All Chicago Tours &amp; Excursions in 2026

A Spectacular Scavenger Hunts Chicago Adventure

1 hour 30 minutesFree Cancellation

USD 15USD 14

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

USD 15USD 14

Dive into Chicago’s Magnificent Mile on an interactive scavenger hunt, perfect for families, friends, or team building! Guided by clues on your phone, you’ll solve puzzles, unlock local legends, and discover iconic sites like the Old Water Tower, Tribune Tower, and bustling Riverwalk—plus hidden gems along the way. Go at your own pace, compete for fun, and see the best of Chicago’s lively downtown in a whole new way. Teams of up to six welcome; no local knowledge required—just curiosity and comfy shoes.

Magnificent Mile Scavenger Hunt: Chicago Walking Tour and Game

Magnificent Mile Scavenger Hunt: Chicago Walking Tour and Game

Chicago O’Hare International Airport is a major hub for travel around the world and services more than 30 million people per year, meaning it’s one of the busiest airports. With so many people, the lines for taxis or other modes of transportation can be overwhelming. Prebook this O'Hare Airport ORD to Chicago Arrival Private Transfer Service and ride smoothly from the airport to your hotel.

Special Offer

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

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

30 minutesFree Cancellation

Uncover the chilling history of Chicago's gangsters and ghosts on this thrilling late-night Halloween walking tour. Delve into the dark secrets of the South Loop, once a vice district, as your historian guide shares captivating tales of Al Capone and the city’s infamous past. Explore haunted locations like the Palmer House and the Chicago Theatre, and hear eerie stories of spirits that linger in Death Alley and along the Chicago Riverwalk. This tour culminates at the Congress Hotel, renowned for its ghostly sightings, making it the perfect way to experience Chicago's haunted history at midnight. - Late-night Halloween walking tour through Chicago's South Loop, ending at midnight. - Hear true stories about notorious gangsters like Al Capone - Visit haunted spots including the Chicago Theatre and Palmer House - End your tour at the Congress Hotel, one of Illinois' most haunted locations

Special Offer

Chicago Gangsters and Ghosts Late Night Halloween Special

Chicago Gangsters and Ghosts Late Night Halloween Special

Walk beneath Chicago’s soaring skyline, hear its hidden stories, then see it shimmer from the water on a lake cruise. From the iconic Bean to the legendary theatre district, this tour brings the city’s spirit to life—one step and wave at a time. Highlights: • Discover downtown Chicago on foot with a 5-Star Private Guide leading the way • Cruise Lake Michigan with included tickets and audio commentary onboard • See breathtaking skyline views and snap iconic photos from the water • Learn the city’s best-kept secrets through fascinating stories and history • Get tailored recommendations on top spots to eat, visit, and explore next Did you know there’s a sculpture in Chicago that reflects the whole skyline? With Rosotravel’s private tour, you'll walk through the city’s most iconic spots, then see it all again from the water on a relaxing lake cruise. It's a fun, personal way to experience the best of Chicago in just a few hours.Reserve your spot ow!

Chicago Downtown Walking Tour & Lake Michigan Cruise Tickets

3 hoursFree Cancellation

USD 263USD 250

This 45-minute self-guided walking tour explores the bizarre history beneath Wicker Park’s elegant surface. Led by a longtime resident, you will discover the neighborhood’s transition from a wealthy enclave to a gritty artist hub and its modern gentrification. Key Highlights: * Radical History: Learn about labor leader Lucy Parsons and the search for hidden bombs in the park. * Beer Baron Row: Hear tragic tales of murder and madness tied to grand Victorian mansions. * Quack Medicine: Discover how Theophilus Noel’s "Vita-Ore" empire funded iconic local architecture. * Mob Intrigue: Visit the former Russian Baths where mobsters met in steam rooms to avoid FBI wires. * Massacre Connections: See where the St. Valentine’s Day Massacre was planned and its getaway car destroyed.

