All Chicago Tours &amp; Excursions in 2026 - page 6

Private Departure Transfer to Chicago Airports (ORD)(MDW)

3.8

(91)

1 hourFree Cancellation

from $90

Bring the kids to LEGOLAND® Discovery Center in Schaumburg for a day of brick-building adventure. With 30,000-square-feet of space this family-friendly attraction has activities for everyone: from an interactive pirate-themed playland to a factory tour where you can actually see how LEGO bricks are made. There's even a mini replica of famous Chi-town landmarks made from nearly 2-million LEGO pieces.

LEGOLAND Discovery Center Chicago Admission Ticket

3.0

(116)

3 hoursFree Cancellation

from $23

Explore the sights and skyscrapers of Chicago’s spectacular Riverwalk on this private, self-led smartphone walking tour. Upon booking, download the app and receive a password to access your tour; once it’s on your phone, it is valid for an entire year. Set off at a time that works best for you: see highlights like the Merchandise Mart, Wrigley Building, Vietnam Veterans Memorial, and much more.

Chicago Riverwalk Self-Guided Walking Tour

4.2

(6)

1 to 2 hoursFree Cancellation

from $15

Immerse yourself in American literary traditions, and enjoy a wide range of interactive exhibitions, during a visit to Chicago’s one-of-a-kind American Writers Museum. Conveniently located on Michigan Avenue, the museum was established in 2017, and is one of the city’s newest highlight institutions. Guarantee your admission, and prevent any travel hassles, by securing your tickets in advance. Once inside, you’ll have time to explore at your own pace.

American Writers Museum Admission Ticket

4.9

(70)

1 to 5 hoursFree Cancellation

from $16

Likely to Sell Out

What do the artists Picasso, Chagall, Miro, and Kapoor all have in common? Incredible public art hiding in plain sight amidst world famous architecture. This 2.5 hour small group (12 Guest Maximum) guided walking tour is perfect for busy sidewalks and getting up close to monumental art! Highlights Include: Edward Kemeys’s “Lions” Juame Plensa’s “Crown Fountain” Anish Kapoor’s “Cloud Gate” (The Bean) Eduardo Kobra’s “Muddy Waters” Pablo Picasso’s “Untitled” Joan Miro’s “Chicago” Alexander Calder’s “Flamingo” Marc Chagall’s “Four Seasons” Louis Comfort Tiffany Art Glass Creation Augustus St. Gaudens “Abraham Lincoln” Marcel Francois Loyau “Clarence Buckingham Fountain”

Downtown Chicago Guided Walking Tour Semi-Private 12ppl Max

(1)

2 hours 30 minutesFree Cancellation

from $52

Price varies by group size

Take a deep dive into Chicago's food scene on a small-group walking tour. Head for several of the city's most-notable eateries, including Billy Goat Tavern, known for its "cheezborger," Pizzeria Uno, birthplace of Chicago’s legendary deep-dish pies; and Al’s Beef, a favorite since 1938. Along the way, hear about the friendly rivalry with New York's pizza scene, Chicago's meatpacking roots, 1920s speakeasies, gangsters, and more.

Chicago Food and Culture Walking Tour

4.6

(17)

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.

from $39

Likely to Sell Out

Chicago's Fireworks Show aboard Tall Ship Windy!

4.8

(14)

1 hour 30 minutes

from $114

Explore Chicago at your own pace with a 48-hour hop-on hop-off bus tour, providing unlimited access to the city's iconic neighborhoods and landmarks. Relax on open-top buses while enjoying engaging audio commentary that reveals the rich history and culture of the Windy City. This tour includes admission to the stunning 360 CHICAGO Observation Deck on the 94th floor of the John Hancock Center, offering breathtaking panoramic views of Lake Michigan and the city skyline. - Unlimited hop-on hop-off access for 48 hours across top Chicago attractions - Audio commentary in multiple languages covers local history and culture - Admission to the 360 CHICAGO Observation Deck for breathtaking views - Perfect for first-time visitors, families, and those seeking flexible exploration Time selected at booking is for 360 CHICAGO admission. Big Bus Hop-on Hop-off Tour available anytime during operating hours.

