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ChicagoSolo travelers' tours

Our most recommended Chicago Solo travelers' tours

Chicago: 360 Chicago Observation Deck Skip-the-Line Ticket

1. Chicago: 360 Chicago Observation Deck Skip-the-Line Ticket

Marvel at the views from 1,000 feet over Chicago’s legendary Michigan Avenue with this ticket to the 360 CHICAGO observation deck on the 94th floor of the John Hancock Center. Save time with skip-the-line access to this popular attraction. Head up to the 360 CHICAGO observation deck to take in breathtaking views of Chicago’s lakefront and view the city skyline from above. Take a peek at 4 neighboring states from this height. Feel the thrill of a 40-second ride in one of North America's fastest elevators to the observation deck to experience what 'Travel & Leisure Magazine' voted one of the best views in America. Enjoy an interactive exhibit on the Ground Floor that highlights Chicago’s rich history and showcases 9 of the city’s culturally unique neighborhoods. On the 94th floor, explore the history and architecture of the magnificent city stretched out before you. To enhance your experience, download the Magnicity App for a guided tour right from your smartphone. The App includes an interactive viewfinder, unique facts, stories and recommendations. Enjoy a thrilling photo opportunity at CloudWalk, a breathtaking 3D mural with the optical illusion of walking in the clouds. Relax and take in the view at the 94th floor’s Cloud Bar which serves up iconic Chicago snacks, neighborhood-inspired Cocktails, and a local brew, Moody Tongue, on tap. By purchasing this timed ticket, you get to skip the ticket desk and present your barcoded voucher to security to be scanned - you may have to wait in a short line at security, then head directly into the Ground Floor Exhibits, and then on to the Elevator Line.

Chicago River Architecture Cruise: Skip-the-Ticket-Office

2. Chicago River Architecture Cruise: Skip-the-Ticket-Office

Skip the lines at the ticket office and climb aboard a state-of-the-art cruise for a 60- or 75-minute cruise of all 3 branches of the Chicago River, and marvel at the architecture that has made the city so legendary. Get an insight into the buildings and engineering of a city that gave birth to the skyscraper and is the spiritual home of modern American architecture. Your expert guide will lead you down the Chicago River to uncover hidden gems, as well the city’s most renowned landmarks, such as the John Hancock building, Trump Tower, Marina City, Willis Tower, and more. Relax with a glass of something cold from the cash bar, as you cruise the Windy City’s waterway, and learn its status as a modern metropolis and one of the world’s most beautiful cities. End your tour in the same place where you boarded the boat.

Chicago: Gangsters and Ghosts 2-Hour Walking Tour

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

See a different side of Chicago on a family-friendly guided tour and hear the tales of the ghosts that haunt the city. Explore the famous Chicago Loop district with your historian guide revealing the many interesting stories hidden behind each turn. Explore the Chicago Loop, known as the vice district during the 1920s and 30s, once the home of speakeasies, secret tunnels and bootleggers. See the places where gangsters such as Al Capone used to party, make deals, and carry out business. Visit haunted locations and old crime scenes including Chicago Riverwalk, Death Alley, and the Chicago Theatre. Peak inside the haunted Palmer House. Finish up at the Congress Hotel, one of the most haunted places in Illinois. Enjoy frequent stops along the way, including a refreshment stop and a restroom break.

Chicago: 360 Chicago Observation Deck Sip and View Ticket

4. Chicago: 360 Chicago Observation Deck Sip and View Ticket

Take in the beautiful views of Chicago as you enjoy a drink from our carefully curated Sip menu. 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 and businesses across Chicago neighborhoods. Get inspired to explore Chicago beyond downtown after watching a short documentary titled 3 of 77 featuring an immersive view of three Chicago 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 in the clouds across a 3D mural complete with an optical illusion – a great photo op!

Chicago: Lake Michigan Skyline Tour & Lake Hopper Cruise

5. Chicago: Lake Michigan Skyline Tour & Lake Hopper Cruise

Immerse yourself in the sights and learn about Chicago’s history and architecture during a cruise on Lake Michigan. Take advantage of skip-the-line entry privileges with a barcoded ticket that lets you proceed directly to the boarding line. Whether you’re a local or a visitor to the city for the first time, taking in the spectacular views of Chicago's skyline from the lake makes for a perfect outing. You’ll see the city as never before while listening to commentary on Chicago's history and architectural gems. Simply hop on board, sit back, relax, and enjoy as you admire Chicago's most significant landmarks and striking buildings that make up the city's skyline that has appeared in so many movies and TV shows. Route: The Skyline Tour and Lake Hopper takes you out onto Lake Michigan, heading both north and south on the lake, you’ll see many of Chicago’s famous landmarks and the classic skyline vista. Enjoy the flexibility to hop-on and hop-off the Skyline Lake loop at either the Museum Campus or Navy Pier.

The Chicago Theatre Marquee Tour

6. The Chicago Theatre Marquee Tour

Go on a history-filled journey, from the inception of this majestic venue in 1921, all the way to its present-day incarnation as a premier entertainment venue. The Marquee Tour encompasses historical and architectural highlights of the building, including the grand lobby, sweeping staircase and majestic auditorium. Tour guests have the chance to stand on the famous Chicago Theatre stage, plus view artist signatures on the dressing room walls, including Frank Sinatra, Dean Martin, Dolly Parton and so many more!

