Chicago
Tours

Our most recommended things to do in Chicago

Chicago River: 1.5-Hour Guided Architecture Cruise

Chicago River: 1.5-Hour Guided Architecture Cruise

Experience more of Chicago by boat than on any other architectural cruise. See architectural highlights and enjoy an open-air deck or climate-controlled interior as you travel the main River and its north and south branches. View all of Chicago's architectural highlights during this comprehensive sightseeing tour. Be entertained by the expert and friendly tour guides as they explain the 130 year-long history behind the skyline, while bartenders and staff keep you comfortable with refreshments.  Choose between the fresh air of the open-air decks or enjoy the comfort of the climate-controlled interiors during your cruise. The tour starts at the Michigan Avenue (DuSable) bridge and goes up the main branch of the Chicago River past Wolf Point. It then cruises along the north and south branches of the river, before heading back past the Chicago Riverwalk towards Lake Michigan. On the way, learn about ornate, historic early skyscrapers like the Wrigley Building and the Tribune Tower, the imposing art deco Merchandise Mart, mid-century skyscrapers like the Mies Van der Rohe AMA Building. Don't miss the circular Marina City Towers, the majestic Willis Tower (formerly the Sears Tower and the tallest building in Chicago) the soaring AON Center, and more modernist structures like Aqua, Trump Tower, Nuveen, and the new Vista Tower. During your cruise, have the opportunity to enjoy a full-service cash bar featuring authentic Chicago products, including local beer and spirits, and Garrett’s Popcorn. Don’t forget to take a selfie at the Grand Staircase at the front of the boat or pose for photos at the picturesque stern or bow of this classic vessel.

Chicago: Willis Tower Skydeck and The Ledge Ticket

Chicago: Willis Tower Skydeck and The Ledge Ticket

Enjoy an unrivaled view over the city of Chicago on a trip up the city's Willis Tower. This famous building, once known as the Sears Tower, is not only home to a Skydeck on the 103rd floor, but it also features The Ledge, a series of 4 glass-paneled boxes that extend out from the building's facade to give visitors a view straight down. As you wind through the ground levels of the Willis Tower, you will be surrounded by museum-quality exhibits highlighting the iconic tower. Learn about Chicago's rich history and culture through these informative visuals. Watch a video presentation, "Reaching for the Sky," where you will be briefed on the history of the building and of architecture in Chicago. Then step into your elevator and you will be amazed at how quickly it ascends. As you travel, your multimedia-equipped elevator will inform you about your vertical progress. Upon reaching the 103rd floor, step out onto the Skydeck, which offers views spanning over 50 miles and across 4 states. Then summon your courage to step out onto The Ledge, a glass balcony that hangs over the edge, for vertigo-inducing views 1,353 feet (about 412 meters) straight down to the city below! Download the Skydeck Mobile App for a free viewfinder which points out many of Chicago’s notable landmarks. Learn more about sights like Navy Pier, Wrigley Field, Grant Park, Art Institute of Chicago, Shedd Aquarium, and Field Museum of Natural History.

Chicago: 45-Minute Family-Friendly Architecture River Cruise

Chicago: 45-Minute Family-Friendly Architecture River Cruise

Admire Chicago’s impressive architecture from a unique perspective aboard a cruise sailing down the Chicago River, which features an indoor and outdoor deck, along with live commentary tailored to entertain the whole family. Treat yourself to a full-service cash bar at your own expense. Experience the best of the Chicago River from Lakeshore Drive to the Willis Tower, navigating along the South branch of the river, before heading back past the Chicago Riverwalk towards Lake Shore Drive and Lake Michigan. Be entertained by the fun and experienced tour guides as they explain the history behind Chicago’s buildings along the river and the exceptional architects who created this ever-changing skyline. Enjoy the most relaxing way to sightsee in Chicago, exploring the city free of traffic, noise, and congestion. Make sure to visit the full-service cash bar featuring authentic Chicago products, including local beer and spirits. Explore the open-air decks that allow you to feel the cooling river breeze and see the city from many vantage points that provide perfect photo opportunities.

Chicago: Navy Pier Centennial Wheel Ticket

Chicago: Navy Pier Centennial Wheel Ticket

Experience the views from the Centennial Wheel at the Historic Navy Pier in Chicago with this attraction ticket. Be suspended over Lake Michigan at the mouth of the Chicago River. Marvel at the Chicago skyline and gaze out over the sparkling waters of Lake Michigan. Choose between two options: With the Regular Barcoded ticket, skip the ticket line and enter the line to board the wheel. The Fastpass Express ticket allows you to skip both lines, and gives you VIP access. Both tickets allow you to visit within 7 days of your scheduled ticket date. Enjoy the Centennial Wheel, which was built in 2016 to celebrate the 100th anniversary of the Navy Pier opening. Featuring 42 gondolas, each holding 8 people, it operates year-round. They also feature LED lighting, padded seats, TV screens, and speakers, as well as panoramic windows on all 4 sides. A ride on the wheel gives you plenty of time to enjoy these panoramic views of Chicago as they unfold around you, and allows you to visit the top three times. Relax and take in the view, or get your camera out to snap pictures of the ever-changing Chicago landscape.

