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GreenMill
Photograph: Martha WilliamsTravel back to a bygone era with live music at the Green Mill.

The 10 best things to do in Uptown

Our staff picked the absolute best of the best to list 10 essential things any visitor must do in the neighborhood

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We compiled the top restaurants in Uptown. We gave you a list of bars that ran far deeper than just Green Mill. We told you where to shop in the neighborhood beyond Target, and let you know that cheap eats means more than the new Sonic. Frankly, there's a lot to do in this overlooked stretch of Red Line territory. It could take days if not weeks to check off everything on those lists. So we made it even easier for your one-day trek to Uptown and Argyle with a to-do list of the essentials. Here are the 10 best things to do in Uptown.

RECOMMENDED: Our complete guide to Uptown

Carol’s Pub
  • Bars
  • Dive bars
  • Uptown

A honky-tonk in Sheridan Park with $1.50 domestics on Mondays, country & western karaoke on Thursdays and the house band Diamondback on weekends, featuring sassy little Reba singin’ and strummin’ rhythm with a darn good gee-tar picker on lead. A pool table in back, greasy grill turning out late-night burgers and Hank-filled jukebox round out the grit fest.

Aragon Ballroom
  • Music
  • Rock and indie
  • Uptown

This beautiful, ornate and capacious space opened as a ballroom in 1926. These days, though, it serves as one of the biggest music venues within the city limits. The 4,500-capacity room hosts acts such as The National, Lorde and deadmau5.

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  • Restaurants
  • Chinese
  • Uptown

For the uninitiated, Lao Sze Chuan is the one that started it all, the restaurant that marked chef and restaurateur Tony Hu’s emergence, the city’s standard-bearer for Szechuanese food (in all its chili-oil and peppercorn glory). It was the first—and so far, only—restaurant that Hu, who immigrated to the United States in 1993, carbon-copied, opening satellites in Downers Grove and Connecticut. This was before the Great Tony Hu Chinatown Conquest of the Late Aughties, which brought Lao Beijing, Lao Shanghai, Lao Hunan, Lao You Ju, Lao Yunnan and Lao Ma La.

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Graceland Cemetery
  • Things to do
  • Literary events
  • Uptown

Since 1860, the Graceland Cemetery has been the final resting place for numerous famous Chicagoans. Pay respect to Roger Ebert, city planner Daniel Burnham, boxer Jack Johnson, the brother of Charles Dickens and many more.

Hopleaf
  • Bars
  • Beer bars
  • Uptown

Thought this was just a bar to belly up to with a Belgian brew in hand? One bite and you’ll know there’s much more. Our perfect night involves sampling the drafts at the bar while slurping down the famous ale-steamed mussels. Beer geeks know this is the place in town to school their palate on craft brews.

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Argyle Night Market
  • Shopping
  • Markets and fairs
  • Uptown

The Argyle Night Market, held Thursday evenings from 5–9pm from July 10–September 4. It includes farm vendors, plus stalls featuring Argyle Street restaurants.

Montrose Beach
  • Things to do
  • Uptown

A fenced-off dog area at this neightborhood beach provides a place for your pooch to run around. Elsewhere, visitors can play volleyball, sit under an umbrella or enjoy the free wifi. Amenities: concessions, kayak rentals, watersports rentals, restrooms, life guard first aid station.

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42 Grams
  • Restaurants
  • American
  • Uptown

It’s BYOB. It uses a ticketing system and each ticket costs $203.68*. That includes taxes and service, but it’s pricey. And worth it. Jake Bickelhaupt is one ballsy chef. 42 Grams follows Elizabeth and Fat Rice as the latest underground restaurant turned brick-and-mortar spot. It’s like Schwa and Goosefoot in that it’s a small neighborhood spot and it’s BYOB. But the voice coming out of the kitchen is inventive, personal and fresh.

Green Mill
  • Bars
  • Cocktail bars
  • Uptown

Al Capone and other gangsters used to hang here in the 1920s, but these days it’s all about the music. Owner Dave Jemilo, who returned the club to its original luster in the 1980s, books smart bebop and mocern jazz with a discriminating ear.

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