Things you HAVE to do in Chicago, Illinois (Winter + Year-round)

A travel guide for the best winter and year-round activities including views, food, drinks, and exercise spots in Chicago, Illinois.

The Windy City, more like Chicag-oh god its cold. Either way Chicago has it all.

Whether you want to taste a flight of Kombucha (gummy bear was my favorite flavor) at the Kombucha Room, play arcade games at Emporium Arcade Bar, or eat a loaded grilled cheese sandwich (the tenderizer is bomb) at Cheesies...Chicago has a little something for everyone.Not to mention, it is full of photographic backdrops.

Since there is so much to tour, I made an easy explore sheet to refer to for your trip.

Some of the best winter activities are:

The best year-round activities include:

  • Take pictures of The Bean
  • Walk around Millennium Park
  • Visit the Art Institute of Chicago and the Field Museum of Natural History
  • Visit Buckingham Fountain
  • Take a photo at the lit up Chicago sign (The Chicago Theater)
  • Shop around Michigan Avenue (coffee shops, treats, clothes)
  • Listen to live music (so many places to listen)
  • Explore the Chicago Riverwalk
  • Take a tour of Chicago architecture via boat
  • See a Comedy Show at Second City
  • Explore lakefront and beaches (great place to exercise)

The best views of the city:

  • The Skydeck at Willis Tower (the ledge 103rd floor, expect a long wait)
  • 360 CHICAGO TILT (94th floor of John Hancock): It is an enclosed moving platform that tilts you out over Michigan Avenue from the 94th Floor. If you go up 2 floors you can get the same view at the Signature Lounge for the price of two drinks.

Tasty food in the city:

  • Eat deep-dish Chicago-style pizza at Pequdo’s, Gino’s East, or Lou Malnati’s
  • Firecakes Donuts where you can get donut ice cream sandwiches
  • Check out coffee shops like Wormhole or Cafe Mustache
  • Eat dumplings at Urbanbelly, Lao She Chuan, or Yolo

Grab some fun drinks at:

  • J Parker
  • Cindy
  • Signature Lounge
  • Whistler
  • Bar Deville
  • Forbidden Root
  • Drumbar at Raffaelo Hotel
  • Noyane Rooftop the Conrad
  • Fountainhead
  • Celeste
  • Gene’s Sausage Shop
  • Taxim
  • Cerise at Virgin Hotels
  • Or if you are really feeling adventurous do the Chicago Bar Decathlon (Bar Crawl)

Get your exercise on by:

  • Walking The 606, which is Chicago’s version of The Highline in NYC. It is an elevated trail that goes through 2.7 miles of the city’s northwest side neighborhoods like Wicker Park, Bucktown, Humboldt Park, and Logan Square
  • Check out Wrigley Field
  • Walk around Alta Vista Terrace District, which is a historic district in Lake View located two blocks north of Wrigley Field. The one-block street was built in 1904 in imitation of the row-house style of London
  • If you really need to get your sweat on, sign up for a free week fitness at one of these fitness locations
  • Take a hike at one of these hiking spots

With so many different things to do and see in the city you will never get bored.

Go explore this incredible city for yourself and let me know what gems you find!