NOV 2023

Unveil Chicago's hidden gems: unique, fun-filled group experiences await.

Searching for the perfect group activities in Chicago for adults can sometimes feel like looking for a needle in a haystack.

You want something fun, engaging, and, most importantly, memorable for everyone involved. 

Whether you're planning a team-building event, a get-together with friends, or just looking to explore the Windy City in a unique way, the quest for the ideal outing can be daunting.

But you can stop worrying now! 

This blog post is your one-stop guide to Chicago's most exciting, diverse, and enjoyable group activities. 

From scenic bike rides along the lakefront to laughter-filled nights at comedy shows, we've scoured the city to bring you the 11 must-try experiences that are perfect for any group. 

Let's dive in and discover the adventures that await you in the heart of the Windy City!

Lakefront bike tour

Cyclist enjoying a bike tour on the Lakefront Trail with Chicago's skyline in view.

Pump those quads with your friends while enjoying breathtaking views of the Windy City!

The Lakefront Trail in Chicago isn't just a path; it's a journey through the heart of the city's scenic beauty. This 18-mile bike trail is your ticket to a day filled with laughter, legwork, and some of Chicago's best views.

With views ranging from the lush greenery of parks to the rhythmic waves of Lake Michigan, the trail is one of the top Chicago Loop tourist attractions

Expect to encounter lively beaches, serene bird sanctuaries, and iconic landmarks like Navy Pier and the Museum Campus. 

This tour is a perfect blend of urban exploration and natural beauty, making it an unforgettable group adventure.

Tips for an awesome bike ride along the Lakefront Trail

  • Start early: Beat the crowd and start your ride early in the morning to enjoy a more peaceful experience.

  • Rent a bike: No bike? No problem! There are plenty of bike rental options (like Bobby’s Bike Hike and Bike & Roll) along the trail.

  • Photo ops: Don't forget to stop at scenic spots for some memorable photos with Lake Michigan in the backdrop.

  • Hydrate and snack: Bring water and some snacks for energy, especially if you plan a full trail ride.

  • Weather check: As you know, Chicago weather can be fickle. Check the forecast and dress appropriately.

Website: Visit its webpage (on the Park District website)

Group outing to Fox in a Box escape room (that’s us!)

Friends collaborating in our (Fox in a Box's) The Bank escape room game in Chicago.

Discover if you have what it takes to crack our escape rooms with your crew!

At Fox in a Box, we're not just about escaping rooms but about creating unforgettable bonding experiences. 

Whether you're with friends, family, or coworkers, our experiences are tailored to test your teamwork, creativity, and problem-solving skills.

Choose from diverse game themes like The Bank, Zodiac, The Prison, and The Bunker.

Our escape experiences are perfect for team building, making memories, and enjoying a different kind of night out in Chicago.

Tips and tricks for the perfect group outing at Fox in a Box escape room

  • Theme selection: Make sure the game theme resonates with everyone in the group. 

  • Group size matters: Consider the optimal group size for each room. Not too many to overcrowd, not too few to underwhelm.

  • Timing is everything: Choose a time that works for everyone. Remember, our escape challenges typically last about an hour.

  • After-game plan: Plan something fun for after the escape. Grabbing a bite at a restaurant near us is a great way to round off the outing.

Website: Visit our home page

Location: Plan your route via Google Maps

Phone: (312) 878-7899

Second City comedy show

Comic performing a standup routine like you can expect at The Second City.

Laugh out loud with the world’s finest comics at The Second City!

At The Second City, every show is a unique experience. From uproarious improv performances to brilliantly crafted sketch comedy, there's something to tickle every funny bone.

With a legacy spanning over 60 years, this iconic venue has been the launching pad for some of the most notable names in comedy, including Tina Fey and Stephen Colbert.

The shows include improv featuring faculty and students, musical improvisations with a twist, and even special themed performances like "Shamilton.”

N.B. - Improv classes at The Second City are a great indoor team building option in Chicago.

Ways to make your Second City outing special and memorable

  • Choose your show: With a diverse lineup, select a show that suits your group.

