Things To Do

*Click to view descriptions under Dine and Discover*

Dine

  • The Violet Hour (Wicker Park)
    An intimate, dimly lit cocktail lounge tucked behind an unmarked door—equal parts moody and elegant. Come for the artful drinks, stay for the atmosphere. A great pre- or post-dinner stop if you’re in the neighborhood.
  • Sushi Rotary Taku (Lincoln Park)
    Endlessly fun and reliably delicious, this is our family’s favorite sushi spot. The conveyor belt is stocked with everything from spicy tuna to mochi—and yes, it’s all-you-can-eat. We’ve made a lot of memories here, and you just might see us making more.
  • First Draft (South Loop)
    Jamie’s favorite go-to for wings, beer, and a laid-back vibe. With an impressive tap list—featuring both local brews and hard-to-find international picks—it’s a perfect spot for catching a game or just relaxing with good food and even better beer.
  • Three Dots and a Dash (River North)
    A hidden tiki speakeasy tucked behind an alley—yes, really. With over-the-top cocktails and tropical vibes, it’s an immersive experience that’s perfect for out-of-towners. Reservations recommended (but so worth it).
  • Wishbone (River North)
    Our favorite breakfast spot—especially Jamie’s. Southern comfort food, generous portions, and flavors that’ll make you wish you had, like, 92,093,853 stomachs just to try everything. Go hungry. Leave happier.

Drift

  • We recommend getting a weekend Ventra pass
  • The Chicago “L” train system
  • Taxis, Uber/Lyft, Divvy bikes are all available through their apps
  • Spot Hero Parking App

Discover

  • Christkindlmarket (Daley Plaza or Wrigleyville)
    A traditional German holiday market filled with mulled wine, hand-crafted ornaments, bratwurst, and cozy vibes. It’s free to walk through and makes for a festive afternoon or evening stroll.
  • Ice Skating at Millennium or Maggie Daley Park
    Skate under the skyline! The Millennium Park rink is just below the Bean, while Maggie Daley has a longer, scenic ice ribbon. Skates are available for rent (reserve in advance if possible).
  • ZooLights at Lincoln Park Zoo
    This annual light show is beautiful, walkable, and free on select nights. There’s hot chocolate, festive music, and holiday-themed photo ops throughout.
  • Field Museum, Art Institute & Shedd Aquarium (Museum Campus + Loop)

If you’re looking to mix a little culture into your visit, Chicago’s museum scene delivers. Marvel at Sue the T. rex and ancient mummies at the Field Museum, stroll through iconic masterpieces (hi, American Gothic) at the Art Institute of Chicago, or spend a cozy afternoon face-to-fin with otters, belugas, and jellyfish at the Shedd Aquarium. All are easily accessible and perfect for a crisp December day.