All Chicago Tours &amp; Excursions in 2026 - page 20

A Spectacular Audio Tour : Wonders of Chicago

1 hour 30 minutesFree Cancellation

"Dive into adventure with Let’s Roam, your go-to for the ultimate app-led adventure hunts! Step into a world where every landmark and hidden gem is waiting to be discovered. Challenge yourself with trivia, tackle brain-teasing puzzles, and embark on an epic journey of exploration! Whether you’re collaborating with your crew or turning up the competition, Let’s Roam Adventure Hunts guarantee a blast for all. Perfect for any occasion—whether it’s a spontaneous outing, a wild bachelorette bash, a festive birthday celebration, or a team-building extravaganza. Each player gets to dive into an interactive role, ensuring every challenge is as thrilling and unique as the next. So, gather your squad, choose your adventure, and let the good times roll! With Let’s Roam, every outing becomes a treasure trove of memories and excitement. Are you ready to conquer the city and create unforgettable experiences? Let’s Roam and make every day an adventure!"

Astounding Chicago Bar Crawl: Chi-Town Showdown

1 hour 30 minutesFree Cancellation

Treat yourself to a VIP arrival in or departure from Chicago during this private pickup or drop-off at Chicago O'Hare Airport (ORD). Enjoy a personalized meet-and-greet from a professionally-trained chauffeur right outside your hotel lobby, private residence, or airport arrivals hall. Ride comfortably in a luxury vehicle with complimentary bottled water. Flight tracking and one hour of free waiting time is included in case of delays.

Arrival Private Transfer: O'Hare Airport ORD to Chicago in Luxury Car

30 minutesFree Cancellation

Price varies by group size

One of the two remaining founding members of the NFL, dating back to 1920, the Chicago Bears are the epitomise NFL history. For an experience filled with tradition and history, look no further than attending a Bears game at the iconic Soldier Field. The Bears are entering a new era, led by former Heisman-Trophy winning quarterback, Caleb Williams. The excitement and electricity in the air Solider Field is noticeable and expectations amongst the Bears passionate fanbase have been raised. Soldier Field, the oldest stadium in the NFL, is a historic venue, located on the shores of Lake Michigan, with a unique architectural blend of the original structure and modern upgrades. The tailgating scene at Soldier Field is vibrant. Fans gather hours before the game to socialize and celebrate, forming a big part of the game day experience. Attending a game is also an opportunity to explore the city, known for its famous deep-dish pizza, you’ll have to get a taste of the real Chicago culture!

Chicago Bears Football Game at Soldier Field

Chicago Bears Football Game at Soldier Field

Experience Chicago in unparalleled style with a 10-mile cruise through the city in a luxury or exotic vehicle. Glide through iconic streets, turning heads at every stop, while taking in the captivating sights of the Windy City. Whether you're a resident or visitor, this exclusive ride offers a fresh perspective of Chicago's vibrant energy and charm. Don’t miss the chance to explore the city like never before—reserve your adventure and drive through Chicago’s heart in true sophistication. All tour vehicles are subject to availability During This Ride You May See Views Of The Following Land Marks: Little Italy Willis Tower Harold Washington Library The Chicago Theatre Millennium Park Grant Park Buckingham Fountain Magnificent Mile Gold Coast Museum of Science & Industry Lake Michigan And much more! We cannot guarantee that all sites on this list will be seen in your tour.

Downtown Chicago City Tour In a Lamborghini[60 Minute Experience]

Turn heads and take in the views with your Premier Chicago Tour Experience! Your journey begins in the passenger seat of an automotive masterpiece. Tour downtown Chicago in an Exotic Sports Car where you'll discover the luxury boutiques of the Magnificent Mile, and enjoy breathtaking waterfront views on Lake Shore Drive. After your scenic tour, enjoy 10 minutes of dedicated photo-op time at the departure point located at the Heart of Downtown Chicago. Whether it’s for social media or a personal keepsake, you’ll have plenty of time to pose with these mechanical works of art against the backdrop of the Windy City before your next adventure begins. More info THE VEHICLES CONSIST OF EXOTIC SPORTS CARS FROM MAKES SUCH AS LAMBORGHINI, FERRARI, MCLAREN, ASTON MARTIN & MORE! Group passenger vehicles consist of Vehicles from make such as Lamborghini, Aston Martin, Rolls-Royce, Bentley & MORE.