360 CHICAGO Observation Deck & Hop-on Hop-off Sightseeing Tour

(1)

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.

from $84

Skip the Line Art Institute of Chicago Tour Semi-Private 8ppl Max

(169)

2 hours 30 minutesFree Cancellation

from $90

Price varies by group size

Set sail for an unforgettable experience on the water with private boat tours and captained rentals along the Chicago River and Lake Michigan. Whether you're looking to explore the city’s historic waterways or enjoy a relaxing cruise with skyline views, we’ve got you covered. Cruise past iconic landmarks like the Wrigley Building on the Chicago River before heading out to Lake Michigan, where you'll take in panoramic views of the city’s world-famous skyline. With a comfortable and stylish cruiser boat, every ride is smooth, scenic, and uniquely Chicago. Want a custom experience? Choose a private boat rental with a licensed captain—ideal for birthdays, date nights, family outings, or simply relaxing with friends. You enjoy the moment, and we handle the navigation. No boating experience needed. Just bring your favorite snacks, drinks, and good vibes—we’ll provide the boat, the captain, and the unforgettable views. Book now and experience Chicago like never before—from the water!

2 to 8 hoursFree Cancellation

4.4

(7)

Chicago City Boat Tours

from $299

Have only a limited amount of time to explore the Windy City? Leave the planning to someone else with this convenient SUV transfer service. Meet your private driver at a time and place that work best for you, and set off: You’ll be dropped off directly at top Chicago landmarks like Navy Pier, Wrigley Field, Michigan Avenue, and Millennium Park, with time for solo sightseeing at each stop.

4-Hour Chicago City Tour by SUV

(2)

4 hoursFree Cancellation

from $800

Get ready to experience Chicago in full color with Tea Around Town. Step aboard our signature pink double-decker bus, beautifully adorned with vibrant wildflowers that bring a whimsical touch to the Windy City streets. Sip fine teas, enjoy delicious treats, and sing along with our entertainers as you journey past Chicago’s most iconic landmarks—from Millennium Park and the Magnificent Mile to the historic Riverwalk.

Tea Around Town Chicago Tea Bus Experience with City Views

1.8

(4)

1 hour 30 minutes

from $76

4.7

(25)

Deep Dish Cooking Class at Pizzeria Uno in Chicago

1 hour 30 minutesFree Cancellation

from $59

Experience the best of the Chicagoland area in style and comfort with our exclusive SUV tours. Discover the city's iconic landmarks, including the breathtaking parks, the famous Cloud Gate (The Bean), world-class museums, and renowned stadiums. Whether you’re attending a concert, exploring historic sites, or enjoying a day at the park, our professional chauffeur service ensures a seamless and luxurious journey. With our SUV tours, you'll have the flexibility to explore at your own pace. Visit top attractions like Millennium Park, the Art Institute of Chicago, and the Field Museum. Enjoy a thrilling game at Wrigley Field or United Center or take in a concert at Allstate Arena. Our chauffeur will drop you off and pick you up at each location, providing you with the utmost convenience. Book your tour today and let us take care of the details. Travel in comfort and make the most of your time in Chicagoland with our premium SUV tour service.

Luxury SUV 4 Hour Sightseeing Tour

4.0

(1)

2 to 4 hoursFree Cancellation

from $350

Discover Chicago like never before with complete freedom to explore at your own rhythm, lingering at fascinating locations or moving swiftly through others as your interests guide you. Our expertly crafted audio experience unveils exclusive historical insights and hidden stories that even longtime residents don't know, transforming you from tourist to insider as you uncover the authentic soul of the Windy City. Unlike rigid group tours that rush you past remarkable details, you'll have the flexibility to choose which attractions captivate you most, creating a personalized journey that matches your curiosity and schedule perfectly. You'll experience the city as locals do – unhurried, authentic, and deeply connected to the stories that shaped this magnificent metropolis, all while enjoying a superior experience that combines the convenience of independence with the depth of expert knowledge.

Chicago Self-Guided Audio Tour

3.9

(9)

3 to 9 hours

from $6

Special Offer

Discover the unique flavor of our Absolutely Chicago E-Bike Tour. Experience the city's rich history, stunning architecture, and breathtaking views as you pedal along on our state-of-the-art electric bikes. From iconic landmarks to hidden gems, this unforgettable adventure combines adventure, warmth, and loads of fun. Immerse yourself in the vibrant atmosphere of Milton Olive Park, the wonder of Soldier Field, and capture unforgettable photos at the majestic Buckingham Fountain. With flexible routes and a focus on hidden treasures, our tour offers a truly unique and memorable experience through the heart of Chicago.

