The Resy Guide to Outdoor Dining in Chicago

Tarantino’s serene sidewalk patio, set beneath twinkle lights on a tree-lined street, has our hearts when it comes to date night. Expect refreshed takes on Italian-American standbys, like grilled polenta with Italian sausage and bell peppers, apricot rack of lamb with mashed sweet potatoes, and rigatoni with mushrooms, sun-dried tomato, prosciutto, peas and cream. Consider making an occasion out of any old Tuesday, when select wines are half off with dinner orders.

The sprawling, 4,000-sq.-ft. patio at this Neapolitan-style pizzeria is the place to go when you just want to lounge over a few quenching frozen cocktails (ahem, rum punch!) and deliciously cheffy pizzas. Lobo offers a tight selection of crisp-edged pies, starters and salads from chef Dan Snowden (Bad Hunter). As August stretches out before us, we’re loving the summery specialty pizza with heirloom tomato, anchovy, burrata and charred spring onion relish.

Perched seven stories up at the chic Ace Hotel, this indoor/outdoor, year-round rooftop serves skyline views to match tasty bites (like cheddar-caramel popcorn and chicken katsu sliders with chili mayo) and fun drinks (like the Tonight, Tonight with mezcal, Campari, red vermouth and orange peel), all set to a soundtrack for good times.

We love the plant-filled, fenced-in beer garden at this hipster favorite in Wicker Park. The scratch-made, veg-friendly comfort food includes a killer brunch menu. The huevos diablos — with fried eggs, jack cheese, hand-pressed corn tostadas, chipotle sauce, black beans and brown rice — is a never-fail hangover cure, best washed down with the vegan Bloody Hammer, comprising Tito’s and house Bloody Mary mix and topped with a fried pickle.

Another favorite (also Italian) al fresco date spot in the city, this Bronzeville staple helmed by owner Peytyn Willborn-Mayes, boasts a roomy side terrace with plenty of seating and overhead covering. To eat expect sturdy Italian American classics, like ravioli Florentine with vodka sauce, steak marsala and grilled pork chops with peppers and onions.

An offshoot of the popular West Town restaurant with the same name, Beatnik On the River is a veritable oasis overlooking the Chicago River. Its lush, transportive patio is outfitted with colorful tile and fringy umbrellas. Grab a Holy Watermelon cocktail with soju and green chile vodka, and a starter round of feta-stuffed medjool dates or scallops with jamón ibérico and settle in.

The sizable patio at this come-as-you-are hangout from Team Scofflaw features well-spaced picnic tables set beneath big umbrellas, edged by a pair of corner fireplaces to warm you on cooler nights. A solid bar food menu of double burgers with American cheese and fried chicken sandwiches rounds out the simple beer list and potent cocktail lineup.

The sunny back patio at this exciting Greek newcomer seats 75, with a greenhouse-style glass enclosure for year-round dining. For now, we’ll take the open summer air, a round of portokali spritzes (Greek sparkling wine, Greek vermouth and tonic), a mezze spread and a gooey, crunchy kataifi pie for good measure.

This longtime Italian-American haunt offers ample sidewalk and patio seating, complete with checkered tablecloths, amber candles, and more Italian-American favorites than you can count. Most tables are set under a retractable awning or umbrellas for shade and shelter from summer rain. Usually packed with locals, the vibe here is always relaxed and neighborhoody.

A backyard oasis in the heart of tree-lined Andersonville, Fiya’s patio teems with plant life and the soothing trickle of a water feature. You’ll find us there all summer, sipping a Hibiscus Cream Garibaldi (gin, Campari, orange juice, hibiscus syrup) and feasting on green falafel, hummus, and blistered pita.

The fine sidewalk patio overlooking Lincoln Square’s Giddings Plaza is ideal for people watching and even the occasional live music performance. Choose from among dozens of sandwiches for all times of day, plus an excellent lineup of craft beer and whiskeys.

The lively, 40-seat patio is back at Diana Dávila’s beloved neighborhood Mexican restaurant. Set beneath bright-red umbrellas with colorful cocktails and an energy to match, this is one of our favorite spots to pass a steamy summer night in Chicago, over platters of queso fundido con birria and fried-oyster tacos.

The brick-walled courtyard patio at this neighborhood bistro is serene and hidden, which also the chill crowd largely comprises regulars. Lounge beneath the trees over seasonally minded French classics like escargot, braised beet and shaved carrot salad and cote de porc with English peas and pork-fat fingerlings.

Experience the Village from a different vantage: Book a seat on its small yet charming sidewalk patio for tried-and-true Italian-American specialties for lunch or dinner in the heart of the Loop. Might we suggest adding wine, whatever the time of day? Italian Village’s list might be the city’s best kept secret.

You have two al fresco options — a sidewalk patio, and a partially covered rooftop deck strewn with twinkle lights — at this lively, family-owned Mexican spot. To eat, expect all sorts of Jalisco-inspired bites, including excellent tacos. The restaurant’s massive agave spirits selection finds its way into delicious cocktails, like the bright, floral mezcal marg, with fruity Banhez mezcal, orange liqueur and lime.

