Chicago
Neighborhood Tours

Enter your dates to find available activities

Our most recommended Chicago 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 o...

    We had a great time! Shorter ride was perfect for young kids. Boat was clean and staff was friendly.

  • Amazing Lakefront Segway Tour of Chicago

    2. 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.

    Great time! Enjoyed the Chicago sites! Enjoyed learning to use the Segway!!! Especially enjoyed seeing so much and a fair price. I enjoyed being so close to the magnificent mile millennium park the Bears stadium the beaches art museum so much more downtown and good restaurants. I almost forgot I enjoyed and the reason I went was to see Buckingham fountain it was really beautiful beautiful day beautiful time beautiful people

  • Chicago: History, Culture and Architecture Walking Tour

    3. 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, either hop on the ‘L’ train or a water taxi o...

    I had an amazing time on this tour! In my opinion, the walking tour allowed me to see so much more of the city, up close and from my own personal viewpoint. The tour guides were very friendly, funny, and knowledgeable. We were even given "Garrett's Popcorn" and "Fannie May Chocolate" as some sweet treats. I highly recommend this tour, and I'm so glad that I did it!!

  • 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 Chin...

    It was interesting and fun. Our tour guide was considerate and funny. Would absolutely do another tour with you.

  • Chicago Underground Donut Tour

    5. 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 t...

    Our guide, Nick, was great! He was knowledgeable, funny, personable and just overall a great part of our experience.

  • Bobby's Bike Hike Chicago: Lakefront Neighborhoods Tour

    6. 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.

    Our guide was awesome! Very knowledgeable and passionate about Chicago as well as our safety! We loved everything about our Bike Hike. The bikes Were easy to handle for all ages and skills. It’s a fun way to see and travel through the city! Think no more about it! Book it! You will love it! We did!!

  • Chicago: Westside Food Tasting Bike Tour with Guide

    7. 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-c...

    Excellent tour! The bikes were good and easy to ride; the food was terrific and the tour guide was attentive, funny and knowledgeable. Highly recommend!!!

  • Chicago: Food, Architecture and History Tour

    8. 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) 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. 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, either hop on the ‘L’ train or a water taxi on the Chicago River (depending on the weather and time of y...

    This was my first time to Chicago this tour was absolutely amazing. Kelly was knowledgeable about everything Chicago..she was able to answer all questions & gave great recommendations. Would highly recommend..

  • Chicago: Downtown Architectural Interiors Tour

    9. Chicago: Downtown Architectural Interiors Tour

    Jump right into beautiful architectural interiors of the Roaring '20s, taking in the class and elegance of a classic Art Deco masterpiece. Go back 50 years to the 1880s and explore the structure and style of one of the most famous and oldest buildings in downtown Chicago. Next, you'll marvel at a vaulted ceiling from the Postmodern era, surrounded by Moorish details. Finally, you'll end looking up at the world's largest Tiffany stained-glass mosaic, and very close to the world-famous Millennium Park with one of the most famous landmarks of Chicago, "The Bean."

    The tour was entertaining and gave me new insights into the fascinating history of Chicago.

  • Chicago: Secret Food Tour

    10. 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.

    This was a great tour and a great value. Good food samplings with a knowledgeable guide. It was a great way to see a little bit of Chicago and sample some of the classic Chicago foods at interesting venues. The food was always ready to serve when we got to the location and the amount of food provided on the tour seemed very reasonable for the price.

Other Sightseeing Options in Chicago

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

What people are saying about Chicago

Overall rating

4.5 / 5

based on 182 reviews

Alicia(tour guide) was the best!! She was super patient with my training and riding as a 1st Time Segway Rider. She was knowledgeable about Chicago's History. She was eager to assist me with photo needs, and she even captured some scenic photo opportunities for me, considering that she has a great eye for photography!! I definitely recommend the Segway Tour and if possible, ask for Alicia as your tour guide!! You won't be disappointed.❤

Great time! Enjoyed the Chicago sites! Enjoyed learning to use the Segway!!! Especially enjoyed seeing so much and a fair price. I enjoyed being so close to the magnificent mile millennium park the Bears stadium the beaches art museum so much more downtown and good restaurants. I almost forgot I enjoyed and the reason I went was to see Buckingham fountain it was really beautiful beautiful day beautiful time beautiful people

I had an amazing time on this tour! In my opinion, the walking tour allowed me to see so much more of the city, up close and from my own personal viewpoint. The tour guides were very friendly, funny, and knowledgeable. We were even given "Garrett's Popcorn" and "Fannie May Chocolate" as some sweet treats. I highly recommend this tour, and I'm so glad that I did it!!

We had a great time! Shorter ride was perfect for young kids. Boat was clean and staff was friendly.

Absolutely loved seeing the architecture of Chicago!