In Your Spare Time
Au Cheval
Au Cheval is our favorite burger spot in the city, located in the West Loop, an area known for its endless restaurant options. The restaurant doesn’t take reservations, but part of the fun is putting in your name and then enjoying some bar hopping nearby while you wait for your table.
Ranalli's Pizza Bar - Lincoln Park, Chicago
Rannali’s is one of our favorite neighborhood spots in Lincoln Park to hang out with friends. It’s the perfect mix of bar vibes and comfort food—especially the pizza. Our go-to order is the hot honey soppressata pizza. There is an additional location in West Loop.
Parlor Pizza Bar West Loop
Parlor Pizza Bar is a fun indoor/outdoor hangout known for its pizzas, lively atmosphere, and weekend Bloody Mary bar—where you can build your own with all the toppings you can dream of. Fun fact: this is actually where Dillon and Maja’s parents met for the first time before a Blackhawks game!
Pizano's Pizza & Pasta
Pizano’s is a casual spot for grabbing classic Chicago-style deep dish or thin crust pizza. With a cozy, laid-back atmosphere and hearty Italian comfort food, it’s a great stop for a low-key lunch or dinner during your weekend in the city. Depending where you are staying, there are multiple locations to choose from.
Pizzeria Portofino
Pizzeria Portofino is a lively, waterfront spot located right on the Chicago River, perfect for when you’re craving both pizza and italian. With beautiful river views, it’s an ideal place to soak up the city while enjoying fresh pastas, wood-fired pizzas, and spritzes. We recommend making a reservation in advance—this popular spot fills up quickly!
Butch McGuire's
Butch McGuire’s is a classic Chicago dive bar and a great place to grab a drink or two.
Topo Gigio Ristorante
Topo Gigio is our favorite date night spot, located in Old Town where you’ll get a real sense of the lively nightlife. They offer endless Italian options with generous portions, making every meal a memorable experience. We recommend walking down Wells Street afterwards!
Eataly
Eataly is one of our favorite spots in the city—it’s part Italian grocery store and part restaurant. You can grab a bite of fresh pasta or pizza, sip on a glass of wine, and pick up some fun ingredients to take home. It's a great place to wander, snack, and enjoy! Located just one block away from The Gwen.
Nisos Prime - Chicago
Nisos Prime is our favorite steakhouse, located in the heart of the West Loop. Our go-to order is splitting the filet and the cacio e pepe—trust us, you won’t regret it.
Tango Sur
Tango Sur is a cozy Argentinian steakhouse tucked away in Lakeview—definitely worth the trip from downtown. It’s one of our go to date night spots, with flavorful steaks, the best empanadas, and a warm, candlelit vibe. Bonus: it’s reasonably priced and BYOB, so don’t forget a bottle of your favorite wine!