Chicago: 360 Chicago Observation Deck General Admission

Chicago: 360 Chicago Observation Deck General Admission

360 CHICAGO Observation Deck sits 1,000 feet over Chicago’s legendary Michigan Avenue. Located on the 94th floor of 875 N. Michigan (formerly the John Hancock Center), 360 CHICAGO gives you the opportunity to experience the best views of the Chicago Skyline and Lake Michigan. 360 CHICAGO’s concourse level includes an interactive exhibit highlighting the history of Chicago and the vibrant cultures that make Chicago diverse and beautiful. Get inspired to explore Chicago beyond downtown through experiences like The City Beautiful and City of Neighborhoods. Travel to the 94th floor in 40-seconds on one of North America’s fastest elevators and step foot onto the observation deck to experience what 'Travel & Leisure Magazine' voted one of the best views in America. Experience 360 CHICAGO Observation Deck with panoramic views of the city, lakefront, and four neighboring states. Download the Magnicity App for a guided tour right from your smartphone. The app includes unique facts, stories, and recommendations to further enjoy Chicago. TILT offers thrill-seekers the chance to see Chicago from a one-of-a-kind view. Step onto TILT and peer out of the building through floor to ceiling windows at a 30-degree angle 1,000 feet above Michigan Ave. TILT is Chicago’s highest thrill ride. CloudBar serves up iconic Chicago snacks, like Garrett’s popcorn, and neighborhood-inspired cocktails with local brewery, Moody Tongue on tap. CloudWalk takes you on a walk through the neighborhoods of Chicago depicted with vibrant colors and joy– a great photo op! *TILT not included in purchase of your general admission ticket. MUST UPGRADE ON SITE.

Chicago: Architecture River Cruise Skip-the-Ticket Line

Chicago: Architecture River Cruise Skip-the-Ticket Line

Skip the ticket lines and step aboard for a 60-minute cruise covering all three branches of the Chicago River. Marvel at the architecture that has cemented Chicago's legendary status. Gain unique insights into the buildings and engineering feats of a city that birthed the skyscraper and is the spiritual home of modern American architecture. Your expert guide will navigate you through the Chicago River, highlighting hidden gems and iconic landmarks such as the John Hancock Building, Trump Tower, Marina City, Willis Tower, and more. As you cruise the Windy City's waterways, relax with a refreshing drink from the cash bar, and soak in the city’s history and its stature as a modern metropolis and one of the world’s most beautiful cities. End your adventure exactly where it began, enriched with newfound knowledge and a deeper appreciation for Chicago’s architectural wonders.

Chicago: Architecture Boat Tour with Drinks

Chicago: Architecture Boat Tour with Drinks

Experience Chicago’s architectural brilliance on an architectural boat tour. Hop on the boat and embark on a guided journey through the Chicago River, immersing yourself in the city's architectural legacy. Listen as your guides share their knowledge of renowned architects and the evolution of Chicago's skyline. Enjoy a front-row seat to iconic landmarks such as the Willis Tower, Wrigley Building, Tribune Tower, and more. With panoramic views of the city, capture stunning photographs and gain a profound appreciation for the city's architectural significance – all while sipping on coffee, tea, lemonade, water, or soft drinks.

Chicago: CityPASS® with Tickets to 5 Top Attractions

Chicago: CityPASS® with Tickets to 5 Top Attractions

Visiting Chicago? Experience 5 must-see attractions, handpicked and packaged together at a 48% savings, with Chicago CityPASS® tickets. Spend less time planning and more time exploring. Visit the attractions at your own pace, in any order. Valid for 9 consecutive days including the first day of use. Get admission to 5 attractions. Includes: •Shedd Aquarium- All-access admission, including all habitats, Animal Spotlights and exhibits, including seasonal Stingray Touch, plus a 4-D Experience (subject to availability) •Skydeck Chicago- Expedited Entry Plus choose 3 of the following: •Shoreline Sightseeing Architecture River Tour- Architecture River Tour •Field Museum- All-Access Pass, including admission to all permanent and regularly priced ticketed exhibitions (specially ticketed exhibitions outside of All-Access Pass may be subject to additional charges) •360 CHICAGO Observation Deck- Express Entry Admission •Museum of Science and Industry- Museum entry (Science Storms, Numbers in Nature: A Mirror Maze, YOU! The Experience, The Blue Paradox, and much more), plus one timed-entry experience (Giant Dome Theater film or Motion Ride) •Art Institute of Chicago - Fast Pass Admission to permanent collection and non-ticketed special exhibitions •Adler Planetarium - All Exhibitions + Two Sky Shows