Bizarre Wicker Park: Medicine and Mobsters Self-Guided Audio Tour

Bizarre Wicker Park: Medicine and Mobsters Self-Guided Audio Tour

45 minutes to 1 hour 15 minutesFree Cancellation

USD 10USD 9

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

Learn from a local as you discover Chicago’s top spots for food, drinks, architecture, and culture. On this tour, you'll explore downtown uncovering their history, iconic landmarks, hidden gems, and must-see photo opportunities. From legendary deep-dish pizza and historic jazz venues to world-famous architecture and vibrant local districts, the local guides provide personalized recommendations for every type of traveler. No need to spend hours planning your trip—this tour is designed to give you the insights, stories, and local knowledge needed to make your Chicago experience unforgettable. * Learn about the essentials of Chicago * Get tailored recommendations from local guides * Take amazing photos at iconic and hidden-gem locations * Get familiar with the city's history, culture, and neighborhoods

Welcome to Chicago: The Essential City Tour with photo stops

1 hour 30 minutesFree Cancellation

Explore Chicago’s historic Loop through the prism of its architecture. This three-hour trek will cover defining moments from 350 years of Chicago’s history, including the first Europeans to come through here, the Great Chicago Fire, the origin of the skyscraper, the 1893 World’s Fair, Prohibition and the creation of Millennium Park. Along the way, you’ll discover some of the Loop’s most beautiful interiors, found in buildings that thousands of people walk past every day, completely unaware of what’s inside…And how things created inside those buildings shaped our current world for the better. You’ll hear the stories of the men and women--including Jean Baptiste Point du Sable, Daniel Burnham, Potter and Bertha Palmer, and Muddy Waters--who made Chicago what it is today, and those, like Jeanne Gang, who are defining Chicago’s architectural future.

Chicago Architecture, History and Culture Loop Walking Tour

3 hoursFree Cancellation

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

2 hours to 2 hours 30 minutesFree Cancellation

SHOOTING&SPINNING IS ALLOWED FROM 18 YEARS OF AGE. In case it is a group, everyone must be 18+ What sets our Date Night Art Experience apart is the perfect blend of excitement, creativity, and connection in a vibrant, interactive setting. You won’t just paint—you’ll shoot paint-filled bombs with a BB gun, spin your canvases to create mesmerizing fluid art patterns, and splash paint freely in a dedicated studio space where messy fun is encouraged. Plus, you can customize playful "hugs" T-shirts as part of the experience. This exclusive combination of dynamic art techniques and uninhibited expression makes the experience energetic, memorable, and deeply engaging. Whether it’s your first date, anniversary, or a special night out, you’ll leave with unique, colorful masterpieces—and unforgettable memories shared in a lively, joyful atmosphere. Book now to turn your date into a creative celebration that’s truly one of a kind!

Romantic Chicago Date Night: A Creative Art Experience

Romantic Chicago Date Night: A Creative Art Experience

1 hour 50 minutesFree Cancellation

USD 449USD 427

Get ready to unleash your creativity at the BYOB Candle-Making Class at Chicago Candle Co. This hands-on workshop invites you to craft stunning, personalized candles from upcycled wine bottles, all while enjoying your favorite drinks. Under the guidance of friendly instructors, you’ll learn the art of glass cutting and soy wax pouring, choosing from a variety of cocktail-inspired scents. Bond with friends or make new ones in a welcoming atmosphere as you create unique pieces that reflect your individual style and eco-friendly values. Perfect for a fun night out or a memorable group activity in the heart of Chicago.

DIY Cocktail Candle and Wine Bottle Cutting Class in Chicago

DIY Cocktail Candle and Wine Bottle Cutting Class in Chicago

Arriving at your destination is effortless with Deenil Experiences’ airport transfer service. Enjoy a smooth ride in a clean, luxurious vehicle, where comfort meets safety. Your professional chauffeur will greet you with a friendly smile, assist with your luggage at the curbside, and provide all necessary details for a stress-free journey. With real-time arrival updates and a complimentary 15-minute grace period, you can relax knowing your travel needs are prioritized. Perfect for families, business travelers, or anyone seeking a reliable transfer experience.

