All Chicago Tours &amp; Excursions in 2026

Chicago By Night River and Lake Cruise

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

Explore a range of interactive exhibits at the Griffin Museum of Science and Industry in Chicago—one of the largest science museums in the country. Rather than simply viewing displays, enjoy hands-on experiences that bring engineering, technology, and natural science to life. Housed in the last remaining building from the 1893 World's Fair, the museum combines historic significance with immersive exhibits, making it an engaging attraction for visitors of all ages.

Griffin Museum of Science and Industry Admission

2 to 4 hoursFree Cancellation

Drunk Dracula Chicago Tickets: Comedy Theatre with Cocktails

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

Immerse yourself in one of Chicago's most vibrant neighborhoods—and head off the tourist trail to discover sights and bites many visitors miss—on this small-group Chinatown food and walking tour. With your guide in the lead, learn about the cuisine of different regions of China, and discover the history of Chicago's Chinatown. Along the way, enjoy a generous array of tastings, from dim sum to Sichuan cuisine and beyond.

Chicago's Chinatown Food and Walking Tour

3 hoursFree Cancellation

See Chicago from a different perspective on this evening cruise that explores the city’s darker side. As twilight settles over the skyline, glide along the Chicago River while hearing chilling tales of disasters, infamous criminals, and eerie legends tied to the city’s past. This relaxed river cruise blends atmospheric storytelling with some of the best nighttime views of Chicago’s renowned skyline and landmarks. Grab a drink from the onboard bar, settle in, and let the city’s shadowy history unfold as you cruise through the heart of downtown. By the end of the journey, you’ll have experienced Chicago’s skyline in a whole new way—while uncovering the chilling events, legends, and mysteries that shaped the city. Please arrive 30 minutes in advance!

Chicago River Ghost & Dark History Night Cruise

Taste some of Chicago's most iconic foods while walking through one of the Prohibition Era’s most fashionable and notorious neighborhoods. Learn about Chicago's world-famous cuisine and the gangsters who ate it all in one special unique tour! Sample Chicago’s deep dish – as well as prime steak and the world famous “Chicago hot dog" all while treading the streets of Capone’s closest friends and dreaded enemies. Highlights include a visit to an old tunnel used by prohibition gangsters in the basement of one of the establishments; a mansion once used as a brothel for gangsters; the Cathedral where gangsters were gunned down by Capone’s men; and a restaurant owned by the man who brought down what was left of the Chicago mafia in the early 2000’s. Gluten-free/vegan/vegetarian options are available (please reach out prior to the tour to inform us of any dietary requirements.)

Chicago: Gangsters and Food Tasting Walking Tour

Price varies by group size

Chicago Explorer Pass: 35+ Things To Do - Includes 360 CHICAGO

1 to 30 days

4.0

(370)

from USD 84

Discover one of the Windy City’s most spooky, gruesome destinations when you book advance tickets to the Medieval Torture Museum. Perfect for Halloween—or any other creepy-crawly occasion—this museum includes a wealth of information about medieval torture practices and devices, plus realistic models to add a macabre edge. Book tickets before you travel for a seamless visiting experience, and make use of an audio guide and included ghost-hunting app.

Medieval Torture Museum Ticket with Audio Guide and Ghost Hunting

Medieval Torture Museum Ticket with Audio Guide and Ghost Hunting

Get to know the Windy City the easy and comfortable way on a small-group minibus tour. Instead of long walks and navigating public transit, see major landmarks like Museum Campus, Buckingham Fountain, the Magnificent Mile, and Millennium Park from an uncrowded minibus with large picture windows. Your driver and guide knows where to find all the best views, and there are plenty of photo stops along the way.

Chicago City Minibus Tour

City Cruises Chicago: Premier Plus Brunch Cruise on Chicago River

Discover the hidden gems of Chicago’s Loop area on a walking tour that showcases the best of the neighborhood’s stunning interiors and architectural must-sees. Step behind the facades to explore beautifully designed interiors—from art deco spaces to stained glass mosaics—as you follow a carefully curated route led by a guide. Along the way, learn about the city’s architecture, art, and history, and experience a side of Chicago often missed by travelers, all from a local’s perspective.

Original Chicago Architecture Interiors Tour: Dazzling Interiors

Enjoy a quintessential Chicago experience—and see more of the city's highlights in less time—on an architecture-themed boat tour of the Chicago River. Pick from multiple convenient start times, and board your vessel directly from the Chicago Riverwalk. Thanks to your trained docent guide, receive a rich introduction to the Windy City’s history, key landmarks, and architectural highlights—and spy landmarks like the Marina City towers and Navy Pier from the water’s edge.

Chicago Architecture Center River Cruise aboard First Lady

Chicago Architecture and True Crime: Halloween Edition

1 hour 30 minutes to 1 hour 45 minutesFree Cancellation

Paint your own street art at Studio WIP

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

Sit back and take in some magic—and enjoy a one-of-a-kind night on the town—during this engaging Chicago show. Show up a few minutes before curtain time to get the best possible seat and start sipping the drinks you brought. Cups and bottle openers are available for your use. Buying your tickets in advance means less waiting for entry; you'll be sure to get the day and time you that fits your schedule.

