The essential outdoor eating guide
Satisfy your hunger for alfresco eats with hot new brunch spots, late-night ice cream shops and everything in between
Best sunshine brunch
1218 W Morse Ave between Lakewood Ave and Sheridan Rd (773-764-8900)
After a couple of $4 pints of Morseland's wicked-potent Bloody Marys, you'll be as drunk as the cast of characters shuffling by the restaurant/bar/live-music venue's sidewalk cafe. Brunch includes prime-rib hash, an excellent red curry chicken salad served in a pita and the Morseland eggs Benedict, which eschews English muffins for chunky crab cakes. Bonus: every table gets a giant bowl of fruit to share.
1520 N Damen Ave between Le Moyne St and Pierce Ave (773-252-1500)
Get out of MOD's slick dining room and onto the patio, where you can be sure you're eating one of the best brunches on the block. Updated, American faves are both comforting and contemporary. It's tough to beat the green-chile hash with a Bloody Mary royale (served with a minican of Miller High Life).
4004 N Southport Ave between Irving Park Rd and Cuyler Ave (773-325-1710)
While other sidewalk seating can feel like you're, well, eating on the sidewalk, Deleece manages to pull off an urban oasis. Maybe it's the lack of foot traffic on this stretch of Southport, or the trees wrapped in white lights. Whatever it is, it's perfect for a Sunday morning with some eggs, coffee and The New York Times.
1952 N Damen Ave between Homer St and Armitage Ave (773-227-2995)
The sculpture that graces Scylla's front patio (rendered by local artist Quang Hong) gets its day in the sun—and so do you—when you have brunch under it on a Sunday morning. But the art is only half the pleasure; goat cheese and raspberry omelettes and crispy waffles with caramelized pineapple make up the other half.
2537 N Kedzie Blvd between Albany Ave and Linden Pl (773-489-9554)
This funky restaurant has one of our favorite seasonally driven menus. Vie for a seat on the sidewalk cafe, where planters spill over with the same herbs you'll find in your eggs Florentine or red-pepper strata. Local organic eggs and sausage pair perfectly with the black sambal Bloody Mary or blackberry Bellini.
3322 N Broadway between Aldine Ave and Buckingham Pl (773-281-7575)
The sidewalk cafe at this pan-Asian eatery is full of advantages: It's more spacious than the tiny dining room, it's got a view (do chiseled boys in tight tees count?) and it brings you that much closer to Valhalla, the wine store across the street you'll run to when you drain your first bottle.
1616 N Damen Ave between North Ave and Concord Pl (773-772-7100)
The beginning of the week is tough, so Feast makes Mondays and Tuesdays more relaxing by going BYOB. If you can snag a garden seat, you'll reap all the voyeuristic benefits of watching passersby on Damen, but without any of the annoyances of sidewalk seating (e.g., no strange dogs begging for food).
6401 S Coast Guard Dr between Marquette and Hayes Drs (773-947-0400)
If you get jealous every time you see a yacht, bring your boatless ass here. This French-Caribbean spot, housed in a former Coast Guard building, has three patios, each right on the lake with a stunning view of the harbor. It's as close to owning a boat as you're going to get.
3763 N Southport Ave between Waveland Ave and Grace St (773-477-5466)
Ever wonder why the tables outside this Argentinian meat parade are always full of people who look so happy? They're drunk. And if you were getting ready to eat a cornucopia of tender, salty, thirst-inducing meats, you'd drink a bottle or three of your own Malbec, too.
Taqueria La Unica
2134 W Cermak Rd between Hoyne Ave and Leavitt St (773-254-7577)
Even if this carryout taco stand did have indoor seating, we'd still munch on its cheap, delicious tacos asadas and chiles rellenos on the outdoor patio. As nice as it is eating under the shade of a sprawling tree, though, it's even nicer knowing that you're supporting a hidden gem.
Best patio for kids to play with their food
Southport Grocery & Cafe
3552 N Southport Ave at Addison St (773-665-0100)
The inside of this sleek breakfast and lunch cafe seems too serene a spot to take our less-than-perfect progeny. So when management throws a few tables out front, we jump at the chance to dig into decadent dishes, like sweet and savory French toast with rosemary-roasted ham. We even sneak a few bites of the kids' bread-pudding pancakes when they're not looking. And we love that they slip in a few healthy sides like fresh fruit, carrot sticks and applesauce onto their plates, too.
