Explore Chicago

Chicago for a Guys Getaway

When we feel the weight of the world on our shoulders, we know it's time to get away and put some work-play balance back in our lives. And what better way than to put aside responsibilities than to make some memories with best buds in the Windy City? We've put together a guide to the best dining, drinking, shopping and adrenaline-inducing activities that are all for the boys.  

Chicago Cut Steakhouse

Prime riverside location, sophisticated surroundings and a menu of chops, shellfish and dry-aged steaks hand-cut on site draw carnivorous crowds to this upscale-casual spot. Late-night dining. B, L (M-F), D (daily), Br (Sa-Su). 

K1 Speed

Adrenaline junkies zoom around the track at this indoor go-kart racing center. Zero-emission go karts can whiz up to 45 miles per hour. Billiards and a bar round out the amenities for corporate team building events, birthday parties and more. Open M-Th noon-10 pm; F 11 am-midnight; Sa 10 am-midnight; Su 10 am-10 pm.

The Tie Bar

Founded in 2004 as a virtual store, The Tie Bar's first physical location is along trendy Armitage Avenue in Lincoln Park. Men can find classic and stylish ties, bow ties, socks, pocket squares, and even select apparel items for affordable prices.


Slink past two unmarked doors to find a whole world of nightlife awaiting in this cavernous space that pays homage to the Prohibition era. Craft cocktails, beer and the largest collection of American Whiskey in North America complement supper club fare reimagined for today’s palette.

Chicago Helicopter Experience

The Chicago Helicopter Experience flies along the lakefront, over Lake Michigan north to Wrigley Field and then south back down to the private downtown heliport. They’re climate-controlled with leather seats and bubble windows. You can purchase an 8x10 of you and your group in front of the helicopter.


There are times we want to wear our favorite button downs but want to look a little more casual. Leaving those typical lengths untucked though results in an outfit that reads more sloppy than laidback. Enter UNTUCKit, a line of men and women’s shirts that fall at that perfect hip length.

Revolution Brewing

This smart Logan Square hangout pulls pints of six house-made beers and serves up a playful bar food menu that ranges from bacon fat popcorn to smoked pulled pork with honey-jalapeno slaw and a tempeh Reuben. Open M-F 11 am-1 am; Sa, Su 10 am-1 am.

Millennium Park

The #1 tourist attraction in the Midwest! Discover a state-of-the-art collection of architecture, landscape design and art that provide the backdrop for hundreds of free cultural programs including concerts, exhibitions, tours, and family activities.

Pritzker Military Museum Library

From Civil War history to wartime fiction to posters of Uncle Sam, this library across from Millennium Park and the Art Institute brims with material that emphasizes the importance of “citizen soldiers” in preserving democracy.

Lou Malnati's

Not Chicago’s biggest name in pizza, but quite possibly the best. Pies sport a flaky, buttery crust and sweet, tomatoey sauce; service is fast and friendly; and the space is comfortable and kid-friendly. Many Chicagoland locations. L, D (daily).

The Red Door Salon Spa

Elizabeth Arden's full-service day spa offers one-stop beauty shopping, from skin care services, facial treatments, waxing and massages to manicures, pedicures, hair treatments and makeup artistry.

SPiN Chicago

In 2009, Susan Sarandon opened SPiN New York, a pingpong social club, opening up a whole new entertainment concept. In 2016, SPiN Chicago debuted sporting 20 tables, a full bar and restaurant and several VIP lounges. M-W 4-11 pm, Th 4 pm-midnight, F 2 pm-2 am, Sa noon-2 am, Su noon-8 pm.