Illinois
Neighborhood Tours

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Our most recommended Illinois Neighborhood Tours

Chicago River: 45-Minute Family-Friendly Architecture Cruise

1. Chicago River: 45-Minute Family-Friendly Architecture Cruise

Admire Chicago’s impressive architecture from a unique perspective aboard a 45-minute cruise sailing down the Chicago River, which features a full-service cash bar and live commentary tailored to entertain the whole family. 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- a perfect way to explore 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.

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Chicago Underground Donut Tour

2. Chicago Underground Donut Tour

Take a donut tour of the windy city, and discover the best Chicago has to offer. At each location, you will taste a curated sample of the best donuts. Some of the stops on this downtown tour include Stan's Donuts, Do-Rite Donuts, and Firecakes Donuts, true donut institutions. This two hour walking tour is led by a passionate donut expert who will guide you to some of Chicago's best donut locales. This tour caters to all size groups, both large and small. The donut tour is great for bachelor and bachelorette parties, birthdays, family reunions, weekend getaways, or even corporate events. There are two versions of the Donut Tour: The Classic Downtown Tour, as well as a local neighborhood tour in Wicker Park. Both are great options if you're excited about donuts. It really just depends on what neighborhood you want to explore: if you want to stay downtown or if you want to venture out to the Wicker Park & Bucktown neighborhoods to see how "the locals do it". In either case, don't hesitate to join the tour. Buy your tickets today!

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Chicago: Food, Architecture and History Tour

3. Chicago: Food, Architecture and History Tour

Start your tour under the dazzling marquee of the Chicago Theater (which you might recognize from the movie-musical Chicago). Your first stop is inside one of the best-preserved spaces built for shopping in Chicago, featuring an unforgettable atrium at its core. Then head towards the Chicago Pedway, a uniquely Chicago feature used by locals and commuters daily. Afterward, head back above-ground near City Hall and head inside to see the classic interior design and architecture. Next, enjoy a sweet treat, and local tradition: Chicago-style popcorn. Weather permitting, take a stroll along the Chicago Riverwalk while taking in views of several soaring buildings, including Marina Towers, the Britannica Building, and the Willis Tower. From there, make your way to another delicious destination where you can sample locally made chocolate from a Chicago staple. Next, take a stroll through the beautiful lakefront parks along Michigan Avenue. End up in the picturesque Millennium Park, home to the iconic Bean sculpture. By then, you’ll hopefully have built up an appetite because it’s time to begin your ultimate food experience.  Travel with your guide up to the River North neighborhood, the original Chicago foodie destination. Start your food tour with a well-known Chicago fare: the Chicago-style hot dog. Every Chicagoan has their own preference as to how the dog should be made, and you’ll get a chance to try your guides’ favorite version. Next up is the world-famous Chicago deep-dish pizza, the staple of the Chicago food scene. Visit a pizza place that’s an icon to Chicago natives to try the real deal for yourself. After you’ve filled up on pizza and hot dogs, take a stroll through two more establishments, each one essential to Chicago’s food culture. Then continue your tasting journey with a classic Chicago sandwich: Italian beef.  Sample this sandwich in a real Chicago institution. Your tour ends here, and your guide will be happy to direct you back to your accommodation or share tips for what else to see and do in the city.

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Chicago: 2.5-Hour Taste of Chinatown Food Walking Tour

4. Chicago: 2.5-Hour Taste of Chinatown Food Walking Tour

Explore the complex layers of Chinese culture and the many contributions these people have made to both Chicago and the world. And what better way to show off Chinese culture then through food? Your guide will take the confusion and language barrier away as you sample your way through a variety of Chinatown's best restaurants and well-kept secret recipes. Start your tour at Phoenix Restaurant and begin with some yummy dim sum dumplings and a traditional Chinese tea tasting. Next, it will be time for a sweet treat - buttery custard tarts from Chinatown's oldest bakery. Then, try a unique and delicious spicy meat sandwich from the Xi'an region. Afterward, stroll through the charming Chinatown Square with its ethnic grocery stores and souvenir shops. Finally, taste a sampling of succulent dry chili chicken, followed by the famous spicy Szechuan hot pot. You'll have traveled all over China but only walked a few blocks on this delicious tour of one of Chicago's most fascinating neighborhoods.

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Chicago: Secret Food Tour

5. Chicago: Secret Food Tour

Sample the culinary delights of Chicago with the help of a fun and enthusiastic foodie guide. Be amazed by the city's eclectic mix of architecture and public art along the way. Taste delicious bites as you explore the city's central Loop district for 3 hours. Get better acquainted with what sets this friendly Midwest metropolis apart from other destinations and get a great insight into the art, architecture and everyday life in the city. Benefit from your guide's local knowledge and get tips to help you sightsee and explore the food and dining scene some more in your own time.

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Amazing Lakefront Segway Tour of Chicago

6. Amazing Lakefront Segway Tour of Chicago

Glide around the streets and parks of Chicago on a leisurely 2.5-hour guided Segway tour. Perfect for Chicago newbies and veterans alike, the tour uncovers quirky facts about one of America’s most energetic destinations. Start your Segway experience at Millennium Park and continue to Grant Park to stop and admire the famous Buckingham Fountain. Ride to Museum Campus to soak up spectacular views of the Chicago skyline and beautiful lakefront. The tour includes a training session to become familiar with the unique self-balancing Segways, before exploring the Windy City in a fun and futuristic fashion. Smart, entertaining tour guides work hard to provide you with the experience of a lifetime, and reward you with expansive views of the sea-like Lake Michigan.

