Chicago Small Group Tours

Artisan Italian Pasta Class in Chicago (Includes 4-Course Meal)

Step into a welcoming kitchen in Chicago for an immersive Italian cooking class hosted through Cozymeal. Limited to 8 guests, this interactive workshop introduc

From $162.00 USD

Bird Tours across Chicago

With over 10 years of birding, Wayne can not only identify birds out in the wild through sight, but also through their many calls! Interested in starting out wi

Candle Making Experience Near Museums & Millennium Park

Step into our vibrant candle-making studio and unleash your creativity! Craft candles with friends and family, blending custom scents in a welcoming space. Take

★ 5.0 (8)

From $75.00 USD

Chicago and All MidWest Self Guided AI Audio Tours for 7 Days

With this AI app, you're no longer restricted to crowded group tours or rigid scripts. Explore iconic Chicago sites like Millennium Park and the Magnificent Mil

★ 5.0 (2)

From $11.75 USD

Chicago BYOT Screen Printing Workshop: Make Your Own Art Tee

Remade in Chicago is the upcycling studio where surplus textiles are transformed into one-of-a-kind wearable art, braided rugs, and hand-stitched quilts. We h

★ 5.0 (5)

Chicago City Tour: Elevated Architecture Tour with Train Ticket Included

Explore Chicago’s amazing architecture from the unique perspective of elevated trains and station platforms. Learn the history behind the famous "L" system and

★ 4.8 (101)

Chicago City Tours See It All No Time Wasted

Skip the corny jokes and never-ending speeches — our shared tours are built for travelers who want the real Chicago, not a stand-up routine. ✔️ Over 20 iconic

★ 3.8 (21)

From $150.00 USD

Chicago City's Iconic Sights and Suburb Gems Tour

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, hi

From $299.00 USD

Chicago Early Skyscraper Walking Tour in the Loop

Step into the birthplace of the modern skyscraper on this immersive walking tour through Chicago’s historic Loop. Discover the stories, innovations, and hidden

From $39.00 USD

Chicago Fire TV Show Set Tour

Get an exclusive behind-the-scenes look at the hit NBC drama Chicago Fire TV Show Set Tour. Visit the actual filming locations where the show comes to life. T

★ 4.9 (80)

Chicago Food Tour: 6 Dishes with Deep Dish Pizza & Beef Sandwich

On our Secret Food Tour: Chicago, you'll enjoy a variety of foods with culinary influences from the people who built this city. You'll experience all the city'

★ 4.9 (1011)

From $84.99 USD

Chicago Foods Tour with The Loop, Skyline, Millennium Park

Delve into Chicago’s one-of-a-kind cuisine and learn something that you would never expect on this small-group Secret Food Tour. Eat your way through the most p

★ 4.6 (5)

From $145.00 USD

Chicago Gangsters and Ghosts Minibus Tour

Uncover the notorious history of Chicago's gangster era on this immersive bus tour that takes you through the city's most infamous landmarks. Visit the Palmer H

From $65.00 USD

Chicago Haunts and Hooligans Tour

Nightly Spirits’ Haunts and Hooligans Tour will illustrate Chicago’s haunted history of secret parlors, underground tunnels, murderous movie theaters and supern

★ 5.0 (41)

From $34.77 USD

Chicago Helicopter Tour: City to Shoreline

Your journey begins with a southeast departure from the Vertiport, offering early views of the city’s iconic skyline. Flying east, you’ll head toward the lakefr

★ 4.5 (25)

From $349.99 USD

Chicago Helicopter Tour: Loop Tour

Take to the skies and experience Chicago from an entirely new perspective on this extended helicopter tour showcasing the city’s most iconic landmarks, neighbor

★ 4.5 (12)

From $209.99 USD

Chicago Highlights Running Tour

Join us for the most memorable experience you will have while visiting Chicago! For runners from around the world, this is definitely a “bucket list” activity.

