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In addition to experiencing the Windy City’s cold weather, there is plenty to do to keep you warm and running around in the winter months! And if you do get a gentle snowfall, it really is a magical sight with the city lights. Winter is the perfect time to prioritize exploring the food and drink scene; therefore following this itinerary you will surely be filling your bellies and hearts. Popular activities include Broadway in Chicago, Millennium Park ice skating, Magnificent Mile shopping and, of course, bar hopping. To limit the walking, I purposely chose restaurants and activities within a small radius in River North. But there are the MUSTS that will bring you outside the neighborhood. 

My itineraries are made with a focus on doing, eating & drinking, which leads to seeing! Make plans easier. The editable templates allow you to add in your own personality, interests and adventures. Or simply download the PDF for a ready to go version. Enjoy!

Notes for Consideration:

  • Always check the weather before packing for Chicago. Layers! Even with that guidance, pack an umbrella and consider it may be 10 degrees colder than expected.
  • Bring comfortable walking shoes.
  • Download a ride share app. Taxis are overpriced and when outside of the downtown area, you will not want to go searching for a taxi.
  • If you can help it, do not drive downtown Chicago. Use public transportation (the L or the Metra).
  • When in doubt, try to make a reservation. Some restaurants do not take them, but others require them weeks or months out.
  • Be ready to eat.

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