Seamless Chicago Airport Transfers with Deenil Experiences

35 minutes to 1 hourFree Cancellation

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

USD 45USD 43

This tour offers a refreshing blend of Chicago’s iconic sights and hidden suburban gems, giving travelers a unique perspective on the city's diverse culture, history, and architecture. Start by marveling at Chicago’s world-renowned skyline, exploring its legendary landmarks, and soaking in the vibrant energy of the city. Then, step beyond the usual tourist path to uncover the hidden treasures nestled in the suburbs. Discover the BAPS Shri Swaminarayan Mandir, an architectural masterpiece showcasing intricate carvings and spiritual serenity; visit the quirky Leaning Tower of Niles, a charming replica of Italy’s famous landmark; experience the awe-inspiring Bahá’í House of Worship, known for its breathtaking design and peaceful ambiance; and stroll through Westfield Old Orchard, a stylish open-air shopping destination offering a blend of modern luxury and relaxed charm. This thoughtfully curated journey bridges the gap between city excitement and suburban surprises. Ready to explore?

Chicago City's Iconic Sights and Suburb Gems Tour

Chicago City's Iconic Sights and Suburb Gems Tour

5 to 10 hoursFree Cancellation

USD 299USD 284

The Bloomingdale Trail was built on a former railway line that once served as the industrial backbone of Chicago's north side. On this self-guided audio tour through Bucktown and Wicker Park, you'll hear how the factories, immigrants, and artists who lined these tracks transformed two scrappy neighbourhoods into some of the city's most sought-after real estate. The tour starts at Walsh Park, the eastern terminus of The 606, named with a nod to Chicago's universal zip code prefix. Further along, you'll stop at the Damen Avenue Arts Plaza, where the Flat Iron Arts Building stands as a reminder of how artists were deliberately recruited to revive a struggling neighbourhood. The tour ends at Western Avenue, the longest continuous city street in the world at 24.5 miles, where the trail continues west into Logan Square and Humboldt Park.

Bucktown and Wicker Park’s 606 Trail: A Walking Tour

Bucktown and Wicker Park’s 606 Trail: A Walking Tour

30 minutes to 1 hourFree Cancellation

Experience the joy of the holiday season aboard the Santa Claus Sleigh Ride Cruises on the Chicago River. This 75-minute ride offers a unique opportunity to enjoy Chicago's stunning winter skyline while creating cherished memories with the family. From November 14 to December 20, join us every Saturday and Sunday for festive fun, including a special visit from Santa himself. Dress warmly, as rides are weather permitting, and come prepared for a delightful outing that supports veterans in need through Shepherd's House. - 75-minute scenic cruise along the Chicago River - Family-friendly experience with a visit from Santa Claus - Available Saturdays and Sundays from November 14 to December 20 - Drinks and snacks available for purchase on board

USD 5USD 5

Special Offer

Santa Claus Sleigh Ride Cruises on the Chicago River

1 hourFree Cancellation

Private Transfer in Chicago (ORD/MDW)

30 minutes to 1 hourFree Cancellation

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

Put on your apron and get ready to turn simple ingredients into seriously satisfying pasta. You’ll begin by preparing fresh pasta dough from scratch, then learn the hands-on techniques for kneading, rolling and shaping it into pasta. Next comes the good stuff: a creamy pumpkin-sage sauce made with pumpkin purée, cream, Parmesan, sage, butter, garlic, nutmeg and black pepper. You’ll learn how to build the sauce, season it and bring it together with your freshly made pasta for a warm, comforting final dish. No fancy pasta skills are required, just a willingness to get your hands a little floury. It’s relaxed, social and deliciously practical, with plenty of satisfaction when you finally sit down to enjoy what you made.

Make Fresh Pasta With a Local Chef in Chicago

USD 75USD 71

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

USD 1,387USD 1,318

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]

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

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Must-Dos in Chicago

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What are people saying about Chicago

Chicago Sightseeing River and Lake Cruise

Donna_H, Oct 2026

These people are doing it right!