From $44.00 USD

Chicago in a Day Walking Tour: Food, History & Architecture

Immerse yourself in Chicago's rich history and vibrant culinary scene on this captivating walking tour. Discover the city's iconic architecture and Prohibition-

★ 4.9 (1377)

From $100.95 USD

Chicago Insider Segway Tour

This is a tour like no other! Our newest Segway adventure is completely unique and will cover the good, the bad, the ugly and the totally weird stories of Chica

★ 4.9 (52)

From $64.80 USD

Chicago Landmarks and Museum Campus Small Group Segway Tour

Looking for fun things to do in Chicago? Explore the city with one of your professional guides on a scenic 6-7 mile tour. Begin your adventure by gliding throug

★ 5.0 (239)

From $70.00 USD

Chicago Local Fashion Designers Shopping Tour with a Stylist

Discover the local shopping scene and its fashion DNA with a professional stylist as you embark on a personalized shopping circuit built to meet your style and

From $150.89 USD

Chicago Loop Food Tour: Taste the Most Iconic Local Eats

Join a local guide for the ultimate foodie adventure in Chicago’s historic Loop, tasting classics like deep‑dish pizza and Chicago‑style hot dogs while discover

★ 4.8 (131)

From $86.68 USD

Chicago Loop Walking Tour

The Loop is the heartbeat of downtown Chicago! It is filled with great architecture, drop-dead gorgeous interiors and fantastic works of art from famous artists

★ 4.9 (57)

Chicago Movie Locations Tour

Discover iconic Chicago movie locations with a private tour, including transportation and hotel pickup and drop-off. Visit the Home Alone house exterior, Wrigle

★ 5.0 (11)

Chicago P.D. TV Show Set Tour

Get an exclusive behind-the-scenes look at the hit NBC drama Chicago P.D. TV Show Set Tour. Visit the actual filming locations where the show comes to life. T

★ 5.0 (33)

Chicago Perfume Making Classes on Magnificent Mile

Step into the world of perfumery and unleash your creativity in a guided workshop! Explore a treasure trove of fragrance notes, from vibrant florals to exotic s

★ 4.9 (90)

From $85.00 USD

Chicago Photo Capture Your Adventure Walking Tour

Discover Chicago's iconic sights on this guided walking tour that highlights five scenic photo spots. With a local guide, enjoy stunning skyline views and learn

From $49.00 USD

Chicago Photo Walk to Bean and Landmarks

We’ll begin our photo walk in Millennium Park with portraits at Cloud Gate (The Bean), one of Chicago’s most iconic landmarks. During our time together, we’ll

★ 5.0 (32)

From $169.00 USD

Chicago Pier Fireworks Segway Tour

See Chicago's weekly summer fireworks display on this spectacular Chicago Segway Tour. You haven't seen Chicago until you have seen it at night while gliding th

★ 4.9 (35)

From $79.92 USD

Chicago River Yoga Walk Tour

This is truly an experience like none other. It is combination of a historical walking tour of the Chicago Riverwalk and Yoga. It is a very non-traditional Yoga

From $44.00 USD

Chicago Riverwalk Architecture Walking Tour

Explore Chicago's iconic skyline on this enlightening Riverwalk architectural tour. Experience the rich tapestry of history and innovation as "you get your step

From $49.00 USD

Chicago Scavenger Hunt Adventure

Turn Chicago into a giant game board with this fun scavenger hunt adventure! This challenge combines the excitement of the Amazing Race with a 3-hour city walki

★ 3.0 (2)

From $49.00 USD

Chicago Scenic Driving Tour

Chicago is a big city with a lot of activities & sightseeing. To tour the city quickly, it requires the help of a knowledgeable local driving guide and that's w

★ 5.0 (23)

Chicago Shoreline Adventure Boat Tour

This tour is the perfect way to experience the shoreline of Chicago in a new and exciting way! Our tour vessel is a former military Williard Marine, which prov

★ 5.0 (40)

