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

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

2 hours 30 minutesFree Cancellation

5.0

(324)

from US$90

Price varies by group size

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

1 hour 15 minutes

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.

(26)

from US$91

3 hours 30 minutesFree Cancellation

Chicago Pizza Tour

Chicago Crime, Mobsters & Ghosts Walking Tour

(481)

from US$89

1 hour 30 minutes to 2 hoursFree Cancellation

4.7

(454)

from US$34

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

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

Price varies by group size

(977)

from US$85

Haunted Chicago: Crime, Ghosts, and Capone Walking Tour

1 hour 30 minutesFree Cancellation

5.0

(354)

from US$35

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

(23)

from US$114

Chicago River 90-Minute Architecture Boat Tour

1 hour 30 minutesFree Cancellation

Admire up-close views of the Chicago skyline—and a fireworks show over the city—on this tiki bar boat tour. In the evening, make your own way to the departure point at the Chicago Riverwalk, hop aboard, and get comfortable in the air-conditioned seating area or on the deck. Purchase cocktails and food from the on-site tiki bar, watch the city float by, and then sit back and take in the show.

(1 838)

from US$37

Chicago River Spectacular Fireworks Show and Tiki Bar Cruise

Chicago River Spectacular Fireworks Show and Tiki Bar Cruise

1 hour 30 minutes

4.0

(33)

from US$53

Chicago Architecture Tour and Speedboat Ride and Lake Michigan

Discover Chicago's world-renowned architecture during this sightseeing cruise. Board a comfortable riverboat for a trip down the Chicago River, viewing landmarks like the Willis Tower and the Tribune Tower while listening to in-depth commentary from your guide. Then board a speedboat for an exciting ride up the shore of Lake Michigan for views of Grant Park, the Museum Campus, and other top sights.

Chicago Seadog River & Lake Architectural Tour

1 hour 15 minutesFree Cancellation

4.5

(284)

from US$42

Nat "King" Cole landmark - Nat lived in this house until he was too big to stay! L.A. and television called him!

African American Heritage Tour of Chicago

4 to 7 hoursFree Cancellation

4.4

(137)

from US$125

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.

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

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

(732)

from US$50

Chicago Fireboat Fireworks Cruise

1 hour 30 minutesFree Cancellation

4.7

(15)

from US$57

Guide discussing A Sunday on La Grande Jatte

Skip-the-line: Art Institute of Chicago Guided Tour

2 hours 30 minutesFree Cancellation

5.0

(591)

from US$84

You get to name your new Exclusive Scent

Chicago Perfume Making Classes on Magnificent Mile

1 hour 15 minutesFree Cancellation

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.

(85)

from US$85

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

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

1 to 2 hoursFree Cancellation

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.

(26)

from US$40

Frank Lloyd Wright Robie House Admission

Frank Lloyd Wright Robie House Admission

1 hourFree Cancellation

4.2

(150)

from US$27

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

(111)

from US$41

Experience Chicago in Style with Our Luxury City Sightseeing Minibus Tour. Indulge in the ultimate Chicago adventure on our top-rated, luxury sightseeing minibus tour. This 2-hour, expertly guided experience takes you through the vibrant heart of the city in a sleek, climate-controlled minibus designed for comfort and class. Marvel at iconic skyline views and the shimmering waters of Lake Michigan from panoramic windows, and enjoy curated photo stops at the city's most breathtaking landmarks. With engaging stories from your private guide and an intimate, upscale atmosphere, this tour offers an unmatched blend of elegance and exploration. Please note, infants 0-3 years old must sit on a lap.

Luxury Minibus Chicago City Tour

2 hoursFree Cancellation

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.

(14)

from US$65

River North Food Walking Tour

Chicago's Ultimate City Bike Tour of Top Downtown Attractions

4.6

(95)

from US$89

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.

Vito's Vault Chicago Speakeasy Dinner Theatre

(259)

from US$59

Price varies by group size

(35)

from US$88

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 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.

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

4 hours 30 minutesFree Cancellation

Discover the architectural soul of Chicago on a thoughtfully curated half-day city tour. Travel through the city’s most influential districts, from historic riverfront landmarks to groundbreaking modern skyscrapers. Explore the Loop’s civic, financial, and architectural core, admire world-renowned towers, and experience Chicago’s most celebrated public spaces. This small-group tour offers a comprehensive introduction to Chicago’s skyline, history, and urban design, concluding with a panoramic skyline view before returning guests to the original pickup point. Ideal for first-time visitors and architecture enthusiasts alike. Explore Chicago’s iconic riverfront skyscrapers and historic bridges See legendary architecture including Willis Tower and Marina City Discover the heart of Chicago’s financial, civic, and architectural power Pass by Millennium Park and spend time at Cloud Gate (The Bean) Enjoy a panoramic Chicago skyline view, included for all guests

(758)

from US$89

Premium Chicago City Tour Small Group ICONIC Landmarks & Skyline

Premium Chicago City Tour Small Group ICONIC Landmarks & Skyline

Chicago Architecture River Cruise

(21)

from US$48

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Top Attractions in Chicago

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What are people saying about Chicago

Isobel_P, Aug 2026

Our tour guide, Sam, was...

