Take a walk through the zoo or head just south to the spot where we got engaged. Hint: it was at the east end of South Pond!
Walk along the river and stop at City Winery for a drink. Bonus points if you get a Bear Hug!
Enjoy the hot honey soppresata pizza on a patio in Lincoln Park.
Pick up a specialty New York–style bagel. The Gold Coast location has a great patio to hang out on.
One of the best parts of this city! Bring a picnic blanket or beach towel and spend an afternoon in the sun with snacks. Oak Street Beach, North Ave Beach, or anywhere in between is always a good time.
Our very first date spot! Family-style Italian food in a lively, fun atmosphere.
A Chicago-inspired boutique with cute clothes, jewelry, accessories, and home items. (Also where the trendy Chicago hat comes from!)
A go-to for burgers, fries, and beer. The Old Town patio is perfect when it’s nice out.
A Michigan State bar and also where we had our first drink as an engaged couple.
Comedy staple in Old Town that never fail to make us laugh.
If you’re feeling adventurous—and love The Bear—this West Town gem is a must. There’s usually a wait, but pickup is an option if you’re in a rush. The Filipino breakfast is a favorite.
A fun, cozy Irish bar that’s great for groups (and comes with darts!).
A Chicago staple with a great vibe and great food. If you’re lucky, you might spot someone from Bachelor Nation.