All Chicago Tours &amp; Excursions in 2026 - page 4

BEST of Chicago Landmarks and Skyline Small Group City Tour

3 hoursFree Cancellation

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

Get a chance to experience the Windy City from multiple vantage points during this two-hour, small-group boat tour in Chicago. Hop aboard a secure and reliable US Navy-built Rigid Inflatable Boat (RIB) for a unique sightseeing experience. Pass by iconic sights such as Navy Pier, Soldier Field, Fort Dearborn, Vietnam Memorial, Wolf Point, Shedd Aquarium, and more, all while comfortably seated in a group capped at only six people.

Small-Group Sightseeing Boat Tour in Chicago

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

Haunted Chicago Booze and Boos Ghost Walking Tour

2 hours 30 minutesFree Cancellation

Experience the adrenaline rush of skydiving without jumping out of a plane at iFly Chicago-Rosemont. With start times available throughout the day, you can easily find a session that fits your busy schedule. Feel confident after a small-group training session, then head into the tunnel for your solo floats. An instructor is present for both 60-second sessions to give you personalized instruction. Afterwards, take home a flight certificate to commemorate your adventure.

Chicago-Rosemont Indoor Skydiving with Two Flights

1 hour 15 minutesFree Cancellation

Souvenirs are a great way to remember a trip, but ones you’ve hand-crafted yourself can be even more special. In this crafting workshop, learn how to create a soy wax candle and customize each with your own personally chosen fragrance. Take home your candle at the end of the course to light at home or keep to cherish the memories. BYOB is allowed during the class for a relaxed experience.

Chicago Candle Making Class On Magnificent Mile

1 hour 15 minutesFree Cancellation

Calling all fans of the paranormal, this evening ghost bus tour of Chicago takes you into the city’s darkest recesses—and reveals a side of the city few others get to experience. Travel with ease between locations where hauntings are reported to have taken place and listen to chilling tales delivered by your guide. The City Cemetery, the site of the notorious St. Valentine’s Day massacre, and more are all included.

Chicago Hauntings Original Ghost Bus Tour

3 hoursFree Cancellation

Sloomoo Institute Chicago: The Ultimate Slime Experience

1 hour to 1 hour 30 minutes

Explore Chicago like a local—and visit the city’s distinctive, characterful neighborhoods, in addition to its major landmarks—on this Half-day tour. Set off from downtown with just a small group for company, and leave the driving to your guide—you’ll explore dozens of Windy City neighborhoods, from Hyde Park and Bronze Ville to Lincoln Park and the Gold Coast. Learn all about Chicago culture and history as you go.

Small Group Tour of Chicago Neighborhoods: North and South Side

4 hours 30 minutesFree Cancellation

Explore one of the country’s great art museums—and discover many of its collection highlights—on this small-group Art Institute of Chicago tour. Meet your guide right out front, and see works from artists the likes of Picasso, Chagall, Seurat, O’Keeffe, and many more. As you go, your guide will share the stories behind the masterpieces, and will help bring the history of the museum and its collection to life.

Skip the Line Chicago Art Institute Tour Semi-Private 12ppl Max

2 hours 30 minutesFree Cancellation

Price varies by group size

Drunk Dracula Chicago: Comedy Theatre with Cocktails

1 hour 30 minutesFree Cancellation

While there are lots of spots across the city where you can try some Chicago deep dish pizza, not many culinary experiences teach you how to make authentic pizzas for yourself before tucking in and enjoying your creations. In this private cooking class, head to a working kitchen where instruction is available in English and Spanish, and get equipped with everything you need to create your perfect pizza.

Deep Dish Cooking Class at Pizzeria Uno in Chicago

1 hour 30 minutesFree Cancellation

Get a fresher perspective on the Windy City—and a traffic-free one—with this Chicago River architecture cruise. As you pass by some of Chicago's most notable buildings, you'll dine on a 3-course lunch, listening to onboard narration about the city's architecture and history along the way. Unlike your standard walking tour, you can expect comfort, great food, and endless photo opportunities.

City Cruises Chicago: River Architectural Lunch Cruise

4.4

(44)

from $85

Take in sweeping views of Chicago from the air during a scenic helicopter flight that offers a premier experience of the Windy City. This private 45-minute flight provides an aerial look at landmarks such as Millennium Park, Navy Park, and Wrigley Field. Ideal for a special occasion, this helicopter tour accommodates up to three people and includes the use of noise-cancelling headsets to hear the pilot clearly.

Private 45-Minute Chicago Skyline Helicopter Tour

Private 45-Minute Chicago Skyline Helicopter Tour

45 minutesFree Cancellation

Set sail for a memorable experience on Lake Michigan with a Signature Chicago Brunch Cruise that is as scenic as it is delicious! You'll savor a chef-prepared buffet and bottomless mimosas while in our comfortable indoor areas. Marvel at unparalleled views of Chicago’s iconic landmarks, such as Willis Tower and Navy Pier from inside or enjoy fresh breezes on the open-air decks. This fun-filled brunch cruise experience for all ages is complete with lively DJ entertainment, dancing, games, and a fully stocked cash bar. Elevate your weekend plans with a one-of-a-kind brunch cruise on the water!