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Chicago: West Loop Underground Donut Tour

7. Chicago: West Loop Underground Donut Tour

Experience the food scene in Chicago on this underground donut tour in West Loop. Learn how each donut location you visit fits into the larger food scene and history of Chicago. Feed your sweet tooth and try donuts from local shops while exploring Restaurant Row. Start at Chicago's French Market that's styled after European markets like those in Barcelona or Paris. Discover all kinds of delicious food and drinks along with the highlight of the trip: donuts. Then, walk along Restaurant Row in Chicago's West Loop. Learn the history of the area on your way to the next stop, Sawada Coffee, a hidden gem of the neighborhood. Next, visit one of the most popular donut shops in the West Loop, Do-Rite Donuts. Try one of their signature donuts, voted the best donut in the city for several years. End at BomboBar and enjoy a big finish to this sweet tour.

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Chicago: History, Culture and Architecture Walking Tour

8. Chicago: History, Culture and Architecture Walking Tour

Start your tour under the dazzling marquee of the Chicago Theater (which you might recognize from the movie-musical Chicago) before heading off into the bustling city. Your first stop is inside one of the best-preserved spaces built for shopping in Chicago, featuring an unforgettable atrium at its core. Then head towards the Chicago Pedway, a uniquely Chicago feature used by locals and commuters daily to move about the city in a network of underground tunnels. Afterward, head back above-ground near City Hall and head inside to see the classic interior design and architecture. Next, enjoy a sweet treat, and local tradition: Chicago-style popcorn. Weather permitting, take a stroll along the Chicago Riverwalk while taking in views of several soaring buildings, including Marina Towers, the Britannica Building, and the Willis Tower. From there, make your way to another delicious destination. Along the way, enjoy views of the world-famous Wrigley Building and the incredible Chicago Tribune building, the heart of Chicago’s thriving and historic journalism industry. Your second tasty confection is locally made chocolate from a Chicago staple. Finally, take a stroll through the beautiful lakefront parks along Michigan Avenue. Round up your tour in the picturesque Millennium Park, home to the iconic Bean sculpture. Here, your guide will conclude your tour and point you in the right direction toward more amazing sights, great lunch spots, or drink recommendations.

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Chicago: Westside Food Tasting Bike Tour with Guide

9. Chicago: Westside Food Tasting Bike Tour with Guide

Go around the world without leaving Chicago! Sample the best of Chicago’s West side neighborhoods decadent food options. Learn the stories of the immigrants from all over the world who helped make Chicago the city it is today, while tasting their delicious foods. Gaze at the historic homes, warehouses, and skyscrapers of Chicago's most historic neighborhoods. Ride along the new elevated 606 trail and the beautiful Lakefront Trail. Begin your tour in Chicago's bustling River North. Cross the iconic Chicago river, then ride through historic meatpacking district Fulton Market, now Chicago's restaurant and tech ground zero. Sample a delicious Mexican torta and a beer at a celebrity chef's new brewpub. Then ride past Google's new headquarters and some beautiful murals before arriving in Ukrainian Village, where you will taste the world's best Polish pierogis. From there, pass gorgeous 19th-century mansions before having another delicious ethnic snack in hipster hot spot Wicker Park. Bike along the new 606 trail, a bike path on a formal elevated rail line, and then sample some delicious ice cream and toffee in Lincoln Park. From there, head to quaint Old Town for a chocolate tasting, and finish off the tour with a beautiful ride down Chicago's world-famous Lakefront Trail.

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Bobby's Bike Hike Chicago: Lakefront Neighborhoods Tour

10. Bobby's Bike Hike Chicago: Lakefront Neighborhoods Tour

Hop on a bike and explore Chicago's lakefront neighborhoods! Bobby's Lakefront Neighborhoods Bicycle Tour is Chicago's longest-running and most popular bike tour. Veer off the beaten path and into the opulent neighborhoods, pristine parks, and packed beaches of the near north-side of Chicago. Explore the Gold Coast mansions, Old Town historic district, Lincoln Park, and the zoo, all on the bike. Pass by North Avenue beach and Chicago's lakefront while an experienced, knowledgeable guide explains the rich history and culture of the area. This tour is designed for all ages and fitness levels. Safety is our top priority, and guests follow bike paths for a majority of the tour. Bikes and helmets are provided.

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Other Sightseeing Options in Illinois

Want to discover all there is to do in Illinois? Click here for a full list.

What people are saying about Illinois

Overall rating

4.5 / 5

based on 182 reviews

We arrived Thursday and we stayed outside of Chicago in Rosemont Hyatt regency. We wanted to see Chicago downtown. We are extremely happy we picked the Architecture Family boat excursion. All my kids wanted and expected different thing. When we got on board a chilly 12-17-2021 boat ride The guide Mr Paul not only filled all our needs of what the city was what things meant and who designed what building and bridge. My kids were all fascinated. Mr Paul is truly an asset to your charming city. He was charming,funny knowledge. Our only regret we did the 45 minute ride and not a longer one. What an amazing time. Thank you MR PAUL and all the employees all very kind and gracious. Thank you Chicago. Becky & Benny. From Leesburg VA

Julia was an excellent guide, who gave us lots of fun information about Chicago! The food was wonderful at all 3 locations, including the dessert as well! It was fun to see the beautiful Macy’s store and the Christkind market. I would highly recommend the tour to anyone visiting during the holiday season.

Ask for Alicia -- best Segway tour guide in Chicago! She also provided an excellent tutorial on use of the Segway before we began our tour. Highly recommend!

It was a super excellent boat ride! Totally recommend it, the guide was funny and easy to understand. Would do it again

Julia was a great guide! She was enthusiastic and knowledgeable about Chicago as she is a local with great tidbits.