2 Hour Chicago Landmarks & Lakefront E-Bike Tour

(4)

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.

from

$61

$72

Chicago Hauntings Original Ghost Bus Tour

3.8

(149)

3 hoursFree Cancellation

from $59

Entry ticket and self-guided audio tour of Skydeck and the city of Chicago are available in a separate app — the WeGoTrip app. You will receive an email from WeGoTrip with the link to download the app with the ticket and the digital guide. The digital guide includes maps, photos, scripts, and audio commentary. You will see Chicago from above and on foot with a Skydeck ticket and self-guided audio touring-app audio tour. Soak up history and panoramas of the place that Frank Sinatra called "My kind of town" and after your visit to the Skydeck, continue your journey on foot, uncovering the stories behind what you saw. Visit Millennium Park, cross the Chicago River and stroll along the Magnificent Mile

Chicago Willis Tower Skydeck Ticket and Audio Tour with City Walk

2 hours

from $79

Flytographer Private Vacation Photo Shoot Connect with a local hand-picked professional photographer in Chicago and capture your most memorable moments during this private photo shoot. Get insider tips on the best things to do in Chicago, including where to eat & what to see from your vacation photographer. Return from your trip with beautiful, high-quality vacation photos — the best souvenir ever. We specialize in: - honeymoons - family trips - engagements - anniversaries - romantic getaways - multi-generational trips - babymoons - solo travellers - and just because! With over 10,000 5-star reviews, Flytographer is the global leader in vacation photography and has captured over 3 million memories for travellers across six continents. We’ve been featured across A-list media, including Conde Nast Traveler, Oprah, Forbes, Travel + Leisure, New York Times, BRIDES, Martha Stewart Weddings, InStyle Magazine, Elle, Buzzfeed, Refinery29, Huffington Post, & many more.

Private Photography Session with Local Photographer in Chicago

(2)

1 hourFree Cancellation

from $325

Step into the heart of Chicago with this in-depth, small-group walking tour of the Loop neighborhood, the heart of the Windy City's downtown. Stop to check out the elevated “L” train, admire historic buildings, discover lesser-known corners of this vibrant area, and view its best-known public artworks, too. You’ll come away with a deeper sense of Chicago’s rich history and architecture.

Chicago Loop Walking Tour

4.9

(55)

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.

from $60

Neon Paint Therapy Experience

30 minutes

from $99

Chicago is renowned for its dynamic dining scene—and this private walking tour offers a personalized introduction to its must-eats. Pick a time that works best for you, and head to Gino’s East: one of the city’s classic deep-dish pizzerias. From there, set off on a tour of the Loop, where you’ll taste sweet and savory treats—and learn about the city’s architecture, history, and culture as you go.

Private Chicago Food Tour with Deep Dish and Beef Sandwich

(64)

3 hoursFree Cancellation

from $225

Price varies by group size

4.1

(38)

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

Discover the vibrant essence of Chicago with a self-guided tour through the Loop, the city’s historic downtown. This journey unveils a blend of striking skyscrapers and hidden architectural gems, allowing you to explore at your own pace. Uncover the rich history from the Great Fire of 1871 to the architectural masterpieces that define the skyline. Stroll past renowned theaters, museums, and captivating public art pieces that contribute to the city’s creative spirit. The Loop offers a unique perspective on Chicago's past and present, whether it's your first visit or a familiar stroll. — Self-guided exploration of Chicago’s historic Loop area — Learn about the city’s architectural innovations and history — Visit iconic landmarks like the Art Institute and Millennium Park — Perfect for first-time visitors or seasoned Chicagoans alike

from $99

The Chicago Loop is the city's epicenter of culture, commerce, and design.

Self-Guided Chicago Loop Tour Explore the City at Your Own Pace

(3)

2 hours to 2 hours 30 minutesFree Cancellation

from $10

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Top Attractions in Chicago

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Attractions

What are people saying about Chicago

Chicago Architectural River Cruise

Heidi_W, Apr 2026

This is the best way to...

This is the best way to acclimate yourself to Chicago. We learned so much from the tour guide and used what we learned all weekend long. The crew was amazing and professional and the complementary drinks especially he hot chocolate was much needed on this cold afternoon.