Our tour guide, Sam, was incredibly knowledgeable and experienced. He was a Chicago native and practically a stand-up comedian. My friends and I were laughing the whole time and learned so much about the history of the Chicago River and its surrounding architecture. Totally recommend, shoutout to Sam!

Chicago Architecture Center River Cruise aboard First Lady

Terra_W, Aug 2026

More information than expected, beautiful excursion

Not only is Chicago architecture amazing, but passing by the buildings and infrastructure lining the river is a beautiful introduction. This company is great! The speaker was a volunteer and she dropped history and other knowledge than just about the variety of building styles and timelines. I am still digesting days later. I cannot wait to visit again and give more time than a half day to this amazing place (I normally hate big cities).

Chicago River 90-Minute Architecture Tour

Diana_E, Aug 2026

6:30pm was the perfect...

6:30pm was the perfect timing to be on the cruise. It was day and sunset has started so the building lights started switching on. The representer was funny and good, not boring at all. Next time we will do the cruise at night to get the different vibe.

Chicago Sightseeing River and Lake Cruise

Ricky_C, Jul 2026

Best Tour I’ve ever had. Very kid friendly.

This was the perfect tour for our first visit. We had the two grandkids, 9 and 12 and they loved it. They really don’t care about history at this age but it was presented in a way they really paid attention. I learned a lot myself. I chose this tour because I liked it was going into Lake Michigan. We do some vacations in Michigan and wanted to let them see Lake Michigan from a different angle. I’ll be back and I’m sticking with this company!! Thank You!

Chicago River 45-Minute Architecture Tour from Magnificent Mile

Lainey_B, Jul 2026

Would not recommend in winter!!!

We went on our tour in January and it was absolutely freezing, the experience was almost unbearable…however, the tour itself and our tour guide were fantastic, and it was a 5 star experience if you factor out the temps that were way below freezing, lol! HIGHLY recommend doing this excursion (when the weather is much nicer!!!!!)

Chicago By Night River and Lake Cruise

Lisa_G, Jul 2026

Very informative and beautiful

Taking the sunset architectural cruise near the Riverwalk was easily one of the highlights of our trip. Seeing the city's iconic skyline transition from the golden hour glow into the beautifully lit evening cityscape is an absolute must-do. The vessel was comfortable, the atmosphere was relaxed, and the tour provided fascinating insights into the history and design behind Chicago's world-famous buildings. If you want a peaceful, breathtaking, and informative way to experience the city from the water, this is it! Highly recommended.

Chicago Lake and River Architecture Tour

Jennifer_M, Jul 2026

Wonderful Saturday afternoon ride!

The 90 minute architecture tour was interesting, well run, and super enjoyable. Molly was our guide and did amazing in her facts and approachable way, added bonus that she is also a teacher! The buildings of Chicago deserve much praise and even though we've done an architecture tour many times, we'll keep coming if they keep being great!

Lake Michigan Sunset Cruise in Chicago

William_M, Jul 2026

We Loved It!

Wonderful experience! Gabby was a great tour guide who provided a lot of history and fun facts about Chicago. She is incredibly knowledgeable. The views were amazing, and the captain provided fantastic opportunities for photos, too! I would highly recommend this sunset cruise to anyone visiting downtown Chicago.

Chicago Crime and Mob Bus Tour

Henry_C, Jul 2026

The host was fantastic...

The host was fantastic and his delivery was spot on. He kept it lighthearted and funny while still making it informative and interesting. I thought this was going to be a gangster tour with a focus on Al Capone, but they presented generations of crime stories, from the Chicago’s origins to the Crack dealing McDonalds employees. I was young when the Tylenol scare occurred and to go past the Walgreens where it happened was also interesting. The only negative feedback I can give is the bus broke down outside of Harry Cary’s and we had to figure out how to get back to the neighborhood we started in. Obviously this was a one off and I would not judge to tour by an unforeseen. Great tour and worth the price of admission.

Lake Michigan Skyline Cruise in Chicago

Anisha_S, Jun 2026

Relaxing Ride

The skyline tour was exactly what I needed after a day of eating and walking about. I was able to book the tour an hour before, which worked for my itinerary and it was affordable. I liked that it is a double decker boat and got to experience the tour from top deck. The day was beautiful and perfect for a tour. The boat was clean, looked presentable, offered cocktails and small snacks(for purchase) and staff were friendly. The tour offered ok views. I was able to capture pictures of the Chicago skyline. My fav part of the ride was how relaxing it was. I would do it again and be sure to nap the next time lol.