All Chicago Tours &amp; Excursions in 2026 - page 18

Chicago Airport Luggage Services Same-Day Delivery and Storage

30 minutesFree Cancellation

$99$94

This self-guided bike tour traces Chicago's reinvention from the ashes of the Great Fire to the skyline that rose in its place, pedaling the Lakefront Trail with Lake Michigan on one side and the city's icons on the other. The route begins near Navy Pier and rolls through Museum Campus, past the Shedd Aquarium, Adler Planetarium, and Field Museum. Buckingham Fountain and the towering Willis Tower come next, followed by Millennium Park's Cloud Gate — Chicago's beloved "Bean." A quick pass through the Loop takes in the Chicago Theatre, State Street, and Union Station before crossing the Chicago River. Stories of the Great Fire and the innovators who rebuilt the city play through your headphones the whole way. Perfect for first-time visitors, casual cyclists, and anyone craving a fresh angle on the city. Download the VoiceMap app and enter the ticket code from your confirmation email to start riding.

Chicago Lakefront Trail: A Self-Guided Bike Tour

Chicago Lakefront Trail: A Self-Guided Bike Tour

1 to 2 hoursFree Cancellation

Little Diners Crew invites young food enthusiasts aged 4-12 to embark on culinary adventures that expand their palates beyond mac-n-cheese and chicken fingers. Each month, kids explore different cuisines at Chicago's best restaurants while interacting with chefs, tasting and rating new dishes, and learning about food preparation and dining etiquette. Meals become memorable experiences as kids discover the world through food.

Little Diners Crew Culinary Adventures for Kids

$105$100

This beginner-friendly chocolate class turns a classic confection into an approachable, rewarding skill. Led by Chef Janet, the experience focuses on teaching essential techniques while keeping the atmosphere relaxed and fun. You’ll learn how to temper chocolate correctly, experiment with popular fillings and use molds to create beautifully shaped treats. Chef Janet breaks everything down step by step, making the process easy to follow even if you’ve never worked with chocolate before. With plenty of tasting, hands-on practice and a supportive environment, this Chicago class is ideal for dessert lovers, curious home cooks or anyone looking for a creative night out that ends on a sweet note.

Fun Chocolate Making Class With a Local Chef in Chicago

Fun Chocolate Making Class With a Local Chef in Chicago

Hanfu Chinese Traditional Costume Try on

1 dayFree 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

Route 66, known as "The Main Street of America", runs through eight states from Chicago to Santa Monica. EN route to Illinois, POR Missouri, Kansas, Oklahoma, Texas, New Mexico, Arizona and California. Along DE way, it connects iconic cities such as St. Louis, Tulsa, Amarillo, Albuquerque, Flagstaff and Los Angeles, offering a unique experience through varied landscapes, from the Midwest Plains to the Southwest Deserts, each with its own history and culture. Route Chicago : 50 points Route DE Chicago to St. Louis : 56 points Route San Luis : 13 points Route DE San Luis to Joplin : 56 points Route Joplin to Oklahoma city : 29 points Route DE Oklahoma City to Amarillo : 27 points Yellow Route to Santa Fe : 39 points Route DE Santa Fe to Las Vegas : 80 points Route DE Las Vegas to Los Angeles : 34 points Total DE DE DE DE l’Or points of interest: 384

Routes POR Route 66 with Audio Guide

6 daysFree Cancellation

See Chicago’s most iconic sights, hear the stories behind the city, and enjoy a comfortable sightseeing experience without the stress of navigating traffic or parking.With us, you’ll explore the highlights of the Windy City with a friendly, knowledgeable guide and comfortable transportation. From the spectacular Chicago skyline to world-famous landmarks, we make it easy to experience the best of Chicago in one memorable journey. Why Book with us? Comfortable transportation Friendly sightseeing guide Great photo opportunities ️Iconic Chicago landmarks Relaxed and enjoyable experience ‍‍‍Great for families, couples, groups, and visitors of all ages Whether this is your first visit to Chicago or you're returning to discover more, we helps you experience the city’s highlights comfortably and conveniently. Sit back, relax, and let us show you Chicago!

Chicago Private SightSeeing Tour

7 hoursFree Cancellation

$89$85

Travel in style with our premium sedan transfer service from downtown Chicago to either O'Hare (ORD) or Midway (MDW) airports. Our luxury sedans offer a private, quiet, and comfortable environment for up to 3 passengers and 3 small bags for business travel or solo trips. Enjoy the professionalism and peace of mind that comes with a dedicated chauffeur who is committed to a stress-free and timely journey. Book your transfer today and experience the difference of a truly professional service.

Sedan Transfer from Chicago to O'Hare (ORD) & Midway (MDW)

Sedan Transfer from Chicago to O'Hare (ORD) & Midway (MDW)

45 minutes to 1 hour 30 minutesFree Cancellation

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

45 minutesFree Cancellation

$90$86

Our transportation service stands out for its reliability, comfort, and private door-to-door experience. Travelers enjoy professional chauffeurs, flight tracking, clean air-conditioned vehicles, luggage assistance, and a smooth direct transfer to Downtown Chicago. Unlike shared transportation, this private service offers personalized pickup, privacy, and a more comfortable travel experience from arrival to drop-off.

