Top Chicago City Tours - page 2

Chicago Bike & Classic Food Tour: Bikes, Bites & Views - Adults

4 hours 30 minutesFree Cancellation

Chicago Family Food and Bike Tour with Top Attractions

4 hoursFree Cancellation

Chicago Architecture River Tour & Hop-on Hop-off Sightseeing Tour

Step into the heart of Chicago with this in-depth, small-group walking tour of the Loop neighborhood, the heart of the Windy City's downtown. Stop to check out the elevated “L” train, admire historic buildings, discover lesser-known corners of this vibrant area, and view its best-known public artworks, too. You’ll come away with a deeper sense of Chicago’s rich history and architecture.

Chicago Loop Walking Tour

Experience Chicago like a true insider on this top-rated walking tour that blends the city’s most iconic food, awe-inspiring architecture, and rich history — all in one unforgettable day. From deep-dish pizza to legendary skyscrapers, you’ll taste, see, and learn what makes the Windy City a world-class destination. Led by expert local guides and limited to just 12 guests, this immersive, small-group tour is the perfect way to discover the real Chicago — not just the tourist spots.

Chicago in a Day Walking Tour: Food, History & Architecture

4 hours 30 minutesFree Cancellation

Price varies by group size

Discover the fascinating history of Chicago from a whole new perspective — on the water! This 120-minute Guided History Tour along the Chicago River brings the city’s past to life through captivating stories, iconic landmarks, and little-known facts that shaped the Windy City into what it is today. • Chicago’s transformation from swamp land to industrial hub to the modern metropolis it is today • The dramatic story of the Great Chicago Fire of 1871 and how the city rebuilt stronger than ever • Tales of Chicago’s most infamous gangsters and Prohibition-era legends • The groundbreaking 1893 World’s Fair and the inventions it introduced to the world • The incredible reversal of the Chicago River — its purpose and lasting impact on the city’s future Step aboard and experience how history, architecture, and innovation flow together on this unforgettable journey through Chicago’s past and present.

BYOB Chicago River Guided History Tour

Explore the hidden side of Downtown Chicago—and see sights that even many locals miss—on a small-group walking tour of the Pedway (an underground network of tunnels that connects Chicago buildings) and the vibrant Loop. Ideal for architecture fans, this tour includes insider stories and landmarks you wouldn't spot on your own—plus a chance to see Windy City icons like the Picasso Statue and Millennium Park.

Chicago Architecture Tour: Underground Pedway and the Loop

Explore Chicago at your own pace with a 48-hour hop-on hop-off bus tour, providing unlimited access to the city's iconic neighborhoods and landmarks. Relax on open-top buses while enjoying engaging audio commentary that reveals the rich history and culture of the Windy City. This tour includes admission to the stunning 360 CHICAGO Observation Deck on the 94th floor of the John Hancock Center, offering breathtaking panoramic views of Lake Michigan and the city skyline. - Unlimited hop-on hop-off access for 48 hours across top Chicago attractions - Audio commentary in multiple languages covers local history and culture - Admission to the 360 CHICAGO Observation Deck for breathtaking views - Perfect for first-time visitors, families, and those seeking flexible exploration Time selected at booking is for 360 CHICAGO admission. Big Bus Hop-on Hop-off Tour available anytime during operating hours.

360 CHICAGO Observation Deck & Hop-on Hop-off Sightseeing Tour

On this small-group Windy City bike tour, you won't just pedal past the lakefront neighborhoods of Chicago's North Side—you'll see more of the city than you could if exploring on your own. Follow a local guide along quiet streets, city parks, and scenic beaches, starting at Lake Shore Drive and continuing along Rush Street and the Magnificent Mile. As you go, glimpse offbeat attractions like the Playboy Mansion, Oprah’s penthouse, and the Victorian houses of Old Town.

Bike Tour of Chicago's Lakefront Neighborhoods

3 hoursFree Cancellation

Special Offer

Explore Chicago by Segway with the benefit of a scenic 7- or 8-mile tour led by your guide. Start with an orientation to operating the Segway and a few minutes to practice. Then roll through the paths of Grant Park to Buckingham Fountain and glide along the Chicago lakefront to view attractions such as Museum Campus, Shedd Aquarium, The Field Museum, and Soldier Field, homefield for the Chicago Bears.

