Updated: April 08, 2024

19 Unique Company Retreat Ideas in Chicago, IL

You found our list of the best company retreat ideas in Chicago, Illinois.

Company retreat ideas in Chicago are locations and activities that provide opportunities for team building, learning, and boosting employee morale during company events. Examples include bowling, food tours, and escape rooms. These ideas are important because they help workers learn about each other and increase employee retention.

These experiences work well as executive retreat options, retreat activities for groups, and company retreats. The activities are similar to Chicago company outings and activities for groups in Chicago.

This article contains:

  • corporate retreat ideas for big groups in Chicago
  • corporate retreat ideas for small groups in Chicago
  • company retreat entertainment ideas in Chicago
  • company retreat locations in Chicago
  • staff retreat activities in Chicago
  • team retreat ideas in Illinois

Here we go!

List of company retreat ideas in Chicago

From Lincoln Park to Sip and Paint to Brooklyn Boulders, the following is a list of the top staff retreat activities in Chicago.

1. Field Day (Team Favorite)

With Field Day, employees participate in interactive outdoor games and form lasting connections. This thrilling activity promotes trust, strengthens relationships, and develops essential workplace skills.

Your Field Day experience includes:

  • a highly skilled host from teambuilding.com will guide you through each activity
  • teams enjoy a mix of nostalgic outdoor games and innovative competitions
  • facilitators can capture team photos to commemorate the event
  • the event will be hosted at a location of your choice
  • we will provide all the necessary materials and equipment for each game

Field Day fosters teamwork, encourages friendly competition, and nurtures camaraderie.

For an unforgettable team building experience, explore the world of Field Day.

Learn more about Field Day.

2. Espionage! (Competitive)

espionage banner

Espionage! transports you to a captivating world of spies, mind-bending puzzles, and strategic challenges.

Here is what to expect during this thrilling event:

  • a talented host from teambuilding.com will lead this 90-minute adventure.
  • compete in a secretive world of spies versus agents.
  • spies try to sabotage the agents’ goals.
  • engage in a series of challenges, including word searches, scavenger hunts, and code unscrambling.
  • have group discussions to unveil the spies’ true identities.
  • we will meet you at your preferred location to host this game of social deduction.

Espionage! challenges your intellect and ignites your team’s competitive spirit. This exercise delivers an unforgettable experience that will strengthen bonds and sharpen strategic thinking.

Learn more about Espionage!

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3. The Art of Storytelling (Boosts Communication)

Our immersive workshop equips your team with essential techniques to build meaningful connections.

The Art of Storytelling includes:

  • a 120-minute session led by accomplished storytellers
  • valuable insights that enhance your team’s storytelling abilities
  • the art of using language, emotion, and structure to create impactful stories
  • captivating communication and presentation skills
  • an environment of openness, vulnerability, and active listening
  • hosted at the location of your choice

Storytelling can have a huge impact on your team. By mastering the art of storytelling, your team will have the power to connect and inspire others through engaging narratives.

Learn more about The Art of Storytelling.

4. StageCoach Improv

Incorporating a StageCoach Improv session into your company’s retreat program is a great way to improve your staff’s soft skills. Working together is essential in improvisation. Every member will contribute to making the team’s skit. StageCoach Improv’s techniques revolve around applied improv, storytelling, and collaboration powered by play.

An improvised skit’s success depends on the performers’ seamless cooperation. Other important “soft skills” for improv include thinking creatively, effectively communicating with others, and having faith in one’s teammates’ abilities. Improvising is a great way to improve teamwork while having fun.

Learn more about StageCoach Improv.

5. The Bridgeport Art Center

The Bridgeport Art Center is a dynamic space offering a wide array of creative classes. The space includes art exhibitions, classes, and studio spaces.

The center hosts various creative classes, such as the following:

  • The Chicago Ceramic Center: Skilled instructors guide participants in clay molding and decorating.
  • Dancing Brush Creativity: Artist Tamara Wasserman offers art classes and workshops.
  • Jeffrey Hirst Fine Art Studio: This artist specializes in encaustic painting, ink painting, and printmaking workshops.
  • Yoga in Vogue Studio: This studio offers yoga and meditation classes in a community-focused setting.
  • Chris Newman Metal Sculpture Classes: Classes offer a unique opportunity to create sculptures using steel, stainless steel, or aluminum.

Overall, The Bridgeport Art Center is a thriving artistic community, and it is a great place to take a class during a retreat. Be sure to explore a diverse range of creative offerings in the heart of Chicago’s South Side.

Learn more about The Bridgeport Art Center.

6. The Forge

The Forge offers different corporate team activities depending on participants’ skill levels. The ziplining option is great for groups looking for a high-speed treetop experience. Your group will be able to zip down a 1000-foot line, rappel down a tower, and rock climb as part of this high ropes challenge.

