After a long, cold winter, you told yourself this would be the summer you’d hit all the hot spots, day drink on a rooftop, maybe have a picnic by the lake. But 10 Saturdays later, all you’ve accomplished is going to a coworker’s wedding, binge watching Fboy Island, and one regrettable bottomless brunch back in May.
Luckily, there are still plenty of warm days ahead. To help you maximize the time that’s left, we curated some spots you should put at the top of your list to cram in as much summery fun as humanly possible. And if you’re an overachiever check out our Summer Guide for even more stuff to do and eat.
Hang Out by the Lake Before It’s Covered in Snow
All the best lakefront places are still open, which means it’s still possible to stare at Lake Michigan and pretend it’s an ocean. And if you binge watched White Lotus but realized you’re never going to be as privileged as those insufferable people, go to the Shore Club. This place on North Avenue Beach has a cabana-style atmosphere with loungy daybeds and some decent Mediterranean food. And unlike the resort in White Lotus, you’ll actually have fun.
Castaways Bar & Grill
If you want to channel your Sisqo Spring Break ’99 fantasy, head to Castaways on North Beach. And while this place is a total sh*tshow, if you want a burger after drinking at the beach all day and/or love hearing radio DJs broadcast Top 40 hits, then this is the place to be.
If Castaways is MTV Spring Break, Waterfront Cafe in Edgewater is Nancy Meyers’ spring break. This outdoor cafe is attached to a coach house next to the Berger Park Cultural Center mansion. It’s quiet and has food like nachos, red pepper spread, and sandwiches. There’s also live acoustic music. It’s basically the beach restaurant equivalent of linen pants.
Reggies On The Beach
For more live music, hit up Reggies on the 63rd street beach. You can expect cocktails, and a party atmosphere where you can stand around in shorts and Tevas without anyone judging you. Or, rent a cabana so you can sit in shorts and Tevas instead.
Where To Eat Along The Lake Shore Path
Eat Something That Says “You’ll Have to Pry Summer Out of My Cold Dead Hands”
For an injection of all the summertime cookouts you didn’t have, go get some BBQ from Soul & Smoke. This outstanding spot has (along with a food truck) two ghost kitchens in Avondale and the South Loop, and a stall in Time Out Market. And not only is the tender, meaty brisket incredible (currently the best in the city), but the sides (like creamy mac and cheese, cornbread muffins, and spicy baked beans) are all just as great as the meat.
Rubi's At Maxwell Street Market
This place is only open from 9am to 3pm on Sundays at the Maxwell Street Market, and this outdoor market has pretty limited dates, so you need to plan ahead. But it’s worth the effort to eat Rubi’s al pastor tacos that come on large handmade tortillas you can see being made in front of you. In your excitement, resist the urge to grab the trompo and run through the market yelling “I’m king of the pastor!” after eating here.
Ice cream is the official dessert of summertime (and, well, life) and we have a lot of good spots in Chicago. But for something iconic, visit Orginal Rainbow Cone. This classic Beverly ice cream shop opened in 1926. It definitely gets points for nostalgia, but at the end of the day, you come here for one thing: the rainbow cone. It’s made with layers of chocolate, strawberry, Palmer House (vanilla with walnuts and cherries), and pistachio ice creams, plus orange sherbet.
Mario’s is a walk-up stand in Little Italy that opened in 1954 and has fantastic Italian ice, which is perfect when you need a break from the richness of creamier sweets. All the flavors are good, but the go-to here is the lemon. It’s the perfect mix of tart and sweet, with little chunks of lemon rind adding freshness. Head here before they close for the season, which is usually mid September.
The Best Ice Cream Shops In Chicago
Sit Outside on a Great New Patio
Ok, hear us out. Babygold Barbecue isn’t in Chicago, it’s actually out in Berwyn. But since you also never took that road trip you planned, this is your opportunity to kill two birds. This new restaurant opened at FitzGeralds, a 40-year old music venue. They just remodeled their outdoor patio, and they have live music nightly, with bands playing everything from jazz to blues to bluegrass. And the music isn’t just what makes this place worth the drive - the BBQ is great, too. The meat has a wonderful smoke, and while the ribs don’t have a bark, they are tender and covered with a sweet sauce we really like.
Diver At The Park
The Diver at the Park is a Tulum-inspired restaurant in Wrigleyville with a large fenced-in beer garden. And as you might have deduced from that description, this is a party patio. The outdoor (and dog-friendly) space is huge, has picnic tables, swings, a vintage camper bar, and serves food like tacos, nachos, and ceviches.
If you just want to sit with friends outside, drink some cocktails, and eat delicious pizza, Pizza Lobo in Logan Square is where you can do this. They serve thin crust pies, and you’ll find great red sauce options like the “amatrice yo-self” (roasted tomato, pancetta, and Calabrian chile), and white pies like the castello bianco - with meatballs, ramps, and parm.
Bar Avec is the rooftop bar on the eighth floor above Avec River North, and it’s a perfect low-key rooftop option for drinks and a light bite that won’t involve a gazillion tourists. The rooftop is shaded, full of plants and trees, and has a great view of downtown. Order a cocktail and small plates like salmon tartare or the brandade, and enjoy the scenery without having to meet up with your extended family at Navy Pier.