Fall in Chicago can be pretty charming - piles of leaves, pumpkins, Mayor Lori Lighfoot wearing a Halloween costume at a press conference, and those dried corn stalks everywhere. Not to mention the wonderfully crisp fall air, which is enjoyable as long as you ignore that it’s foreshadowing the arctic winds heading our way. Here are 11 restaurants, bars, and pop-ups that will help you take advantage of this time of year.
Pre-pandemic, we’d go to The Darling in the West Loop for drinks, live performances, and to sit inside a space designed to look like Luigi’s Mansion. Now you can come here to have cocktails and small plates in their “rose garden.” That’s the name of their outdoor patio area that’s filled with private greenhouses that you can reserve for two to four people. And while the little shelters are actually pretty warm (like a....greenhouse), they do have blankets in case you get cold.
Jojo's Shake Bar
For the month of October, Jojo’s in River North has turned its large outdoor patio into a giant pumpkin patch. So you can indeed pick pumpkins, but more importantly you can eat their over-the-top desserts (like caramel apples, shakes, pies, and shakes topped with pie) in a glass dome.
OK, so how much this will appeal to you will depend on how much you enjoy working out. The outdoor dining space at Bandit (and at sister restaurant Bar Siena across the street) double as locations for their Weekend Workout Series. They host a variety of outdoor classes run by different fitness boutiques around the city, followed by brunch on the patio (which is tented and has lots of heaters). Plus, they also have “Camp Dineamic” during the weekend that focuses on a bunch of different activities for kids.
Replay Lincoln Park
Replay in Lincoln Park is going full-on theme for October. This arcade bar has an outdoor, socially-distanced Stranger Things themed pop-up. The patio is decorated to look like the places from the show (like the Upside Down), and serves things like Eggo waffles, chicken nuggets, and cocktails like “The Mind Flayer.” Plus, they also have a drive-through haunted house in the alley behind the bar.
We appreciate the huge outdoor patio at Park & Field no matter what time of year it is. But fall is our favorite because it’s the best time to relax on the Adirondack chairs and make s’mores around one of their multiple fire pits. It feels kind of like camping, but here we can also watch sports on one of their outdoor TVs.
This year The Dawson added a wood-burning stone fireplace to its fenced-in patio. That, plus the trees covering the large outdoor space, create the kind of rustic environment we want after watching Yellowstone or a season of Alone. And if the fireplace isn’t enough to keep you warm, they also have blankets and outdoor heaters.
The Moonlighter is like a hybrid of Park and Field and The Dawson. This place has two stone wood-burning fireplaces that feel like they belong in a home on the frontier, but also a bunch of TVs so you can watch the game outside. Like a mullet: rustic in the front, sporty the back.
The team behind Machine Engineered Dining & Drink in Wicker Park opened Elsewhere, a pop-up in River North. If you’re familiar with Machine, you know this place is really into flowers (they have a flower shop inside their restaurant) and elaborate cocktails (the kind that comes with a sugar cage and tiny hammer). And you’ll find all of these things at Evermore, which is basically a secret garden-y type spot in a parking lot. Along with a long drink menu, they also have small plates.
Old Grounds Social
The all-season outdoor space at Old Ground Social is filled with couches, firepits, twinkle lights, plant walls, TVs, and giant dice. Does it look a little like the set of a social experiment show on Netflix? Maybe. But coming here for drinks and a burger is a nice change of pace from your apartment. Plus, they occasionally have deep-fried Oreos.
This 3,000-square-foot rooftop bar in Wicker Park has a lot of space for cool stuff to do besides eating and drinking. On Mondays, Tuesdays, and Thursdays. they have movie night (with spooky movies for October) and every Wednesday they have their rooftop concert series, where they play shows on giant screens and have a light show. All socially distanced, of course. Oh, and they also have heated “haunted cabins”, which are both creepy and unique.
Perhaps the most unique thing about Daisies is just how great the food is. That said, they do have a very cute pumpkin patch on their patio with pumpkins, hay, those dried corn stalk things, and everything else that makes us feel like it’s autumn in the Midwest. Plus, there are heaters. Get the sweet potato panini.