ORD Airport to Downtown Chicago Private Transfer

ORD Airport to Downtown Chicago Private Transfer

40 minutesFree Cancellation

Six days to enjoy the beautiful scenery of the three major lakes in the Great Lakes region of the United States, all of which are located in Lake Michigan in the United States, Lake Superior, the largest freshwater lake in the world, and Lake Huron. Famous cities along the five great lakes: Chicago, Milwaukee and Traverse City along Lake Michigan, Green Bay along Green Bay, and Sault Ste. Mackinac Island, which was once selected as one of the top ten most beautiful islands in the world. Room Details All hotel rooms are based on two Full / Double beds or one King/Queen bed depends on what rooms are availiable at the hotel on the day. The maximum occupancy per room is four travelers. One Room Selection If you are a party of more than four guests or desire to have separate rooms, please create separate bookings. Avoid traveling in a different bus? If you have more than one booking, please provide all confirmation numbers once your bookings are complete.

Chicago Milwaukee and Lakes 6 Day Tour

6 daysFree Cancellation

THE MERCEDES SPRINTER EXECUTIVE VIP VAN OFFERS SEATING FOR 13 PASSENGERS, WITH LUGGAGE CAPACITY FOR 5 CHECKED-IN BAGS AND 5 CARRY-ON ITEMS. Luxurious Fleet: Our fleet consists of top-of-the-line luxury vehicles, meticulously maintained to provide the utmost comfort and style during your journey. Whether you're traveling solo, with a group, or for a special occasion, we have the perfect vehicle to suit your needs. Professional Drivers: Our drivers are not only highly skilled behind the wheel but also epitomize professionalism and courtesy. They prioritize your safety and satisfaction, ensuring a smooth and enjoyable ride from pick-up to drop-off.

Mercedes VIP Van O'Hare/Midway Airport (Curbside)Chicago 1-Way

Mercedes VIP Van O'Hare/Midway Airport (Curbside)Chicago 1-Way

1 hour to 1 hour 30 minutesFree Cancellation

Our tours have varying difficulty levels to accommodate different skill levels. We take every safety precaution available to prioritize your well-being. Our routes that take you to must-see attractions and beautiful destinations. The Bahāʾī temple that we will pass is listed on the National Register of Historic Places and the only Bahāʾī place of worship in North America. This weekend vacation to Milwaukee is a vibrant mix of urban excitement and nature. Notable spots that riders can visit are the Milwaukee Art Museum, the National Bobblehead Hall of Fame Museum, and the Black Holocaust Museum. The city is also home to over 40 breweries, with iconic names like Schlitz and Pabst leading the way. On the ride you'll traverse mostly flat terrain that shifts between suburban areas and secluded bike paths. Expect southward winds along the lake, be prepared to experience some headwinds during your ride. Roads: 79% paved, 21% trails Distance: 74.6 miles Elevation: +963 ft/ - 1,058 ft

Unforgettable Small Group Biking Tours from Chicago to Milwaukee

1 day 10 hoursFree Cancellation

$349$332

One of the “original six”, dating way back to 1926, the Chicago Blackhawks are the epitomise NHL history. For an experience filled with tradition and history, look no further than attending a Blackhawks game at the iconic United Center. The Blackhawks are going through somewhat of a transition phase, led by superstar youngster Connor Beard, winner of the 2024 Calder Memorial trophy for the best NHL rookie. The team are looking to return to previous heights that have seen the franchise win 6 Stanley Cup titles. With a capacity of over 23,000, the United Center is designed for maximum fan engagement, featuring excellent sightlines and modern amenities. The giant LED scoreboard ensures that you won't miss a moment of the action, while the state-of-the-art sound system amplifies the crowd's excitement, making every goal feel monumental! Don't miss out on this opportunity of a lifetime to experience the NHL live in a venue that has become synonymous with Chicago’s vibrant sports culture!

Chicago Blackhawks Ice Hockey Game at United Center

Chicago Blackhawks Ice Hockey Game at United Center

Discover the unique journey of Pope Leo XIV through Chicago on this interactive bus tour. Visit his childhood home and childhood church in the suburb of Dolton on this one of a kind experience. This tour not only showcases the Pope's life but also intertwines the vibrant culture of Chicago, making it a must for both visitors and locals. Enjoy exclusive insights from knowledgeable guides while engaging with the city's rich history and faith. - Guided bus tour through Chicago’s historical sites related to Pope Leo XIV - Pickup at Holy Name Cathedral in the heart of the city

Chicago Pope Leo XIV's Roots Tour

2 hours 30 minutesFree Cancellation

$79$75

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

Discover Chicago’s infamous gangster past on a private, fully personalized tour through the city’s historic Prohibition-era streets. Travel in comfort with your English-speaking driver, who shares captivating stories about Al Capone, rival gangs, speakeasies, and legendary crime events of the 1920s and 1930s. Begin at Biograph Theater, where John Dillinger was shot, then visit the St. Valentine’s Day Massacre site, a pivotal moment in Al Capone’s rise. Explore Holy Name Cathedral, the Cook County Criminal Court Building, and Harry Caray’s Italian Steakhouse, all linked to Chicago’s mob history. Conclude in the Chicago Loop, uncovering hidden speakeasies and secret nightlife spots from the Prohibition era. With a flexible, door-to-door itinerary, this private tour offers an immersive, thrilling look into the city’s dramatic gangster history.

