Only have a weekend in Chicago? Our hospitable Midwestern instinct is to beg you to stay longer, but luckily, you can pack a lot of Chicago into 48 hours. America’s third-largest city is brimming with one-of-a-kind sites: From prohibition-era speakeasies and stunning architectural gems to hole-in-the-wall taco joints and Michelin starred restaurants, there are endless reasons to visit Chicago. But you already knew that. Take a big bite of Chicago culture with this well-rounded smorgasbord of things to do, see, eat and drink in the city by the lake. And come back for a longer stay next time, won’t you?
Kick off your weekend with a show at Chicago’s iconic home to sketch comedy and longtime Saturday Night Live talent incubator. The lineup of shows at the Second City changes every few months, but the ongoing Mainstage and e.t.c. stage shows—both written in-house—are consistently hilarious choices.
Close out the evening with a visit to another local landmark. The Green Mill, originally opened in 1907, was a favorite of Al Capone’s, allegedly because of its clear views to the front and back doors. Grab a cocktail at this Uptown jazz club and don’t forget to snap a photo (or better yet, a Boomerang) of the flickering marquee out front on your way out.
Head to Michigan Avenue to check out one of Chicago’s best brunches. Cherry Circle Room is tucked away inside the Chicago Athletic Association Hotel, formerly a men's club that reopened in 2015 to become one of Chicago's hippest spots. After your meal, take the elevator up to Cindy’s, the hotel’s rooftop bar, for sweeping views of Millennium Park and the lakefront as well as excellent cocktails.
Cross the street to wander around Chicago's beloved Millennium Park, which opened in 2004. There's no shame in snapping a selfie in front of Cloud Gate (a.k.a. the Bean) before checking out Frank Gehry’s stunning Jay Pritzker Pavilion. It's touristy, sure, but believe us when we say that locals love the Bean, too.
Take the pedestrian walkway from Millennium Park to the Art Institute of Chicago, which houses some of the most important works in art history. Admire the vast impressionist and American collections, the impossibly tiny Thorne Rooms and contemporary works in the Modern Wing, which opened in 2009. It's easy to spend hours exploring the Art Institute's galleries.
Take the Pink Line to Pilsen for an outstanding taco dinner at Carnitas Uruapan, an unpretentious storefront joint. As the name suggests, this place specializes in chunks of tender, slow-cooked pork. It's served by the pound alongside corn tortillas and salsa so you can assemble your own tacos.
For over 35 years, Wrigleyville's Smart Bar has been the heart and soul of Chicago’s robust house-music tradition. The 400-capacity dance club is tucked below Metro Chicago and hosts a lineup of cutting-edge DJs spinning house, techno and electro beats. Plus, if you feel like dancing the night away, Smart Bar stays open till 4am.
There are tons of exciting restaurants in Logan Square, but Lula Cafe never disappoints. The neighborhood staple was specializing in farm-to-table eats before it was a thing, and that philosophy still holds true today. Look out for seasonal dishes like coconut brioche French toast and egg noodles in savory mushroom broth.
Head inside to check out the Garfield Park Conservatory, which was described as “landscape art under glass” when it opened more than a century ago. Good news for your wallet: The light-filled space is free and open to the public every day of the year. The conservatory features some 600 flora species, including succulents, lush ferns and blooming flowers.
Whether it’s window shopping or actual shopping, an afternoon wandering Milwaukee Avenue in Wicker Park is an excellent way to end your trip. Go crate-digging at Reckless Records, shop vintage treasures at Una Mae’s and Vintage Underground, step into a lush wonderland at Asrai Garden and stroll through stacks of tattered volumes at Myopic Bookstore.
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