Top Things to Do In Chicago For Groomsmen As Featured On WGN Spotlight

By  Tommy Peske
Updated on 04/18/24
Top Things to Do In Chicago For Groomsmen As Featured On WGN Spotlight

Top Things to Do In Chicago For Groomsmen As Featured On WGN Spotlight

By  Tommy Peske
Updated on 04/18/24
Groom Hacks

Part of the Groom Hacks

Top Things to Do In Chicago For Groomsmen As Featured On WGN Spotlight

By  Tommy Peske
Updated on 04/18/24

Your big day is almost here! And all your friends are together for the first time in a long time. How cool?!

But before the wedding day, what do you do? How do you take advantage of this get-together and make sure your groom squad is entertained in Chi-Town?

Fun Things To Do In Chicago For Adults

Chicago is a big city with plenty of things to do, from world-renowned architecture to remarkable museums, a lively river scene, a gorgeous lakefront, and more.

The Groom Club editor, Dustin Sitar, recently sat down with WGN Spotlight Chicago to share our top picks for Chicago wedding events for grooms and their groom crews. 

Here are some of the most fun things to do in Chicago.

The Bachelor Party

The Bachelor Party

Let’s start with the bachelor party. It’s likely the first of the events you’ll want to plan. And who knows when you and your friends will be together the next time, so make the most of your bachelor party with these suggestions.

We recommend The Barrel Run in Chicago for those who appreciate spirits and quirky transportation. Take part in ultra-cool tours of Chicago breweries, wineries, and distilleries—in the comfort of their barrel bus! 

Alternatively, suppose you’re looking for things to do in Chicago at night. In that case, you can pop into some of Chicago’s welcoming watering holes, sample the local drinks, and enjoy your favorite type of music.


The Bachelor Party:: Go Kartin

Looking for a faster-paced event, maybe something more adrenaline-rushing?

K1 Speed go-kart racing is a fun option for those who want to channel their inner NASCAR driver and end any debate about the best driver within your friend group.

Another “cool” option on a hot day is a Chicago Tiki Boat bachelor party cruise on Lake Michigan. Roll with the waves and party with your closest friends.

Any of these activities is a perfect way to kick off your wedding events with your groom crew.

Pre-wedding Activity

A pre-ceremony get-together with your groomsmen on the day of your wedding is becoming a popular trend, especially for those coming from out of town for the wedding. 

Chicago has plenty of excellent options for relaxing with your friends before you say, “I do.” 

Get Some Breakfast, Relax on the Green, or Throw Some Darts

Get Some Breakfast, Relax on the Green, or Throw Some Darts

A fantastic meal is a great way to start your day of celebration with your crew. 

The Breakfast Club and Grill, a Chicago icon for over 30 years, is an excellent place to fuel up with mouthwatering breakfast options.

Pre-wedding Activity: Diversey

Once your crew is fortified for the day, you can explore Chicago’s lakefront by stopping at Diversey Driving Range to play some minigolf, putting greens, and even heated driving ranges for those frosty days. 

Lastly, try your hand at Flight Club Darts over a few cocktails or beers before getting ready for your big with your groom crew. Still looking for more things to do in Chicago? We’ve got your back.

Other Cool Things To Do In Chicago

These are just a few of the top things to do in Chicago. Check out Chicago cultural centers, miles of lakeshore parks, or a walk through Grant Park for something more toned down.

You’ll find a broad mix of pricey, moderate, and free things to do in Chicago.  

Scout Out Lake Michigan

Exploring Lake Michigan is one of the best things to do in Chicago. Chicago has revitalized the lakefront with miles of parkland to enjoy for free. It offers you and your buddies spectacular skyline and lakefront views, bike trails, or rollerblading, depending on what you and your groomsmen are into.

Your groom crew can choose to bask and swim on several beaches and participate in water and beach volleyball activities. If you’re celebrating with your crew in summer or fall, you’ll likely find a festival or event happening on the shores to add to the fun.

Try an evening dinner or cocktail cruise on Lake Michigan departing from Navy Pier. It is one of the most relaxing and enjoyable things in Chicago. The pier also has the fantastic Centennial Wheel, where you can learn more about the city while taking in some incredible sights. 

If you’re still looking for more water-related fun, look toward the Chicago River! The river runs through downtown Chicago, offering gorgeous views and a thriving riverfront filled with restaurants. 