4729 N Lincoln Ave between Leland and Lawrence Aves (773-989-5595)
This Lincoln Square mainstay has plenty of all-ages favorites: buttery croissants, decadent mac and cheese, homemade pizzas and a dessert case that thrills both young and old. The patio overlooks pretty Giddings Plaza, so when your kids have reached the point where they can't sit still, they can join other restless little ones romping around while you finish your food in peace.
Kitsch'n on Roscoe
2005 W Roscoe St between Damen and Seeley Aves (773-248-7372)
The enclosed backyard patio is a big favorite with families who want to avoid street traffic. They also appreciate the plastic carafe of water, bread basket and paper and crayons brought to the table as soon as you sit down. Parents come to satisfy cravings for comfort food like meatloaf and chicken and waffles. Kids dig the throwback lunch boxes filled with burgers, quesadillas and other typical pint-size picks—relics to them, sweet nostalgia to Mom and Dad.
Artopolis Bakery, Cafe and Agora
306 S Halsted St between Jackson Blvd and Van Buren St (312-559-9000)
For parents with young kids, this place nails it: The food is inexpensive, you get it fast, and it tastes great. The signature artopitas—flaky puff-pastry rounds with fillings like ham and kasseri cheese, and chicken and mozzarella—make perfect kiddie fare. Adults dig into fresh salads, sandwiches and traditional Greek dishes like roasted lamb and moussaka. The best part: The popular patio that overlooks Halsted Street is usually pretty noisy, so no one will notice a few shrieks and squeals coming from your table.
Medici on 57th
1327 E 57th St between Kenwood and Kimbark Aves (773-667-7394)
Your kids won't get to scrawl all over the graffiti-covered walls downstairs at this Hyde Park institution if you head to the rooftop patio, but the fresh air will do you all some good. The tykes can pick from a kids menu of staples like pizza, hotdogs, grilled cheese and PB&J, while you can go for one of the fresh and filling salads and then ruin your perfectly healthy meal with the irresistible sweets from the bakery.
Best sugar fix under the stars
Bobtail Soda Fountain
2951 N Broadway at Wellington Ave (773-880-7372)
What would an old-school soda fountain be without an outdoor spot to watch the world go by? Late-night hours (till 11pm weekdays, midnight weekends) mean you can get a post-dinner jolt from the caffeinated "cream espress" milk shake (vanilla and espresso). Or grab a scoop of the Lakeview Bourbon Barhopper (chocolate ice cream with bourbon) to get a jump on the night's festivities.
958 W Armitage Ave at Sheffield Ave (773-388-1880)
Get your after-dinner drink here (it's open until 11pm), where the glass case is amply stocked with all the typical teahouse pick-me-ups—scones, biscotti, croissants—but the best sugar rush comes in liquid form. Snag a sidewalk table, down a sweet and spicy iced chai and you'll be ready to hit the bars in no time.
Original Rainbow Cone
9233 S Western Ave between 91st St and 92nd Pl (773-238-7075)
For 79 years, the awning-covered picnic tables of this Southwest Side ice-cream shop have been packed with locals feeding their sweet tooth. It has added smoked brisket and pulled pork sandwiches to the menu this year, but the classic Rainbow Cone is what keeps us coming back until 10:30pm. The five-flavor cone features slices of chocolate, strawberry, Palmer House (vanilla with cherries and walnuts), pistachio and orange sherbet stacked one on top of the other for an unbeatable classic.
1733 S Halsted St between 17th and 18th Sts (312-829-4150)
The walls of this cute coffee shop are full of work from local Pilsen artists, but the real masterpiece is the chocoflan, chocolate cake topped with flan and baked. It's a combination almost as genius as cookies and cream, and it tastes even better when you eat it on the patio out back.
Zephyr Ice Cream Restaurant
1777 W Wilson Ave between Ravenswood and Hermitage Aves (773-728-6070)
It's Art Deco galore inside this aptly named spot, but come summer, the sidewalk cafe is where we'd rather be. Table service means you're not just buying a cone and scrambling for a seat—you'll order your French fried ice cream or ten-scoop War of the Worlds from a server, and minutes later it'll appear before your very eyes. If you lap it up and feel like sticking around, you can partake of the full bar until midnight weekdays and 1am weekends.
