20 Fun Client Entertainment Ideas in Chicago, IL

By: | Updated: February 13, 2024

Here is our list of the best client entertainment ideas in Chicago, IL.

Client entertainment ideas in Chicago are experiences and fun activities to impress your clients in the city. For example, you can dine at Sunda New Asian or catch a show at the Chicago Magic Lounge. The purpose of these ideas is to help you decide the best way to appreciate your clients and foster your business relationship.

These ideas are similar to Chicago group outings and corporate events in Chicago. Client entertainment is a topic that appears in many books on customer experience and fulfills a similar purpose to luxury corporate gifting.

This list includes:

  • VIP client entertainment ideas in Chicago, Illinois
  • client appreciation event venues in Chicago, IL
  • places to bring clients in Chicago
  • client meeting spaces in Chicago

Let’s get to it!

List of client entertainment ideas in Chicago

Hosting client appreciation events and outings will demonstrate your commitment and make your guests feel special. From visiting United Center for a music concert to booking a mixology class at Hollow Leg, here are fun ways to entertain clients in Chicago.

1. Mix n’ Mingle (Client Favorite)

Mix n’ Mingle is an immersive 90-minute event designed to start meaningful conversations and build strong relationships.

Here is what you can expect during the Mix n’ Mingle experience:

  • We will meet you at the venue of your choice with all the necessary supplies.
  • An expert host from teambuilding.com will skillfully guide you through a series of interactive exercises and activities.
  • Thoughtfully crafted exercises will break the ice, spark engaging conversations, and foster genuine connections.
  • Engage in group discussions and collaborative team challenges.
  • Encourage effective collaboration, communication, and sharing.
  • Discover shared interests, common goals, and unique perspectives.

By going beyond surface interactions, you will unlock the power of networking and create lasting connections.

Learn more about Mix n’ Mingle.

2. The Great Guac Off™️ (Highly Rated)

Guacamole making competition

During The Great Guac Off, participants face off against each other in a friendly and flavorful guacamole-making competition!

Here is what to expect at this avocado-based celebration:

  • Experienced hosts and co-hosts from teambuilding.com will meet you at the location you choose.
  • We will bring delicious guacamole ingredients and a variety of dippers.
  • To add an exciting twist, hosts can introduce a secret ingredient.
  • First, hosts will lead engaging warm-up games and icebreakers.
  • Then, teams will dive into avocado trivia and thrilling mini-games.
  • Finally, participants will showcase their culinary skills by creating magnificent guacamole masterpieces.
  • Participants will give each guacamole creation a unique name, and a panel of judges will taste and score each entry.
  • At the end of the competition, a champion guacamole maker will win!

The Great Guac Off satisfies taste buds while creating strong bonds and improving communication skills.

Learn more about The Great Guac Off.

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3. Ultimate Trivia Showdown (Popular)

With Ultimate Trivia Showdown, you can experience an exhilarating night of fun and games! This 90-minute activity offers engaging questions and friendly competition, which is great for entertaining clients.

Here is what this event includes:

  • A captivating host from teambuilding.com will lead the event.
  • Put your knowledge to the test with interactive questions, games, and puzzles.
  • Engage in a variety of thrilling activities, including Majority Rules, General Knowledge Trivia, The Champion Challenge, and Smarty Pants Ultimate Trivia.
  • Questions will span various topics, from pop culture to science to history.
  • Choose a venue of your choice, and we will come fully equipped with all the necessary materials.

Clients love interactive activities, so consider Ultimate Trivia Showdown for your next bonding event!

Learn more about Ultimate Trivia Showdown.

4. United Center

United Center is an indoor arena and home to the Chicago Bulls and the Chicago Blackhawks. The arena is a famous ground for hosting fun shows performed by artists like Post Malone, Kevin Hart, Mary J. Blige, Lizzo, and Kid Cudi. Also, you can get tickets to watch a basketball or hockey match on a game day.