This rad little South Side bar, with a solid craft beer list and excellent drinking food, is a magnet for good times and good people. A colorful mural overlooks the smallish sidewalk patio, which is edged with wood benches and set beneath leafy trees. More info here.

With ample (as in 6,000 sq. ft.) outdoor room that includes a bocce court and vintage camper bar, crowd-pleasing snacks, plenty of local craft brews and expert cocktails — including seasonal slushies — we’re fairly sure you won’t find a better place for weekend revelry all summer long.

Chicagoans now have three glorious Parson’s patios to choose from: the original Logan Square outpost, Lincoln Park and this newest in West Town. In whatever hood you settle beneath those signature red-and-white umbrellas, a Negroni slushy is a must. A round of hush puppies and perhaps a fried chicken sandwich will ensure you can order two.

Gaijin’s covered front patio beneath the rumbling El is an ideal setting for lively cocktails and the restaurant’s specialty: okonomiyaki, the savory Japanese pancakes topped cleverly with tempura shrimp and corn, or slow-cooked beef, roasted garlic and bonito. Pickled add-ons are a must; chef and owner Paul Virant is a master preserver. The patio also sports a walk-up window where you can get kakigori to go.

This modern Korean barbecue’s roomy back deck, set beneath a custom mural of First Lady Michelle Obama, was already high on our list for al fresco musts this summer. And a recent, well-deserved Bib Gourmand designation only heightens the hankering to make it a regular haunt. Yes, there’s expert, crackly-skinned fire chicken and savory grilled LA galbi, but don’t sleep on the veggie dishes.

One of our favorite spots for al fresco hangs is back after a lengthy hiatus. This Midwestern tavern’s serene sidewalk patio sits on a tree-lined street just off of bustling Kedzie Blvd. The boozy cocktails are impeccably calibrated as always, like the Longman manhattan with Wild Turkey, Punt e Mes and aromatic bitters. We’ll take a round of broiled oysters with crab butter, too, and keep ‘em coming. PSA: Visits are limited to 90 minutes, and no pets on the patio for now, please.

With limited indoor seating at its sophomore South Side outpost, this cheery minichain is all about patio season. With ample space, painted-wood picnic tables and a quintessential summer-in-the-city vibe, you’ll find us there till September, washing down our garlic-shrimp tacos with rosemary-tinged margaritas. It’s first come, first served, 11:30 a.m. to 9 p.m. daily; order at the counter before grabbing a table, please. Call 773-823-9410 for availability. And read about their very unique, very throwback approach to pandemic survival (which will hopefully return) . There’s also limited dining with counter orders at the Wicker Park original. More info here.

Take in sweeping views of Lake Michigan and our fair city’s iconic skyline from this elegant 22nd floor perch. Vu’s sprawling, all-season rooftop lounge includes fire pits, two bars, a karaoke room and upmarket bites like parmesan fries and seasonal charcuterie boards, perfect for passing while you sip prickly jalapeño margaritas in the sunshine.

As its name suggests, this delightful Venezuelan storefront on West Armitage is all about the arepas: squishy cornmeal cakes bursting with hearty fillings like shredded beef, black beans and sweet plantains. The private patio is comfy and lined with hedges, allowing plenty of elbow space to lean into these glorious handhelds. Call 773-543 3000 for reservations or to-go orders, and find more details here.

This cozy Italian eatery serves up homemade pasta like tender gnocchi with pesto and chicken and soulful, hearty proteins like veal osso bucco on a sidewalk patio that’s now available to reserve, as with their indoor tables. Heaters stand at the ready should the evening turn chilly.

This easygoing neighborhood eatery offers plenty of awning-covered high-top seats on its roomy (heated!) patio. Come for a bright Rose Bill cocktail, with dry gin, grapefruit liqueur, cherry syrup and sparkling rose topper. Stay for chef Ken Carter’s upmarket Midwestern comforts, including tamari-glazed chicken wings, squash and chicories panzanella and an excellent double cheeseburger with American cheese and arugula.

A handful of sidewalk patio tables, sectioned off with planters, await at Sarah Grueneberg’s inviting pastificio in the heart of the buzzing West Loop. Once there, commence with a quenching Aperol spritz and round of ‘nduja arancini while you choose your inevitable pasta order. There’s a reason Grueneberg’s cooking is always in high demand, and now you can appreciate it outdoors.

A huge, hidden tree-lined beer garden sits adjacent to this longtime neighborhood spot, which by the way serves excellent thick, charred cheeseburgers (we’re partial to the Moody Bleu), plus easy-drinking beers and sweet, no-nonsense cocktails. More info here.

Carlos Gaytan’s acclaimed French-Mexican eatery features a 40-seat covered patio beneath strings of bulb lights and edged with big copper planters. The focused menu packs vibrant, creative dishes like corn masa tetelas (triangular pockets) stuffed with tinga de pollo, and lamb neck barbacoa with mint jocoque (fermented milk) and pinto bean purée. Quenching sips include the Zamora, with spiced berry shrub, lemon and Topo Chico (we like adding a measure of mezcal). Reservations are recommended.