1655 W Cortland Ave between Marshfield Ave and Paulina St (773-862-5263)
This cute-as-a-button casual American spot has done well despite its odd location (a bit hidden off of the beaten Bucktown path) due to its cozy feel and moderate prices. That coziness carries over into the sidewalk seating, where you can get a surprisingly tasty burger on a crusty dinner-roll-like bun with strips of bacon and grilled onions.
Smith & Wollensky
318 N State St between Wacker Dr and Carroll Ave (312-670-9900)
It shouldn't be a shock that a 12-buck burger is good, but this one's damn good, and we'd gladly pay that price for the unbeatable view from the outdoor terrace overlooking the Chicago River. The half-pound burger is made from the trimmings of prime beef that's dry-aged on premises, grilled impeccably to your specifications and served with a pile of house-made fries. The only bummer is that it's only on the outdoor menu during lunch.
Daily Bar & Grill
4650 N Lincoln Ave at Wilson Ave (773-561-6198)
Bright yellow walls, gray slate floors and flowers blooming everywhere make this sun-drenched patio on bustling Lincoln Avenue the perfect spot for a great burger. This place has two: the Daily burger, a half-pound of Black Angus beef on a toasted bun with lettuce, tomato and onions; and the belt-busting Sunday Edition, which piles on bacon, gooey cheese and grilled mushrooms and onions.
1700 N Damen Ave at Wabansia Ave (773-489-6212)
We get so caught up in conversation with friends over the signature S'moretini and the ridiculous-but-tasty tropical-teaser cocktails that it never dawned on us to try the burgers. Good thing we did, because they're the best on the block. The half-pound of Black Angus beef is cooked perfectly medium-rare and served on a buttered and grilled bun, which is key. We're torn between the blue cheese and the brie with caramelized onions, so try them both and decide for yourself.
733 S Dearborn St between Harrison and Polk Sts (312-461-1116)
Don't get us wrong, we're not knocking "The Famous Hackney Burger" (a name that's trademarked, by the way), but unless you order the blue cheese version (in which they mash the cheese into the meat before it's grilled, resulting in melty goodness), the preformed patty won't live up to its 65 years of hype. So we go for the blue and sit on this South Loop sidewalk patio wishing we had a way to get to Glenview, where the original location (Hackney's on Harms) has a beautiful, giant outdoor deck flanked by huge oaks that make our city trees look like twigs.
Best upscale eats
800 N Michigan Ave between Chicago Ave and Pearson St (312-239-4030)
According to the menu, the word GARDEN stands for (chef Sandro) Gamba Artistically Redesigns Dining Experience in NoMI. But that's the only ridiculous thing about this classy space, where diners sit among plenty of planters on the fanciest patio furniture you've ever seen. Throw in a menu of lighter fare, like golden tomato gazpacho and lime-marinated calamari, and you've got the perfect summer spot for when your parents come to town.
4518 N Lincoln Ave between Sunnyside and Wilson Aves (773-271-6100)
We applaud chef Michael Altenberg's reverence for organics, devour his French bistro classics like roasted chicken (among the best in town) and steak frites, and linger as long as possible in this perfectly pretty garden. Trees, colorful lush foliage and a winding brick path make for a serene Euro-country feel and the best spot around for a flute of champagne or a pint of Belgian beer.
The Peninsula Chicago, 108 E Superior St between Rush St and Michigan Ave (312-573-6618)
Normally we don't condone paying through the nose for Chinese food when Chinatown options abound, but this gorgeous rooftop patio, brimming with fresh flowers and offering a view of the historic Water Tower, is hard to beat. And the elevated takes on five-spiced duck, drunken baby chicken and wok-tossed lobster mostly surpass expectations.
2610 N Cannon Dr between Fullerton Pkwy and Lake Shore Dr (773-477-5845)
Okay, so technically you're not eating outside, but when the giant French doors swing open and you're only a few feet from a pond in the middle of Lincoln Park, you're as close to nature as it gets. Even more so when you sample chef Bruce Sherman's elevated contemporary menu, concocted with as much locally grown organic food as he can get his hands on.