Reserving luxurious seating for your guests during an event is one of the VIP client entertainment ideas in Chicago, Illinois. Depending on your selected seating option, your clients can access VIP parking, catering, a private in-suite bathroom, and a dedicated hostess or chef.

Your clients will have a great time at United Center, whether you visit on a game day or relax in a dining area. You can maximize the fun by further exploring the United Center Atrium, which is home to the 1800 Market, Madhouse Team Store, and a statue of Michael Jordan. Before or after your event, you can also stop for a meal at Queenie’s Supper Club.

Learn more about United Center.

5. Chicago Magic Lounge

Chicago Magic Lounge is a theater and speakeasy bar in the city. Your guests will enjoy a magical night at this venue. While you marvel at the magic performance, you can also sip craft cocktails and small plates served at the venue. Chicago Magic Lounge opens daily and features top magicians like Rebecca Spectre, Mike Caveney, Tina Lenert, and Mark King.

The venue has cabaret-style seating with a convenient view of the stage from different areas. You and your clients will likely share a table with other guests. Additionally, you can rent a space in the theater to host an unforgettable client appreciation event.

Learn more about Chicago Magic Lounge.

6. Zanies Chicago

Zanies Chicago is a well-reviewed comedy club and 21+ venue in the city. The showroom welcomes talented comedians on stage, including Chris Red, Joe Machi, CJ Sullivan, and Justin Whitehead. Reserving a show performed by your guests’ favorite artist is one of the fun client entertainment ideas in Chicago.

In most cases, the show will last about 90 minutes, and theater seating is available on a first-come, first-served basis. Zanies Chicago hosts tons of events your guests will love. You can watch top comedians practice in the Super 6 Showcase or enjoy a Saturday late-night show called After Hours.

Learn more about Zanies Chicago.

7. City Mini Golf

City Mini Golf conveniently sits in the center of Maggie Daley Park, within walking distance of Cloud Gate and Pritzker Pavilion. To liven up visitors’ experience, the center provides a mystery spinner on the course, giving several instructions like:

  • “Play with your putter behind your back”
  • “Use your hand for the first hit”
  • “Have a player stand on the green as an obstacle”

With these fun instructions, you and your clients will surely share moments of laughter. Additionally, the center regularly changes obstacles to create a unique experience every visits. You can come along with food or stop for grabs at Rink Cafe.

Learn more about City Mini Golf.

8. Hollow Leg

Hollow Leg provides hands-on mixology classes ideal for entertaining clients in Chicago. During the session, you will master the art and science behind crafting balanced cocktails that suit your palate. If your clients do not drink, then the bar can customize the cocktail ingredients to exclude alcohol.

Hollow Leg offers various package options for a private event. You can reserve an exclusive spirit tasting, learn how to make bitters, or play “cocktail whisperers” with your guests. In the latter event, the bar will create several cocktail options for your guest to pick a favorite and enjoy the selection throughout the event. Hollow Leg guarantees a good drink and a great time to make your guests’ day.

Learn more about Hollow Leg Mixology Classes.

9. Cocoa + Co.

Cocoa + Co. is a cafe and bakery serving various treats like pastries, chocolate bars, hot cocoa, and coffee. This cafe is among the fun places to bring clients in Chicago. You can reserve a private tasting class or a tea party for your guests. The tasting experience will last 60 minutes and include a variety of chocolates to expand your palate.

The cafe also hosts “choctail” parties, where you and your clients socialize and enjoy a custom chocolate menu within 90 to 120 minutes.

Learn more about Cocoa + Co.

10. Waveland Bowl

Waveland Bowl is a bowling alley and event venue with cosmic bowling and arcade games. Each lane can accommodate about six players and is reservable for two hours.

Also, you can extend the fun to the billiard room with several pool tables. After a game, you and your guest can retreat to Alley Dogs, a restaurant at the venue offering a menu of favorite American selections.

Learn more about Waveland Bowl.

