Chicago Three Day Winter Itinerary

Chicago winters have a bad reputation, generally. But, as cold as it can get, it is truly one of the most special times to visit. The holiday season is magical in Chicago. And even when the season is over, it is an incredible city to cozy up in without the crowds of summer. Bottom line, Chicago knows how to do winter right. Whether this be a staycation, or a first time trip to Chicago, we hope you enjoy this three day itinerary to visiting Chicago in Winter.

Below is a three day itinerary to visiting Chicago in the winter.

Chicago Three Day Winter Itinerary

Day 1: Get in the Holiday Spirit

  • Start your day with a coffee and pastry at our favorite Gold Coast coffee shop, Dollop
  • Make your way down the Magnificent Mile to enjoy the lights, do some shopping and check out the largest Starbucks in the world
  • Enjoy the festive Christkindlmarket in the loop for lunch with tons of unique vendors (many straight from Germany). I highly recommend the Glühwein and the Raclette sandwich.
  • Visit the beautiful Christmas trees at both Millennium Park and the Wrigley Building Terrace for some great photo opportunities.
  • While you’re there, try ice skating at the Millennium Park ice rink. Is there anything more festive than ice skating in the middle of Chicago?
  • After ice skating, you’ll be hungry for dinner. Make a reservation at our favorite restaurant in Chicago, Chicago Pizza and Oven Grinders. You may have heard of them for their famous pizza pot pie (don’t forget to get an order of Mediterranean bread, too!)
  • End your day with a hot winter cocktail at Butch McGuire’s. The quintessential Chicago Holiday Bar.
Chicago Pizza and Oven Grinders- Pizza pot pie
Butch McGuire’s

Day 2: Treat Yourself

  • Begin your day in elegance with breakfast at the Lobby at the Peninsula. We love the holiday decor here. (Pro-tip, head up to the rooftop bar, Z-Bar after breakfast for some fabulous views of the city)
  • Spend time at the world famous Art Institute of Chicago This is our favorite Chicago Museum and currently has some great exhibitions.
  • Enjoy dinner at a historic Daniel Burnham building, The Exchange. Aside from the incredible architecture of the building, the food is impressive and it is a great place to cozy up in the winter months.
  • Head down the street to the Chicago Athletic Association to have a cocktail in the stunning Drawing Room or play some games in the Game Room (wine, popcorn and shuffleboard- what more could you want?)
Lobby at the Peninsula
The Atrium at The Exchange
The Game Room at the Chicago Athletic Association

Day 3: Hop around the Hot Spots

  • Start your day with brunch at trendy Cira in Fulton Market. I absolutely love the waffles here (pictured below).
  • After brunch spend some time walking around Randolph street and Fulton Market. This is one of my favorite areas to shop and explore.
  • Stop into Eataly to shop for authentic Italian ingredients to bring home, while sipping on wine (….and maybe enjoy a charcuterie board as well.)
  • Head out to Wicker Park for a delicious Spanish dinner at Mama Delia’s (be sure to try the paella- some of the best we’ve ever had!)
  • Have a cocktail (or two) at a cozy speakeasy nearby, The Violet Hour
Mama Delia’s

Where to Stay

There is an overwhelming amount of hotels to stay in Chicago, but here are a few we would highly recommend:

Side note: reach out to us first to book at Since we are travel advisors now, many times we are able to get you a discounted rate!

  • The Viceroy -Located in the heart of Gold Coast with some great dining and bar options.
  • Chicago Athletic Association– Located across from Millennium Park in the Loop.
  • The Robey -Located in Wicker Park in Chicago’s Flatiron Building.
  • The Hoxton – Located in Fulton Market with a few great restaurants inside.
  • Hotel Zachary -Located in Wrigleyville with a trendy restaurant and views of Wrigley Field.

Let us know if you visit Chicago in the winter and what you loved about our Chicago three day winter itinerary. Comment if you have more Chicago in winter recommendations to add!

Published by happilyaway

We are a married couple living in Chicago, and we are obsessed with traveling (probably like you). Unlike many travel bloggers, we have no intention on quitting our jobs and traveling full time because we actually love our jobs (shocker- I know) and we have a sweet puppy that we can't bear to leave for for than 3 weeks at a time. This hasn't stopped us from making all of our travel dreams come true. We are excited to share our adventures with you and help show you how you too, can travel the world- even while working full time. Emilie & Chris

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