1119 W Taylor St at May St (312-226-6479)
The pomp and circumstance at this classic French spot (surprisingly, smack dab in the middle of Little Italy) is part of its charm. But things are bound to be more relaxed in the quiet, almost-hidden garden because digging into pate and champagne surrounded by lush foliage never feels stuffy. It just feels right.
W Lakeshore-Chicago 644 N Lake Shore Dr at Ontario St (312-255-4460)
We're not sure which we like more—having a front row seat for the weekly waterfront fireworks over Navy Pier or devouring incredible global small plates like serrano-wrapped shrimp skewers and crispy lamb cigars. The outdoor tables are a hot commodity once the fireworks start blasting (Wednesdays at 9:30pm and Saturdays at 10:15pm), so request one in advance.
Best alfresco Italian
136 N LaSalle St between Court Pl and Randolph St (312-696-2420)
The servers here will bring you bowls of cappelletti, chef Dean Zanella's nonna's famous gnocchi and a pair of sunglasses so you don't have to squint when taking in the sweeping view down La Salle toward the Board of Trade building.
1359 W Taylor St at Loomis St (312-491-1414)
The hostess at this stylish Little Italy spot may send you up to the rooftop patio to grab a drink while you wait to be seated. But once you get up there and watch people scarfing down the farfalle con prosciutto at the candlelit tables, why would you want to return to the dining room?
1359 W Taylor St between Ada and Loomis Sts(312-491-1414)
We've yet to find a better brick-oven pizza in town. It's thin (but not New York–style) and truly Italian, with bubbled edges, tangy fresh tomato sauce, slices of fresh mozzarella (not that shredded fake stuff) and just-picked basil. We like it so much we'll eat it on this ambitious outdoor patio that offers little more than a glimpse of chef Bruno Abate's Vespa and the craggly buildings of the meatpacking district.
2144 W Division St between Hoyne Ave and Leavitt St (773-342-1011)
The sidewalk seating in front of Letizia's is just fine for coffee. But at night we head for the giant, beautiful back patio at the adjacent new wine bar. Trees, a bubbling fountain, rose bushes and brick pathways make this the perfect spot to sample more than three dozen wines by the glass and order up crispy Roman-style pizza, fancy bruschetta and cheese plates.
1805 W Division St between Wood and Honore Sts (773-235-8888)
Think sidewalk spots along Division are divey hangs for local hipsters? This high-quality sushi star blows that theory. We've always had good luck asking servers what's freshest, and we're not ashamed to admit they've got us hooked on their nontraditional rolls, like the House Crunch. Added bonus: Outside, you can escape the ubiquitous sushi-bar house music.
2020 W Division St between Damen and Hoyne Aves (773-862-8500)
When we want high-end sushi without the high-end scene, we head for the simple outdoor tables here and dig into house specialties. Signatures items like yukke toro (fatty tuna tartare with quail egg) and kani nigiri (seaweed filled with baked spicy crab) aren't exclusive to this locale (Mirai shares its head chef with Japonais), but the funky neighborhood and surrounding post-dinner bar choices are.
504 N Wells St between Illinois St and Grand Ave (312-595-2300)
If you caught last week's outdoor drinking guide, you've already read our accolades for one of the nicest rooftop decks around. But we thought we'd mention it again because we sampled the sushi and found that not only is this plush patio perfect for a nightcap (or night-starter), but it's great for sashimi as well. We're not crazy about the rice, so skip the nigiri in favor of slick cuts of the day's fresh catch.
600 W Chicago Ave at Larrabee St (312-822-9600)
This swank spot is the closest thing we have to Ian Schrager's beautiful Delano Hotel in Miami, except that this breezy outdoor space sits on the banks of the Chicago River. The only thing fresher than the hotties in white-on-white designer summer wear is the impeccable sushi.
1400 N Wells St at Schiller St (312-664-3663)
Long before Chicago's great sushi boom, this Old Town stalwart (opened in '69) taught us how to tell nigiri from sashimi and miso from udon. The garden patio out back is loaded with fresh flowers and, like the friendly staff, somehow raises the comfort level for those intimidated by the sushi scene.