City Cruises Chicago: Signature Brunch Cruise on Lake Michigan

Chicago Haunted Interior Architecture Ghost Tour

1 hour 30 minutes to 1 hour 45 minutesFree Cancellation

Paint ""Therapy"" is allowed for individuals aged 18 and over. In the case of a group, all participants must be 18 or older Engage in a vibrant explosion of creativity with the Neon Paint Therapy Experience at Shot Of Art. This immersive 30-minute activity invites adults aged 18 and over to unleash their artistic flair while surrounded by glowing neon lights and energetic vibes. Armed with water guns filled with neon paint, participants can freely express themselves on canvas and walls, creating a unique masterpiece. With premium clothes protection provided, enjoy the thrill of painting without worry. Capture the moment and let your imagination run wild in this exhilarating art session.

Neon Paint Therapy Experience

Lincoln Park Hauntings Ghost Investigation Tour

2 hours 15 minutesFree Cancellation

The Experience is more than a food tour. It is an immersive cultural experience that combines food, history, architecture, and storytelling in one of Chicago’s most influential neighborhoods. Guests will enjoy curated tastings from locally owned Black restaurants while learning about the people, businesses, and historical moments that helped shape Chicago’s Black cultural landscape. Along the route, we visit significant landmarks, including the site where Barack and Michelle Obama’s love story began, historic community gathering spaces, public art, and locations connected to the neighborhood’s rich legacy of entrepreneurship, music, education, and civil rights. Unlike traditional food tours that focus primarily on dining, this experience connects each tasting to the larger story of the community, providing travelers with insider knowledge and meaningful cultural context.

Explore Chicago Black Culinary Heritage

2 hours 45 minutesFree Cancellation

Admire a side of Chicago that few other visitors get to experience—and enjoy a relaxing trip out on the water, tailored to your party—with this private sailboat charter and sailing tour. You and up to five other guests will have the exclusive use of a sailboat, complete with a captain for the duration of your tour. Sail on Lake Michigan and enjoy the sights of Chicago’s striking skyline. If you want, you can even take a turn at the helm.

Private Sailing on Beautiful Lake Michigan - Navy Pier, Chicago

Step into the shadows of Chicago’s past on this adults-only haunted pub crawl, where ghost stories, historic landmarks, and legendary nightlife collide. Beginning near the iconic Palmolive Building, this guided experience takes you through the city’s Gold Coast and beyond, uncovering the eerie aftermath of the Great Chicago Fire and the restless spirits it may have left behind. Along the way, you’ll visit a curated mix of historic sites and local bars, blending chilling storytelling with time to grab a drink and soak in the atmosphere. Adults 21+ only, must have valid I.D.

Burning Spirits Haunted Pub Crawl

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

Skip the lines to the iconic Art Institute of Chicago and marvel at world-famous masterpieces by Monet, Van Gogh, and Picasso. Dive into a treasure trove of art, history, and culture at one of the oldest and most celebrated museums in the U.S. Tour is available in following language: English Spanish & French Highlights: • Private Tour of the Art Institute of Chicago • 5-Star Licensed Guide fluent in your chosen language • Skip-the-Line Tickets to the Art Institute of Chicago • Insightful stories about world-famous masterpieces, including works by Monet, Van Gogh, and Picasso • Expert guidance through Impressionist, Post-Impressionist, and Modern Art collections Discover the rich art and cultural heritage of Chicago with Rosotravel on an exclusive private tour with Skip-the-Line Tickets to the iconic Art Institute. Enjoy the luxury of a personalized itinerary led by a Licensed Private Guide. Uncover the magic of Chicago’s artistic treasures today!

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

Price varies by group size

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Must-Dos in Chicago

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What are people saying about Chicago

Chicago River 90-Minute Architecture Tour

Vonda_B, Oct 2026

I Loved this tour!

This is a very popular tour. It sells out fast so best to get tickets in advance. The tour is very lovely (especially on a nice day). I enjoyed our tour guide. He was funny, entertaining and very knowledgeable. Seeing Chicago's architecture from the river was amazing!

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 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 River 45-Minute Architecture Tour from Magnificent Mile

Janelle_M, Sept 2026

This tour was...

This tour was informative, funny, and a great introduction to this part of the city. Like the buildings, it blended history with more modern events. The tour began and ended just on time, and allowed plenty of time for photos. I would consider doing the longer tour next time because I liked this one so much!

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

Chicago Architecture Center River Cruise aboard First Lady

Carmen_W, Sept 2026

Informative, Worthwhile, and Accessible

The tour guide Patricia was excellent: Not only was she very knowledgeable about the architecture itself, she had an engaging presentational style and could translate the architectural principles into common language. The pre-boarding staff and the staff on the boat were all extremely courteous and helpful. My husband has limited mobility, and they were very gracious in helping him board and disembark and also storing the walker. For anyone who does have limited mobility, note that there are 3 flights of stairs down to the boat from the main street entry on East Wacker. There is a ramp a couple blocks further and we used that route to come back onto the street level.

Chicago Lake and River Architecture Tour

cyngrimm2, Aug 2026

The key is the tour guide

We went on the architectural tour, and our tour guide was Kenny. He did an amazing job, so if you can get him as your tour guide, I highly recommend him! It was raining when we started, but thankfully it cleared up and turned into a beautiful day. We absolutely loved the tour! I would definitely recommend it—it’s such a great experience and a wonderful way to see and learn about the city.