Chicago is an amazing food city. From Michelin-starred restaurants to hole-in-the-wall treasures, the city is nothing short of a food mecca.
That being said, it’s hard to enjoy by yourself; after all, sharing food with someone takes a great amount of respect (and generosity). Here’s a list of suggestions for your next food-centered date with that special someone, depending on what season it is.
SPRING: Get Shaved Snow and Explore Navy Pier
Bear with me, Chicago natives. While Navy Pier has long been thought of as a lame tourist trap, its recent renovation has made it a much less cheesy spot, not to mention it now has a brand new Snow Dragon Shavery.
Feast on adorable macaron ice cream sandwiches, bubble tea, and shaved snow while revisiting your childhood on Navy Pier’s amusement rides. Who can resist a good old-fashioned Ferris wheel ride? It doesn’t get more textbook romantic than that.
SUMMER: Get Caramel Pie from Beatrix To-Go and Walk to Millennium Park
One of Beatrix’s most famous desserts is its caramel pie. It’s silky, creamy, and the perfect balance of sweet and a hint of caramel bitterness. It also comes in a cute little pie-shaped container that’s easy to hold and perfect for eating out of while walking around Millennium Park.
While the trek from Beatrix to Millennium Park is around 20 minutes, you pass through the heart of downtown Chicago and the Chicago River, a breathtaking sight especially after dinner.
Millennium Park includes the famous Cloud Gate sculpture, AKA “The Bean,” but if you’re not in the mood for tourist traps, Jay Pritzker Pavilion usually has free concerts and movies during the weekends in the summer.
It’s also worth mentioning that the pavilion is BYOB. So, grab a slice of pie and a bottle of wine and prepare for a relaxing night of music and summer laziness.
FALL: Brunch at M. Henry and A Visit to the Lincoln Park Conservatory
While M. Henry is quite a ways north in the city, it’s well worth the trek. It’s most famous for its bliss cakes, a super fluffy and thick version of a pancake. It’s stuffed with a fruit-infused marscapone cream and is coated with a crunchy oat topping and fruit compote. It’s a must-try for brunch aficionados.
Afterwards, if you’re still hungry, you can go across the street to La Baguette Bakery, a bakery that offers insane value for gigantic pastries. You’ll find traditional Mexican breads and desserts along with your typical cupcakes and cookies.
To walk off all that food, I suggest heading to the Lincoln Park Conservatory, a glass-domed structure filled with a variety of exotic plants. It’s a beautiful spot to briefly get away from chilly fall weather, and the fact that admission is free is another huge plus.
WINTER: Christkindlmarket in Daley Plaza
Christkindlmarket is a traditional German Christmas marketplace that is set up every December in the heart of Daley Plaza. With delicious offerings ranging from mulled wine in a boot and traditional gingerbread to assorted mixed nuts and potato pancakes, it’s hard to leave hungry.
If you’re looking for a one-of-a-kind Christmas gift, there are shops filled with handmade ornaments, trinkets, and toys. Even with the Chicago cold, this marketplace brings plenty of Christmas cheer, and there will be plenty to talk about as you stroll around with your date.