Chicago Winter Weekend Itinerary

I’m starting a series I’ve been wanting to do forever focused on visiting Chicago during the four different seasons. My plan is to highlight different things to do and places to eat that are fitting for that particular season. I’ve formatted this post like an itinerary and tried my best to remain geographically and logistically conscious since Chicago and it’s charming neighborhoods can be challenging to navigate if you aren’t familiar with the city. I want these itineraries to represent the best of Chicago and therefore will not being taking COVID restrictions into consideration.

I’m kicking off the series with a Winter Weekend in Chicago guide. I’ll start by saying I know this isn’t the most popular time to visit the Windy City but Chicago can still be charming even when it’s freezing cold outside. Plus, there are tons of indoor activities to see and do where you won’t even notice the weather. Ultimately, there are so many incredible restaurants and amazing things to do in our city that I can’t possibly mention them all but hopefully this helps as a nice starting point if you’re looking to plan a trip to Chicago in the future.

Winter Weekend in Chicago

  • Friday
    • Check into hotel: Palmer House
      • I picked a hotel in the Chicago loop because it’s pretty central to the areas in this itinerary and walking distance to many of the activities. Of course there are tons of great hotels in this area of the city if you’re looking for alternatives.
    • Dinner at Topo Gigio
      • Topo Gigio is one of my favorite Italian restaurants in Chicago. However, if you’re in the mood for a different food genre, consider Twin Anchors, Adobo Grill or Broken English Taco Pub. All are in Old Town and walking distance to Second City.
    • Comedy show atThe Second City
      • TheSecond City is a Chicago staple and where many great comedians got their start including Steve Carell, Stephen Colbert, Chris Farley, Tina Fey, Amy Poehler, the list goes on! They usually offer an early and late show and almost always sell out so be sure to grab your tickets ahead of time.
    • Drinks/Out in Old Town
      • Old Town is one of my favorite late night bar scenes in Chicago. Just across the street from The Second City or a few minutes walk down Wells Street and you’ll find yourself plenty of options to grab a drink or late night snack. A few favorites include: Benchmark, The Vig and Happy Camper but you really can’t go wrong.
  • Saturday
    • Brunch at Wild Berry Pancakes & Cafe
      • A warm, hearty brunch will be necessary after a fun night out in Old Town. I picked Wild Berry Pancakes & Cafe because the food is delicious and it’s only a 10 minute walk from Palmer House.
    • Ice Skating at Maggie Daley Park or Millennium Park
      • Millennium Park and Maggie Daley Park are both so pretty and surrounded by the city. What better way to soak in the views than with a fun winter activity like ice skating?! Just be sure to reserve your spot ahead time because the weekends fill up fast.
    • Drinks at Cindy’s
      • A short walk across the street from the park is Cindy’s, the rooftop restaurant in the Chicago Athletic Association Hotel. Even though it’s cold, the views are spectacular from Cindy’s and it’s a great place to grab a drink and warm up after ice skating.
    • Dinner at The Publican
    • Drinks/Out in Fulton Market
  • Sunday
    • Walk down the Magnificent Mile
      • Start down by the Palmer House and work your way north on Michigan Ave. You’ll pass by Millennium Park [again] and can admire the impressive Cloud Gate sculpture [aka the Bean], stop to see the stunning city views as you cross over the Chicago River and pop into different retail stores along the way.
    • Lunch at London House
      • Stop and grab a quick lunch at London House which offers spectacular views of the city and river. This is also a great spot to visit during the warmer months when you can better take advantage of the rooftop.
    • Visit The Art Institute of Chicago
      • On your return trip, I highly recommend stopping to stroll through The Art Institute of Chicago. I’m not a big museum person but I really enjoyed touring The Art Institute. It is definitely worth seeing.
    • Head home
      • Check out of the hotel and head home!

Chicago really is a beautiful city filled with so much history and character. If you visit during the winter and enjoy it, I highly recommend coming back during another season because it only gets better and I’m sure you’ll come to love this city as much as I do!



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