Tucked atop always-jammed Roots Pizza, this seasonal, 85-seat rooftop oasis pulls culinary inspiration from its own organic onsite garden. You’ll find some enclosed, air-conditioned seating for those extra-steamy Chicago summer nights. Chef Bryan Collante’s Asian-inflected menu includes chicken-fried cornish hen with togarashi and gai lan, whole black bass cooked in banana leaf and ube sundaes served in custardy bubble waffles. Reservations are recommended.

This fun-loving restaurant housed in the former Black Bull space boasts a sprawling patio in front of its bright-pink facade, perfect for people watching on harried Division Street. Chef Marcos Campos beguiles with exquisite regional Spanish fare, from top-notch mackerel conserveras with shishitos, to Iberian pork cheeks braised in red wine. But it’s the bar program that will really grab you by the hand, with more than 35 selections of sherry from across Spain, phenomenal wine pours, plus a solid offering of gin and tonics and zero-proof cocktails.

This elegant Southern restaurant ranks high on our list of beautifully appointed dining rooms and bars, thanks to chef and owner Erick Williams’s curated selection of fine art and interior design elements that reverberate with meaning. But come summertime, the sidewalk patio offers diners fresh air and views of vibrant Hyde Park, while we feast on fried-green tomatoes piled with succulent shrimp étouffée, blackened catfish and Carolina gold rice, and deliciously throwback peanut-butter pie with dark chocolate.

Chef Won Kim’s funky counter-serve spot opens its roomy, concrete paradise of a patio from Thursday to Sunday with adjacent bar/bottle shop Maria’s Packaged Goods. Inventive Polish-Korean mashup fare includes pierogies with tamari sour cream, and a Ko-Po bulgogi beef sandwich with ssam mayo, baby swiss, sauteed onions and shishitos on brioche bun. Plus, there’s plenty of local beers to choose from, including one of our all-time faves, Marz Community Brewing’s Jungle Boogie, a vibrant pale wheat ale spiked with rooibos tea. Call ahead at 773-890-0588 for availability. More info here.

Tucked behind this cozy, taxidermy-filled watering hole lies, without doubt, one of the city’s best patios. It’s a roomy, stone paved, urban backyard with a firepit and mobile bar beneath a canopy of twinkly lights. Table sizes cap at six, and drinkers are limited to two hours — plenty of time to sip one or two of the four daily-rotating cocktails, like the summery mezcal jammer, with mango and citrusy Carpano Classico and lime. Reservations are strongly recommended.

The spacious sidewalk patio at this excellent cantina and margarita bar is back open in Pilsen. Grab a seat in the sunshine or beneath the bulb lights after hours for spiced-up Mexican classics like carne asada fries and quenching flavored margaritas from tamarindo to spicy mango. Open Tuesday and Thursday through Sunday. Visits are limited to two hours; and it’s for sure BYO blanket on chilly nights! Call ahead at 312-829-1147 for availability.

Dine on classic Piedmontese fare like luscious carne cruda, meaty ragu with house fettuccine, and prosciutto-wrapped rabbit loins from chef Cameron Grant on the backyard patio hidden behind this Logan Square restaurant. Ask for a bottle recommendation from the curated regional wine list; there’s something delicious for every budget.

This Greektown standby sports a downright whimsical patio with its retractable roof, Greek columns and bubbling waterfall. To eat, expect a wide range of Greek-American standbys, from creamy, garlic-spiked spreads with pita to gyros and hearty oven-baked moussakas.

This bi-level Asian brewpub features a greenery-edged roof deck with a partly-covered section in case of rain. Chef Bo Fowler’s food menu takes inspiration from Vietnam to the streets of Chengdu, China with culinary-inspired beers to match: think calamansi-tinged wit and jasmine tea-infused kolsch.

This lively cantina brings fresh Mexican street fare like pibil-marinated chicken tacos on house tortillas to Downers Grove, with a lively patio that acts like an extension of the dining room thanks to roll-down glass windows. Heads up: there’s also a taco takeout window.

This Chatham restaurant and event space boasts a roomy rooftop deck with weekly DJ sets and a pop-up menu (currently) from Uncle Reg’s Café, which includes jerk chicken and pork tips, crisp fried catfish, and thick-cut corned beef sandwiches.

Newly-debuted for alfresco season, Scofflaw’s beautiful, walled-in patio is all dressed for a garden party in pretty white wicker and fringed white umbrellas. You’ll find wryly elegant (mostly) gin-focused cocktails to match — like the Neptune, made with genever, falernum, orgeat, passion fruit, and lemon.

The open-air setting at this modern Mexican cantina features patio seating for up to 64, with imaginative Mexican dishes from chef Guillermo Reyes (Mi Tocaya Antojeria), agave-focused drinks and a tlayuda (open-faced fried tortillas) menu starting at 10 p.m. for night owls.