All Chicago Tours &amp; Excursions in 2026 - page 3

Art Institute of Chicago Skip-the-Line Exclusive Guided Tour

2 hours 30 minutesFree Cancellation

5.0

(334)

from USD 90

Price varies by group size

Stop off the bus at Chicago Landmark Building with Prohibition Era History

Chicago Night Crimes Tour by Bus

2 hours to 2 hours 30 minutesFree Cancellation

See the towers, piers and iconic landmarks along the Chicago River on an architectural cruise through the heart of the city. Enjoy complimentary refreshments on deck as you cruise down the historic waterway, while listening to fun stories and facts throughout the tour. Spot gargoyles that keep watch high above the city, and buildings that range from Neoclassical to Art Deco. Take in over fifty sites from Lake Point Tower to the Navy Pier, and see the Second City from the water.

(511)

from USD 55

Chicago Architectural River Cruise

Chicago River 90-Minute Architecture Boat Tour

4.6

(853)

from USD 50

Likely to Sell Out

Vito's Vault Chicago Speakeasy Dinner Theatre

(1,865)

from USD 37

Price varies by group size

(38)

from USD 88

Chicago's Lake Michigan Downtown Kayak Rental at Ohio Street Beach

Escape the bustle of the city during this one or two-hour kayak rental along Lake Michigan in downtown Chicago. Experience the serene waters of the iconic lake as you paddle at your own pace in a single or tandem kayak, enjoying views of Chicago’s famous skyline. Take breaks along nearby urban beachfronts, with the option to extend your rental time. Stand-up paddleboards are also available for rental.

Chicago's Lake Michigan Downtown Kayak Rental at Ohio Street Beach

1 to 2 hoursFree Cancellation

Kick back and enjoy a great meal while taking in the sights of Chicago's most famed landmarks on this scenic lunch cruise along Lake Michigan. See and photograph the dramatic city skyline, Navy Pier, Soldier Field, and Shedd Aquarium. The cruise includes a delicious buffet lunch with salads, entrees, desserts, and unlimited nonalcoholic beverages. There's also a DJ, games, and a dance floor to keep your group entertained.

(26)

from USD 40

City Cruises Chicago: Signature Lunch Cruise on Lake Michigan

City Cruises Chicago: Signature Lunch Cruise on Lake Michigan

2 hoursFree Cancellation

4.0

(380)

from USD 63

Book in advance to take this popular tour that details the mob history of Chicago during the Prohibition Era (1920s-1930s). Learn about the exploits of gangsters like Capone, Dillinger, Moran, and others as you travel by minibus to sites like the Biograph Theater, Holy Name Cathedral, and St. Valentine's Day Massacre. Your guide adopts gangster attire and characteristics that add dramatic flair to the historical commentary.

Chicago's Original Gangster Tour by Bus

1 hour 45 minutesFree Cancellation

4.6

(171)

from USD 48

Enjoy an unforgettable evening on Lake Michigan with the Chicago Fireworks Cruise. Witness the stunning skyline as you glide across the water, leading up to the spectacular fireworks display at Navy Pier. This 1.5-hour cruise offers a unique perspective of the city while providing a relaxed atmosphere for friends and family to gather and enjoy the show. Boarding begins 15 minutes prior to departure, so arrive early to secure your spot and make the most of this dazzling experience. - 1.5-hour cruise featuring panoramic views of Chicago's skyline - Marvel at the iconic fireworks show off Navy Pier - Departing and returning to 111 N Lake Shore Drive

Chicago Fireboat Fireworks Cruise

Chicago dogs, deep-dish pizza, brownies, and craft beer are all sampled on this half-day bike tour through the Windy City. Cover about 13 miles (21 km), following your guide at a moderate pace through Chicago neighborhoods. On the day tour, ride through Wrigleyville, Old Town, Lincoln Park, and Gold Coast. On the night tour, visit Chicago’s Riverwalk, Millennium Park, Buckingham Fountain and the Lakefront Trail. As you go, stop for generous food and beer tasters.

