Explore Our Neck of the Woods (Old Town & Gold Coast)

Kathleen and Andrew both spent the past few years living in the Old Town/Gold Coast neighborhood which has served as the location for many dates! Feeling a little hungry? Head to Nookies for breakfast classics, Small Cheval for burgers and fries, or Cafe Sushi for some BYOB sushi. Need a laugh? Catch an improv show at Second City or a comedy act at Zanies. Bring some cash and grab a drink at Old Town Ale House after to experience Anthony Bourdain’s favorite bar in Chicago.

Play Tourist (Mag Mile, River North, & the Loop)

The Drake is situated right at the end of Chicago’s famous Mag Mile! Head South on Michigan Ave. to pop in and out of shops or just admire the grand window displays. Keep heading down Michigan Ave. and you’ll run into the Riverwalk, Millennium Park (home of the Bean), and the Art Institute! Warm up with some classic deep dish at any of the many Lou Malnati’s (Andrew's pick) or Giordano's (Kathleen's pick) locations, try an Italian Beef at Mr. Beef’s (where they filmed The Bear), or grab a Chicago dog with all the fixings at Portillos!

Experience One of Our Favorite Dates (Wicker Park)

When searching for the perfect date spot, Kathleen and Andrew often settle on Big-Mini Putt Club for fun drinks and friendly competition (read: Kathleen always wins). Head West of the River to Chicago’s Wicker Park neighborhood. While there, you can partake in mini golf or just explore the quirky shops on Milwaukee Ave. When you eventually get hungry, venture to Tortello for handmade pasta, Piece for New Haven-style pizza and award-winning beer, or Mott St. for one of the best burgers in town. There are plenty of bars to stop by or you can venture to the top of the Robey Hotel for delicious cocktails and views of the city!

Savor the Holidays (Lincoln Park & Lakeview)

Some of Kathleen and Andrew’s favorite memories with family, friends, and each other have taken place in Lincoln Park and Lakeview. Catch one of the last nights of Zoo Lights at Lincoln Park Zoo, visit the Christkindlmarket outside of Wrigley Field, or take a stroll on Armitage Avenue for some post-Christmas shopping. Warm up at Cafe Ba-Ba-Reeba! for Spanish tapas, sip on a Watermelon Margarita at Old Pueblo Cantina, or tackle a juicy steak at Tango Sur.