All Chicago Tours &amp; Excursions in 2026

Chicago River 90-Minute Architecture Tour

Get a front row perspective on the exquisite buildings that line the Chicago River during a 45-minute architecture cruise. Hear live commentary about the history and architectural heritage of Chicago on this family-friendly tour, which highlights landmarks such as the Chicago Riverwalk, Michigan Avenue Bridge, Wrigley Building, and Willis Tower. Sit on the open-air top deck or the sheltered bottom deck for the ultimate view of Chicago.

Chicago River 45-Minute Architecture Tour from Magnificent Mile

45 minutesFree Cancellation

Drink in a one-of-a-kind perspective on the Windy City when you go for an evening cruise, perfectly timed to coincide with the sunset. Hop aboard your open-top vessel (with an enclosed and climate-controlled lounge) in the heart of the Magnificent Mile, and cruise along the Chicago River. Then, see the skyline from a distance, and watch the skyscrapers light up, when you continue to Lake Michigan for a sunset viewing.

Lake Michigan Sunset Cruise in Chicago

Marvel at Chicago's iconic architecture and lakefront from a unique perspective with this 30-minute immersive ride. With drone footage, helicopter-mounted cameras, and other custom media, Flyover Chicago creates the sensation of flying above and through the city to take in its highlights from above. Get up close to details atop the highest skyscrapers and learn about Chicago's history and cityscape during the ride.

30 minutesFree Cancellation

Flyover in Chicago

Get the most out of your trip to Chicago as you enjoy discount access to five of the city’s top attractions with the CityPASS®. This easy-to-use mobile ticket grants you free entry into top-tier sights including the Chicago's most famous aquarium and Skydeck Chicago, plus your choice of admission to three of the following attractions: Field Museum, Art Institute of Chicago, Museum of Science and Industry, 360 CHICAGO Observation Deck, Adler Planetarium, or Shoreline Sightseeing Architecture River Tour.

from US$144

Admire some of the Windy City's most iconic views—and enjoy a time-saving, relaxing way to sightsee—aboard this pet-friendly Chicago River architecture boat tour. With commentary from your onboard guide, watch the spectacular skyline glide by, including dozens of notable buildings, like the Wrigley Building and the John Hancock Building. In just one tour, you cover multiple branches of the Chicago River and learn insider facts and stories you'd otherwise miss.

Chicago Architecture River Cruise

1 hour to 1 hour 30 minutesFree Cancellation

Visit the Skydeck, located on the 103rd floor of the Willis Tower (formerly the Sears Tower), with ease thanks to this prebooked ticket option. Avoid long lines at the ticket office and enter directly to access the highest point in Chicago. Peruse interactive displays and exhibits showcasing Chicago's history. Then walk out on to the Ledge, a glass balcony that offers unimpeded views of Navy Pier and Wrigley Field.

Skydeck - Willis Tower Admission

30 minutes to 1 hour 30 minutesFree Cancellation

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

Tower above the Windy City’s world-famous skyline with pre-booked admission to 360 Chicago—a great way to avoid long ticket lines. Ascend one of the tallest buildings in North America aboard its lightning-fast elevator, and be rewarded with bird’s-eye views of Chicago and Lake Michigan. You can also upgrade to the Sip and View ticket, which includes one drink at the newly renovated CloudBar. Once onsite, you can purchase tickets to TILT, 360 Chicago's top attraction.

360 CHICAGO Observation Deck Admission

1 to 4 hoursFree Cancellation

3.9

(1 314)

from US$27

See Chicago your way with flexible hop-on hop-off tickets designed to suit every sightseeing style. Explore the Windy City at your own pace, hopping off to visit top attractions such as Millennium Park, Navy Pier, the Magnificent Mile, and the Chicago Riverwalk while enjoying onboard commentary that adds context to what you see. Perfect for first-time visitors or those short on time, this tour offers flexibility and ensures you don’t miss any of Chicago’s highlights. You can also upgrade your experience to enjoy extra sightseeing time and a panoramic sunset tour for unforgettable skyline views.