Chicago: Hop-on Hop-off Sightseeing Tour by Open-top Bus

Chicago: Hop-on Hop-off Sightseeing Tour by Open-top Bus

Experience the best of Chicago at your own pace from the unique vantage point of a Big Bus tour. Board our open-top, double-decker bus as you take a relaxing ride through the city's most iconic landmarks, from the Magnificent Mile to Millennium Park. Hop on and off at our convenient stops throughout the city to discover Chicago's vibrant neighborhoods and world-famous attractions including 360 CHICAGO, Willis Tower, the Chicago Riverwalk, Museum Campus, The Bean, and more. Spend your day shopping on Magnificent Mile, riding the Ferris Wheel at Navy Pier, or sampling authentic Chicago Deep Dish Pizza. With our flexible and convenient tour, create your own itinerary and explore the city at your own pace. Track bus arrivals in real time with our free downloadable app so you always know when the next bus is coming. Marvel at the stunning skyline as you enjoy professional digital commentary in multiple languages, with earbuds provided. Hear expert insight into Chicago's rich history and culture, as well as tips on the best places to eat, drink, and shop. Maximize your Big Bus experience with our 4 Self-Guided Audio Walking Tours, designed to complement the downtown tour route. Simply download the app and explore at your own pace. All tours start and end at a Big Bus Stop. Choose from fascinating topics including Architecture, Chicago Riverwalk, Public Art, and more! Top hop-on hop-off sights include: • Navy Pier • Millennium Park • Skydeck Chicago & Willis Tower • Chicago Riverwalk • Museum Campus • 360 CHICAGO • Chicago River Cruises • And more!

Chicago: Gangsters and Ghosts Guided Walking Tour

Chicago: Gangsters and Ghosts Guided Walking Tour

Discover a different side of Chicago on a family-friendly guided tour, either on foot or by bus. Hear the tales of the ghosts, and gangsters, that haunt the city. Explore the Chicago South Loop district with your historian guide, uncovering the many mysteries hidden behind every turn. Meet your guide and kick off your guided walk through Chicago's notorious South Loop, known as a vice district during the 1920s and 30s. Stroll through his now upmarket area of the city which was once home to underground speakeasies, secret tunnels, and bootleggers. Hear the true stories of Chicago's bloody past and the gangsters who caused havoc in the city. See the places notorious figures such as Al Capone used to party, make deals, and carry out "business". You will also enjoy a short rest stop at a famous former gangster hangout. Discover the legends of the ghosts that are said to lure along the Chicago Riverwalk and the aptly named Death Alley. Stop at haunted locations including Palmer House, and the Chicago Theatre, before finishing with a visit to the Congress Hotel, one of the most haunted places in Illinois.

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Insider guides to Chicago

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Must-try food in Chicago: 12 yummy dishes to remember
Must-try food in Chicago: 12 yummy dishes to remember

The vibrant food scene in Chicago reflects its rich history and diverse culture. When visiting the Windy City, exploring its culinary delights is a must. From iconic Chicago deep-dish pizzas to mouthwatering fish and pork tacos, there are numerous foods to try. Enjoy a river or lake cruise to sample some of the best food in Chicago, complete with three-course meals and beverages. Walking tours offer another great way to discover popular food spots while visiting hidden gems or iconic landmarks like the Willis Tower and Navy Pier. Here are 12 foods you must eat on your Chicago vacation.

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Chicago in summer: best things to do and see
Chicago in summer: best things to do and see

If you're visiting Chicago in summer, you should add cruises to your must-do activities. Viewing the city on a boat is one of the best experiences you will have in the city.

Couples will also find Chicago summer activities pleasant. They can learn about the city on a speedboat as they take in the thrill of the water.

Families shouldn't shy away from Chicago tours in the summer. If you have kids, consider going for guided tours through The Pedway. To learn more about the city, you can also learn about famous gangster hangouts or take Segway trips.

Create your Chicago summer itinerary full of activities that appeal to you with our top experiences below.

