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

Small Group Bike Tours From Chicago to Lake Geneva

2 daysFree Cancellation

from $449

Your private luxury tour experience begins with a prompt pickup in downtown Chicago. Step inside the climate-controlled cabin of a world-class Rolls-Royce. Your professional chauffeur will navigate the bustling streets of the Windy City. Glance through the panoramic windows at towering skyscrapers like the Willis Tower. Coast down Michigan Avenue to admire the luxury boutiques of the Magnificent Mile. Pass by the architectural marvels of the Loop and the lakefront beauty of Grant Park. This tour itinerary maximizes your time in the city. It is ideal for couples celebrating an anniversary, travelers on a tight schedule, or anyone seeking a VIP Chicago experience. Avoid the crowds of standard tour buses. Enjoy the privacy, comfort, and prestige of DS Luxury Rolls-Royce Tour.

Downtown Chicago City Tour in a Rolls Royce[60 Minute Experience]

Downtown Chicago City Tour in a Rolls Royce[60 Minute Experience]

1 hour

3.5

from $195

Chicago: Luggage Storage Close to Museum of Contemporary Art

Experience the freedom of exploring without the extra weighting in Chicago. Our luggage storage service ensures your belongings are secure, allowing you to enjoy the wonders of your destination with peace of mind. Whether you're waiting for a late flight, have arrived early for your stay, or simply want to explore without the burden of your bags, our service is the perfect solution. Store your bags at prime locations near major attractions, transport hubs, and popular areas, making your travel experience smoother and more enjoyable.

Chicago: Luggage Storage Close to Museum of Contemporary Art

1 dayFree Cancellation

from $10

Chicago O`Hare Airport (ORD) to Chicago: Arrival Private Transfer

Book your private arrival transfer from Chicago O`Hare Airport (ORD) to Chicago. Avoid the hassle of waiting in long taxi or shared shuttle queues and use our private, door-to-door airport transfer. Your driver will be waiting for you at the scheduled time, and you can travel comfortably to your destination. We track your flight. Our driver greets you with a name plate. We provide door-to-door service. There are no hidden charges. We use clean cars and professional drivers.

Chicago O`Hare Airport (ORD) to Chicago: Arrival Private Transfer

30 minutesFree Cancellation

from $101

Discover Hollywood magic in the heart of the Midwest on the Chicago Suburbs Movie Sites Tour. Visit real filming locations from classics like Ferris Bueller’s Day Off and Home Alone to modern hits like The Dark Knight. Led by a local actor guide, explore iconic homes, schools, and streets while hearing behind-the-scenes stories and fun film trivia. Perfect for movie lovers and anyone wanting a fresh, cinematic look at the Chicago suburbs.

Chicago Suburbs Movie Sites Private Tour

Chicago Suburbs Movie Sites Private Tour

2 to 3 hours

4.5

from $270

To me, one can appreciate a given building, or piece of public sculpture, far better when a tour guide explains the historical and cultural context. What was important in that era, and what was the architecture of that era thus trying express? I do know a lot about this. Thus, you will gain this information about each point of interest. I have taken other tours here, and I just do not hear a word from that point of view. This tour will be like an open history book to an America that no longer exists: Roman and Greek architectural styles, as well as French and British-influenced styles. Of course, you will see the latest in office building architectural styles from around the world, for those of you who just love the modern era as well.

Architectural and Historical Private Tour in Downtown Chicago

Architectural and Historical Private Tour in Downtown Chicago

2 hours 20 minutes to 2 hours 30 minutesFree Cancellation

from $199

Let’s Roam leads the way as the top app-led adventure hunt company! Explore the city’s top landmarks and uncover hidden gems while tackling trivia questions and overcoming challenges. Whether you're collaborating with your team or sparking friendly competition, you’ll discover new facts and forge unforgettable memories. Let’s Roam Adventure Hunts are perfect for any occasion—from everyday fun to bachelorette parties, birthdays, corporate team building events, and beyond! Each participant selects an interactive role, with challenges tailored to every adventurer's spirit.

