The Second City is one of the world's premier comedy club, comedy theater, and school of improvisation. They have live shows every night. Some notable alumni include Bill Murray, Steve Carell, Chris Farley, Tina Fey, Amy Poehler and Keegan-Michael Key. Make sure to buy tickets in advance because they typically will sell out!

A unique spot in the West Loop with two unique nine-hole mini-golf courses, swanky bars and lounges to enjoy cocktails. The Puttery is a fun interactive activity everyone is sure to enjoy!

There are various museums to explore throughout the city. A few notable ones are the Art Institute of Chicago, The Field Museum, Museum of Science and Industry and the Museum of Contemporary Art.

Bar Siena: This is one of Taylor’s favorite places in the city. You can’t go wrong with any of their starters but Taylor’s favorite is the burrata. There are so many good dishes to choose from that sharing plates to taste multiple items is the way to go!

Il Porcellino: A classic Italian restaurant in River North. This spot is one of Brad’s favorite places to get gnocchi in the city! Make sure to get the Tuscan cheese bread as a starter!

Nancy’s: Nancy’s is a neighborhood staple for us. If you have been at their place and ordered in pizza, you can guarantee it came from Nancy’s. We may be biased but some of the best thin crust pizza in the city.

Peaqods: While everyone has their take on the best deep dish pizza in the city, we think this place takes the cake. Be prepared to wear stretchy pants because you will need them if you can make it through 2 slices.

Green Street Meats: While this doesn’t compare to KC barbecue, it’s one of our favorites in the city. Get your own sandwich or share a few things. The frito pie can’t be beat.

Bub City: Another BBQ spot we enjoy but with live music!

La Josie: An upscale Mexican restaurant in the West Loop. Tasty margs and a lot of tacos to choose from. Don’t skip the guac!

Ema: If Mediterranean is your jam, you should definitely check out Ema or it’s sister restaurant Aba. Both amazing and you can’t go wrong with anything on the menu. Highly recommend making a reservation.

Maple & Ash: An upscale steakhouse in the city where we celebrated our 5th Anniversary. You can’t go wrong with any of the steaks on the menu but make sure you get a side of mashed potatoes!

Au Cheval: One of the best burgers in the city. They don’t take reservations so plan for a bit of a wait. We put our name in and then head to Lonewolf or Haymarket for a drink while we wait for a table.

Theory: Our go to spot to watch all of Iowa’s heartbreaking losses.

Blind Bar: A speakeasy in the West Loop that you enter through a barber shop. Upscale cocktails and live music.

Goose Island

Maplewood