Chicago Hop-on Hop-off Sightseeing Tour by Open-top Bus

Chicago Hop-on Hop-off Sightseeing Tour by Open-top Bus

Chicago's Navy Pier Centennial Wheel Ticket

15 minutesFree Cancellation

Eat your way through downtown Chicago on a walking food tour. Visit Millennium Park, the Palmer House Hotel, and other city landmarks and taste quintessential Chicago foods such as deep-dish pizza, hot dogs, and chocolate brownies. All food tastings are included, and the tour covers an easy 1.5 miles (2.4 km) suitable for most fitness levels. A bike or kayak rental is also included in the tour cost.

Chicago Favorites Ultimate Food and Walking Tour

3 hoursFree Cancellation

Chicago River 90-Minute Architecture Boat Tour

Chicago Lake and River Architecture Tour

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

1 to 30 days

4.0

(367)

from US$84

We invite you to step inside the city’s most exclusive, jaw-dropping architectural treasures. Led by an expert local storyteller, you’ll discover breathtaking hidden spaces, from Frank Lloyd Wright’s sunlit masterpiece inside the Rookery to the world's largest Tiffany stained-glass domes at the Cultural Center and Marshall Field Building. Walk through the stunning Gilded Age luxury of the Palmer House and iconic movie backdrops along La Salle Street at a relaxed, conversational pace. We combine world-class history with photo vantage points, ending with personalized local recommendations. Don’t just see Chicago, experience it from the inside out.

Chicago's Secret Interiors Architectural Walking Tour

Chicago's Secret Interiors Architectural Walking Tour

Witness Chicago’s stunning skyline from above on this exhilarating helicopter tour. Departing from the Vertiport, the flight offers breathtaking views of the city’s iconic architecture, including Soldier Field and the Shedd Aquarium, as well as the picturesque Lake Michigan shoreline. This unforgettable experience showcases 8 key points of interest along a scenic 10-mile route, perfect for photography enthusiasts and those seeking a unique perspective of the Windy City. - 10-mile scenic helicopter flight over Chicago's skyline - Fly past famous landmarks like Soilder Field and Chinatown - Minimum of 2 passengers required, maximum of 3 per flight - Free parking available at the Vertiport Chicago

Chicago Skyline Snap Tour Helicopter Flight Over Chicago

7 to 10 minutesFree Cancellation

The best views of Chicago can be yours at 360 Chicago Observation Deck! Perched 94 stories above the Windy City in the former John Hancock Building, 360 Chicago provides commanding views of Lake Michigan and Chicago’s towering skyscrapers. Located in the heart of downtown on Michigan Avenue, the observatory is steps away from other top Chicago attractions. It will be the high point (literally) of your Chicago trip! Upgrade to the Sip and View ticket, which includes one drink at the newly renovated CloudBar. The Sip menu includes a rotating selection of beer, wine and cocktails. Once onsite, you can purchase tickets to TILT, a thrill ride that offers visitors unique, downward facing views from 1,030 feet. You may also choose to upgrade your Sip and View ticket from the Sip Menu to the Elevated Menu for an additional $8. *TILT not included in purchase

360 Chicago Observation Deck Sip and View Ticket

4.0

(111)

from US$44

We are the original, top-rated Gangsters and Ghosts tour! Hear the tales of the ghosts, and gangsters, that haunt the city. Explore the Chicago South Loop district with your historian guide, uncovering the many mysteries hidden behind every turn. Walk through Chicago's notorious South Loop, known as a vice district during the 1920s and 30s. Stroll through this now upmarket area of the city which was once home to underground speakeasies, secret tunnels, and bootleggers. Hear the true stories of Chicago's bloody past and the gangsters who caused havoc in the city. See the places notorious figures such as Al Capone used to party, make deals, and carry out "business". Discover the legends of the ghosts that are said to lure along the Chicago Riverwalk and the aptly named Death Alley. Stop at haunted locations including Palmer House, and the Chicago Theatre, before finishing outside the Congress Hotel, one of the most haunted places in Illinois.