Amazing Scavenger Hunt: Time For a Go in Chicago

Amazing Scavenger Hunt: Time For a Go in Chicago

1 hour 30 minutesFree Cancellation

from $15

Your Private Ride Awaits – Executive Sedan Service from O'Hare

Whether you're flying in for business or leisure, We ensures your journey is as smooth and stylish as your destination. Here's why travelers trust us: Luxury Fleet for Every Occasion Choose from executive sedans, SUVs, Sprinter vans, and minibuses Immaculately maintained, climate-controlled, and equipped with premium amenities Punctual & Reliable Real-time flight tracking ensures on-time pickups—even if your flight is early or delayed Chauffeurs arrive early and plan routes to avoid traffic delays Professional Chauffeurs Courteous, licensed, and experienced drivers Dressed professionally and trained in customer service and safety Easy Booking & Real-Time Updates Book online in minutes with instant confirmation Receive driver details and live tracking before your ride Perfect for Business & Leisure Ideal for corporate travel, family vacations, weddings, and group events Discreet, comfortable, and tailored to your needs

Private Sedan Transfer from O'Hare and Midway Airport to Chicago

1 hourFree Cancellation

from $120

Unleash your creativity at a private Art Splash painting session in Chicago. Perfect for group celebrations, birthdays, or corporate events, this 40-minute experience lets you get hands-on with bold paints, premium tools, and a 12x16 canvas to take home. Protective clothing is provided—so you can embrace the splash, layer colors, and express yourself freestyle, no art skills needed! Your group gets a private room and expert guidance, ensuring an unforgettable, laughter-filled activity for anywhere from 6 to 80 people. Just arrive ready for creative fun and leave with a unique piece of art (allow up to five days for full drying).

Private Art Splash: Chicago Group Painting Experience

Private Art Splash: Chicago Group Painting Experience

40 minutes

Celebrate the beauty of spring and the rich history of the National Cherry Blossom Festival, commemorating the 1912 gift of 3,000 cherry trees from Tokyo to Washington, D.C. Visit iconic landmarks like the Lincoln Memorial, Vietnam Veterans Memorial, White House, and U.S. Capitol. Stroll through East Potomac Park, enjoying the blossoms along the scenic 4.4-mile Hains Point Loop Trail, with views of the Martin Luther King, Jr. Memorial, Franklin D. Roosevelt Memorial, and more. Special Note: The 2025 National Cherry Blossom Festival will take place from March 20 to April 13, though bloom timing may vary depending on weather conditions. Immerse yourself in the vibrant beauty of D.C.’s cherry blossoms and explore the city’s rich history on this unforgettable tour!

from $70

Chicago to Washington D.C. Cherry Blossom 3-Day Tour

Chicago to Washington D.C. Cherry Blossom 3-Day Tour

3 daysFree Cancellation

4.5

from $496

Step into the birthplace of the modern skyscraper on this immersive walking tour through Chicago’s historic Loop. Discover the stories, innovations, and hidden details behind the buildings that shaped the modern city. What makes this experience unique: • Small-group tour for a more personal experience • Story-driven guiding that brings Chicago’s architecture to life • Focus on early skyscrapers and hidden architectural details • Visit iconic landmarks in the historic Loop • One complimentary copy of my book, Chicago Beyond the Bean, is included per booking.

Chicago Early Skyscraper Walking Tour in the Loop

Chicago Early Skyscraper Walking Tour in the Loop

Savor the flavors of Mexico’s Yucatan Peninsula, right in Chicago—and feel like a local when you dine in your host’s own home—during this small-group dinner experience. Be sure to come hungry: alongside a small group of diners, you’ll savor a multi-course menu of Yucatan classics, from a tropical starter to pibil tacos and beyond. In between, enjoy cocktails and the chance to converse with your host and fellow guests.

from $39

Likely to Sell Out

Yucatan Delights by a Michelin Star-Trained Chef in Chicago

Explore the vibrant neighborhoods of Chicago with engaging tours that delve into the rich history and culture of areas like Bridgeport /Stockyard Tour, led by Historian Dilla, who uncovers the unique stories and contributions of these communities, providing an authentic experience of Chicago's diverse heritage. Whether you're a history buff or simply curious about local culture, these tours offer fascinating insights into the Windy City's past and present. The tours vary in duration but typically last around 2 hours, making them perfect for a quick but enriching adventure. - Discover the history and culture of Chicago's neighborhoods - Tours available in Bridgeport /Stockyard Tour - Led by knowledgeable Historian Dilla for an authentic experience