If you want amazing company retreat entertainment ideas in Chicago, then The Forge has you covered. Laser tag, ax throwing, archery tag, and mountain biking are all part of The Forge’s Outdoor Rec & Nature Adventure Package. Whatever package you choose, your team’s experience at The Forge will be memorable.

Learn more about The Forge.

7. Chicago Dine Around

Corporate retreats that include cooking lessons or contests are a fun way to bring your team closer together. Chicago Dine Around provides culinary experiences for corporate groups, such as a progressive dining tour that will take your group to a new restaurant for each dish, allowing them to mix and transfer tables at each location. Up to 560 individuals may join the trip over its three-hour duration, making it one of the preferred corporate retreat ideas for big groups in Chicago.

The hosts also offer interactive workshops where your team can learn to cook deep-dish pizza, mixed cocktails, or traditional Italian food, in addition to an architectural dining tour that includes a sail down the Chicago River. Be sure to check out Chicago Dine Around when looking for team retreat ideas in Illinois!

Learn more about Chicago Dine Around.

8. Frank Lloyd Wright Home and Studio Tour

Iconic architect Frank Lloyd Wright created innovative designs that combined nature and structure. Visitors to the Chicago area can see the place where this movement began. This home was the first building Wright had complete artistic control over, and his style is evident in the construction. Wright completed building this studio and house in 1889, and he created more than 150 projects there.  Attendees can tour just inside the house or include a walk of the surrounding area. A guide leads the interior tour, spending 60 minutes discussing the home where Prairie-style architecture was born. The neighborhood tour is a 45-minute self-guided audio walk where guests can see some of the homes Wright designed. History and design lovers will surely love this stop during your Chicago retreat. 

Learn more about the Frank Lloyd Wright Home and Studio Tour.

9. Paintball Explosion

Paintball Explosion is an adventure-packed theme park offering a range of thrilling activities. The extensive maps include indoor and outdoor paintball fields like Nuketown, Code Black, Mutiny, Shipment, Biohazard, Turmoil, and Nam Field. Paintball enthusiasts can choose from traditional paintball, low-impact paintball, or airsoft.

For corporate outings, Paintball Explosion offers an affordable team building experience for individuals of all ages and fitness levels. The firm provides all the necessary equipment, making it accessible and fun. Party packages are available for different group sizes, and you can enhance your party with extras like cake cutting, party bags, customized dog tags, T-shirts, and even a personal videographer.

The park also provides information for those new to paintball, covering the game’s basics, gear, and how to play. The company emphasizes safety and offers rental equipment for newcomers. Paintball Explosion’s knowledgeable staff ensures a thrilling yet secure experience.

Learn more about Paintball Explosion.

10. Chicago Cares

You can make a statement about your company’s commitment to social responsibility by collaborating with a group like Chicago Cares during your retreat. Numerous volunteer opportunities exist, allowing you to practice your company’s principles with efforts that benefit the local community. The staff at Chicago Cares can assist you in finding the ideal volunteer opportunity for your group of any size, whether you are interested in planting trees or organizing a neighborhood cleanup.

Learn more about Chicago Cares.

11. Brooklyn Boulders

Groups may learn to work together by taking a climbing workshop. Besides teaching you how to boulder and auto-belay, the staff at Brooklyn Boulders will lead you in activities designed to improve your communication and problem-solving skills. You can pick from a number of exciting options to test and motivate your group. In addition, you will have access to various amenities in one convenient location, including conference rooms, coworking spaces, showers, and designated places for yoga and meditation.

Learn more about Brooklyn Boulders.

12. Loyola University Retreat and Ecology Center

The Loyola University Retreat & Ecology Center is located about an hour’s drive from downtown Chicago and is a great place to relax and unwind. The location has hotel rooms, dorm rooms, and several conference rooms, making it ideal for a weekend retreat away from the city. The facility also offers sustainable cooking demonstrations and ropes and zip line courses for team building at this facility. In addition, there are 98 acres of land for outdoor activities, including hiking and birdwatching.

Learn more about The Loyola University Retreat & Ecology Center.

13. The West Loop

Located just minutes from Chicago’s central business district, The West Loop is quickly becoming one of the most popular dining districts in the country. Bonci’s Pizza, Cemitas Puebla, and Kuma’s Corner are just a few of the stops along Chicago Food Planet’s Gateway to the West Loop Food Tour. This activity will offer your group a behind-the-scenes peek at the city’s culinary revolution as they eat in renowned restaurants and creative eateries. This retreat idea is a great choice year-round but even better in the summer when the streets of the West Loop come alive with partygoers and style-conscious tourists.

Learn more about The West Loop.

14. North Avenue Beach

Chicago receives a significant portion of the snow that falls on the state of Illinois each winter, lending credence to the stereotype that it is a frigid, windy location. However, winter does not last forever. Going to the beaches during the summer in Chicago may make for a memorable experience. North Avenue Beach is among the best beaches around.