Chicago Gangsters and Ghosts Walking Tour

Chicago Gangsters and Ghosts Walking Tour

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

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

Chicago Crime and Mob Bus Tour

1 hour 30 minutes to 2 hoursFree Cancellation

Discover more of Chicago beyond downtown with this convenient South Side open-top shuttle transfer. Travel from central Chicago to some of the city’s most important cultural and historic destinations, including Jackson Park, the Obama Presidential Center campus, and the Griffin Museum of Science & Industry. Enjoy an easy ride south without arranging taxis, rideshares, or public transit connections. The shuttle first stops near the Obama Presidential Center and Jackson Park, giving you access to one of Chicago’s most historic lakefront spaces. Explore the area at your own pace, take photos, or continue your visit independently. The route also serves the Griffin Museum of Science & Industry, one of Chicago’s most popular attractions and one of the largest science museums in the world. This is a great option for travelers who want a simple, affordable way to visit Chicago’s South Side highlights from downtown. Choose a one-way transfer or an all-day ticket for added flexibility.

Roundtrip Shuttle to South Side and Obama Presidential Center

30 minutesFree Cancellation

Explore Chicago's buzzing food scene—and see some of its best-known landmarks on the way—on this two-in-one walking tour. The small group size offers are more intimate experience as you stroll around the vibrant Loop area, spotting highlights from the Willis Tower to the Rookery building. Indulge in a variety of famous Chicago foods, from deep-dish pizza to the world-famous dipped Italian beef sandwiches.

Chicago Food Tour: 6 Dishes with Deep Dish Pizza & Beef Sandwich

3 hoursFree Cancellation

Price varies by group size

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Lake Michigan Skyline Cruise in Chicago

Francesco_R, Sept 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 River 90-Minute Architecture Tour

Francesco_R, Sept 2026

If You Enjoy History, Architecture, Boat Rides, and a Good Drink, Then This Is The Tour For You!

Excellent boat ride that takes you to three far points along the Chicago River, including as far as where the Great Chicago Fire began and as far north as to where the river meet Lake Michigan. Throughout the ride you are given an impressive lecture on the variety of buildings that tower high over you, along with the history of Chicago that coincides with the architecture. The boat comes along with a bar and snacks to buy from as you enjoy the narrative, cruising along the river. If you love architecture, history, boat rides, and a nice beverage all in one, choose this tour. I recommend their hot apple cider with cinnamon stick— it really goes great with the weather and experience. The staff is super friendly and with a great sense of humor. The program covers almost everything significant of Chicago’s history.

Lake Michigan Sunset Cruise in Chicago

Susanna_M, Sept 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 Sightseeing River and Lake Cruise

Kim_D, Sept 2026

Worth Every Dollar Spent

This was a well worth the time and money spent on a water boat. Juniper who was the speaker on the boat let us know all kinds of good information and told us about some good history about the buildings and even some information about Lake Michigan . She talked about the Navy Pier to . My husband and I really enjoyed the ride looking at the beautiful lake and Downtown Chicago. We would totally recommend this 1 1/2 ride to all who would like a great ride with no shake up and hear some good knowledge from the staff on the boat. (Thanks Juniper)

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 Architecture River Cruise

beatrice_o, Sept 2026

Highly recommend

We really enjoyed the architectural tour. It was my favorite thing from our Chicago trip. Charley made it informational but also had a good time getting to know all the buildings and history of Chicagos skyline. Will def be back! I do recommend booking during sunset hour! We did the 90 min tour at 6:30pm

Chicago River 45-Minute Architecture Tour from Magnificent Mile

Noah_G, Sept 2026

Just buy the ticket

Todd was excellent! Pay attention and ask questions because the tour guides are very knowledgeable. The scenery up and down the Chicago river is unmatched. The unique architecture and stories behind them are incredible. The boat is not fast, so take your time looking up and down each building. Sunset is the best time to go! Everything was lit up pink for Dolly Parton as well.

Chicago By Night River and Lake Cruise

Deidre_S, Aug 2026

A great experience

First Lady boat ride was a great experience. You will start on the Chicago river and merge into the Michigan lake. The view was amazing I mean amazing especially at night! The con was it can get a little bit chilly at night so bring a jacket. They sell blankets if you were to get cold and they also have a bar so you can sip and enjoy the ride. I would definitely recommend it.