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Best places to visit in Chicago: top attractions you don't want to miss
Best places to visit in Chicago: top attractions you don't want to miss

They don't call it the Mecca of the Midwest for nothing. Illinois' largest city is also home to some of the country's most important sights. From must-visit Chicago landmarks and monuments to incredible art museums, the Windy City rewards visitors of all tastes. Get ahead of your trip with these 20 must-see attractions, covering everything from Al Capone's HQ and the Magnificent Mile to the world-famous Art Institute of Chicago.

As the birthplace of the skyscraper, every Chicago itinerary must include a close look at the city’s architecture too. You can explore the iconic skyline at the John Hancock Building or ascend the Willis Tower for a bird’s-eye view. Visiting Chi-town with kids? The Museum of Ice Cream will be the highlight of their vacation. Whatever you pick, you can't go wrong with this list of Chicago’s best places to visit.

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8 epic things to do in Chicago at night
8 epic things to do in Chicago at night

The Windy City is known for its magnificent architecture, open green spaces, and delightful gastronomy scene, and it really comes alive after dark. Take in city views lit up from the water or a sky-high observation deck. Head to one of Chicago’s many sporting venues and cheer on the home team. Follow the footsteps of notorious gangsters like Al Capone and visit spooky haunts and hidden speakeasies. Or witness a dazzling fireworks display over Lake Michigan from a historic pier. Whatever your interest, this list of epic things to do in Chicago at night has you covered.

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Our most recommended things to do in Chicago

Chicago River: 1.5-Hour Guided Architecture Cruise

Chicago River: 1.5-Hour Guided Architecture Cruise

Experience more of Chicago by boat than on any other architectural cruise. See architectural highlights and enjoy an open-air deck or climate-controlled interior as you travel the main River and its north and south branches. View all of Chicago's architectural highlights during this comprehensive sightseeing tour. Be entertained by the expert and friendly tour guides as they explain the 130 year-long history behind the skyline, while bartenders and staff keep you comfortable with refreshments.  Choose between the fresh air of the open-air decks or enjoy the comfort of the climate-controlled interiors during your cruise. The tour starts at the Michigan Avenue (DuSable) bridge and goes up the main branch of the Chicago River past Wolf Point. It then cruises along the north and south branches of the river, before heading back past the Chicago Riverwalk towards Lake Michigan. On the way, learn about ornate, historic early skyscrapers like the Wrigley Building and the Tribune Tower, the imposing art deco Merchandise Mart, mid-century skyscrapers like the Mies Van der Rohe AMA Building. Don't miss the circular Marina City Towers, the majestic Willis Tower (formerly the Sears Tower and the tallest building in Chicago) the soaring AON Center, and more modernist structures like Aqua, Trump Tower, Nuveen, and the new Vista Tower. During your cruise, have the opportunity to enjoy a full-service cash bar featuring authentic Chicago products, including local beer and spirits, and Garrett’s Popcorn. Don’t forget to take a selfie at the Grand Staircase at the front of the boat or pose for photos at the picturesque stern or bow of this classic vessel.

Chicago: Willis Tower Skydeck and The Ledge Ticket

Chicago: Willis Tower Skydeck and The Ledge Ticket

Enjoy an unrivaled view over the city of Chicago on a trip up the city's Willis Tower. This famous building, once known as the Sears Tower, is not only home to a Skydeck on the 103rd floor, but it also features The Ledge, a series of 4 glass-paneled boxes that extend out from the building's facade to give visitors a view straight down. As you wind through the ground levels of the Willis Tower, you will be surrounded by museum-quality exhibits highlighting the iconic tower. Learn about Chicago's rich history and culture through these informative visuals. Watch a video presentation, "Reaching for the Sky," where you will be briefed on the history of the building and of architecture in Chicago. Then step into your elevator and you will be amazed at how quickly it ascends. As you travel, your multimedia-equipped elevator will inform you about your vertical progress. Upon reaching the 103rd floor, step out onto the Skydeck, which offers views spanning over 50 miles and across 4 states. Then summon your courage to step out onto The Ledge, a glass balcony that hangs over the edge, for vertigo-inducing views 1,353 feet (about 412 meters) straight down to the city below! Download the Skydeck Mobile App for a free viewfinder which points out many of Chicago’s notable landmarks. Learn more about sights like Navy Pier, Wrigley Field, Grant Park, Art Institute of Chicago, Shedd Aquarium, and Field Museum of Natural History.

