It’s not that there’s anything wrong with The Bean (or Cloud Gate, if we’re getting technical). The Bean is great. It’s cool looking, and honestly totally worth the crowd to get a picture of how weird it makes your reflection look. That said, every minute you spend with The Bean is a minute you could be spending somewhere a little less crowded and a little more Chicago. Here’s how to spend a weekend like you know the place.
WHAT TO EAT
We’re not going to tell you to skip the deep-dish pizza and Chicago-style hotdogs. We would never. We just want make sure you’re doing it right.
Built in 1948, this drive-in diner is about as old-school-kitsch as it gets. You can’t miss it, as it’s topped by two huge anthropomorphic hotdogs swooning over each other. It’s also one of the best places to get an authentic Chicago hot dog. Drive-in ordering is really where it’s at here; pull up to a menu, flip a switch, place your order, and let them bring it to you. A note for the uninitiated: If you put ketchup on your hot dog, they’re going to judge you. Superdawg Drive-In, 6363 North Milwaukee Ave., Chicago, IL, (773) 763-0660, superdawg.com
Pequod’s is Chicago deep-dish pizza with a twist. Unlike anything you’ll get at Uno’s, Pequod’s signature take on Chicago-style pizza has a caramelized cheese crust. And that is an addition worth exploring. Pequod’s Pizza, 2207 North Clybourn Ave., Chicago, IL, (773) 327-1512, pequodspizza.com
There are two reasons to go to Diner Grill, and they’re both great. The first is you want to have a super-retro dining experience (Diner Grill has just ten bar stools facing the grill, where you can watch your delightfully greasy food being made). The second reason is that it’s 4 a.m., and you want a cheeseburger. A hotspot for the post-bar crowd, Diner Grill is open 24 hours for dine-in and carryout. Diner Grill, 1635 W. Irving Park Rd., Chicago, IL, (773) 248-2030
WHERE TO STAY
Forget Marriott or Hyatt—Chicago is full of one-of-a-kind places to sleep.
Looking for a slice of history? Check out the Hotel Burnham, built in 1895 and located in the Reliance Building, a U.S. National History Landmark right in the Loop. It’s been home to some dubious characters: Al Capone’s “Dentist” (read: drug dealer) used to work out of room 809. It’s a beautiful building full of stories and close to basically everything. Hotel Burnham, 1 W. Washington St., Chicago, IL, (866) 690-1986, burnhamhotel.com
Soho House Chicago
If you’re more interested in seeing the newest Chicago has to offer, Soho House Chicago is right up your alley. This former belting factory was renovated into one of Chicago’s newest and niftiest places to stay. It’s hard to say what’s coolest about it: the rooftop featuring a 60-foot swimming pool and a killer view, or the gymnasium where you can take MMA classes and fight in a professional boxing ring. Soho House Chicago, 113 N. Green Street, Chicago, IL (312) 521-8000, sohohousechicago.com
WHAT TO DO
Unless you’re there with kids or you really, really love touristy stuff (no judgment), skip Navy Pier. Instead, hit up…
Lincoln Park Zoo
It’s hard to recommend a zoo to a Cincinnatian, but this one is great. It’s also free, and any trip can use a no-cost activity. Since it’s in the heart of Lincoln Park, once you’re done checking out the animals you can stroll through beautiful gardens and check out the nearby lakefront. Lincoln Park Zoo, 2200 N. Cannon Dr., Chicago, IL, (312) 742-2000, lpzoo.org
Museum of Science and Industry
The best museums are the ones where you get to touch stuff. The Museum of Science and Industry prides itself on its interactivity, so there’s never a boring minute. Go through the disorienting Mirror Maze, create digital fireworks, ride through a coal mine. This is a “so much to do and so little time to do it” kind of museum, no matter how much time you have. Museum of Science and Industry, 5700 S. Lake Shore Dr., (773) 684-1414, msichicago.org
This post has been updated.