From $90.00 USD

Chicago Skyline Snap Tour Helicopter Flight Over Chicago

Witness Chicago’s stunning skyline from above on this exhilarating helicopter tour. Departing from the Vertiport, the flight offers breathtaking views of the ci

★ 3.8 (19)

From $149.99 USD

Chicago Small Group City Tour

Experience Chicago like never before on your all-inclusive small group city tour, led by an expert guide. Discover iconic landmarks, hidden gems, and vibrant ne

From $465.00 USD

Chicago to Mackinac Island Scenic 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 thro

From $685.00 USD

Chicago to Milwaukee Day Trip with Brewery Tour & City Highlights

Escape Chicago for a day and experience Milwaukee’s culture, food, and legendary beer scene. This curated day trip includes highlights such as the Harley-Davids

★ 4.5 (12)

Chicago Tour South Side

The Blue-Collar side of Chicago many call it! This tour will show The Ford Factory, home of the steel mills, the blue-collar neighborhoods and many places on th

★ 4.5 (47)

Chicago Walking Tour: Art Deco Skyscrapers Loop

View Art Deco masterpieces built in the heart of Chicago’s financial district during the Roaring '20s. Learn how Art Deco reflected the era’s fun-loving optimis

★ 4.8 (193)

Chicago Walking Tour: Historic Skyscrapers

Chicago is home to some of the world’s earliest skyscrapers. Get an up-close look at these 19th Century marvels, learn about innovations used to build them and

★ 4.8 (72)

Chicago Walking Tour: The Magnificent Mile

Discover how a dirt road known as Pine Street transformed into a "Paris on the Prairie" and later into the Magnificent Mile, the city’s premier shopping distric

★ 4.9 (51)

Chicago Walking Tour: Tiffany Treasures

Learn about the life and work of Louis Comfort Tiffany as we visit some of Chicago’s most magnificent art-glass and mosaic installations, each designed and craf

★ 4.7 (47)

Chicago's Gold Coast Hidden History: A Self-Guided Audio Walk

Amy Bizzarri, author of 111 Places in Chicago That You Must Not Miss, takes you on a fascinating self-guided audio tour of hidden historical spots in Chicago's

★ 4.4 (8)

From $8.09 USD

Chicago's Original Gangster Tour by Bus

Our guides present an accurate account of the activities in Chicago during the 1920's and 1930's (Prohibition Era). You will hear about the exploits of Capone,

★ 4.6 (179)

From $48.00 USD

Chicago's West Side Foodie Ride Bike Tour

Take a detour off the beaten path, and explore the flavors of Chicago’s delicious West Side with Bobbys's Bike Hike & Food Tours, America's longest running city

★ 4.9 (114)

From $99.00 USD

Chicago-Milwaukee Small Group Tour

Discover the charm of Milwaukee on a small group day trip from Chicago! Enjoy a guided city tour, explore iconic landmarks, and experience the legendary Miller

From $485.00 USD

Chicago-Rosemont Indoor Skydiving with Two Flights

Feel the thrill of skydiving without jumping out of an airplane. It's true! Head to iFLY Chicago in Rosemont, a premier indoor skydiving facility powered by a s

★ 4.4 (34)

From $126.00 USD

Classic Chicago Food Lovers Tour in River North

Get a taste of Chicago on this small-group walking food tour and explore the specialties of River North neighborhood. Dive deeper into the culinary history of t

From $136.00 USD

DIY Cocktail Candle and Wine Bottle Cutting Class in Chicago

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 ca

Downtown Chicago Guided Walking Tour Semi-Private 12ppl Max

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.