  • Arrive early: Get there early for good seats and soak up the vibrant atmosphere.

  • Dinner plans: Consider dining at nearby restaurants before or after the show for a complete night out.

  • Laugh freely: Be open to the unexpected nature of improv and enjoy the spontaneous humor.

Website: Visit their website

Location: Plan your route via Google Maps

Phone: (312) 337-3992

Music night at the Jazz Showcase

Man skillfully playing a trumpet during a live jazz performance.

Immerse yourself in soulful melodies and sway into the night at the Jazz Showcase!

Nestled in the heart of Chicago's South Loop neighborhood, the Jazz Showcase isn't just about jazz; it's about experiencing a piece of musical history. 

Hosting the greatest names in jazz, from Dizzy Gillespie to Ira Sullivan, the Showcase has been a beacon for jazz enthusiasts for decades.

The club's intimate 170-seat setting ensures an up-close and personal encounter with the music - no wonder it’s a top favorite with Chicago tourists.

And with live performances seven nights a week, including their family-friendly 4 pm Sunday Matinee, there's always a rhythm waiting to match your schedule.

Tips for a swingin' night at the Jazz Showcase

  • Pick your performance: Check out their online calendar to choose a night that resonates with your jazz preferences.

  • Time it right: Shows typically run at 8 pm and 10 pm, with a special 4 pm Sunday Matinee. Plan accordingly for the full experience.

  • Budget for fun: Average drink costs are around $12, with both lot and metered street parking available for convenience.

  • Student and musician perks: Take advantage of discounts and special parking rates available on select nights.

Website: Visit their website

Location: Plan your route via Google Maps

Phone: (312) 360-0234

Chicago food tour

Freshly baked Chicago-style pizza in front of an oven.

Dive into the heart of Chicago's culinary scene with your friends and coworkers!

There's no better way to bond than over food, and a food tour of the Windy City offers just that - a mouthwatering journey through our culinary landscape. 

From deep-dish pizza & legendary Chicago-style hot dogs to local favorites like spicy Szechuan dishes from Chinatown & unique Nordic flavors from Andersonville's charming taverns, explore must-try Chicago dishes that define our cuisine and culture.

Tour historic neighborhoods, from the bustling streets of Pilsen, known for its authentic Mexican flavors, to the vibrant corners of Greektown, and into the heart of Andersonville on your culinary quest.

Savor these tips for a flavorful Chicago food tour

  • Diverse tastes: Be open to trying a range of flavors. Chicago’s culinary scene is a melting pot of cultures.

  • Pace yourself: With so many delicious stops, remember to pace your eating.

  • Dress Comfortably: Comfortable shoes are a must as you'll be walking between food spots.

  • Dietary preferences: Inform your tour guide of any dietary restrictions in advance.

  • Weather preparedness: Check the weather forecast and dress accordingly – the tour will take you through various neighborhoods.

Architecture tour down the Chicago River

Breathtaking view of Chicago's skyline from a boat on the Chicago River.

Glide along the Chicago River and marvel at the towering architectural wonders of the Windy City!

Embark on an architectural odyssey with Chicago's most famous river cruise, a must-do for both locals and visitors. 

Organized by the Architecture Center, this cruise offers a captivating narrative about Chicago's rich architectural history, with up-close views of iconic buildings like the Willis…err, Sears Tower, the Wrigley Building, and the Tribune Tower.

Whether you're an architecture buff or just looking for a unique way to see the city, try the cruise out!

Blueprint for a picture-perfect Architectural River Cruise

  • Weather-wise wardrobe: Chicago's weather can be unpredictable, so dress in layers and be prepared for a breezy ride on the river.

  • Camera-ready: Bring a camera or smartphone for some amazing skyline shots.

  • Be on time: Arrive a bit early to secure the best viewing spots on the boat.

  • Listen and learn: Engage with the guide's narrative to fully appreciate the architectural splendors you're witnessing.


Man actively volunteering at a local charity in Chicago.

Give back to the community by lending a helping hand at our local charities!

Volunteering in Chicago is a way for friends, family, or coworkers to come together and make a meaningful impact. 