4.5

(17)

from USD 57

From deep-dish to hot dogs, taste Chicago Classic Dishes on our Chicago Food & Bike Tour. Ride by Bicycle, learn the stories, and savor every stop on the best Food & Bike Tour in Chicago.

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

4 hours 30 minutesFree Cancellation

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.

(764)

from USD 89

Skyline Queen showcasing the Chicago Skyline!

Chicago Sightseeing River and Lake Cruise

Chicago's Ultimate City Bike Tour of Top Downtown Attractions

4.7

(704)

from USD 46

Amazing skyline and lakefront views await on our Chicago Bike Tour. Experience the city’s beauty up close on a Bicycle Tour in Chicago that blends culture, history, and unforgettable scenery.

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.

(269)

from USD 59

The Chicago River, as seen from our stop on wacky Wacker Drive

Chicago City Tour with Architecture River Cruise Option

2 to 4 hoursFree Cancellation

Sail on Tall Ship Windy, join us for our "Chicago Skyline Sail"

(733)

from USD 50

1 hour 15 minutes

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

(26)

from USD 91

2 hoursFree Cancellation

4.1

(49)

from USD 99

Chicago's Delicious Downtown Donut Tour with 8 Amazing Tastings

Sample some of the Windy City's tastiest donuts—and head to locals-loved dessert destinations that most visitors miss—on this one-of-a-kind walking tour. With your guide in the lead, head to a number of Chicago’s tastiest donut bakeries, all while exploring the city's vibrant downtown Loop neighborhood. All tastings are included in the tour cost, and vegan, gluten-, and nut-free options are also available upon request.

Chicago's Delicious Downtown Donut Tour with 8 Amazing Tastings

2 hoursFree Cancellation

The Field Museum of Natural History is one of Chicago’s most-visited museums—and this package deal offers a way to beat the crowds and see its top exhibitions without stress. Secure your tickets before you travel, arrive an hour before the galleries open to the public, and explore in the company of a museum docent. You’ll see collection highlights like Sue the Tyrannosaurus Rex, the Griffin Halls of Evolving Planet, and much more.

(1,494)

from USD 70

Field Museum of Natural History Early Access Ticket

Field Museum of Natural History Early Access Ticket

2 to 4 hoursFree Cancellation

4.5

(58)

from USD 73

Chicago's Fireworks Show aboard Tall Ship Windy!

Enjoy the most Unforgettable Fireworks Cruise in Chicago! A SPECIAL EVENT SAIL! Treat yourself to Navy Pier’s spectacular fireworks display from the best seats in town! Grab a cool drink from our full bar, relax, and enjoy a leisurely evening sail past the brilliant and beautiful Chicago nighttime skyline. Windy provides the accompanying sound track, over the ship sound system coordinated fireworks display, amazing show! Rain or Shine event. no umbrellas are allowed to be opened underway. Tall Ship Windy, located on Navy Pier, and we have a ticket booth and dock, in front of the Billy Goat Bar and Grill. Arrive early, as fireworks crowds are huge! expect travel delays.

Chicago's Fireworks Show aboard Tall Ship Windy!

1 hour 30 minutes

4.7

(24)

from USD 114

Frank Lloyd Wright Robie House Admission

Discover one of Chicago’s top architectural marvels when you explore Frank Lloyd Wright’s UNESCO-listed Frederick C. Robie House, located right on the University of Chicago’s campus. Considered a masterpiece of Prairie School architecture, the building is famed for its cantilevered roof and rich wood details. Save money when you book tickets to the house in advance; call ahead to reserve a space on one of the museum’s frequent, small-group public tours.

Frank Lloyd Wright Robie House Admission

1 hourFree Cancellation

4.2

(152)

from USD 27

Likely to Sell Out

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

1 to 2 hours

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.

(111)

from USD 41

3 hours 30 minutesFree Cancellation

Chicago Pizza 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.

(481)

from USD 89

Smiles ear to ear as you ride our Chicago Bike Tour through scenic Lakefront Neighborhoods. Fresh air, open paths, and lake views make this the ultimate Bicycle Tour in Chicago.

Bike Tour of Chicago's Lakefront Neighborhoods

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.