2-Hour Chicago Lakefront & Museum Campus Segway Tour

Take to the skies and experience Chicago from an entirely new perspective on this extended helicopter tour showcasing the city’s most iconic landmarks, neighborhoods, and waterfront views. The flight begins near the Chicago Fire Practice Facility before heading over Chinatown, where colorful architecture and historic streets create a striking aerial view. From there, you’ll pass McCormick Place, the largest convention center in North America, stretching along the lakefront and highlighting the scale of Chicago’s downtown footprint. Continuing north, you’ll fly over Northerly Island and Soldier Field, followed by the heart of the Museum Campus, where the Field Museum and Adler Planetarium sit against the backdrop of Lake Michigan. Grant Park comes into view next, often called Chicago’s front yard, leading to an aerial look at Millennium Park and the unmistakable curves of The Bean.

Chicago Helicopter Tour: Loop Tour

12 to 15 minutesFree Cancellation

Experience Chicago at its most magical—and admire views that few other visitors get to see—on this evening Segway tour. Visit popular Grant Park and see Buckingham Fountain’s summertime light show, with an illuminated Windy City skyline as the perfect backdrop. Then, glide along the lakefront, and admire Chicago's weekly summer fireworks display at Navy Pier from a secret location. Guided Segway training plus the use of a helmet are included.

Chicago Pier Fireworks Segway Tour

Outside of Italy, few places in the world are as famous for their pizza as Chicago. Eat like a local as you travel off the beaten path to savor the city's best pizza, traveling by bus so you can cover more food hot spots in less time. Discover the science behind ingredient selection and baking as you sample slices from historic pizzerias, and take away plenty of tips to enhance your eating in Chicago.

3 hours 30 minutesFree Cancellation

Chicago Pizza Tour

Skip navigating around the city with a map and guidebook and explore Chicago's iconic landmarks in just a few hours on this sightseeing tour led by an expert guide. Board a comfortable, large-windowed minibus and explore Downtown and North Side neighborhoods, stopping to visit several locations and hear about the historical and cultural factors that make Chicago unique. Upgrade your tour with a popular open-top boat tour on the Chicago River that focuses on the city's renowned architecture.

Chicago City Tour with Architecture River Cruise Option

2 to 4 hoursFree Cancellation

Get a chance to experience the Windy City from multiple vantage points during this two-hour, small-group boat tour in Chicago. Hop aboard a secure and reliable US Navy-built Rigid Inflatable Boat (RIB) for a unique sightseeing experience. Pass by iconic sights such as Navy Pier, Soldier Field, Fort Dearborn, Vietnam Memorial, Wolf Point, Shedd Aquarium, and more, all while comfortably seated in a group capped at only six people.

Small-Group Sightseeing Boat Tour in Chicago

Taste food from around the world—and immerse yourself in some of the Windy City's most characterful, locally beloved neighborhoods—on this half-day biking and tasting tour of Chicago. With just a small group for company, you'll follow your guide through the city streets, stopping for views of Chicago’s famous architecture and seeing more than you could if traveling on foot. In between, stop for bites like Polish pierogis, locally made chocolates, and Mexican tacos.

Chicago's West Side Foodie Ride Bike Tour

4 hoursFree Cancellation

This walking tour is a feast for the eyes, combining art, architecture, and history as you navigate through bustling downtown Chicago. In a small group, you’ll marvel at skyscrapers and mosaic murals as you discover stories and secrets about the city’s past. See the stunning interiors and exteriors of noteworthy buildings and leave with a comprehensive understanding of the city’s downtown.

Walkin' with Colin: Chicago History-Mystery-Comedy-Tragedy Tour

Get to know the foodie Chicago neighborhood made famous by "The Bear"—and taste your way through some of the Windy City's best bites—on this small-group walking tour of River North. Visit locals-loved hotspots that represent the best of the city's dining scene, and Be sure to come hungry: You'll try everything from tacos and Italian beef sandwiches to deep-dish pizza, all while learning about the neighborhood's history and food culture.

