• Sipster Team

7 Ways to Do Fall in Chicago Right, Social-Distance Style

Usually fall in Chicago brings seasonal brews on tap, sweet and spooky craft cocktails, outrageous pop-up bars and insane deals on pitchers and bloody marys during football games. Making the most of our outdoor spaces has kept the Windy City social scene alive during the summer of COVID, but there’s already a chill in the air! This fall season brings our last chances to get some socially distant meet-ups in before the frigid winter winds and snow are back to keep us indoors.

Soon you’ll be able to check the SIP app to see what’s poppin’ at Chicago’s bars and restaurants. But until then, we’ve learned a few tricks for planning safe and social outings in the city—check out our “bucket list” for fall in Chicago:

1. Drink a Local Oktoberfest in an Outdoor Beer Garden

You may or may not be able to find polka music or Bavarian soft pretzels, but Chicago has plenty of beer gardens where you can enjoy a seasonal brew in the crisp fall air. Several local breweries distribute signature fall flavors; watch out for Oktoberfests from Revolution Brewing, Metropolitan, Burnt City and Half Acre as well as Hoodie Weather Lager from Forbidden Root Brewing Co.

2. Happy Hour on the Riverwalk

With plenty of nooks and crannies inside and outside, the Riverwalk is a sure bet no matter what the weather decides to do! Sip on a glass of red at City Winery Chicago Riverwalk, grab a beer at the Chicago Brewhouse, choose between cocktails or coffee at Tiny Tapp, or take in some tunes at Beat Kitchen on the Riverwalk. If you’re feeling adventurous, rent kayaks or a paddleboat to get out on the water!


In the Midwest, we love our football. You don’t have to go to the stadium to have a good old-fashioned tailgate party! You don’t really need a truck with a tailgate either, but it helps. Grill some brats and burgers, fill the crockpot with something cheesy and make sure you’ve got a cooler (or a keg) full of beer. And don’t forget something a little stronger for touchdown shots!

4. Enjoy some Live Music, Outdoors

Chicagoans know that as summer turns into fall, our days to enjoy the outdoors are numbered. If you know where to look, there are still some opportunities to get your live music fix on rooftops, patios and in other outdoor spaces. Surprise someone special with tickets to a romantic Candlelight classical music concert, and don’t forget to bring a comfy sweater.

5. Stock Up on Seasonal Produce and Treats

Chicago City Markets are essential businesses! Fall is the time to buy pumpkins, squash, kale, cauliflower, broccoli, brussels sprouts, leeks, kohlrabi and other cold-weather crops. Pick up some of your favorites for healthy and hearty soups and stews. And if you’re looking for fresh apple cider donuts, the farmer’s market is probably your best bet!

6. See some Fall Colors

Any park near you will probably have some pretty fall foliage, but the ones on this list are worthy of making a day trip. The Chicago Botanic Garden, Morton Arboretum and Lincoln Park top the list. For a sweet Saturday afternoon date, pick up warm drinks or head home afterward to fix up a hot mulled wine and get cozy.

7. Dig Into some Pumpkin (or Apple or Pecan) Pie

There’s nothing quite like a big slice of pie slathered in whipped cream. This classic fall comfort food can be found at several local spots for delivery or takeout. Stalk them on social media first to find out what flavors are available, as they may change on a daily basis—the anticipation is part of the fun!

Have a fantastic fall, and download the SIP app to stay on top of drink deals in Chicago as soon as bars and restaurants are back to business as usual!

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