Better yet—treat your groomsmen to a choice of boat tours on the river highlighting Chicago’s architectural wonders. If you are more adventurous, there are also kayaks you can rent and paddle your way down the river.

Peruse the Art Institute of Chicago

The Art Institute of Chicago is a tour de force in the art world, housing masterpieces from ancient to modern times. It is the perfect place for your groom’s crew that loves art, even if they want to recreate some movie scenes from Ferris Bueller’s Day Off. Lastly, this is only 1 of 64 museums that Chicago has to offer!

(P.S. Did you know that Route 66 starts right in front of the Art Institute?) 

The Art Institute of Chicago has much to offer and is a great place to visit. It is also centrally located between Grant Park and Millenium Park—a genuine walker’s paradise! Check out the ever-popular centerpiece of Millenium Park, a sculpture named The Cloud Gate, known more affectionately as “The Bean.” It’s an ideal photo spot for a group selfie.

Catch a Game and More

Chicago’s sports scene is unlike any other.

The United Center is the home arena for the Chicago Bulls and the Chicago Blackhawks. You and your groomsmen can visit and see where sports legends like Michael Jordan and Bobby Hull, made history. 

More into baseball? Chicago is a powerhouse housing both the Chicago Cubs and the Chicago White Sox. Both teams have amazing parks to visit and are a shoe-in to be a blast for you and your crew. 

If you like football, catch a Bears game at Soldier Field and partake in the tailgating before the game with the rest of the fans for a once-in-a-lifetime experience.  

Best yet, all these parks and arenas hold world-class concerts, so be sure to check it out and buy your tickets ASAP!

Don't Forget Gifts for Your Crew

Traditionally, the groom also gifts their groomsmen for standing with them on the most important day of their life. But what should you get them? Buying locally makes your groom crew’s gifts memorable and supports the local community. We suggest you consider these local vendors below:

Koval is a fabulous couple-built Chicago-based distillery with one-of-a-kind products that any of your groomsmen will enjoy. 

The distillery has a rich history, being the first distillery in Chicago in two centuries. And yes, you can give your groom crew the tour and a taste of history.

The distillery is famous for its tasty craft drinks. Gift your friends some whiskey or gin that comes straight from the grain. Bourbon is a classic, while Cranberry Gin offers an unexpected twist.

Ashland Leather features Horween leather, a Windy City icon for over a hundred years. 

The brand focuses on the finest leathers with hand-crafted products like lush wallets, holders, belts, and watch straps in all shapes and sizes that your groomsmen will love.

To give the products an edge, they’re all named after famous Chicago gangsters and can be personalized. 

Fannie May is a treat for anyone with a sweet tooth.

The business has been a Chicago classic since the 1920s, providing delicious chocolates, sweets, and other treats. Stop by to pick or make your own box—there are even gift baskets for your groomsmen.


Where should my groomsmen or groom crew stay while visiting Chicago?

Chicago offers a wide range of hotels, pricing, and even some great Airbnb options! If someone wants to be in the city’s heart, tell them to stay in the Loop, but you may have some buddies who want to be closer to something more authentically Chicago. We suggest Wicker Park, West Loop, and Wrigleyville for great nightlife, food, and cozy neighborhood vibes. 

Are there any budget-friendly things to do in Chicago? 

Lincoln Park Zoo is FREE! It even offers several events, like ‘Night at the Zoo,’ which is exclusive for adults and features food and drink vendors from all over the city. 

Any ideas for a unique Chicago experience? 

Of course! The John Hancock Center is an architectural masterpiece with 100 floors. It will give your buddies a 360° view of the city and Lake Michigan. You can eat at multiple restaurants within the center if you’re hungry. The skyscraper also has a massage parlor and a souvenir shop.

Chicago: Your Groom Crew Kind of Town

With these suggestions, make Chicago “Your Groom Crew’s Kind of Town” and create great memories for all. Whether your groom crew is large or small, Chicago offers a wealth of activities that can make your appreciation of them fun and memorable. 

Subscribe to The Groom Club’s newsletter for more information on more things to do with your groomsmen before your wedding, what gifts to give your groomsmen, and more! The Groom Club is here to help and to ensure you and your crew have a great time together. 

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