Chicago Gangsters and Prohibition Private History Tour

Chicago Gangsters and Prohibition Private History Tour

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

Step into the vibrant, resilient heart of Chicago's South Side. On this immersive journey through Bronzeville, you will uncover the epic story of the Great Migration—a time when millions of African Americans fled the Jim Crow South to build a self-sustaining 'Black Metropolis'. From the birthplace of gospel music to the headquarters of a newspaper that changed the nation, discover the triumphs of entrepreneurship, the brilliance of cultural innovation, and the unyielding spirit of a community that shaped modern America. A 3.9 km self-guided tour with 7 stops over 121 min Ideal for travelers interested in Identity, Migration & Globalization and History & Memory Immersively told in a podcast style by experts and locals Matching audio content, AI guide and navigation through the app

Podcast Tour Chicago The Promised Land and the Black Metropolis

2 hours 1 minuteFree Cancellation

$7$7

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.

Yucatan Delights by a Michelin Star-Trained Chef in Chicago

Private Transfer from O’Hare Airport to Downtown Chicago

1 hour 15 minutesFree Cancellation

Here's what you can expect during your 1.5-hour private room experience: Shooting/Spinning Art Experience: Collaborate with your group to create a masterpiece on a large canvas (24x36 inches) using our unique Shooting/Spinning technique. Each team of seven people will work together to shoot down balloons filled with paint, then watch as we spin your canvas to create mesmerizing abstract art. Art Room Experience: Indulge your inner artist as you each create your own masterpiece on a personal canvas (16x20 inches). Choose your colors, unleash your creativity, and bring your vision to life in our inviting art room. Paint: High-quality acrylic paints provided for all your artistic endeavors. Premium Clothes Protection: Keep your party attire clean and stylish with our premium clothes protection, ensuring a worry-free painting experience. Book your party at Shot of Art today and prepare for an unforgettable experience!

Art Boom 3 in 1 : Adults-Only Private Art Experience in Chicago

1 hour 30 minutesFree Cancellation

Explore Chicago's cinematic history through a thrilling scavenger hunt that takes you to 12 iconic movie locations across the Loop and River North. Participants will engage with the city’s vibrant architecture and learn about its role in popular films, from classic comedies to dramatic stories. The hunt encourages teamwork as you answer questions, upload photos, and guess locations to earn points. Helpful hints in the form of movie clips and photographs will guide you along the way. Unleash your inner film buff and discover the magic of Chicago’s film scene while enjoying a fun-filled adventure with friends or family.

Chicago Movie Landmarks Scavenger Hunt

Chicago River 90-Minute Architecture Tour

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Must-Dos in Chicago

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What are people saying about Chicago

Courtney_P, Oct 2026

Great Tour!!!

Loved this Chicago River Architecture Boat tour! I live in Chicago and took friends who were visiting from out of state on this tour. We all really enjoyed hearing about Chicago history, the buildings, and architecture, and we learned a lot. Our tour guide was great - easy to understand, knowledgeable, and entertaining. Highly recommend!

Chicago Architecture Center River Cruise aboard First Lady

shaykele_h, Oct 2026

I Hope You Get Edie!

If you like history, then this the excursion for you! Edie, our docent, did a phenomenal job giving us a timeline of not only the architectural movement of Chicago, but of the Chicago River and Lake Michigan! A more beautiful day in Chicago couldn’t have been ordered!

Chicago Architecture River Cruise

Nelly_B, Oct 2026

Great experience

My dad and I were visiting Chicago for the first time and we loved this tour! You could tell our tour guide Jack was super passionate about the city and we really appreciated his knowledge! We would highly recommend this tour to anyone visiting chocago

Chicago River 45-Minute Architecture Tour from Magnificent Mile

Divine_R, Oct 2026

Best Tourist Activity I’ve Ever Done

Really well done, genuinely captures that energy and culture of the city. Hits on way more than just the generic architecture and tourist aspects of Chicago which made the experience the best tourist activity I’ve ever participated in. Still at awe in how they made us feel like we were flying over Chicago

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 Favorites Ultimate Food and Walking Tour

Eunice_T, Sept 2026

Great Tour with a fantastic tour guide

Our tour guide, Casandra, was great. She shared some great information about the history of Chicago and provided answers to other questions that we inquired about. The food stops were great. I enjoyed the pizza, hotdog, popcorn, beef sandwich, and brownie. We were definitely full by the time our tour ended. Thanks for a great experience.

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 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