Downtown Chicago City Tour in a Super Car [30 Minute Experience]

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.

Chicago River Spectacular Fireworks Show and Tiki Bar Cruise

Chicago River Tiki Bar Party Cruise from Chicago River Wednesdays

Special Offer

Become an official Chicago Explorer with the Kids Loop Treasure Hunt. This engaging scavenger hunt invites young adventurers to navigate through the iconic landmarks of Chicago, solving clever clues and completing fun challenges. Discover hidden gems from impressive silver sculptures to historic theaters while capturing memories along the way. There's no rush, just plenty of time to work as a team, think like detectives, and uncover the secrets of the city. Each clue solved brings you closer to becoming Chicago Loop Champions. The adventure awaits your first clue is ready.

Chicago Kids Loop Scavenger Hunt

1 hour 30 minutesFree Cancellation

from

$10

Per group

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Must-Dos in Chicago

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What are people saying about Chicago

Chicago River 90-Minute Architecture Tour

Alexa_R, Oct 2026

So much fun!!

I did the night boat tour and it was cool to see the city lit up. The tour guide was incredibly knowledgeable. My group would have been ok doing a 45 minute tour instead of the 90 minute tour, but we did get to see some really cool buildings! Also, if you want to make sure you are able to sit with your group, show up early otherwise your seat options will be limited.

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 Architecture River Cruise

Mark_V, Sept 2026

Great tour , until it was time to exit the boat

Great tour. The young lady giving the tour was absolutely great, speaking in English and Spanish. Then the tour ended and she stood by the exit saying goodbye with her hand out with two five dollar bills rolled up in her fingers as a sign to leave her a tip. Very disappointed

Flyover in Chicago

Angela_S, Sept 2026

Flying rollercoaster of fun around downtown Chicago

If you’re good with heights and motion, it is an AMAZING experience and way to see downtown Chicago. I recommend doing Flyover after you’ve been around downtown. day or two so you recognize some of the buildings as you fly. The one thing that would make it better is if they had a little better customer service and communicated about the number of stairs or even verbally offered an elevator option instead of just ushering everyone to the stairs. There are already a lot of stairs in Chicago so taking what seemed like 2-3 flights of stairs (as in going down to the L) was a surprise. The ride made up for this. It was so cool to fly all around the riverfront and downtown area. At one point, I put my hands in the air because it felt like we were on a rollercoaster drop. So much fun!

Chicago River 45-Minute Architecture Tour from Magnificent Mile

Monique_E, Sept 2026

Lights..Camera...Action

Lights...camera...action Had a wonderful experience with my 17yr old son. This was something different vs that we were going to go during the day. However the night ride was amazing you get to see all the beautiful buildings lit up along the river trail. The speaker is available giving you the history of each architectured buildings. Bring your camera and/or phone and snap away. Get there early to get a good seat

Chicago Sightseeing River and Lake Cruise

Jack_H, Sept 2026

The best part of Chicago

We did a tour guided by Cole yesterday and he did a fantastic job. His energy kept the tour entertaining and upbeat. You obtained a great deal of history involving the water system, the architecture and more while enjoying all the wonderful views. We had the option of sitting inside or outside. We also enjoyed some beverages from the bar and the bartender was also pleasant. I highly recommend the boat tour when you visit Chicago.

Chicago Architecture Center River Cruise aboard First Lady

Cindy_H, Sept 2026

Wonderful, informative boat cruise.

Was in Chicago for the weekend with my daughter and we took this particular trip. Our guide, Patricia, was great! She was very knowledgeable about the architecture and history of Chicago. Was very interesting and informative. Would recommend this particular excursion!

Chicago River 90-Minute Architecture Boat Tour

Beth_C, Sept 2026

Boats and Tours Architecture Tour

We lucked out on the weather rain was forecast but it didn’t come until late afternoon and we were the first tour at 10 am. If it’s a cool morning bring a jacket. The best views are from the top open air deck. The lower deck has windows but fewer chairs so if it’s bad weather get there early. The tour guide we had did a wonderful job.

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