Drinks at Weegee's. Photo by Adam Jason Cohen

Cities

Avoid Amateur Hour in the Windy City

Skip the long lines and weekend warriors & go where the locals hang.

Going out in Chicago can be a blast, but locals know the best way to avoid long lines and overenthusiastic weekend warriors is to step out on a weekday or venture off the beaten path. While the city is an ideal place to get weekend-wild, there’s plenty to do throughout the week to avoid the deluge of thirsty amateurs on Friday and Saturday nights. From dance nights on Tuesday, slow jams on Thursday, and Friday night karaoke to day-drinking at Sunday brunch—this list has you covered, every day of the week, whether you’re here to visit Chicago or looking for what to do as a local.

Monday

Maria’s Packaged Goods
960 W 31st St

Start your week with a few sips at Maria’s Packaged Goods in Bridgeport. Named after Maria Marszewski, a onetime hairdresser from Busan, South Korea, who’ve passed on the restaurant to her sons, Maria’s has been a classic “slashie” (half community tavern/half liquor store) since 1986. On any day of the week, you’ll find exactly what you’re looking for at Maria’s: good tunes, strong cocktails, and about 200 beers to choose from. The recent addition of Kimski, the adjoining counter-service joint, means you can pair Korean-Polish street food with your beverage of choice. Kimchi fried rice and a Marszewski Mule? Now that’s a good Monday night.

The bar at Danny’s.
photo by Adam Jason Cohen

Tuesday

Danny’s
1951 W Dickens Ave

A little-known secret is that Tuesday is the best night for dancing in Chicago, and Danny’s is a big reason why. Tucked away on a residential street in Bucktown, Danny’s would be easy to miss if it weren’t for its neon Schlitz sign. The tavern is set on the first floor of a residential building, and the interior makes a busy night feel reminiscent of the best house parties where the rooms are dark, the music is loud, and the bodies are moving. If you’re lucky enough to visit on the third Tuesday of the month, there’s Night Moves, a monthly disco, house, and funk party. If you miss Night Moves, check out Smiths Night, an equally danceable event every fourth Tuesday.

Wednesday

The Promontory
5311 S Lake Park Ave West

With a calendar packed with events like dancehall parties, Afrofusion nights, and the Moth storyslams, it’s impossible to choose the best day of the week for a visit to the Promontory in Hyde Park. Still, the bar at this restaurant and music venue is the perfect spot to end hump day amongst the Promontory’s grown-up and sexy clientele. A seasonal cocktail menu means you can enjoy a hot buttered rum during Chicago’s brutal winters and cool off with a frozen gin and tonic in the summer. For those staying dry, the menu also offers thoughtful nonalcoholic options, like a lemonade with smoked blackberries or a pear nectar mocktail with pineapple and cinnamon.

Thursday

The Whistler
2421 N Milwaukee Ave

Every third Thursday of the month in Logan Square, a line forms outside of a bar called the Whistler. The bar is no stranger to weekend lines, but this particular line is for Slo ’Mo, a night of slow jams for queer fam. You know the artists by name: Sade, Janet, Prince. What you don’t know is how loose a Thursday night can get. Arrive early and chill on the patio till the dance floor gets live or snag a seat by the bar while you watch folks of all identities unite under a collective love of the body roll. Either way, don’t be late.

Friday

Alice’s Lounge
3556 W Belmont Ave

In Avondale, Alice’s Lounge is the karaoke bar for all those who scoff at karaoke. There’s nothing particularly cool about this dive. It isn’t design-forward, there isn’t a carefully curated beer list, and you won’t find much else to do on this strip of Belmont Avenue. In short, it doesn’t have the trappings of typical places on travel lists like this. What it does have is Fred, Chicago’s best (and perhaps the world’s best) karaoke DJ. He’s ornery, sure, but his love of karaoke shines through his air-guitar accompaniment, backup vocals, and unenthusiastic commentary on each performance. Expect to hear renditions of the latest Top 40 hits, classic rock standards, and favorites from the ’90s through the early aughts. Most nights, Alice herself will be behind the bar slinging cold Okocims till 4 a.m., so practice your scales and leave your judgment at the door.

Take some time to lounge at Weegee’s.
photo by Adam Jason Cohen

Saturday

Weegee’s Lounge
3659 W Armitage Ave

After dancing and singing your way through the week, you’re ready for a chill Saturday night. Enter Weegee’s Lounge. Named after NYC crime photographer and photojournalist Weegee, this moody Logan Square joint gestures toward the 1940s without feeling contrived, and the era-appropriate music is never too loud. Weegee’s has all the things you want out of a Saturday night (like shuffleboard, a photo booth, and an airy beer garden) and none of the things you don’t want (like bros, lines, and high prices).

Sunday 

Café Marie-Jeanne
1001 N California Ave

While we can all agree that getting out of bed after a night (or week) of drinking sounds miserable, sometimes brunch is a necessary evil. Café Marie-Jeanne’s “curatives” menu offers healing concoctions when you’re having a rough Sunday morning, while drinks from the cocktail menu like “The Day After Amaro” help you pick up where you left off on Saturday night. Equally as important is the à la carte brunch menu, from which combinations are endless. Lamb sausage with eggs and cheddar grits? Hell yeah. Smoked trout with baby lettuce and home fries? You got it. Caviar toast with sautéed calf brains and fried chicken livers? Uh . . . okay. Anyway, there’s nothing quite like some French-inspired bites and a little daytime drinking to wrap up a fun-filled weekend.

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