Chicago Lakefront: Seadog Speedboat Ride

7. Chicago Lakefront: Seadog Speedboat Ride

This half-hour Seadog Speedboat ride along Chicago’s lakefront is one of the best ways to view the city’s skyline while learning about the city. Combine an exciting speedboat ride with informative and amusing stories about the world-famous Windy City. As you depart Chicago's Navy Pier, your captain will tell you interesting facts about the pier and the lakefront as he cranks up the music and races to key lakefront landmarks. Stop near the picturesque lakefront park of the Chicago Museum campus, where you’ll learn about the architecture and history of Chicago. Admire views of the Magnificent Mile neighborhood, including the Buckingham Fountain, Sears Tower, Grant Park, and Chicago's largest shopping district. Listen to the thrilling sound of the turbo engines as you race around the Lake Michigan waterfront and back to the Navy Pier. Upgrade to the Extreme Thrill Ride Option and experience exhilarating speeds and full 360° spins. This jet-propelled ride blasts off to start and splashes down to stop. Experience full-throttle slalom runs, sharp twists and turns, and the raw power of Seadog Extreme's 1400 HP engines.

Chicago: 75-Minute Architecture Cruise by Speedboat

8. Chicago: 75-Minute Architecture Cruise by Speedboat

Climb aboard a speedboat for a thrilling river and lake cruise around some of Chicago’s architectural gems. Gain insights into the city's most famous landmarks from your guide. Admire sights like Willis Tower, Tribune Tower, and Buckingham Fountain. Depart from the former Navy training center of Navy Pier on the shores of Lake Michigan on a tour along the lakefront. Sail through the locks and along the Chicago River all the way to the second tallest building in the USA, Willis Tower (formerly Sears Tower). Get up close to Chicago’s most iconic buildings and unique architecture, and enjoy amazing views and an entertaining narration as part of the exciting ride. Learn the fascinating history of structures like the neo-Gothic Tribune Tower and the Lyric Opera of Chicago. Cruise the lakefront of Lake Michigan to see monuments and attractions such as Buckingham Fountain, Grant Park, Chicago Harbor, and the Chicago Museum Campus.

Chicago: Go City All-Inclusive Pass with 25+ Attractions

9. Chicago: Go City All-Inclusive Pass with 25+ Attractions

The Chicago All-Inclusive Pass by Go City provides free admission to the city’s top activities, attractions, and tours, offering the ultimate in convenience and savings. Choose durations of 1, 2, 3, or 5 days at a low, pre-paid price and save up to 50%* compared to buying individual attraction tickets. Take a trip up to SkyDeck Chicago, visit the Field Museum, have fun at Navy Pier, and enjoy a cruise. All these and more are included with your Chicago All-Inclusive Pass. The Chicago All-Inclusive Pass comes with a digital guide including useful attraction information. Use it to help you decide what to do, where to go, and how to get there. Activities, attractions, and tours included with the Chicago All-Inclusive Pass: • Shedd Aquarium (reservations required) • SkyDeck Chicago (reservations required) • Hop-On Hop-Off Big Bus Chicago: 1-Day Classic Tour • 360 CHICAGO • Adler Planetarium • Museum of Science and Industry • Field Museum • Architectural River and Lake Tour • Chicago Children's Museum • LEGOLAND Discovery Center • Bike and Roll Chicago: 2-Hour Bike Rental • Chicago History Museum • Lincoln Park Zoo Rides • Museum of Contemporary Art • Robie House • Frank Lloyd Wright Home and Studio Tour • Ernest Hemingway Birthplace Home • 10pin Chicago 90-minute Bowling & Pizza (reservations required) • American Writers Museum • Lakefront Speedboat Tour • Extreme Thrill Ride • Downtown Chicago TV & Movie Sites Walking Tour (reservations required) • Chicago Theatre Marquee Tour • Chicago Must-See Architecture Walking Tour (reservations required) • Mobsters and Haunted Mysteries Walking Tour (reservations required) • $20 Food and Drinks Credit at The Cauldron Chicago • The Forge Adventure Park • Chicago Pizza and Drink Combo Attractions and tours are subject to change. Check the digital guide included on your confirmation voucher for the full list of inclusions, opening times, and reservation instructions. *Savings based on itineraries on Go City website.

Chicago: Seadog Speedboat Fireworks Cruise on Lake Michigan

10. Chicago: Seadog Speedboat Fireworks Cruise on Lake Michigan

Enjoy a summer or autumn evening on this Chicago Seadog Speedboat Fireworks Cruise on Lake Michigan. This popular 60-minute narrated tour ensures you have the best views of this magnificent fireworks display. Every seat on the Seadog Speedboat Fireworks Cruise has amazing panoramic views of Chicago's historical skyline. Whether you are looking for a romantic evening, a night out with friends, or simply appreciate the art of pyrotechnics, this tour will have everyone of all ages leaving with a smile. Come and visit all of the possibilities that Chicago has to offer by enjoying a magical Fireworks Cruise on Lake Michigan. These memories are made to last a lifetime! Join us on Wednesday and Saturday evenings during the summer months for an unforgettable memory.

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What people are saying about Chicago

Overall rating

4.5 / 5

based on 991 reviews

Awesome tour with an awesome guide ! Baylor’s enthusiasm and friendliness really sold it and she even managed to give me goosebumps with the way she told some of the stories! :)

Our guide Ty was super cool and handled the whole tour well. I'll definitely tell all my friends who visit Chicago to take this tour.

Conor was very knowledgeable and the tour was a great pace with lots of info!

Our docent was extremely knowledgeable and the tour was well worth it.

Loved it!!! No crowds or long lines!! Love Chicago in the winter!!