Chicago River 90-Minute Architecture Tour

Tina_M, Apr 2026

Best 90-minute tour on the Chicago river

Experience was absolutely amazing! The weather was perfect! Our tour guide Alicia is the best, super knowledgeable about the architecture, Architects and the history of Chicago. I highly recommend this and suggest taking the 90 minute tour. It’s worth it!

Chicago Architecture River Cruise

Stacey_W, Apr 2026

Worth every penny!

Love this cruise! I would do it EVERY time I visit Chicago if I had the opportunity. Always learn something new. Our guide was very knowledgable. I love seeing the reflections of the mirrored buildings on each other. Such a beautiful skyline. It was a bit chilly October 31, but wear a winter coat, hat and gloves and you're good to go!

Chicago River 45-Minute Architecture Tour from Magnificent Mile

Louann_M, Apr 2026

super enjoyable and informative architectural rivercruisr

I followed my maps but when I arrived the boat entrance wasn't marked well, but otherwise the whole experience was great! it was very easy boarding and getting a seat, the staff were all so nice…the tour was just long enough and the gal tour guide was lovely with an english accent, nice to listen to. We learned a lot about Chicago’s history along with timeline of the buildings how they were built and special building materials used, super interesting and well done. it was a lovely day as well which made it so nice, I highly recommend, is my first time to Chicago, great thing to do for all ages!

Flyover in Chicago

Sharon_S, Apr 2026

Great Experience...Flyover Chicago!

This was a great experience. You really feel that you are flying over Chicago. The ride is not "scary" as my daughter thought it would be (I think she was imagining a rollercoaster of some sort). You will get to see all of the highlights of Chicago and more...not spoiling it for you...go check it out!

City Cruises Chicago: Premier Plus Brunch Cruise on Chicago River

Amena_S, Apr 2026

Top tier experience

It was amazing from start to finish. Very aesthetically pleasing and service and food was top tier. Our server Heather was a perfect 10 across the board. Her recommendations, her spirit, her genuine energy was a breath of fresh air. She helped us with food selections, which were amazing down to photo opportunities. She even led us to the amazing bartender Keisha who made the best bottomless mimosas to say the least. We had to stop by the bar to let Ms Keisha know how well she mixed those cocktails. This was truly an amazing birthday brunch experience. Great way to start my birthday!!!

Chicago Favorites Ultimate Food and Walking Tour

Marsha_M, Apr 2026

5 STARS ASK FOR MICKY. Great entertainment

This food tour is more than just eating! Micky is a top notch guide and you learn the history and legends about Chicago. All the Food was fantastic! There are just enough places that you don't get too much. The nice walk around after each stop was timed well. The entire tour was entertaining. Ask for Micky as your guide.

Chicago Architecture Center River Cruise aboard First Lady

Emmanouela_T, Mar 2026

It was a wonderful...

It was a wonderful experience with very carefully guidance! There was a good amount of information shared about the buildings and the city of Chicago in general with enough details to catch the curiosity and interest of more expert audience (eg my mother who is an architect) as well as audience that is not related to architecture and engineering. Well worth it and highly recommended!

Field Museum of Natural History Admission Tickets

Julie_C, Mar 2026

Too Much for 1 Day

There is so much to see and explore. Get rest before coming and go see the things you’re interested in first. There is so much to see and experience that it can’t be done in a single day. My kids have very different tastes and we split up. There was something of intense interest for both.

Chicago Crime and Mob Bus Tour

Jean_P, Mar 2026

My birthday experience

This was our first bus tour in Chicago. The address was for a library, so we went inside. The library worker told us a bus would be out front, so we asked one of the bus drivers and he was the driver for our tour. It was a beautiful day, and also my birthday, and we enjoyed the tour very much. Jay, was the guide and she was very knowledgeable and offered many tidbits to the tour.

Lake Michigan Sunset Cruise in Chicago

Lauren_T, Oct 2025

Our tour guide, John, was...

Our tour guide, John, was full of energy and provided plenty of knowledge about Chicago history while making it a fun environment. The music was a variety of genres so there is something for everyone. We didn’t purchase any beverages while on the cruise, but they did let us know it was available. Worth the money for sure! Picture worthy.