★ 5.0 (5)

From $55.00 USD

Exclusive Sushi-Making Class in Chicago (Includes 3-Course Meal)

Discover the fundamentals of sushi-making in Chicago during this immersive class hosted through Cozymeal. Limited to 8 guests, the workshop showcases the precis

Express Chicago Photo Tour of Landmarks

Let’s take photos at one of Chicago’s most famous spots - the bright red CHICAGO sign at the Chicago Theatre! During this 30-40 minute photo walk, I’ll help you

From $99.00 USD

Frank Lloyd Wright Robie House Admission

The Frederick C. Robie House on the University of Chicago campus is considered one of the most important buildings in the history of American architecture. This

★ 4.2 (159)

From $27.00 USD

Golden Hour Motorized Paddleboard Tours w/ Mobile DJ

One of a kind experience you can only find in Chicago. Motorized paddle boards take the stress out of paddling. LED-lights make the boards illuminate the water

★ 5.0 (2)

From $105.00 USD

Great Lakes & Mackinac Island 4-Day Small Group Tour from Chicago

Take in three of the Great Lakes and a string of classic Midwest towns on this four-day small-group loop out of Chicago. Travel up the western shore of Lake Mic

★ 5.0 (2)

From $1,125.00 USD

Hanfu Chinese Traditional Costume Try on

Discover the elegance and beauty of Hanfu, the traditional  clothing of ancient China, in this one-of-a-kind cultural experience here at our Chinatown Visitor C

From $20.00 USD

Haunted Chicago Booze and Boos Ghost Walking Tour

Join this Chicago haunted pub tour which is a combination ghost tour and pub crawl that will take you on a walking tour to explore the fascinating history of Ch

★ 4.9 (330)

From $35.87 USD

Haunted Ghosts & The Chicago Outfit Segway Tour

Looking for a unique Chicago tour? Glide into the city’s dark past with our unique Segway tour, where ghosts, gangsters, and true crime come to life. Cruise to

★ 4.7 (38)

From $75.48 USD

Historic Homes and Cottages of Wicker Park Walking Tour

Much of the historical information shared on this tour is unknown to most attendees. This tour also shows everything from the gritty to the pretty, from the mun

★ 5.0 (51)

From $45.00 USD

History and Architecture of Chicago Loop Walking Tour

Discover the amazing history and architecture of Chicago with expert tour guide Dave Lineal. Walking among gigantic towers of downtown, we will learn why and ho

★ 5.0 (24)

From $33.00 USD

History of the Jazz Age at Chicago Art Deco Architecture Tour

Dive into the center of the architectural boom of the roaring 1920s and take a chance to enjoy the grand facades of the Art Deco skyscrapers on this guided walk

From $67.00 USD

Inside Tour of Chicago’s Fine Arts Building

Take a time travel journey inside Chicago's best-kept secret: a 125-year-old architectural marvel. This extraordinary building was envisioned by renowned archit

★ 4.9 (28)

From $45.00 USD

Italian Ravioli Cooking Class in Chicago (Includes 4-Course Meal)

Get to grips with Italian pasta in this Florentine-inspired hands-on class in Chicago, hosted through Cozymeal, which connects you with top-rated local chefs. C

From $145.00 USD

Lakefront Segway Tour in Chicago

Segways are amazingly fun, and Chicago's lakefront, parks, and skyline are absolutely gorgeous! Add our smart, entertaining tour guides to the mix, and you have

★ 4.6 (151)

From $70.00 USD

Learn To Make Mole The Real Mexican Way Before Lunch

With a deep knowledge of Mexican cuisine and a passion for cooking with authentic ingredients, Carla brings the art of Mole-making to your table. Each dish is c

From $185.72 USD

Mediterranean Cooking Class in Chicago (Includes 3-Course Meal)

Fresh, vibrant and built on ingredients you can find anywhere – this Mediterranean cooking class in Chicago, hosted through Cozymeal, which connects you with to

From $110.00 USD

One Day Galena and Dubuque Tour from Chicago

Explore the charming towns of Dubuque and Galena on this enriching day trip from Chicago. Begin your journey along the scenic Mississippi River in Dubuque, wher

★ 3.0 (2)