Chicago: 45-Minute Family-Friendly Architecture River Cruise

Chicago: 45-Minute Family-Friendly Architecture River Cruise

Admire Chicago’s impressive architecture from a unique perspective aboard a cruise sailing down the Chicago River, which features an indoor and outdoor deck, along with live commentary tailored to entertain the whole family. Treat yourself to a full-service cash bar at your own expense. Experience the best of the Chicago River from Lakeshore Drive to the Willis Tower, navigating along the South branch of the river, before heading back past the Chicago Riverwalk towards Lake Shore Drive and Lake Michigan. Be entertained by the fun and experienced tour guides as they explain the history behind Chicago’s buildings along the river and the exceptional architects who created this ever-changing skyline. Enjoy the most relaxing way to sightsee in Chicago, exploring the city free of traffic, noise, and congestion. Make sure to visit the full-service cash bar featuring authentic Chicago products, including local beer and spirits. Explore the open-air decks that allow you to feel the cooling river breeze and see the city from many vantage points that provide perfect photo opportunities.

Chicago: Navy Pier Centennial Wheel Ticket

Chicago: Navy Pier Centennial Wheel Ticket

Experience the views from the Centennial Wheel at the Historic Navy Pier in Chicago with this attraction ticket. Be suspended over Lake Michigan at the mouth of the Chicago River. Marvel at the Chicago skyline and gaze out over the sparkling waters of Lake Michigan. Choose between two options: With the Regular Barcoded ticket, skip the ticket line and enter the line to board the wheel. The Fastpass Express ticket allows you to skip both lines, and gives you VIP access. Both tickets allow you to visit within 7 days of your scheduled ticket date. Enjoy the Centennial Wheel, which was built in 2016 to celebrate the 100th anniversary of the Navy Pier opening. Featuring 42 gondolas, each holding 8 people, it operates year-round. They also feature LED lighting, padded seats, TV screens, and speakers, as well as panoramic windows on all 4 sides. A ride on the wheel gives you plenty of time to enjoy these panoramic views of Chicago as they unfold around you, and allows you to visit the top three times. Relax and take in the view, or get your camera out to snap pictures of the ever-changing Chicago landscape.

Chicago: 360 Chicago Observation Deck General Admission

Chicago: 360 Chicago Observation Deck General Admission

360 CHICAGO Observation Deck sits 1,000 feet over Chicago’s legendary Michigan Avenue. Located on the 94th floor of 875 N. Michigan (formerly the John Hancock Center), 360 CHICAGO gives you the opportunity to experience the best views of the Chicago Skyline and Lake Michigan. 360 CHICAGO’s concourse level includes an interactive exhibit highlighting the history of Chicago and the vibrant cultures that make Chicago diverse and beautiful. Get inspired to explore Chicago beyond downtown through experiences like The City Beautiful and City of Neighborhoods. Travel to the 94th floor in 40-seconds on one of North America’s fastest elevators and step foot onto the observation deck to experience what 'Travel & Leisure Magazine' voted one of the best views in America. Experience 360 CHICAGO Observation Deck with panoramic views of the city, lakefront, and four neighboring states. Download the Magnicity App for a guided tour right from your smartphone. The app includes unique facts, stories, and recommendations to further enjoy Chicago. TILT offers thrill-seekers the chance to see Chicago from a one-of-a-kind view. Step onto TILT and peer out of the building through floor to ceiling windows at a 30-degree angle 1,000 feet above Michigan Ave. TILT is Chicago’s highest thrill ride. CloudBar serves up iconic Chicago snacks, like Garrett’s popcorn, and neighborhood-inspired cocktails with local brewery, Moody Tongue on tap. CloudWalk takes you on a walk through the neighborhoods of Chicago depicted with vibrant colors and joy– a great photo op! *TILT not included in purchase of your general admission ticket. MUST UPGRADE ON SITE.

Chicago: Architecture River Cruise Skip-the-Ticket Line

Chicago: Architecture River Cruise Skip-the-Ticket Line

Skip the ticket lines and step aboard for a 60-minute cruise covering all three branches of the Chicago River. Marvel at the architecture that has cemented Chicago's legendary status. Gain unique insights into the buildings and engineering feats of a city that birthed the skyscraper and is the spiritual home of modern American architecture. Your expert guide will navigate you through the Chicago River, highlighting hidden gems and iconic landmarks such as the John Hancock Building, Trump Tower, Marina City, Willis Tower, and more. As you cruise the Windy City's waterways, relax with a refreshing drink from the cash bar, and soak in the city’s history and its stature as a modern metropolis and one of the world’s most beautiful cities. End your adventure exactly where it began, enriched with newfound knowledge and a deeper appreciation for Chicago’s architectural wonders.

Chicago: Architecture Boat Tour with Drinks

Chicago: Architecture Boat Tour with Drinks

Experience Chicago’s architectural brilliance on an architectural boat tour. Hop on the boat and embark on a guided journey through the Chicago River, immersing yourself in the city's architectural legacy. Listen as your guides share their knowledge of renowned architects and the evolution of Chicago's skyline. Enjoy a front-row seat to iconic landmarks such as the Willis Tower, Wrigley Building, Tribune Tower, and more. With panoramic views of the city, capture stunning photographs and gain a profound appreciation for the city's architectural significance – all while sipping on coffee, tea, lemonade, water, or soft drinks.