(1)

from $205

2 Hour Bridgeport /Stockyard Chicago Tour

2 Hour Bridgeport /Stockyard Chicago Tour

Explore the charm of Mackinac Island on this delightful journey from Chicago. Experience a blend of history, culture, and stunning landscapes as you travel through the Great Lakes region. Discover the island's unique features, where cars are absent, allowing horse-drawn carriages to roam freely among Victorian architecture and beautiful scenery. Enjoy iconic sites like Fort Mackinac and Arch Rock while wandering through quaint downtown shops and savoring famous fudge. This tour is designed for families, couples, and solo travelers looking for a serene getaway filled with natural beauty and cultural richness. - Scenic travel through the picturesque Great Lakes region - Discover Mackinac Island's charm without car traffic - Visit Fort Mackinac, Arch Rock, and local boutiques - Ideal for families, couples, and solo adventurers seeking relaxation

from $45

Chicago to Mackinac Island Scenic Tour

16 to 17 hoursFree Cancellation

3.0

from $685

Custom Chicago Walking Tours

1 to 3 hoursFree Cancellation

from $20

Private SUV Transfer from O'Hare Midway Airport to Chicago

1 hourFree Cancellation

from $200

Explore the historic Loop District of Chicago on a private walking tour that delves into the city's architectural legacy. With an expert guide, visit iconic skyscrapers and stunning lobbies, learning the fascinating stories behind their designs. This 2.5-hour tour is perfect for architecture enthusiasts and curious travelers alike, providing a unique perspective on the birthplace of modern skyscrapers. Whether you’re a local or a visitor, discover why Chicago's skyline is renowned worldwide. - Private tour lasting 2.5 hours, perfect for families and small groups - Visit landmark buildings like The Sullivan Center and The Rookery - Expert local guide shares insider knowledge about architectural history - Flexible meeting points available for your convenience

Private Chicago Loop Architecture Walking Tour

Private Chicago Loop Architecture Walking Tour

2 hours to 2 hours 30 minutesFree Cancellation

(5)

from $180

Explore the vibrant neighborhoods of Chicago with engaging tours that delve into the rich history and culture of areas like Chatham, led by Historian Dilla, who uncovers the unique stories and contributions of these communities, providing an authentic experience of Chicago's diverse heritage. Whether you're a history buff or simply curious about local culture, these tours offer fascinating insights into the Windy City's past and present. The tours vary in duration but typically last around 2 hours, making them perfect for a quick but enriching adventure. - Discover the history and culture of Chicago's neighborhoods - Tours available in Chatham - Led by knowledgeable Historian Dilla for an authentic experience

2 Hour Chatham, Chicago Tour

Discover the very best of New York City in one unforgettable experience! From the majestic Statue of Liberty and the historic Brooklyn Bridge to famous neighborhoods, hidden gems, and picture-perfect skyline views — this tour captures it all. Enjoy guided stops at iconic landmarks, learn fascinating stories from your local guide, and experience the true energy of the city that never sleeps. Perfect for first-time visitors or anyone wanting to see it all, this experience blends history, culture, and unbeatable photo ops at every turn. Come ready to explore, snap amazing pictures, and make lasting memories on the ultimate NYC adventure!

from $45

2 to 7 hoursFree Cancellation

Chicago VIP Private Tour

4.5

from $499

Live the mythical Route 66 as it should be: at your own pace, with freedom and with the feeling of being walking a living history. This audio guide accompanies you from Chicago to Los Angeles, transforming each stretch of road into an experience full of context, curiosities and stories that give meaning to the journey. You don’t just drive – you understand the landscapes, cities and small towns that marked the American dream. No schedules, no groups and no rush, just you, the road and a voice that guides you at the right time. If you’ve always dreamed of doing Route 66 for real, this audio guide is the most authentic and simple way to live it.

Guided Audio Road Trip Route 66

6 daysFree Cancellation

1.0

(1)

from $29

Enjoy a stress-free game day with your 5-hour private hourly service. Skip parking hassles and stadium traffic while your professional chauffeur handles the driving. Travel in comfort and style with your choice of Sedan, SUV, Sprinter Van, or Minibus — perfect for groups from 6 to 23 passengers. Your vehicle is exclusively yours for 5 hours, giving you the freedom to make multiple stops, tailgate, or celebrate after the game. With door-to-door pickup from your hotel, residence, or airport, bottled water onboard, and a luxury fleet designed for comfort, you can focus on the excitement of the event while we take care of the rest.

