Waterfront Café (Edgewater)
Open only in summer, the Waterfront Café is a hidden lakefront-dining gem nestled in beautiful Berger Park. Spend just a few minutes seated under their patio lights with the lake breeze on your face and you’ll feel transported to the casual beach vacation you’ve been dreaming about. Forget that you’re still in Edgewater as you choose from their extensive beer, wine and cocktail list. The menu has a wide range of classic American and British fare such as fish and chips, or a chicken avocado wrap named after the 48th ward of Chicago that houses this cozy cafe. Enjoy live music five nights per week and keep an eye out for their ticketed, themed dinner events.
6219 N Sheridan Road, Chicago, IL, USA +1 773 761-3294
Streeterville Social (Streeterville)
The summer season in downtown Chicago begs for rooftop options, and this sprawling restaurant and bar atop the Loews Hotel offers you the best of everything. Enjoy dinner on the bistro side, indulging in everything from fish tacos to churros, then cross over to the terrace side where you’ll find 9,000 square feet of open leisure space for ending the evening with a relaxing round of drinks. Several dozen plush couches are the perfect place to plop down with a cocktail or grab a cold beer and try your hand at their giant jenga or corn hole sets. Set against a stunning backdrop of pure Chicago skyline, Streeterville Social will be your new go-to favorite.
455 North Park Drive, Chicago, IL, USA +1 312 840 6617
If Andersonville is on your list of neighborhoods to explore, we don’t blame you. This specialty Italian restaurant is one of the area’s many highlights, just steps from the main street of shopping and nightlife. Sample any of Anteprima’s classic Italian fare that changes throughout the year depending on market availability. Try their pepper-crusted tuna or tagliatelle on the picturesque back patio with a full glass of wine before hitting the town.
5316 N Clark St, Chicago, IL, USA +1 773 506 9990
Heartland Café (Rogers Park)
Trek up to the far North Side for a stop at the quaint and friendly Heartland Café, a favorite among local residents that boasts of its ‘good wholesome food for the mind and body.’ It has a comforting way of welcoming you like family even if it’s your first visit to Rogers Park. The place is split between cafe and grocery store, both offering a wide range of vegetarian, vegan, organic and gluten-free food options. Dine indoors at the bar or outside under their canopy of lights on a warm summer evening, and swing by during the week for bingo, trivia and open mic events.
7000 N Glenwood Ave, Chicago, IL, USA +1 773 465 8005
Sheffield’s Beer and Wine Garden (Lakeview)
Hit the Lakeview staple Sheffield’s after you take in a Cubs game down the street at Wrigley Field for their signature smoked dishes and endless beer list. The servers are prepared to recommend the perfect beer, so be sure to arrive both hungry and thirsty. Expect a good amount of typical barbecue fare, like their Bucket-O-Bones babyback ribs and Buffalo Chicken Rolls. Dine out in the picnic-style beer garden or in one of their three different bar areas. Swing by during one of their live music events or themed brunches for the full summertime experience.
3258 N Sheffield Ave, Chicago, IL, USA +1 773 281 4989
90 Miles Cuban Café (Logan Square)
This Chicago favorite is named after the 90-mile distance between Key West, Florida and Cuba. But you don’t have to go all that way for authentic Cuban fare, just stop in at one of Chicago’s three 90 Miles locations. Make sure to visit them in Logan Square for indoor and outdoor patio seating complete with weekly flamenco shows while you dine. Try a house special like Fricase de Pollo or Puerco Rotizado that were both featured on Diners, Drive-Ins and Dives. Keep in mind that it’s BYOB, but they do have several tasty sangria and mojito mixes waiting for you.
2540 W Armitage Ave, Chicago, IL, USA +1 773 227 2822
Bridge House Tavern (Loop)
Patio restaurants and cafes line the edges of the Chicago River that winds its way through downtown, but only Bridge House Tavern gives you the best of every world. Come for the spectacular city views and casual atmosphere, but stay for the tasty and low-cost gastro-pub grub. They host a special every day of the week, like $5 Bloody Marys and mimosas on the weekends and a $14 burger-and-beer deal on Tuesdays. Don’t feel intimidated by the posh steakhouses that surround it; just come as you are for any meal. Even a passing boat can pull up and grab a bite!
321 N Clark St, Chicago, IL, USA +1 312 644 0283
Enoteca Roma Ristorante (Wicker Park)
From the street, this cramped restaurant in Wicker Park doesn’t look like much. But Enoteca Roma’s authentic cuisine served on the expansive back garden will almost make you feel like you’ve traded the busy city for the Italian countryside. Owners Fabio and Letizia serve up their own family recipes straight from Italy in their seasonally-changing menu. They offer weekly specials but have also mastered the classics. So order yourself a big bowl of pasta and an even bigger glass of wine while you enjoy the sunset over the patio.
2146 W Division St, Chicago, IL, USA +1 773 772 7700