11. Headquarters Beercade

Headquarters Beercade is a fun venue in the River North neighborhood where you can have a few drinks and chat with your clients. Pinball and arcade games are available to heighten the fun for your guests. You will find an extensive list of classical games to play, from Kang Fu Masters and Galaga to Mortal Kombat 2 and Street Fighter 11.

Headquarters Beercade is a vibrant venue that also hosts trivia games on a scheduled basis. The trivia will test your knowledge of popular movies like Harry Potter, Hocus Pocus, Jurassic Park, and Big Mouth. You can access this arcade bar all year round.

Learn more about Headquarters Beercade.

12. Chicago Bath House

Chicago Bath House is a traditional bathhouse conveniently located in the Wicker Park neighborhood. The location provides relaxing services, including spa treatments, massages, tanning, and a sauna.

This bathhouse has a cold pool, traditional Banya, Schvitz, and a hot room. The center raises the room’s temperature by heating boulders inside a brick or granite oven. Also, you and your guests can have a body scrub service while in the hot room.

Chicago Bath House is one of the nice client meeting spaces in Chicago, featuring flatscreens, free wifi, and an occupancy capacity of 20 guests. At the end of your treatments, you can treat your client to traditional cuisine at the bath house’s restaurant.

Learn more about Chicago Bath House.

13. Lillstreet Art Center

Lillstreet Art Center is a creative studio that serves the Chicago area. The center host art parties great for entertaining clients. Your experience will last about three hours, and the center will take care of the needed art supplies. Also, professional artists will be available to guide your clients through a fun and memorable experience.

Lillstreet Art Center hosts private workshops on screen printing, ceramics, and metal & jewels. Also, a dedicated events team will help you customize the program to your guests’ liking.

Learn more about Lillstreet Art Center.

14. Sunda New Asian

Sunda New Asian is one of the client appreciation event venues in Chicago, IL. The restaurant is an award-winning kitchen that creates a unique culinary experience for diners by twisting Southeast Asian traditional cuisine and flavors. Sudan offers a commendable selection of beverages, including fine wines, cocktails, and Asian beers. Your guests will enjoy the restaurant’s unique dishes and vibrant atmosphere.

You can reserve a party room for a private dining experience. Also, the restaurant can customize your event to include amusements like celebrity appearances, photo booths, and live band performances.

Sunda offers happy hour at the bar on Mondays through Fridays. Additionally, you can impress your clients by booking the monthly sushi rolling class to learn the steps for preparing traditional meals within 90 minutes.

Learn more about Sunda New Asian.

15. BATL Chicago

BATL Chicago is an ax-throwing facility and entertainment center in the city. The center offers several ax-throwing packages that range between one and two hours. Although the venue does not serve food, you are free to arrange for catering and bring the meals on-site. Alternatively, you can pre-order your food online and receive your meal in your lanes.

If you need a dedicated ax coach to guide your clients throughout, then you should book the Premium Package. After an exciting tournament, you can dine in a seating area and chat with your clients.

Learn more about BATL Chicago.

16. Revolution Brewing

Revolution Brewing is one of the largest breweries in Illinois. The company organizes private and public tours lasting 45 minutes and ending with a beer tasting. The company will provide an expert guide and protective goggles to ensure you have a safe and insightful experience.

At the end of the tour, you chat with your guests while sharing snacks and sods. Revolution Brewing is one of the nice client entertainment spaces in Chicago. The company provides social event packages with a custom menu, a seated buffet, and access to a built-in stage. The brewery has a vibrant atmosphere that will make the day memorable for your clients, whether you only tour the facility or dine at the taproom.

Learn more about Revolution Brewing.

17. Chicago’s First Lady Cruises

Chicago’s First Lady Cruise provides well-maintained vessels that can accommodate large and small groups in the city. Reserving a private yacht party with this cruise service is one of the VIP client entertainment ideas in Chicago.