Chicago: CityPASS® with Tickets to 5 Top Attractions

Chicago: CityPASS® with Tickets to 5 Top Attractions

Visiting Chicago? Experience 5 must-see attractions, handpicked and packaged together at a 48% savings, with Chicago CityPASS® tickets. Spend less time planning and more time exploring. Visit the attractions at your own pace, in any order. Valid for 9 consecutive days including the first day of use. Get admission to 5 attractions. Includes: •Shedd Aquarium- All-access admission, including all habitats, Animal Spotlights and exhibits, including seasonal Stingray Touch, plus a 4-D Experience (subject to availability) •Skydeck Chicago- Expedited Entry Plus choose 3 of the following: •Shoreline Sightseeing Architecture River Tour- Architecture River Tour •Field Museum- All-Access Pass, including admission to all permanent and regularly priced ticketed exhibitions (specially ticketed exhibitions outside of All-Access Pass may be subject to additional charges) •360 CHICAGO Observation Deck- Express Entry Admission •Museum of Science and Industry- Museum entry (Science Storms, Numbers in Nature: A Mirror Maze, YOU! The Experience, The Blue Paradox, and much more), plus one timed-entry experience (Giant Dome Theater film or Motion Ride) •Art Institute of Chicago - Fast Pass Admission to permanent collection and non-ticketed special exhibitions •Adler Planetarium - All Exhibitions + Two Sky Shows

Chicago: Hop-on Hop-off Sightseeing Tour by Open-top Bus

Chicago: Hop-on Hop-off Sightseeing Tour by Open-top Bus

Experience the best of Chicago at your own pace from the unique vantage point of a Big Bus tour. Board our open-top, double-decker bus as you take a relaxing ride through the city's most iconic landmarks, from the Magnificent Mile to Millennium Park. Hop on and off at our convenient stops throughout the city to discover Chicago's vibrant neighborhoods and world-famous attractions including 360 CHICAGO, Willis Tower, the Chicago Riverwalk, Museum Campus, The Bean, and more. Spend your day shopping on Magnificent Mile, riding the Ferris Wheel at Navy Pier, or sampling authentic Chicago Deep Dish Pizza. With our flexible and convenient tour, create your own itinerary and explore the city at your own pace. Track bus arrivals in real time with our free downloadable app so you always know when the next bus is coming. Marvel at the stunning skyline as you enjoy professional digital commentary in multiple languages, with earbuds provided. Hear expert insight into Chicago's rich history and culture, as well as tips on the best places to eat, drink, and shop. Maximize your Big Bus experience with our 4 Self-Guided Audio Walking Tours, designed to complement the downtown tour route. Simply download the app and explore at your own pace. All tours start and end at a Big Bus Stop. Choose from fascinating topics including Architecture, Chicago Riverwalk, Public Art, and more! Top hop-on hop-off sights include: • Navy Pier • Millennium Park • Skydeck Chicago & Willis Tower • Chicago Riverwalk • Museum Campus • 360 CHICAGO • Chicago River Cruises • And more!

Chicago: Gangsters and Ghosts Guided Walking Tour

Chicago: Gangsters and Ghosts Guided Walking Tour

Discover a different side of Chicago on a family-friendly guided tour, either on foot or by bus. Hear the tales of the ghosts, and gangsters, that haunt the city. Explore the Chicago South Loop district with your historian guide, uncovering the many mysteries hidden behind every turn. Meet your guide and kick off your guided walk through Chicago's notorious South Loop, known as a vice district during the 1920s and 30s. Stroll through his now upmarket area of the city which was once home to underground speakeasies, secret tunnels, and bootleggers. Hear the true stories of Chicago's bloody past and the gangsters who caused havoc in the city. See the places notorious figures such as Al Capone used to party, make deals, and carry out "business". You will also enjoy a short rest stop at a famous former gangster hangout. Discover the legends of the ghosts that are said to lure along the Chicago Riverwalk and the aptly named Death Alley. Stop at haunted locations including Palmer House, and the Chicago Theatre, before finishing with a visit to the Congress Hotel, one of the most haunted places in Illinois.

Frequently asked questions about Chicago

What top attractions are a must-see in Chicago?

The must-see attractions in Chicago are:

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What are the best day trips and excursions from Chicago?

The best day trips and excursions from Chicago are:

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What are the best inexpensive tours in Chicago?

