Begin your date with an art deco walking tour right along Chicago's Riverfront. Admire the enormous Merchandise Mart and terra cotta facades as you work up an appetite. Then, head over to Goddess and the Baker currently whipping up mini pumpkin pies, caramel pretzel cupcakes, and hot spiced apple cider. True love is sure to start with a mini pumpkin pie!
Photo Credit: Barry Butler
Bundle up and head to the river for the award-winning Chicago Architecture Foundation Center River Cruise aboard Chicago's First Lady. It’s arguably one of the best ways to see fall foliage, to hear about Chicago's masterpieces, and a great opportunity to hold hands. Bonus: hot apple cider (spiked or not!) is now available! We cruise through November 24th.
Photo Credit: @apoorva_shivaram
Enjoy a brisk walk past brownstones on your way to Lincoln Park, followed by Fall Fest in Lincoln Park Zoo, which has professional pumpkin carving and hay bales galore. Later, head over to the pond for skyline views, the perfect background for a selfie together. End the day with dinner at Cafe Ba-Ba-Reeba, which is less than a mile from the park!
Grab your honey and start haggling at several indoor farmers markets that stay open year round! Logan Square Farmers Market has live music as well as gelato and baked cheese, so it's truly the place to be! With a wide variety of colorful fruits and veggies, it’s ideal for grabbing a gourd or pumpkin to decorate your space.
Photo Credit: Glenwood Sunday Market
View the changing leaves as you stroll through Grant Park, arm in arm with your main squeeze. Grab apple cider donuts at Stan's Donuts and sit down on a bench to people-watch. Alexa, play "Autumn Leaves," by Ed Sheeran.
Photo Credit: Curbed Chicago
A treasure trove of stained glass and red brick, this Hyde Park home uses Wright's signature autumn palette, which is why it makes for a lovely fall afternoon with a friend. You could also join the Autumn After Hours events each Friday in Fall, which includes wine and live music. Wine, architecture, and your crush? Sounds like a terrific evening.
Photo Credit: Urban Matter
Travel outside the city to explore 13 miles of hiking trails overlooking the Illinois River. With flowing springs and waterfalls, viewpoints perferct for picnics and rich history, Starved Rock State Park is just up the adventurous couple's alley. Oh my gourd, what a delightful day!
Photo Credit: Michele Valenta
After a day of wandering around Chicago, all you want to do is sit down on the couch with a classic! Cue up Harry Potter and the Prisoner of Azkaban, an obvious choice for its autumn colors and countless shots of Hagrid's pumpkin patch. Want to take your fandom to the next level? Make butterbeer!
Photo Credit:Poison Nightmares
Perhaps the most instagrammable place in Chicago, the wndr museum is made up of mirrored walls and a sequin tunnel. Too rainy or cold outside? Put some mascara on and go to the wndr museum, where you’re guaranteed a good photo. And if you're on a date, you automatically have someone to take your photo!
Photo Credit: Anna Miller
Nothing says Fall in Chicago quite like cozying up with a drink near a fireplace. Order a cheese flight and sample alcoholic ciders at The Northman as the evening winds down. Or, choose from the Fall menu of gin-focused cocktails at Scofflaw. And if you stay until midnight, you'll be treated to a warm chocolate-chip cookie.
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Photo Credit: Scofflaw
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