Osito Logo
Your EventsSign In

Chicago Group Travel

Discover best locations, activities and hotels in Chicago. Enjoy convenient group booking for a fun and memorable holiday!

The easiest way to plan your Chicago group travel

Explore Activities
Browse and find the most popular spots to go, things to do, and places to stay.
Get Smart Proposals
Osito finds and compares the best venues for your group travel, saving you hours of back and forth for free, no markups.
Save & earn rewards!
Osito negotiates the best rates and books directly with venues. Plus you earn rewards!
Chicago is calling!
Here are the favourite destinations for groups
Popular Destinations
Millennium Park
Navy Pier
Art Institute of Chicago
Chicago Riverwalk
Wrigley Field
Lincoln Park Zoo
Millennium Park
Millennium Park is a stunning urban oasis nestled in the heart of Chicago. With its iconic Cloud Gate sculpture, lush gardens, outdoor art installations, and serene Lurie Garden, this park offers a perfect backdrop for group gatherings and leisurely strolls. Enjoy live music at the Jay Pritzker Pavilion or have a picnic on the Great Lawn with your friends and family, creating unforgettable memories in this picturesque setting.
Millennium Park
Navy Pier
Navy Pier is a vibrant waterfront destination that offers a plethora of entertainment options for group travelers. From the iconic Ferris wheel and the Chicago Shakespeare Theater to the diverse dining and shopping options, there is something for everyone to enjoy. Take a leisurely boat cruise on Lake Michigan, catch a fireworks show, or simply soak in the stunning views of the city skyline with your group, making Navy Pier a must-visit attraction in Chicago.
Navy Pier
Art Institute of Chicago
The Art Institute of Chicago is a cultural treasure trove that beckons art enthusiasts and history buffs alike. Wander through its halls lined with masterpieces by renowned artists like Monet, Picasso, and O'Keeffe, and immerse yourself in the world of creativity and beauty. With guided tours and interactive exhibits available, exploring the museum with your group promises a enriching and inspiring experience that fosters conversations and shared appreciation for art and culture.
Art Institute of Chicago
Chicago Riverwalk
The Chicago Riverwalk is a scenic promenade that runs along the Chicago River, offering breathtaking views of the city's architecture and waterfront charm. Stroll along the walkway lined with cafes, bars, and public art installations, and soak in the vibrant atmosphere of this revitalized urban space. Whether you opt for a leisurely boat tour, a kayaking adventure, or simply a relaxing afternoon by the water, the Riverwalk provides a picturesque setting for group outings and bonding moments.
Chicago Riverwalk
Wrigley Field
Wrigley Field is an iconic sports venue that exudes history, charm, and the spirit of Chicago's beloved Cubs. Gather your group of sports enthusiasts and experience the thrill of a live baseball game at this legendary stadium, cheering alongside fellow fans and savoring the electric atmosphere. Indulge in classic ballpark snacks, soak in the nostalgia of the ivy-covered walls, and create lasting memories of camaraderie and team spirit at Wrigley Field.
Wrigley Field
Lincoln Park Zoo
Lincoln Park Zoo is a delightful escape into nature located within the bustling city of Chicago. Home to a diverse array of animals from around the world, this free zoo offers a unique opportunity for group travelers to connect with wildlife and enjoy a day of exploration and discovery. Wander through the lush gardens, attend animal feedings and talks, and marvel at the beauty of nature with your group, creating a fun and educational experience for all ages.
Lincoln Park Zoo
Discover Chicago: Top things to do
Great ideas and activities for your group
Private architectural boat tour on the Chicago River
Group dining at the iconic deep-dish pizza place
Visit to the Art Institute of Chicago for a guided tour
Evening at a comedy show at The Second City
Day trip to Millennium Park for group activities
Exploration of Navy Pier, including rides and entertainment
Chicago: A suggested 4-day itinerary
Here's a sample schedule for a 4 day group travel in Chicago
Day 1
Check-in at hotel, group lunch at local eatery
Visit to the Art Institute of Chicago for a guided tour
Dinner at Lou Malnati's Pizzeria
Day 2
Morning work session in hotel meeting room
Private architectural boat tour on the Chicago River
Evening at a comedy show at The Second City
Day 3
Day trip to Millennium Park for group activities
Exploration of Navy Pier, including rides and entertainment
Group dinner at a renowned local restaurant
Day 4
Check-out and departure