These are the best activities when you are visiting Chicago on a budget:

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Insider tips: Explore Chicago like a local

Megan & Aram is a travel blog that focuses mostly on travel in the Nordics and Eastern Europe with the occasional trip beyond those regions. We love coffee, promoting small businesses, and sports.

What should I do on my first trip to Chicago?

Chicago is the third largest city in the United States and there is an endless number of things to do for every type of visitor. If you're visiting Chicago for the first time, start your day at Milennium Park and The Bean - which has, over time, become a symbol of the city. If you're lucky, you may even get to experience a free concert or gathering there during your trip! Don't leave the area before heading out onto Navy Pier for a few photos.

You can't visit Chicago as a first-timer without heading to The Skydeck at Willis Tower. What was previously known as the Sears Tower is now the Willis Tower and is one of the tallest buildings in the Americas! You can step out onto the glass-bottom Skydeck for an epic view of the city and since you'll be 1,353 into the air, you will be able to see everything!

Some museums worth checking out are the Art Institute of Chicago and the Museum of Science and Industry.

If you need an escape from the city, there are plenty of day trips from Chicago that will give you the downtime you need.

What are some hidden gems to see in Chicago?

Chicago is teeming with hidden gems and one of the best places to visit to experience one of the city's most underrated places is the 606 - a park and trail system that has been transformed from its days as an old railroad line. The 2.7-mile trail goes through the city connecting various neighborhoods. Another hidden gem is Promontory Point which is located in Burnham Park. This man-made peninsula offers some of the top views in the city - and you can see the skyline and Lake Michigan while sitting in a relaxing spot. Chicago also has some of the coolest neighborhoods and districts of any US city! And, many of these neighborhoods have large concentrations of different ethnic groups, making it like a trip around the globe without ever leaving the Midwest city.

How much time should I spend in Chicago?

You can see the best of Chicago on a long weekend trip, but a week is an ideal amount of time if you're really wanting to explore the city deeper. You can see the main highlights on a long weekend trip, though. To maximize your time, sign up for city tours and utilize the 'L', or metro system.

What food is Chicago known for?

It would be remiss of me to mention the food of Chicago and not start off with deep-dish pizza! Originating at Pizzeria Uno in 1943, this style of pizza is beloved by residents of the Windy City and it has become Chicago's most iconic dish! Some other foods to try when visiting are Chicago style hot dogs (made famous during the Great Depression), Italian beef, and Chicago BBQ. You can also dive into the city's Eastern European history with some tasty perogies and potato pancakes.

What is the best way to get around Chicago?

While renting a car may be the most ideal option for those looking to take day trips, Chicago is a very well-connected city that lends itself to walking and public transportation!

You will find plenty of taxis, public buses, and bike sharing options within Chicago. The city is also home to the L-train, or the city's metro operated by the Chicago Transit Authority. The L-train stands for 'elevated train' and it serves over 140 stations on its 8 train lines.

What are the best months to visit Chicago?

Winter can be brutally cold in Chicago (and snowy), making the best time to visit the city summer (or the shoulder season). The summers in Chicago are never exceptionally hot and the greenery makes the area pleasant and inviting. Lake Michigan also offers plenty of opportunities during the summer months, as well. You can swim on its beaches or take a boat out into the lake.

What are the best neighborhoods to visit in Chicago?

Chicago has some of the most dynamic neighborhoods of any city I have ever been in! Every one has something interesting and unique to offer! Some of the most popular neighborhoods are Wicker Park (lots of cool bars and cafes), Logan Square (young professionals and hip establishments), Andersonville (known for its Swedish history and Midsommarfest), Pilsen (known for its art scene), Ukrainian Village (lots of Ukrainian history, art museums, and businesses), Lincoln Square (German history with many Bavarian bakeries, etc), and more.

What are the best neighborhoods for food?

Lincoln Park is a favorite Chicago district for food lovers! One thing that the neighborhood is famous for is its brunch options! You can find many international restaurants here - but brunch is a big deal in Lincoln Park and you can find everything from vegetarian brunch options to French toast flights and DIY mimosas!

Another area of the city known for its trend-setting food options is the West Loop. The West Loop is located in the former meatpacking district and now has so much to offer food lovers - from fine dining restaurants to celebrity chefs opening up new concepts to Chicago residents.

If you love Mexican food - head to Pilsen and indulge in some of the city's best Mexican restaurants.

What are the best neighborhoods for shopping?

Chicago is a shopper's paradise and you will find delightful shopping everywhere! Michigan Avenue is the city's most famous shopping thoroughfare - with shops lining the streets and mega malls located along one of the city's busiest streets. The Shops at North Bridge and the 900 North Michigan Shops are some of the places to check out when there. Beyond Michigan Avenue, you can find great shopping on Armitage Avenue in Lincoln Park and cool vintage finds on Belmont Avenue at The Belmont Army. There are also many other second-hand shops and indie stores if you head east on Belmont.