From bustling soup kitchens to serene community gardens, the city offers a variety of family bonding activities and opportunities to support a good cause.

Top Chicago volunteer opportunities to explore with your group

Talk with your team, settle on a niche, and search for relevant volunteering opportunities in the Windy City.

Explore street art in Pilsen

Two people admiring vibrant street art in the Pilsen neighborhood of Chicago.

Uncover the colorful streets of Pilsen and witness the urban canvas that brings our community's stories to life!

Just as Pilsen's food scene offers a taste of its rich Mexican heritage, its street art paints a vivid picture of the neighborhood's Latino roots. 

Stroll along 16th and 18th Streets to see how artists like Hector Duarte and Jeff Maldonado have transformed these spaces into a vibrant celebration of Mexican-American culture and history. 

This artistic journey through Pilsen is more than just sightseeing; it's an immersive cultural experience in the heart of Chicago.

Making the most out of your Pilsen group outing in Chicago - tips and tricks

  • Camera-ready: Bring your camera! These murals make for stunning photographs and memorable backdrops.

  • Art meets history: Keep an eye out for murals that tell the story of Pilsen's cultural evolution.

  • Comfy footwear: You'll walk a lot, so wear comfortable shoes.

  • Local insights: Engage with local artists or guides to gain deeper insights into the artworks.

  • Support local: Visit nearby cafes and shops to support the community that fosters this vibrant art scene.

Head for the Navy Pier

Scenic view of Navy Pier, showcasing its vibrant atmosphere.

Have a group outing at the Navy Pier and soak in the lively vibes of one of our most beloved landmarks!

Navy Pier, an iconic Chicago landmark, is a quintessential addition to any Chicago group outing for adults. 

Ride the famous Centennial Wheel for stunning skyline views, choose from the numerous food options, or join in on the fun of the Navy Pier Pressure Scavenger Hunt

Seasonal fireworks and cultural events add to the Pier's allure.

With something for everyone, the Navy Pier promises a memorable group experience for adults in Chicago.

Tips for an amazing Navy Pier meetup

  • Ride the Centennial Wheel: An iconic part of the Chicago skyline, this Ferris wheel offers breathtaking views.

  • Diverse dining: From classic Chicago fare to innovative culinary delights, Navy Pier's food scene has something for everyone.

  • Scavenger hunt fun: Participate in the Navy Pier Pressure Scavenger Hunt for an interactive and entertaining group experience.

  • Catch the fireworks: Plan your visit around the summer or winter fireworks (like the New Year’s Eve fireworks) for a spectacular end to your day.

Website: Visit their website

Location: Plan your route via Google Maps

Phone: (312) 595-7437

Day out at the Shedd Aquarium

Visitors enjoying the view of marine life at a large exhibit in the Shedd Aquarium.

Get up close (and sometimes personal) with the wonders of the ocean at the Shedd Aquarium!

Discover the wonders of aquatic life at the Shedd Aquarium, a highlight of Chicago group activities for adults. 

Encounter playful sea otters, glide alongside stingrays, and marvel at the vibrant fish that call this place home. 

Interactive experiences like touching starfish and immersive exhibits bring you face-to-face with the beauty of the underwater world. Specifically, check out what they added as part of the 2023 overhaul.

A visit to the Shedd is an engaging journey through marine life, perfect for any group exploring the heart of Chicago's aquatic treasures.

Making waves: tips for an unforgettable visit to the Shedd Aquarium

  • Plan ahead: Check online for special events or temporary exhibits to make the most of your visit.

  • Interactive experiences: Don't miss out on the hands-on touch tanks and educational talks for an engaging visit.

  • Underwater wonders: The new Caribbean Tunnel and “Changing Oceans” galleries are must-sees for their immersive experiences.

  • Photography fun: Carry a camera to capture the vibrant marine life, but remember, no flash photography to protect the animals.

  • Stay informed: Learn about the aquarium's conservation efforts and how you can contribute to marine life preservation.

Website: Visit their website

Location: Plan your route via Google Maps

Phone: (312) 939-2438

Kayaking down the Chicago River