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36 Hours in Chicago (From a Local)

The New York Times travel section recently updated their 36 Hours in Chicago guide, and it’s a pretty solid way to spend a quick weekend in our fair city. From classics like an architecture tour on the river to a comedy show at Second City to more innovative suggestions like a stop at the new American Writers Museum, there are certainly worse ways to take in all that Chicago has to offer. In fact, I may take a few of the suggestions myself and check out some of the restaurants they call out by name!

But it all got me thinking: how would I recommend someone spend a day and a half in Chicago? I grew up here; the museums and the lake and that skyline were all a part of the backdrop of my childhood. Just another day in the city. Moving back as an adult, I spent the first couple of years exploring as much as I could, learning my way around and getting my own feel for all the different neighborhoods.

These days, I get in most of my home-town tourism when I’m showing out-of-town friends and family around (which (happily!) happens more times than I can count in any given season). And then there was that stint when I actually was a tour guide, walking groups of eager, attentive travelers through Chicago history and its film connections.

Given all that, I feel like I’m as qualified as any to offer some ideas about where to go, what to see, what to do and what to eat if you’ve only got a quick few days to explore. Here’s how I’d spend 36 Hours in Chicago:

Friday Afternoon

Whether you arrive at Midway or O’Hare, if you drive in or coast in on a train, you’ll want to start your weekend with an adventure in the heart of the city. Make your way downtown and start at The Bean (also known as Cloudgate, but no one in Chicago calls it that. Nor do we call it Chi-town. Just FYI.). It’s worth seeing this iconic sculpture and Millennium Park that surrounds it; it’s like seeing the Statue of Liberty in New York. You want to be able to say you have. 

If it’s nice out, snag a bike from one of the nearby Divvy stations and make your way east from Michigan Avenue to the Lake Shore trail, a stretch of path that runs north and south along Lake Michigan. Head in either direction for amazing views of both the city skyline and the lake. If it’s not a great day for outdoor activities, never fear: Chicagoans are amazing at finding things to do indoors. For the artsy, do take an hour or two to wander the Art Institute of Chicago; there are certainly a few gems in there. Otherwise, head across Michigan Avenue to the Chicago Athletic Association Hotel, where you have a bunch of options for cocktails and a spot to chill. I recommend The Game Room, where there’s checkers built into the tables, shuffleboard and ping-pong tables for the taking, and a great selection of drinks and food. 

Friday Evening

Jump in an Uber or take the Pink/Green line trains out to Morgan St. to get to the West Loop. There are enough restaurants in this neighborhood that you could spend your day and a half just eating your way through them all, but I say stop at Maude’s Liquor Bar, a bustling French bistro off Randolph. With classics like mussels and cassoulet plus a decent selection of more standard fare, it’s a great spot to start your food tour of the city. And though reservations are recommended, you’ll actually have a shot at getting a table, unlike other popular places lining “restaurant row” (I’m looking at you, The Girl & The Goat and Au Cheval…). 

Save room for dessert, though, and head over a block to get a decadent treat from BomboBar, the walk-up, takeaway concept from parent restaurant Bar Siena. You might miss it if you don’t know it’s there (which now you do!), and that would be a bummer. Sure, you could get a sandwich or coffee, but what you’re really here for is a Bomboloni, a freshly made donut with your choice of filling that’s served in a little bottle you inject into the pastry. Sounds silly, but my goodness is it amazing.

Bombo Bar
Image direct from Bombo Bar

Friday Late Night

Once you’re well fed (and sugared up!), there’s still plenty of fun to be had in Chicago on a Friday night. Bars are open late, so you could head over to The Drifter, an actual speakeasy hidden behind a bookcase at the Green Door Tavern, for a custom cocktail and a bit of a show. But I think it’d be more fun to snag tickets to the late-night show at Chicago Magic Lounge. A fairly new addition to the city (it opened in 2015), there are a handful of shows throughout the week, but on a Friday night you can catch the classic show in their 120-seat cabaret. Converted from a 1940s laundromat, the illusion starts right at the front door, as you enter…through the laundromat!

Saturday Morning

There are a million places you could get brunch in Chicago, from Beatrix to Xoco to Jam to…you get the idea. But I’m going to recommend a Chicago classic, one that isn’t fancy but is delightful (and BYOB): Yolk. Wherever you stay in the city, there’s a Yolk nearby, and any of them will do. Be sure to arrive hungry, as every meal here is a hearty meal. I love the skillets and omelettes, though if you prefer a sweeter way to start your day, they’re known for a selection of decadent pancake dishes, too. Bring a bottle of bubbly and ask for their juice options to create your very own mimosas.

