For a lighter, airy aesthetic, follow up with dinner at Tony Mantuano’s Michelin-starred Spiaggia.Close out the night with sing-a-longs at the Zebra Lounge piano bar, or maybe elsewhere...Later on, Reggies is around the corner for rooftop drinks and/or a rock show.Scavenge for vintage finds and partake in a monthly supper club Sometimes the best way to get to know people is by the type of junk they’re willing to put in their apartments.For dining in this 'hood, you’ll find the infamous Kuma’s Corner for some of the best burgers in the city (as long as you and your date can withstand the Slayer-grade metal on repeat) or Honey Butter Fried Chicken, where you can grab food to go for a picnic in Brands Park down the street.
Palmisano Park (also known as “Mount Bridgeport” or Stone Quarry) has 27 acres of paths through wetlands to roam with your Sugar Shack sweets.
You’ll want to walk off that breakfast, so continue for a stroll through Ronan Park’s Multicultural Sculpture Park & Healing Garden or the trails around the North Park Village Nature Center.
In the evening, dine at Angelo’s Wine Bar (or Ixcateco Grill if you’re looking for a great BYOB spot) followed by Break Room Brewery a couple blocks over.
Those looking to take their relationship to the next level should consider booking a Chicago Helicopter Experience over the city, but obviously not if your date is terrified of heights.
Spend the afternoon at Whirly Ball Chicago’s giant complex, which has happy hour specials Sun-Wed, bowling, laser tag, and three courts for that crazy game combining lacrosse, basketball, and bumper cars.