River North Food Walking Tour

3 hoursFree Cancellation

Chicago's Ultimate City Bike Tour of Top Downtown Attractions

3 hoursFree Cancellation

Special Offer

See the best of the Windy City, all in just half a day—and learn the stories behind its best-known sights—on this private tour. In the morning, meet your driver at your Downtown hotel, hop aboard your private vehicle, and set off with a tour guide in tow. You can look forward to seeing sights like Grant Park, Navy Pier, and Buckingham Fountain—and stopping for photo opportunities along the way.

Private Chicago Guided Tour with Hotel Pickup

4 hoursFree Cancellation

Price varies by group size

Experience Chicago in a new way on this small-group Segway tour. Visit Chicago’s "front yard," and see more of the sights in less time. Glide along the fragrant floral paths of Grant Park to the famous Buckingham Fountain. Then, travel along the banks of Lake Michigan to the Museum Campus for top-notch views of the city’s iconic skyline. Guided Segway training and helmets are included, making this a beginner-friendly tour.

Chicago Landmarks and Museum Campus Small Group Segway Tour

Enjoy a fun and scenic 90-minute Cycleboat Cruise along the beautiful Chicago River! Take in stunning skyline views as you pedal, relax, and sip your favorite drinks with friends, family, or that special someone. • 1.5-hour cruise up and down the iconic Chicago River • Comfortable boat with 10 cycle stations and bench seating at the front • Maximum capacity of 16 passengers — perfect for smaller groups or couples • BYOB! Bring your own beverages and snacks to enjoy onboard • Departs from the Water Plaza on the Chicago Riverwalk (between Wells Street and LaSalle Street bridges) Whether you want a lively group outing or a relaxing ride through the city, this Cycleboat Cruise is one of the most unique ways to see Chicago from the water — no full-boat rental required!

Chicago River Cycleboat Cruise

1 hour 30 minutesFree Cancellation

See Chicago through the eyes of Al Capone and the Everleigh Sisters at your own pace with this affordable walking tour. • Walk in the footsteps of the gangsters, bootleggers, hoodlums, gunmen, and crooked cops and politicians who made up what was known as the “Chicago Outfit” • Hear from producer Richard Junger, an urban historian, professor and author passionate about Chicago • Do it all in 45 minutes or linger at stops along the way with complete control over when you start and finish • Get unlimited use before your booking date and after it • Use the virtual tour option at home Once you’ve booked, you’ll receive a ticket with instructions and a unique code listed under “Before You Go”. Then simply install the VoiceMap app and enter your code. The app displays directions to the starting point, and when you’re in the right place, just pop in your headphones and tap start. VoiceMap has automatic GPS playback, with turn-by-turn directions. It also works offline.

Chicago’s Ragtime & Jazz Eras: A Self-Guided Audio Tour

Discover many of Chicago’s best-known landmarks—and see the city dressed up in its festive best—on this holiday walking tour of the Windy City. Come bundled and join your guide and small group to explore the famous Christkindlmarket. Then continue to discover Millennium Park’s ice rink and Christmas tree, stroll the Magnificent Mile’s glowing lights, and more while you hear fun facts and cultural insights from your guide.

Chicago Seasonal Stroll Walking Tour of Holiday Attractions

Lake Michigan Skyline Cruise in Chicago

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Top Attractions in Chicago

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Attractions

What are people saying about Chicago

Francesco_R, Sep 2026

Awesome View, Fun Boat Ride, and Excellent Narration— Must Try!

This ride does not go out into Lake Michigan; it goes up to the barrier between the port and the rest of the lake. However, it was still a very fun ride. The boat staff are very courteous and professional, and services include drinks and snacks available for purchase. This tour is exactly as the title advertises, for you get to ride out on the lake’s waters while presented with numerous, impressive views of Chicago’s city, especially at sunset where the bright yellow and orange glare shines across and between the building gaps of the city— as if you see a vast silhouette of a city in said glow. Most of the boat ride is smooth, albeit there are a few fun bumps and easy dips. Along with the ride and panorama you get a historical and geographical narration of Lake Michigan and its ties to Chicago. It is a presentation that enriches the experience altogether. Very much worth the price and time!