5-Hour Sports Event Chauffeured Service in Chicagoland

5 hoursFree Cancellation

from $500

We understand the importance of ensuring a hassle-free transfer experience. Our private airport transfer service allows you just that. Book our private airport transfer service and enjoy a safe, reliable, comfortable, and convenient journey from your accommodation in Chicago to O'Hare International Airport (ORD). Let us take care of your transportation needs, allowing you to focus on enjoying your trip to the fullest.

Private One-Way Airport Transfer From Chicago To O'Hare Airport

Private One-Way Airport Transfer From Chicago To O'Hare Airport

45 minutesFree Cancellation

from $93

Discover Chicago in a fun new way—and combine your sightseeing with a lively scavenger hunt—on this 2-in-1 excursion. With your smartphone in hand, set off at a time that works best for you on this self-led tour. Prompted by the game, explore the Windy City's vibrant Loop neighborhood. Spot historic buildings, famous streets, and other local landmarks along the way, all while your party solves clues and challenges.

Chicago Scavenger Hunt Adventure

3 hoursFree Cancellation

3.0

(2)

from $49

For sightseers looking to put a spooky spin on their night and avoid the overpacked city tours that tell history most of us already know, this Chicago Family-Friendly Ghost Tour is just the thing. Stop at popular Chicago attractions, including the Flying Dragon sculpture, the Chicago Stock Exchange Arch, the Abraham Lincoln statue, and Buckingham Fountain, while a guide tells you ghost stories along the way.

Haunted Chicago: Lincoln Park Ghost & History Walking Tour

Haunted Chicago: Lincoln Park Ghost & History Walking Tour

1 hour 30 minutesFree Cancellation

4.1

(12)

from $30

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Top Attractions in Chicago

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Attractions

What are people saying about Chicago

Chicago River 90-Minute Architecture Tour

Imani_F, Aug 2026

A Must See & Do!!

The architectural boat tour was amazing. It gave us an exceptional view of the beautiful buildings along the Chicago river. Spiro was the absolute best guide; he was funny and gave a cool history lesson on the architecture origins and even the history of the city of Chicago itself! He is an asset to the company, for sure!! Will be trying the sunset ride on my next visit!

Chicago Architecture River Cruise

Jayme_K, Jul 2026

Chicago River at Night

We had an amazing experience on the Chicago Architecture River Tour at night! Seeing the city’s skyline illuminated from the river was absolutely stunning. Our tour guide was fantastic, engaging, incredibly knowledgeable, and shared so many interesting facts and stories about Chicago’s architecture and history. The entire experience was relaxing, informative, and one of the highlights of our trip. I highly recommend this tour to anyone visiting Chicago!

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 Favorites Ultimate Food and Walking Tour

Steve_C, Jul 2026

Great way to eat yourself around the city

Great range of foods. Good local knowledge and Molly was really enthusiastic about her home town, this showed throughout the tour. My wife had become vegetarian a few months before the 2 swapped choices were good and sorted with no fuss. We both left feeling full and knowing a lot more about Chicago

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 Architecture Center River Cruise aboard First Lady

Monica_Z, Jul 2026

Chicago First Lady river cruise

The First Lady architecture cruise was fantastic! It is a great tour to do when first arriving in Chicago to get a nice layout of the city and the river. We learned a lot from the docent onboard and he gave us a lot of places to visit on foot afterwards. Highly recommend!

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.

Chicago Lake and River Architecture Tour

Ioana_C, Jul 2026

Best tour of Chicago river and lake.

Best combination of lake and river tours. The Chicago skyline is wonderful to see it in its entire length and beauty from Lake Michigan. The tour guide was very knowledgeable and had a wonderful story to tell at “every corner”. Toilets were clean and there was no problem finding where to sit. We did not buy anything from the bar but everything looked clean and nice. Total duration of the tour is one and a half hours spent approximately half-half between the lake and the river part. Fun fact: lake is a couple of feet higher than the river and you can see that when crossing over during the tour. Chicago river flow direction was altered in the early 1900 to flow away from the lake and keep chicagos source of clean water intact.

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.