The “F*ck It’s Almost Fall” Guide
Where to go when you realize summer is slipping away and you’ve completely wasted it.
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 Formula 1: Drive To Survive, 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 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.
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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.
photo credit: Brian Kinyon
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.
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
Watch Live Music Outside Before No One Wants To Go Outside Ever Again
photo credit: Sarah Larson
A hundred years ago, this tiny bar in Bucktown was a go-to spot for locals looking to break some Prohibition laws. Now, it’s still slinging beer (legally) but has also become one of the city’s most beloved performance venues. In the summer they host performances on their small front porch. There, in an intimate open-air setting, you can hear anything from rock trios to the melodious twang of a solo banjo. Paired with one of their cheap beers on tap and it makes for a perfect, laidback Chicago summer night. Check here for their performance calendar.
Just off of the Morse Red Line is Le Piano, a Rogers Park jazz bar. And they have outdoor summer performances as part of Chicago’s Alfresco program. With an outdoor piano set up, they host musicians covering a wide range of genres including classical, jazz, and blues. In addition to cocktails and wine, Le Piano also serves food, with dishes like lamb chops or chicken with a tarragon wine sauce.
photo credit: Sam Rice
Ina Mae Tavern & Packaged Goods
For Booze and Blues, head to Ina Mae Tavern in Wicker Park on Thursdays. From 7pm-10pm, they have $10 Old Fashioneds and a live blues set. You can also order from their delicious southern menu, which has staples like fried chicken, po' boys, and beignets.
The Best Spots To Listen To Live Music Outside This Summer
Hang Out On A Great New Patio
The Wiener's Circle
The Wiener’s Circle? The iconic hot dog stand that hasn’t changed in over 30 years? On a guide with the word "new" in it? Indeed. This iconic Lincoln Park spot that’s famous for its take-no-shit staff and wild late-night atmosphere now has a spacious back patio, and it’s wonderful. The partially-covered backyard has tons of tables, a full bar, mini basketball court, ping pong table, TVs, and heaters. Just know that you can’t order food from the bar, so hit up the regular ol’ Wiener Circle line for a char dog and some good-natured verbal abuse—then head towards that great new patio.
The Duplex in Logan Square serves food from different restaurants every six months, which always makes this place feel new. Right now they’re serving Latin American food from Cacahuates (with dishes like mushroom chile rellenos and chorizo con queso) and Mediterranean-inspired things like shrimp pita and Greek fries from Kalista. This place feels more like hanging out at a bar with great food than a restaurant—they have live djs and activities like game nights. There’s a large sidewalk patio, and this place is great if the decision to get together is impromptu, because there is a very good chance you will be able to just show up and get a table.
photo credit: Kim Kovacik
Because of its fantastic funk and soul soundtrack, delicious food, and long wine list, we already had plenty of reasons to hang out at a Bronzeville Winery for as long as possible. But now this American restaurant in Bronzeville has a great sidewalk patio that's surrounded by lots of plants. And we can't think of a better way to spend a summer evening than listening to Earth Wind & Fire with some caramelized watermelon with a glass of pinot grigio.
They’re still setting up tables in the middle of Chicago streets, and that's where you'll find the patio at Jaleo in River North. This is the fifth location of this casual Spanish restaurant that opened in D.C. back in 1993, and Jaleo's colorful, busy River North space can definitely give you chain restaurant vibes. But that concern will disappear fast thanks to the attentive service and great food. The menu includes tapas, paellas, sangrias, and a long list of Spanish wines. And the crowd—while a mixed bag of tourists—is clearly having some fun. It’s a great spot for dinner and drinks before going out downtown, or if you just want to get together with some friends and not worry about how loud you’re being.
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.
The Best Patios In Chicago
Check Out A Festival
Nothing makes you feel like you took full advantage of Chicago's three months of decent weather like leaping over beer puddles while balancing a paper plate stacked with food in one hand. Luckily we have over 6,934 street festivals to choose from each weekend, and there are plenty left in September and October.