After breakfast, make your way to the Lincoln Park area to the Chicago History Museum. This is easily one of the most underrated spots in the city, and definitely worth a few hours of your time. From an original El train car to an immersive walk through Chicago’s blues history, you’ll discover much more about the Windy City than the story of the fire or the how the river turns green every St. Patrick’s Day. Be sure to check out what exhibitions are rotating through; in my experience they’re always worth checking out. 

Saturday Midday

By now, you’ll be in the Old Town neighborhood, a bit of Chicago that looks like it’s right out of a Dickens novel—look closely and you’ll see a cobblestone alley or two. Wander up and down Wells St. between Division and North Ave. for some window shopping and general neighborhood sightseeing. While you’re there, I recommend stopping for lunch at Small Cheval (cousin to the sought after “best burger in Chicago” at Au Cheval) if it’s not too busy. If it is, you’ll do fine at La Fournette, a hole-in-the-wall French bakery with soups, sandwiches, baguettes, macarons and any other sweet treat your heart desires.

Between lunch and dinner, you’ll want to try to see a bit more of the city. My idea of a nice afternoon includes a walk through the Lincoln Park Zoo, Chicago’s big, free zoo with all the classics: giraffes and rhinos and even a brand new habitat for their polar bears. If it’s the holiday season, that means it’ll get dark out early enough to check out Zoolights, their annual holiday display. Animals and Christmas? Win! Just across the park from the zoo is the Lincoln Hotel, where you can head up to the rooftop bar, the J. Parker, to enjoy a cocktail with breathtaking views of the city (and the zoo you just visited). 

Saturday Night

Saturday night in Chicago means finding a great spot for dinner, and like brunch, there’s no shortage of options. You could head back to Randolph St., but consider exploring a new neighborhood if you’re feeling adventurous.  You could head out to Pequod’s Pizza for a taste of real Chicago pizza (please, please avoid Lou Malnati’s and Giordano’s…), or class it up a bit and head north to Band of Bohemia, a simply stunning re-furbed warehouse in Ravenswood with a Michelin star. Technically a brewpub, you can let the chef take the lead and enjoy their tasting menu, or select from starters, entrees and sides that’ll make you swoon. 

Now that you’re up on the northside, make your way over to Lakeview, the neighborhood that Music Box Theatre, Chicago’s best cinema, calls home. Founded in 1929, the main theater is as grand as it was ninety years ago, and today there are modern additions like a lounge space to chill before or after your film and a small second screening room that often features some exceptional arthouse fare. But for this weekend, check out their Midnight Movie screening schedule, which will probably include something like Rocky Horror Picture Show or the cult hit (for some reason) The Room. The schedule changes from week to week, and if you’re up for a late night, whatever they’re showing is likely worth staying up for. 

Image courtesy of Music Box Theatre

Sunday Morning

Your weekend in Chicago is winding down, and if you’ve followed along on this itinerary so far, you’ve been on the go pretty much the whole time. So it’s understandable if by this point you’re looking for a simple Sunday morning. Skip the long brunch lines and go for a straightforward (but wholly delicious) breakfast at Bang Bang Pie & Biscuits (two locations!).  One of their breakfast biscuits (with and egg!) and a hot cup of coffee makes for a lovely Sunday morning. Throw in a copy of the Sunday Tribune and you might just pass for a Chicagoan.

If you’ve still got time before you head back home, I’ll wrap up my 36 hours with one recommendation that does overlap with the New York Times. They list the American Writer’s Museum as a stop early in their weekend, and while it is a cool place to check out, it won’t take you more than an hour or so to wander the small—but mighty!—exhibits on writers and writing. You can pop over for a bit on your way out of town, getting one last glimpse of downtown before you go.

Honorable Mentions

There is so much to do in Chicago, I couldn’t possibly list everything. If you’re looking for a great view, order a cocktail at the Signature Lounge on the 96th floor of the Hancock Building. You’ll save the $40 it costs to go to the top of the Sears Tower and get a view of the skyline that actually includes that iconic high-rise. If you really want to experience the best meal in Chicago (and have about $300 or so per person to spare), plan well in advance to experience Alinea, a three Michelin star restaurant with Chef Grant Achatz at the helm. It’s hard to choose just one show to see in Chicago’s massive theater scene, but it’s worth looking at what’s currently playing, from Broadway in Chicago to the Belmont Theatre District. 

How will you spend your next visit to Chicago?

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