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Uptown
Profile
Uptown is growing, developing, and redefining itself. But here’s the best part: it hasn’t yet hit the fever pitch of some other up-and-coming neighborhoods, so it’s kind of like you’re getting in on the ground floor. And that ground floor can be pretty awesome.
First off, the neighborhood gives you a super diverse mix of food at your doorstep, from Ethiopian to Vietnamese, plus American brunch, Chinese barbecue, fresh sushi, and sizzling pub burgers. Then there are the historic and cultural gems, like the jazzy Green Mill or stately Riviera Theatre, as well as all the offerings in the Asia on Argyle district. On top of that, Uptown has some of the nicest 20th-century Art Deco architecture in the entire city — but stroll just a few minutes down the street to enjoy the sandy shores of Lake Michigan, complete with the Lakefront Trail, multiple beaches, and a dog park. There are restored Victorian homes and brand-new modern apartments at surprisingly affordable prices, all in an area with just enough edgy charm to keep things interesting.
Uptown is glitzy theaters and dimly-lit jazz shows. It’s summer afternoons at Montrose Beach, spent soaking up the sunshine and enjoying the sparkling views. It’s sampling Vietnamese delicacies along West Argyle, then popping into the Fat Cat for a 40s-inspired cocktail. Discovering Uptown is kind of like the feeling you get when you try a new cuisine, and realize it just became your favorite food.
Backstory
The original plans for Uptown were grand: to create a new central Chicago, ready to rival the other great cities of America’s Northeast. Showy buildings, entertainment hubs, and chic residences sprang up, promising something big in this community six miles north of downtown.
For years, Uptown was a center of nightlife and jazz music, and was very popular during Prohibition. But the neighborhood was hit hard by 1929’s catastrophic stock market crash — and the Great Depression that followed. Magnificent hotels and single-family homes were split into smaller units, buildings fell into disrepair, and expanding transportation sent people off to other neighborhoods.
But now, after years of flying under the radar, Uptown is seeing a major revival. Buildings are getting restored and revitalized, new housing options are popping up left and right, and this super diverse area continues to redefine itself over time.
Local Fare
- Tiztal Cafe: Head here for an extensive breakfast and brunch menu, fusing American comfort food and Mexican cuisine. Enjoy some chilaquiles in their cute, eclectic patio.
- Sun Wah BBQ: Something of an Uptown institution, this Chinese classic has seen its fair share of influential diners, including Mayor of Flavortown himself, Guy Fieri. If there’s one thing to try, it’s the Beijing Duck Dinner, using every part of the duck to create a multi-course feast.
- Kie-Gol-Lanee: Oaxacan-inspired kitchen. Their chocolatey-spiced mole is the perfect way to warm up on a cold evening.
- Nha Hang Vietnam Restaurant: A tiny, cozy, family-run spot serving seriously home-cooked flavors. The pho is delicious, but so is everything else on the menu.
- Demera: Incredible Ethiopian food, plus with a full bar with cocktails and house-made honey wine. Don’t skip the coffee — they roast their own beans on location.
- Tesfa: A family-run, casual Ethiopian restaurant with three different kinds of injera. Perfect for a group dinner, just call ahead to reserve a table.
- Tweet: Big plates of brunch classics using lots of organic ingredients, served with plenty of mimosas or bloody marys. The entire space is decked out in original artwork hand-picked by the founder
Things to Do
- Neighborhood Events: Uptown has several festivals throughout the year. For instance, there’s Argyle Night Market, a series of weekly Asian food markets during the summer. There’s also the Annual Taste of Uptown, a restaurant crawl where you get a food passport stamped after each sampling.
- Green Mill: Tucked inside one of the neighborhood’s long-standing Art Deco structures, this jazz bar was a favorite of Al Capone. There are live shows nightly, with a full calendar on their website. Cash only.
- Montrose Beach: There’s a mix of sand, grass, trails, and paved pathways — as well as a cute dog park and nearby dining options.
- The People’s Music School: An amazing organization that offers free music education to underserved students. You can attend regular family-friendly concerts that range from student recitals to professional orchestras and more.
- Aragon Ballroom and Riviera Theater: Both built in the early 1900s, these are not just beautiful buildings — they’re also some of the best places in town to catch a live concert.
- Asia on Argyle: Head to this district to pick up Asian groceries, or grab a bite at one of the many stellar restaurants. In the summertime you can swing through the weekly Argyle Night Market, and each year there’s a big Lunar New Year celebration.
Sights to See
Graceland Cemetery: This massive cemetery is the burial site of many famous Chicagoans. But it’s also a certified arboretum, giving it a park-like feel with tons of trees and greenery.
Transportation
Uptown has two L stations — Argyle for the Red Line, and Wilson for both Red and Purple Express, which can make commuting to the Loop a breeze. There’s also a Metra station in Ravenswood to the west, the bike-friendly 18-mile Lakefront Trail to the east, and multiple bus routes in between.
- the Loop: ~35 min by public transit
- the Lake (Montrose Beach): ~20 min walk
- O’Hare: ~60 min by public transit
- Midway: ~60 min by public transit