Boasting arguably the most stacked dining and drinking scene in the city, the northwest side hipster haven of Logan Square also serves up chic shopping, one of the city’s best public spaces and more. 
Where To Eat
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3025 W. Diversey Ave. / Website
This no-nonsense, no-reservations wine bar and eatery has been gaining accolades since it opened nearly 10 years ago—so it’s no big surprise that it was named among the city’s 2023 crop of Michelin Bib Gourmand recipients.
See Also: The Ultimate Chicago Neighborhood Guide
2375 N. Milwaukee Ave. / Website
Vegetables play a leading role at chef-partner Joe Frillman’s charming 70-seat Logan Square spot, but he also taps into his talent for pasta making, which he discovered working at Balena and The Bristol. Look for seasonal pastas ranging from pappardelle with mushroom ragu to addictive whole wheat tagliatelle with walnuts.
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3209 W. Armitage Ave. / Website
From Jonah crab salad with waffle fries and cocktail sauce to bucatini with bacon, jalapeno and anchovy, crowd-pleasing, whip-smart cuisine is on the menu at chef Jason Vincent’s beloved neighborhood fave. Pro tip: The team’s next door Pizza Matta is low-key one of the city’s best pie joints.
See Also: The Ultimate Guide To The West Loop
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2507 W. Armitage Ave. / Website
Omakase restaurants are a dime a dozen in Chicago these days, but few can stand up to chef Otto Phan’s exquisite tasting menu, an intimate seafood journey of 2.5-3 hours that is sensational—and seriously expensive at a whopping $440-$490 before beverages.
2200 N. California Ave. / Website
Charcuterie and salumi is an art form at this hot spot—and the stunning meat and cheese boards are masterpieces in themselves, exquisitely arranged with toothsome selections like succulent spreadable ‘nduja, spicy saucisson l’ail and artisanal cheeses with all the accompaniments, from almonds and olives to seasonal jam and grainy mustard.
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2657 N. Kedzie Ave. / Website
One of the ’hood’s great hangouts, this lively farm-to-table restaurant and whiskey bar beckons with soul-satisfying grub (the wild boar sloppy joe is a classic) and expertly made cocktails. Want to stay a while? Six casual but smartly appointed rooms upstairs are available by the night.
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2537 N. Kedzie Blvd. / Website
This iconic, community-focused dining destination from chef Jason Hammel and Amalea Tshilds offers mostly organic, very veg-friendly farm-to-table plates like chickpea and fennel tagine and steak tartare with smoked beets and crispy lentils.
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2800 W. Logan Blvd. / Website
Chef Diana Davila and team serve up creative takes on classic Mexican dishes like elote-style spaghetti squash, broccolini al carbon and charred salsa- and beer-braised chicken thighs.
2824 W. Armitage Ave. / Website
Inspired by the Piemonte region of northern Italy, this cozy and convivial spot from Aldo Zaninotto offers delectable plates like bagna cauda, gnocchi with prosciutto, peas and kale, and Slagel Farms lamb with crispy potato wedges and gremolata.
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3059 W. Diversey Ave. / Website
Indian flavors with a global perspective add up to toothsome plates like the signature butter chicken calzone, lamb kebab pizza and a brunch Bombay sandwich with smoked beet and salted jalapeno.
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2728 W. Armitage Ave. / Website
This rustic neighborhood spot takes inspiration from the traditions of the Alps, which translates to a smartly curated selection of charcuterie and cheese plus comforting plates of three-mushroom risotto and slow roasted pork shoulder.
What To See & Do
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Bloomingdale Avenue between Ashland and Ridgeway avenues / Website
Officially known as the Bloomingdale Trail, this former rail line is now a 2.7-mile system of parks and trails that has given the city’s northwest side much-needed green space for walkers, bikers and families to explore.
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2047 N. Milwaukee Ave. / Website
Billing itself as “Chicago’s most eclectic music venue,” this 1500-capacity club has hosted everyone from experimental indie band Animal Collective to drag performer Shea Coulée.