(259)

from USD 59

River North Food Walking Tour

4.6

(96)

from USD 89

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Top Attractions in Chicago

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Attractions

What are people saying about Chicago

Flyover in Chicago

Charnique_W, Aug 2026

10/10 highly recommended

My daughter and I loved this experience. Purchasing our ticket on Viator was so much easier, I absolutely loved how it showed up on my phone screen as a reminder of the event for the day when added to my wallet. The place was clean and the staff was nice. We went on a weekday so the line was short and we got in, in less than 5 mins. I would definitely do this again!!!!

Chicago River 90-Minute Architecture Tour

Eddie_M, Aug 2026

Amazing guide made the tour memorable!

The tour was amazing, our guide was very knowledgeable about the buildings and kept us engaged the entire tour. It was a beautiful day, but we chose to sit on the lower deck to have some shade. It was a little difficult to the guide sitting in the bow. Adding a speaker in that area would make the tour equally enjoyable for every passenger. I'm sorry that I don't recall the guides name. She really deserves her flowers.

Chicago Architecture River Cruise

Breah_C, Aug 2026

This was so enjoyable! We...

This was so enjoyable! We did the 8:30pm tour, which I would highly recommend. The entire city is lit up making for the most breathtaking views. Sam S was our guide (the best guide for sure) and his knowledge along with charismatic presentation truly made the entire experience top notch. With the availability of the bar and snacks on deck, I could have stayed on board for hours. The information given during the tour were things I truly had never heard before and kept my attention the entire time. It was a very smooth ride and the boat seemed to make no noise at all allowing for no issues hearing Sam S or the quiet sounds of the city around. 100/10 experience!

Chicago Architecture Center River Cruise aboard First Lady

Judith_L, Aug 2026

Architecture tour worth doing again

Michael the mapmaker was a fantastic docent for the tour, and we had a perfect summer day for this tour. He was full of historical tidbits and knowledge about the skyscrapers throughout downtown Chicago. I’ve been on this tour before, and Michael and the weather made it well worth repeating.

Chicago Sightseeing River and Lake Cruise

Kyanna_R, Aug 2026

This tour was amazing and...

This tour was amazing and beautiful. 10/10 worth the money. Nice views. The tour guide was extremely knowledgeable on the architecture of Chicago. We got stuck BUUUUT the boat crew remained calm and got us back safely. They gave us a refund before we got back to shore. I would recommend getting new wine because the wine that was there was really nasty lol.

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.

Chicago Lake and River Architecture Tour

Liliana_B, Aug 2026

Could not recommend Emma enough!!

Emma our tour guide to the fantastic job! It was such a fun and engaging tour and we got to see so much of Chicago in the hour and a half. The AC worked well and you were able to get drinks while I’m bored and of course, go in and out as you please. The bathrooms were clean and the stuff was all very helpful and knowledgeable. Highly recommend!

Chicago River 45-Minute Architecture Tour from Magnificent Mile

Katie_T, Aug 2026

Excellent educational tour for all ages

Very educational. We had a group of 8 ranging from 50’s down to a 3 and 4 year old and it was just the right amount of time for them. We did the 9:00 one and John Miller did an excellent job being enthusiastic so early in the morning. Looks as if he truly enjoys his job.

Chicago Favorites Ultimate Food and Walking Tour

Debra_K, Aug 2026

Delicious food and history come together!

This food tour was an excellent combination of delicious Chicago specialties with historical and cultural perspectives. Molly, our guide, shared her well informed perspectives iwith her passion and love for the city. Her storytelling was compelling and entertaining. This tour is a must do and time well spent while you are in Chicago.

Lake Michigan Skyline Cruise in Chicago

Stanley_A, July 2026

We had a great experience...

We had a great experience on the Skyline Cruise in Chicago. The staff was extremely friendly and welcoming from start to finish. The boat ride was smooth, and the views of the city were absolutely beautiful. We also enjoyed learning about Chicago’s landmarks and history throughout the tour. I would highly recommend this cruise to anyone visiting Chicago—it’s a relaxing, scenic, and educational experience!