You have a list of our Outdoor Greatest Hits. But what about the new places? After all, you can only go to Parson’s so many times. When you find yourself getting mad that someone else is sitting at “your” picnic table, it’s a sign that it’s time to try something different. Who knows - one of these might turn into your new favorite spot.
Eating at Mi Tocaya is an all-around good idea no matter what time of year it is. The Mexican food is fantastic, and the atmosphere is always upbeat and fun. During the summer, you get the added benefit of being able to eat on the patio - which has trees and other green things (including delicious guacamole). Order a few tacos or some of the small plates, like pork albondigas or nopales and burrata, and stay for as long as you possibly can.
This is not your casual weeknight spot - Gibsons Italia is an outdoor dining power move. It looks and feels expensive, and has an impressive view of the Chicago River. Sit either on the second floor patio or on the third floor, which has a retractable roof. Just don’t let the “Italia” in the name distract you - you should stick with the steaks here, along with anything else that looks like it belongs on the menu of the original Gibsons steakhouse.
Walking into this casual Southern bar and restaurant feels like entering a narrow hallway. But if you keep walking, eventually you’ll reach the awesome back patio, which is where you want to be. There’s a long cocktail menu, and their food specialty is tamales that are simmered in a chile broth instead of steamed. These come in a few different varieties, like spicy brisket and even a vegan option. Also a good idea: coming here on the weekend for day drinking and brunch.
The inside of Clever Rabbit is very dark. That’s fine in the winter, but during the summer, you want to eat the vegetable-focused food here with the benefit of sunlight on the large front patio. Come with friends and share the cartoonishly large crudite platter - and if you’re a meat-eater, know that there’s a great burger, too. A likeable spot for vegetarians and non-vegetarians alike.
Theater On The Lake is an event space that’s right on Lake Michigan, with a lawn leading up to the water. But the restaurant (complete with patio) is open to the public. Come here for a burger and snacks - we especially like the pimento cheese spread - with a view of the lake. It’s way better than fighting the crowds at North Beach.
When you want your summer to feel like a Country Time lemonade commercial, go to Daisies. The menu of Midwestern-inspired food revolves around seasonal produce, and it’s the type of restaurant where they’ll tell you where the lettuce came from that day. Sit in the quiet back courtyard and order a bunch of vegetable-heavy pastas, like beet agnolotti or a tajarin with white beans and cracklins. To really get into the theme, order the onion dip as an appetizer.
The Southport stretch in Lakeview is a family-heavy area, and this Italian spot fits right in - the outdoor patio has plenty of room between tables for strollers and/or tantrums about stolen crayons. Come here for brunch or dinner and definitely order a pizza (the wood-fired Neapolitan pies have a chewy but still crispy crust), as well as some pasta.
You know all about the outdoor juggernaut that is Big Star in Wicker Park. And the new location in Wrigleyville has a pretty fantastic patio as well - plus a view of Wrigley Field. The menu has the same solid tacos and cocktails you’ll find at the original, plus some excellent nacho-like “hot chips.” Just be sure to check the Cubs schedule before you plan a trip.
The Moonlighter has a huge outdoor space with multiple fireplaces that works for all seasons. But the extensive menu of bar food like waffle fries, nachos, and burgers makes it feel like an ideal summertime hangout - it has pool party and backyard BBQ written all over it. Add in a few pitchers of house cocktails, and your group will want to stay all night.
When we think of rooftop bars, we generally think of places located in high-rises downtown. Great views, but the altitude sickness and gale force winds can get tiresome. Pearl’s in Edgewater isn’t very high up, but the roof still has a fantastic view without being overly breezy. The Southern menu has a mix of Cajun classics like po’boys and jambalaya as well as very good barbecue. Sit on the rooftop with a po’boy and a Hurricane.
This is a casual spot in the West Loop that serves mostly small plates, like avocado hummus and goat tostadas. Unlike most of the other places in the neighborhood, it’s typically not crowded - so during the summer, you can really take your time over cocktails on the back patio.
Some background on Burt’s, which is technically in Morton Grove: It was started by the original owner of Pequod’s (so the pizza is almost identical), and subsequently developed a cult following. New owners took over last year and updated the space, but kept the same recipes. So now there’s great pizza, a full bar, and a large outdoor patio. We highly recommend going on a mini road trip and bringing as many friends as you can find/make at short notice. Your mental Chicago pizza map (and your summer) won’t be complete until you do.