What neighborhood should I stay in when I visit Chicago?

If you're a first-time visitor to Chicago, you will want to stay downtown and near many of the main sights and museums. Other good and safe options are Lakeview, The Loop, and Lincoln Park. All are well connected by public transportation. However, if you're looking for a more 'local' experience, check out hotel options in Logan Square, Lincoln Square, and Wicker Park. There are plenty of food options and hip bars and hang out in!

What's are 4 best tips for a person traveling to Chicago?

1) Don't let yourself get overwhelmed. This is the US' third most populous city and it is a lot to take in! Plan your trip ahead and then try to stay in one area and explore it deeply. You can save additional sights and areas for a future trip.

2) Heading to Chicago in winter? Bundle up! They don't call it the Windy City for nothing! It is cold, windy, and snowy! But, you will still find plenty to do in the city during the winter months that it is always worth a visit!

3) If you're visiting different neighborhoods, research the history of the place and find pieces of those history throughout. For example, if you're visiting Andersonville, you will quickly realize that it has extensive Swedish history. Stop into Swedish bakeries and shops and see how this culture has meshed together with Chicago's throughout the years. It truly is one of the things that makes the Midwest city so unique!

4) Take the L-train! This transport option is cheap, efficient, and the best way to get around the city. You can save so much money by avoiding driving around and parking and just taking the L around.

What should people avoid doing in Chicago?

Avoid thinking that this city is similar to Los Angeles and New York. Chicago retains that Midwestern 'down-to-earth' charm that can get lost a bit on the coasts. The city is sports-centric and bars are super social and friendly. Be sure to go in ready to meet people and make some new friends along the way!

Another thing to avoid is eating at the chain restaurants. While these places are predictable and offer a 'secure' experience - Chicago has some insanely good food options and there is no better way to learn about the city than through its food!

What are your top 5 favourite GetYourGuide experiences in Chicago?

1) Chicago River: 1.5-Hour Guided Architecture Cruise

2) Chicago: Willis Tower Skydeck and The Ledge Ticket

3) Chicago: Gangsters and Ghosts 2-Hour Walking Tour

4) Chicago Lakefront: Seadog Speedboat Ride

5) Chicago: Favorite Foods Guided Walking Tour

What is one thing that surprised you about Chicago?

I have been to Chicago more times than I can count, but the one thing that always surprises me is how friendly everyone is! Big cities tend to be a little unfriendly but Chicago is the absolute opposite. Every time I head there, I meet new people and make new connections and it is difficult to leave. I wouldn't be surprised if I ended up moving there one day and calling the Windy City my home.

What are the best annual events in Chicago?

Chicago has several events annually and one of the city's most popular is the Taste of Chicago, the largest food festival in the world! You'll find a lot of live music, food, and more! It is a must-visit summer festival in Chicago. The city also has several music festivals not only dedicated to popular bands, but also different genres of music. You can head to the Chicago Jazz Festival or the Chicago Blues Festival and see how both styles of music have made an impact on Illinois' largest city.

Top Attractions in Chicago

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What people are saying about Chicago

Overall rating

4.6
(16,697 reviews)

Everything was good . We have to talk to the customer service for help because when we need to reserve the were no spaces available , but they explain that we just need to go straight to the place and show the tickets and we did and everything went just right . We have no problems and save with this instead of buying direct with the business . We definitely recommend it , we have try this in London , NY , San Francisco , and others places , and always works .

What an amazing tour! As a lover of walking tours with a distaste for the cold, this was a great way to experience Chicago regardless of the weather. It turned out to be a beautiful day but we were able to stop inside lovely buildings for a bit of warmth and history. The guide engaged all the guests in the small group and we learned so much. Highly recommend as something to do if visiting Chicago in the winter.

The Chicago CityPASS was absolutely excellent! It provided seamless entry to top attractions, saved time with skip-the-line benefits, and offered great value for the price. Everything about the experience was well-organized, and it made exploring the city so much easier and more enjoyable. Highly recommend for anyone visiting Chicago!

I loved the tour. Matthew, our guide, connected the exteriors and interiors of the buildings in a beautiful way, combining his observations of physical details with the history and intentions of the architects and their buildings. He showed us how to think about what buildings demonstrate about their time and place. Absolutely great.

The science of it all was amazing. The upside down picture. The hanging from a balcony. My favorite the Michael Jackson " lean. I sent that picture of my three granddaughters to all my family and friends. Thank you for the experience.