Your experience will include a customized menu and an opportunity to enjoy a 360 degrees perspective of the city from the top deck. In the end, your clients will watch breathtaking summer fireworks. You can also add different entertainments to enhance your guests’ experience, like hiring a DJ, renting casino games, or hosting a live band.

Your clients will have a fantastic experience on the vessel, whether you decide to cruise Lake Michigan or the Chicago River.

Learn more about Chicago’s First Lady Cruises.

18. Lincoln Park Conservatory Tour

Lincoln Park Conservatory is a botanical garden situated near Lake Michigan. You can reserve a tour to explore the conservatory with your guests. During the experience, you will learn about the garden’s exotic plants and visit the Palm House, Fern Room, and Orchid House.

The docent-led tour will extend to the Lily Pool, which opens seasonally. Here, your clients can relax, learn about the native wildflowers, and have a scenic walk around the North Pond Nature Sanctuary. Lily Pool is one of the client entertainment event venues in Chicago and an excellent choice if your guests prefer an outdoor space. However, there are no shaded areas at the location. So you should dress according to the weather and prepare umbrellas during the wet season.

Learn more about Lincoln Park Conservatory Tour.

19. Eaglewood Resort & Spa

Eaglewood Resort & Spa is a highly-rated resort in a village near Chicago. The resort has well-maintained amenities you can use to entertain your guests, from a spa and golf course to a dining area. A great time is sure for your guests at this destination while relaxing on the patio with a fire pit or dining at Praire River Restaurant.

The golf course at Eaglewood features 18 holes and a scenic landscape. Also, several packages, private golf lessons, and club rentals are available. Eaglewood resort features state-of-the-art technology, ballrooms, a conference concierge, over 25 meeting rooms, and a private golf simulator with more than 15 courses.

Learn more about Eaglewood Resort & Spa.

20. National Museum of Mexican Art

Touring the National Museum of Mexican Art is among the fun client entertainment ideas in Chicago. An art appreciation day at this destination will fascinate your clients and provide a learning opportunity. The museum is home to exhibits that will take you back to over 3,500 years of history.

You can also explore the art and cultural representations by Chicano, Mexican, and Latino artists. From old-school photographs and priced artifacts to paintings and textiles, you will find many impressive artworks to explore. The institution also recounts stories of talented artists like Carlos Cortéz, Rosario Cabrera, Agustin Victor Casasola, and Jean Charlot. Admission to the museum is free.

Learn more about the National Museum of Mexican Art.


Clients are vital in business. Therefore, you would want to maintain a good relationship with your clients and show how much you care. Chicago is among the vibrant places in Illinois, with tons of experiences to impress guests. The city is home to unique destinations, including one of the oldest Bath House in the United States. Also, the city has over 600 parks and an average of 189 sunny days to enjoy the vibrant atmosphere outdoors. With many attractions, activities, and iconic destinations, you will hardly run out of ways to entertain your clients in Chicago.

Next, check out fun group activities in Chicago and Chicago private event venues.

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FAQ: Client entertainment ideas in Chicago, Illinois

Here are answers to questions about client entertainment ideas in Chicago.

What are the best client entertainment ideas in Chicago, IL?

The best entertainment ideas for clients in Chicago include watching a show at Chicago Magic Lounge and touring the Lincoln Park Conservatory.

How do you entertain clients in Chicago?

You can visit one of Chicago’s destinations to impress your clients, whether a stadium or fine dining. Also, researching the entertainment offered at your selected venue is a great idea. You can plan extra entertainment like hosting a live band, a celebrity, or DJ if allowed at your reserved location. During the planning process, you should consider the time and date convenient for your guests, including dietary requirements and your client’s preferred entertainment.

What are some good places to take clients in Chicago?

Some good places to take clients in Chicago are Headquarters Beercade, Waveland Bowl, Zanies Chicago, United Center, Chicago Bath House, and Chicago’s First Lady Cruises.

Author avatar


People & Culture Director at teambuilding.com.
Grace is the Director of People & Culture at teambuilding.com. 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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