At this beach, you can swim or go out on a boat, rent a bike, kayak, paddleboard, jet ski, or water tube. You can do yoga early or play volleyball in the evening. The large beach home, styled like a blue and white ocean liner, also has plenty of room for inside recreation. The venue has almost 22,000 square feet, and while you are not enjoying its various attractions, you may gaze in awe at the shimmering waters below. As one of Chicago’s most fantastic shorelines, the beach is one of the best company retreat locations in Chicago.

Learn more about North Avenue Beach.

15. Sip and Paint

Team members may channel their inner creativity freely during a private painting lesson at Sip and Paint Chicago. Sip and Paint will offer your group an instructor to help you learn the basics. The hosts will provide all the materials you need to create art. This location does not provide any refreshments, but participants can bring their own drinks. This activity is good for groups looking to get artsy.

Learn more about Sip and Paint.

16. Brew & Grow

For a company retreat activity that includes food and drink, you can book a beer-making course with Brew & Grow. The providers will supply every piece of equipment for your group to learn to brew. The best part is that you will try different beers at different stops. You may tailor one of their packages to fit your financial or time-related needs. In addition, the sessions can help encourage participation and discussion between your team members. This activity is a great retreat event in Chicago.

Learn more about Brew & Grow.

17. Lincoln Park

Lincoln Park is the most popular park in Illinois and one of the busiest in the whole country. Only New York’s Central Park receives more tourists each year. The first aspect you will notice is the presence of so many attractions. Your team will have several museums, theaters, concert halls, conservatories, botanical gardens, and other cultural institutions to explore.

You can opt for regular activities like dining and shopping during your retreat. You can also try unique activities like shooting arrows at a range or riding horses over the hills. The scenery of Lincoln Park is among the best in the city. Here, between the willow trees, lily ponds, and tulip gardens, is a welcome respite from the city’s towering skyscrapers. Lincoln Park provides an ideal combination of urban conveniences and natural beauty.

Learn more about Lincoln Park.

18. Chicago Sailboat and Yacht Charters

You could have a corporate sailing workshop if you have a significant budget and prefer corporate retreat ideas for small groups in Chicago. Team building sailing courses offered by Chicago Sailboat and Yacht Charters help participants develop a wide range of abilities vital to forming and maintaining a high-performing group. The company collaborates with expert facilitators and creates a program tailored to your group’s unique needs. Sailing is a great way to develop skills, including active listening, skill acquisition, clear communication, and teamwork.

Learn more about Chicago Sailboat and Yacht Charters.

19. The Untouchable Tour

Chicago is the exception to the rule that Illinois is not a hub of mob activity. During Prohibition, the city served as the epicenter for infamous gangsters like Al Capone, Bugs Moran, and Baby Face Nelson, who rose to prominence via illegal activities like including bootlegging and gunrunning. Naturally, the city offers a plethora of “mob tours” meant to sate the insatiable need for information on these celebrities.

Tthe Untouchable Tour is the first and still the greatest of its kind. The tour operators will pose as gangsters from the 1920s and 1930s, complete with period clothing and accents. You will go to the spots where mobsters made shady deals. Additionally, you will visit the location of the 1929 St. Valentine’s Day Massacre.

If planning a retreat, then you should consider including the Untouchable Tour. The activity will acquaint you with the streets and sidewalks of downtown Chicago and provide an exciting glimpse into the city’s dark past.

Learn more about The Untouchable Tour.


Whether local or across the country, teams would do well to organize a retreat in the Chicago region. Chicago is an excellent destination for a weekend retreat, thanks to its world-class art and cuisine culture and plenty of outdoor activities. Retreat activities in Chicago can help bring your company closer and increase employee retention.

Next, check out Chicago team building ideas and corporate events in Chicago.

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FAQ: Company retreat ideas in Chicago, Illinois

Here are frequently asked questions about company retreat ideas in Chicago.

What are some good corporate retreat ideas in Chicago?

Some good corporate retreat ideas in Chicago include The West Loop and Chicago Cares. Since these activities promote so many aspects of effective teamwork, they are a great option for corporate team building. However, in Chicago, you must consider the changing of the seasons. Having fun in the great outdoors is a great way to spend the summer, but come fall and winter, you should consider indoor options.

How do you plan a fun team retreat in Chicago?

Planning a fun team retreat in Chicago requires you to involve other group members in the process. You need to decide your goals for the retreat. What you want to accomplish during your retreat will determine many other details, such as the length of time spent away from the office, the location of your retreat, and the activities you choose.

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People & Culture Director at teambuilding.com.
Grace is the Director of People & Culture at TeamBuilding. She studied Industrial and Labor Relations at Cornell University, Information Science at East China Normal University and earned an MBA at Washington State University.

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