I've been on many water excursions in different cities, and one of the things I most appreciated about this experience was the amount of staff available at the very onset.... while you're walking around the very busy streets of Chicago, boats are everywhere, people are everywhere, but your ticket is for one particular thing at a particular time, and you need to find it! Their employees were in easily recognizable clothing, and were extremely helpful and friendly. Having already walked 15,000 steps that day on a jacked knee, hunting endlessly for the right spot or going the wrong direction can really put a damper on the experience. Downright frustrating! Well, this did not happen here. I found the crew very hard-working and organized, they were truly dedicated to everyone having the best time possible. Worth every dime and I would recommend it!

Chicago By Night River and Lake Cruise

Melissa_F, Oct 2026

Great tour of the river and Lake

This cruise was fantastic. I have done just a river cruise before but this was better. I loved hearing about the architecture in the river areas but also going out onto the lake was fabulous. You get to transverse through the lock that takes you out into Lake Michigan and learn about the the skyline from the East and West sections of the lake. Our tour guide was fabulous, informative and funny.

Chicago Favorites Ultimate Food and Walking Tour

Jessica_S, Oct 2026

Biggest Bang for Your Buck

A great way to pack a day’s worth of food and history into a few hours. Food? Delicious! Tour? Awesome! Guide? Epic! Cassandra (Caddie) brought the history of Chicago’s food, architecture, and art to life with her energetic and entertaining delivery. She was friendly and funny, making the hours fly by. As a solo traveler I was made to feel part of the group which was so comforting. I also can’t wait to take a bike ride around the river and lake with the included bike rental! This tour really packs in so much bang for your buck! 20/10 Highly Recommend!

Chicago River 90 Minute Architecture Tour

Kevin_M, Oct 2026

Highly recommended boat tour.

The tour guide was engaging and had a really good sense of humour. His knowledge of “his” city was in depth and he told the stories with enthusiasm educating the people onboard. The bar was easily accessible and the prices were reasonable. Saw some interesting buildings and changes in architecture throughout.

Chicago Architecture Center River Cruise aboard First Lady

Mary_M, Oct 2026

Absolutely lived up to the hype!

An exceptional tour from start to finish. We took the 11:00 AM slot and had perfect weather, which made for stunning photos of the skyline. The CAC docent was fantastic, delivering a masterclass in Chicago history and architecture without it ever feeling dry. The boat was spacious, clean, and very well-run. Booking through Viator was seamless. Don't look at any other boat tours—this is the official one you want to choose.

Chicago River 45-Minute Architecture Tour from Magnificent Mile

Jeanine_O, Oct 2026

Fabulous way to spend an evening!

The night cruise along Chicago River was awesome. Kay, our tour guide was knowledgeable and funny and made the 45 minutes fly by! What was a happy surprise was that ALL passengers had a seat up top. Looked like so many, but they did it right. I would do it again during the day as well to see the contrast. Great value for your your dollar!

Chicago Architecture River Cruise

Dwella_G, Oct 2026

A must do experience in Chicago.

When planning your Chicago itinerary, put this tour at the top of your list. The Chicago Architecture River Cruise was a must-see experience. The weather was great. Our tour guide was very knowledgeable about the city and its buildings, which made the experience enjoyable. It’s nice for all ages. Make sure you dress warmly.

Chicago River 90-Minute Architecture Boat Tour

Chris_S, Oct 2026

David is the best in the city!

This was an excellent tour. The the ride was comfortable, though. I would’ve liked something a little bit better than folding chairs, but everybody had space it was a very stable comfortable ride. David was absolutely fantastic. I cannot say enough good things about him as the tour guide. His knowledge was excellent. His timing was fantastic. He was personable. He was funny. If I come back, I’ll probably go see him again even though it will be a repeat experience because he was just that enjoyable highly recommend 10/10

Chicago Lake and River Architecture Tour

Gregory_L, Oct 2026

Great experience on the river

This is the second time we have experienced the architectural river tour. Learned new stuff and the crew aboard the boat was friendly and accommodating as they were the last time. This is definitely an interesting and economical experience for anyone who lives here and wants to learn more of Chicago’s history or someone from out of town that just wants a nice afternoon. !