Chicago Crime and Mob Bus Tour

Leslie_P, Sep 2026

It would be a crime to miss this tour!

I have taken several Viator tours, and they NEVER disappoint! The Mob and Crime Tour was no exception! Jay possesses an impressive knowledge on the subject, and the presentation was balanced to provide people with limited knowledge of Chicago history a good foundation in the subject, yet offered plenty of specific, anecdotal, and trivial facts to further inform and educate guests familiar with "the players" and events of crime in Chicago. The pacing of the presentation was excellent, and information was delivered in an entertaining and interesting way. Jay was quite skillful at adjusting the presentation to coincide with sites as the bus was driving by. I appreciated the fact that participants were able to leave the bus at the Biograph Theater to spend a little time rather than just driving by. That was a highlight of the tour! All of my other Viable tours have been walking tours -- this was my first bus tour. The bus was clean and comfortable and the driver did a great job navigating traffic -- way to go, Tommy! Jay & Tommy make a great team, and did their very best to make the tour fun & informative. Thanks to both of you for a great tour! I highly recommend this tour --you won't be sorry!

Lake Michigan Sunset Cruise in Chicago

Susanna_M, Sep 2026

Fun way to see the city from the lake

Not an architecture tour so don’t take this if that is what you’re looking for. A great way to see the sites at night. A very enjoyable evening and Bobby are guide was knowledgeable and available to everyone for any question they may have had! Highly recommend this tour!

Chicago River 90-Minute Architecture Tour

Travita_F, Sep 2026

I Love Architecture! Who Knew??!!

This tour was awesome!! My husband and I learned so much about Chicago’s history and the gorgeous architecture. I didn’t know I was into architecture until I took this tour! Our guide was knowledgeable, informative and funny. He even checked in on us personally during the break. The seats were comfortable and we would definitely recommend this tour to anyone visiting Chicago.

Chicago's Chinatown Food and Walking Tour

Allison_B, Sep 2026

Do yourself a favor!!!

My bestie and I loved this tour! Our guide, Valerie, was so sweet and passionate about the food. We met so many nice people from group members to shop owners, and every dish was delightful! She even helped me find some Mooncake for me to bring home to my daughter. I highly recommend this tour, and you will be very lucky if you get Valerie as your guide!

Chicago Favorites Ultimate Food and Walking Tour

Michelle_B, Sep 2026

Highly Recommend

We’ve done at least a dozen food tours across the U.S. and were very impressed with this Chicago tour. Our guide, Gabe, did an awesome job; sharing plenty of city knowledge, humor, and keeping the tour flowing. The food stops themselves were a great balance of Chicago favorites. Even our 10 yr old son enjoyed it. We would definitely recommend!

Chicago River 45-Minute Architecture Tour from Magnificent Mile

Evelynn_T, Sep 2026

Recommended by locals

I went with my friend in town and boyfriend. I am a southside native and looking for a touristy thing to do in the city. It was 95 degrees out but we still had so much fun. The breeze helped and they sell drinks. Would recommend for anyone looking to learn more about our beautiful city.

Chicago in a Day Walking Tour: Food, History & Architecture

mazndene, Aug 2026

Great tour guide and experience.

Great tour, David our guide was very knowledgeable. He took us to places we never would have looked at but WOW. Food was a real bonus it will fill you up. The popcorn stop was an eye opener who would have thought cheese and caramel would be so tasty 😂. Would definitely recommend this tour Chicago is an amazing city and thanks to David it was such an enjoyable experience.

Chicago Night Crimes Tour by Bus

Wesley_S, Jul 2026

Fascinating Tour!

What an interesting, and fascinating tour. The rich history of Chicago's mob crimes, while off putting to some, makes for a unique tour experience. If you enjoy learning about crime history, or even heard of Al Capone and the beer wars, Dillinger, Nitty, this is the tour for you. The guide was great, plus it's at night so you get to see the downtown at night which is stunning.