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2040 N. Milwaukee Ave. / Website
Hannibal Buress, Natasha Legerro and Kumail Nanjiani are among the notable talents who have graced the stage of this longtime comedy club, which fills three stages with standup, sketch comedy and more.
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2646 N. Milwaukee Ave. / Website
This classic movie house opened in 1915 and has been a community staple ever since. Expect a lineup of independent-leaning arthouse fare, Tuesday trivia nights in the lounge and late-night showings of classics like Taxi Driver and Donnie Darko.
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3420 W. Armitage Ave. / Website
A must-visit destination for blues fans since 1984, this iconic music destination boasts a welcoming vibe and a spectrum of performers ranging from traditional to modern.
Where To Shop
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2523 N. Kedzie Blvd. / Website
This dog-friendly, community-minded bookstore focuses on contemporary fiction and nonfiction and draws a community crowd for book clubs, author readings, storytelling and more.
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2317 N. Milwaukee Ave. / Website
A smartly curated mix of emerging and established designers populate the racks of this upscale women’s boutique, which focuses on personalized service to help customers build or round out their wardrobe.
3505 W. Fullerton Ave. / Website
Discover a hypercurated selection of chic home goods from around the globe—think exquisite Japanese measuring cups and British tree swings—at this eminently browseable storefront.
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3131 W. Logan Blvd. / Website
Dubbed “Chicago’s handmade marketplace,” this eclectic, female-owned storefront features wares from more than 300 Windy City artisans—think everything from jewelry and home accessories to apparel, zines and more.
Hit The Town
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3143 W. Logan Blvd. / Website
This award-winning cocktail bar is one of the city’s fave mixology spots and serves an array of classics, seasonal libations, spirit-free drinks and more, plus creative takes on bar snacks (duck snickerdoodles anyone?).
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2165 N. Western Ave. / Website
Chef Jason Vincent and his Giant teammates are the brains behind this colorful, playful hangout, which serves tropical-meets-botanical cocktails alongside craveable riffs on Chinese-American fare like crab rangoon and orange chili chicken.
2812 W. Palmer St. / Website
This sultry, low-lit mixology haven is hidden behind an unmarked door next to its sibling Lardon, but that hasn’t stopped Chicago cocktail lovers from packing the place for its ubercreative libations from day one.
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2952 W. Armitage Ave. / Website
Negroni slushies anyone? Oh, and one of the best fried chicken sandwiches in the city, plus killer hush puppies, milkshakes and more, all on on of Logan Square's chillest-yet-sceniest patios.
3201 W. Armitage Ave. / Website
Gin is the focus of this neighborhood fave, though you’ll find plenty of other spirits haunting the smart cocktail list, along with a surprisingly toothsome food menu with plates like fire chicken scallion pancake and black sesame beignets with miso caramel.
2456 N. California Ave. / Website
Downstairs from always-hopping Italian joint Testaccio, this swank wine bar offers a little taste of Paris with red velvet banquettes from legendary Chicago brasserie La Sardine and a Champagne-centric wine list.
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2758 W. Fullerton Ave. / Website
Stylish atmosphere and top-notch classic and creative cocktails (not to mention an inviting patio plus nibbles by Umamicue) make this a Logan Square go-to.
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2421 N. Milwaukee Ave. / Website
This hipster bar is many things—record label, gallery and performance venue among them—but it’s best known for its smart, creative list of cocktails, which it’s been shaking up since 2008.
Where To Stay
2444 N. Elston Ave. / Website
Fitness fanatics are in heaven at this recently built boutique property on the site of Midtown Athletic Club, where guests get full access to the location’s pools, tennis courts, yoga studio, boxing gym and more, all just a few miles northwest of downtown.
See Also: The Ultimate Chicago Neighborhood Guide
Photography by: Top photo by Eduardo Fonseca Arraes/Getty Images; Daisies photo by Neil Burger; Lardon photo by Clayton Hauck; Osteria Langhe photo by Kristen Mendiola; FELT photo by Wade Hall; Meadowlark photo by Clayton Hauck
