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13 Things to Do in Chicago This Weekend (That Will Look Good on Instagram)

From biking around town to taste-testing the best deep-dish—did it really ever happen if you didn't 'gram it?

Go on a Bike Ride

You don't have to be one of those guys who rides Lake Shore Drive in head-to-toe spandex to enjoy biking around the city. Chicago has so many accessible routes that take you around beautiful lagoons, cultural detours and even brewery pit stops. Just don't make us get all mom on you and promise us you'll wear a helmet. (Via Thrillist)

Try a Hip New Workout

Sure, we’d all like to work out more. But who can make that happen when the gym is so inconvenient and Netflix is just so damn convenient? The answer is closer than you think—literally. We’ve found the top workouts in ten Chicago neighborhoods to help make breaking a sweat a little more effortless.


Get Your Friends Together for a Bar Crawl

Presenting the great Chicago Bar Decathlon, organized by geographic proximity as you fan your way outward from Downtown. You may not take home a gold medal, but we do recommend having Advil on hand for the day after. (Via Thrillist)

Go for Afternoon Tea (Yep, It’s Cool Again)

We never need an excuse to eat pastries, but afternoon tea is an awfully good one. The petits fours, the cookies, the scones—they’re all included along with stacks of dainty sandwiches and pots of premium tea. Best of all: All you need is a friend and a reservation, and your afternoon tiny-cake consumption is set. Here's where to make afternoon tea reservations in Chicago


Pull Up to the Counter at an Old-School Diner

There are few experiences more comforting than sitting in a diner, sipping on a cup of hot coffee and digging into an omelette that even the hottest brunch spot can't rival. Thankfully, there are some surviving greasy spoons around Chicago. Come hungry. (Via Thrillist)

Take a Hike

We don’t know quite how to break this to you, but it’s come to our attention that Illinois is rather, um, flat. But hey, what we lack in mountain ranges we make up for in literally everything else, and we’re home to more than enough natural wonders to suppress that occasional and unsettling urge to climb a steep incline. Here, seven of our favorite places to channel our inner green goddess.


Book an Easy, Romantic Getaway

From romantic stays in a former brewery/tree house to a weekend retreat in a train caboose with an outdoor hot tub, these ten Midwest destinations offer way more romance than another night of GrubHub and rosé. (Via Thrillist)

Eat at One of Chicago’s Amazing New Food Halls

Decision paralysis is a real thing, especially when it comes to eating out. Do you want a burger or ramen? What about sushi? Fortunately, Chicago’s growing food hall trend gives you a bevy of eateries that offer all of the above. Now you know where to go—but see if you can decide what to order at these five top food halls.


Get Spooked

It's not just the traffic on the Dan Ryan that's scary; Chicago is home to lots of supposedly haunted spots—including, apparently, Oprah's Harpo studio (whaaat?). It doesn't have to be Halloween to get in a good scare. Here are some of Chicago's spookiest places. (Via Thrillist)

Transport Yourself Back in Time at an Old-Fashioned Ice-Cream Shop

Call us crazy, but a milkshake just tastes better when it’s served out of an old-fashioned soda-fountain glass. That’s why we searched high and low for Chicago’s best old-school ice-cream parlors. Here are five spots that dish up the retro charm as readily as the sugar cones.


Hit the Road

It’s amazing how quickly three hours go by when that “next episode” button keeps popping up. But with the same amount of time in the car, you can transport yourself to romantic retreats, majestic waterfalls and (yesss) wineries. Forget battling the security lines at O’Hare—these five road trips are our top picks for your next weekend getaway.

Fill Up on Dumplings

Dumplings: These self-contained, edible little parcels are some of our favorite cold-weather treats. From the savory filling to the light-as-air wrapper (fried or steamed—we love both), it’s a perfect food from start to finish. If you agree, try one of Chicago’s nine best dumplings, which we’ve ranked below.


Taste-Test the Best Deep-Dish You Haven’t Already Heard Of

We surveyed the city far and wide to come up with a list of the very best deep-dish pizzas in Chicago, leaving off some famous names and including some you've probably never heard of. Happy gorging, Chicago-style. (Via Thrillist)