From $450.00 USD

Premium Chicago City Tour Small Group ICONIC Landmarks & Skyline

Discover the architectural soul of Chicago on a thoughtfully curated half-day city tour. Travel through the city’s most influential districts, from historic riv

★ 4.9 (31)

From $48.00 USD

Private Chicago Photography Class for Stunning City Shots

Chicago has architecture that stops you in your tracks, a lakefront that stretches to the horizon and neighborhoods full of color and character. With instructio

From $175.00 USD

Private Luxury 6-Pax SUV Limo Transfer from or to Chicagoland Airport and Suburb

Enjoy convenient private transportation between Midway or O'Hare International Airport and your hotel in the comfort of a private 4 door 6 Passenger Luxury SUV

★ 3.0 (2)

From $210.00 USD

River North Food Walking Tour

On our 3 hour food walking tour of Chicago, you will taste delectable foods from 5 different delicious places. Tease your tastebuds as you savor foods from Chic

★ 4.6 (96)

From $89.00 USD

Shameless TV Show Location Tour

Experience the ultimate Private Shameless TV Location Tour with the convenience of hotel pick and drop-off, allowing you to sit back, relax and enjoy the ride w

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

The Art Institute of Chicago attracts nearly as many visitors as other leading galleries like the Met, Louvre & British Museum. On this 2.5 hour semi-private (1

★ 5.0 (248)

From $90.10 USD

Skip-the-line: Art Institute of Chicago Guided Tour

Beat the crowds with an expert art historian guide on this exclusive early morning tour. Immerse yourself among the masterpieces housed within the acclaimed mus

★ 5.0 (629)

From $71.40 USD

Small Group Bike Tours From Chicago to Lake Geneva

The route to Lake Geneva follows the incredible coastline of Lake Michigan and eventually into the rolling green hills of Wisconsin. Your group will stop to see

From $449.00 USD

Small Group Tour of Chicago Neighborhoods: North and South Side

This unique tour of Chicago will allow for tourist to see most of Chicago’s 77 neighborhoods and city parks. There is no other tour that tours multiple neighbor

★ 4.5 (54)

Small-Group Sightseeing Boat Tour in Chicago

The ultimate custom sightseeing experience in Chicago! Enjoy the City from great vantage points and photograph the world-famous skyline. We zip you to many sigh

★ 5.0 (119)

From $89.00 USD

Spanish Paella Cooking Class in Chicago (Includes 3-Course Meal)

Tapas, paella and flan – this hands-on Spanish cooking class in Chicago, hosted through Cozymeal, which connects you with top-rated local chefs, takes you throu

From $110.00 USD

The Art Institute in Chicago Highlights Tour & Photoshoot

Discover the Art Institute in a unique way that blends art, storytelling, and photography. After a warm welcome, we'll head inside with tickets included & begin

★ 5.0 (5)

From $101.00 USD

The Escape Game Chicago: Epic 60-Minute Adventures in River North

Our Chicago location is right off of the famed Michigan Ave next to countless entertainment and dining options, perfect for pairing an escape room with dinner a

★ 5.0 (444)

From $47.95 USD

Unforgettable Small Group Biking Tours from Chicago to Milwaukee

Our tours have varying difficulty levels to accommodate different skill levels. We take every safety precaution available to prioritize your well-being. Our rou

From $349.00 USD

Walkin' with Colin: Chicago History-Mystery-Comedy-Tragedy Tour

Embark on a profound, downtown walk-around, to discover incredible stories and secrets of the city on this not to miss feet on the street experience! During our

★ 5.0 (245)

From $44.00 USD

Workers Cottages of Oldtown Triangle Walking Tour

This tour will show you many of these delightful cottages and the different styles they were designed and constructed in. You will also learn about their histor

★ 5.0 (57)

From $45.00 USD

Yucatan Delights by a Michelin Star-Trained Chef in Chicago

Each dish is crafted with the freshest ingredients and a focus on traditional cooking techniques, resulting in a dining experience that is both authentic and de