Trickery Chicago Magic Show

See the Second City from the water with a sightseeing cruise along the Chicago River and the Lake Michigan shoreline, offering a unique perspective of towering skyscrapers and historic architecture. This tour offers stories about the city’s history and culture as you pass by Chicago's landmarks, museums, and buildings. Capture unforgettable images of the city skyline from Lake Michigan, ensuring a unique look at Chicago, perfect for all ages.

Chicago Sightseeing River and Lake Cruise

Zoom along the shoreline of Lake Michigan, zipping past famous landmarks as you go, during this exhilarating speedboat ride in Chicago. Climb aboard your 2,000-horsepower speed boat at Navy Pier, then hang on for the ride of a lifetime, as you zip past famous attractions like the Willis Tower, Grant Park, and Buckingham Fountain, pausing to learn a little about the history and architecture of the Windy City along the way.

Lake Michigan 30 Minute Speedboat Ride

30 minutesFree Cancellation

See the towers and iconic landmarks along the Chicago River on an architectural cruise through the heart of the city. Enjoy complimentary non-alcoholic refreshments on deck as you cruise down the historic waterway, while listening to fun stories and facts throughout the tour. Spot buildings that range from Neoclassical to Art Deco, take in over fifty sites, and see the Second City from the water.

Chicago Architectural River Cruise

Chicago Lake and River Architecture Tour

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

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Must-Dos in Chicago

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What are people saying about Chicago

Flyover in Chicago

Sandra_B, Oct 2026

Fly Over Chicago.

⭐⭐⭐⭐⭐ An Incredible Experience! Flyover Chicago was absolutely amazing! From beginning to end, it was such a fun and exhilarating experience. The breathtaking scenery, incredible visuals, and sensation of soaring through the air made it feel like I was actually flying. Whether you’re visiting Chicago or live in the area, this is an attraction you shouldn’t miss. I would absolutely do it again. I only wish it lasted a little longer.

Chicago River 45-Minute Architecture Tour from Magnificent Mile

Cheryl_E, Oct 2026

It was evening and...

It was evening and drizzly/rainy. The buildings could not always be seen as they drifted in and out of clouds (magical and mysterious). The tour guide also shared lots of fun trivia and history. It was my two teen children's favorite Chicago experience. Highly recommend!

Chicago River 90 Minute Architecture Tour

Andrew_G, Oct 2026

Better than you would think!

The guides are well informed and engaging. It was a lovely sunny day so what could be wrong with the setting? Suprisingly interesting and engaging. Nice way to see the city. They were also very accommodating for handicapped. Which is greatly appreciated.

Chicago Architecture Center River Cruise aboard First Lady

Fran_S, Oct 2026

Best activity once you arrive in downtown Chicago!

I’ve taken this tour two times this year while entertaining family and coworkers from our of town and they absolutely love the tour. The tour operators are so well educated and do such a wonderful job at moderating and really showcasing Just how beautiful Chicago is for all its architecture and would recommend this to anybody visiting the city!

Chicago Sightseeing River and Lake Cruise

Nahrain_C, Oct 2026

Beautiful Chicago Experience

The boat guided was wonderful. The narration of Chicago's architectural history was interesting and informative. Everyone on board was friendly and accommodating. My only drawback was that it was not handicap accessible (not that I saw, anyway). Taking 2 flights of stairs down and then up again afterward is not easy for seniors or people with leg injuries/medical issues.

Chicago Architecture River Cruise

Rachel_G, Oct 2026

Cool experience and take your dogs if you can!

This was a really cool experience and a great way to see the Chicago River and the Chicago skyline. The history was interesting and Mac our guide was great and super informative. We traveled with our 2 dogs and the boat was gentle enough that you barely felt like you were moving. Money well spent!

Chicago By Night River and Lake Cruise

Ravi_V, Oct 2026

It was a really good...

It was a really good experience. It got a bit cold when we got to Lake Michigan, but that was expected. It was great to listen to the history of the awesome architecture in Chicago. Anna, our guide was fantastic. She was extremely articulate and kept the tour interesting and funny at the same time. Cheers!

Chicago River 90-Minute Architecture Boat Tour

Sharolyn_B, Oct 2026

The dock is a bit run...

The dock is a bit run down. There are at least porta-potties. The seating on top of the boat is folding chairs, but pretty comfy ones. But the tour guide was just amazing! So knowledgeable, and he gave a really good mix of historical facts, interesting happenings, Chicago culture, and humor. Very enjoyable!

Chicago Crime and Mob Bus Tour

Su_O, Sept 2026

Best Crime Tour in Town

Our first time in Chicago and my daughter really wanted to see the crime tour. We had an amazing time driving thru Chicago and listing to the stories. We stopped in 3 locations and was able to get out of the bus and explore. See the actual "crime scene" We did it on Sunday morning, so traffic and places were not as crowded. TOTALLY WORTH IT

Chicago Lake and River Architecture Tour

Tamara_P, Sept 2026

This was a perfect ...

This was a perfect activity for anyone who loves to see the history of Chicago and experience the beauty of the outdoors on the river and lake., we loved it , the tour guide was not only knowledgeable but funny as well ! We enjoyed it and would recommend anyone to do this trip it was about and 1 1/2 hours which was the perfect amount of time .highly recommend!