Chicago Itineraries

So you found yourself with a day or two in Chicago and you want to fill your free time with some fun stuff and great food- you’ve come to the right place! I have a variety of activities that you can add to your Windy-City list, read the full Chicago post for more details and stories of my visit. If you are only able to visit for one day, or for two days, see the two separate itineraries below to best accommodate your schedule.

One-Day Itinerary 

If you only have one day in Chicago, here are the top 5 things to do:

  1. Stop to pick up a quick breakfast at Stan’s Doughnuts.
  2. Take an Architecture Boat Cruise- Chicago Line Cruises
  3. Take a stroll through Millennium Park to see Cloud Gate aka “The Bean,” and other sculptures, and Buckingham Fountain (11 minute walk from Millennium Park).
  4. Schedule the Chicago Pizza and Cocktail Tour.
  5. End your night with a drink or dessert at The Signature Room
Map for your “Chicago One-day Itinerary”

Two-Day Itinerary 

Day 1:

  1. Stop to pick up a quick breakfast at Stan’s Doughnuts.
  2. Take an Architecture Boat Cruise- Chicago Line Cruises
  3. Engage your inner child, play and explore the Navy Pier.
  4. Go to Giordano’s for lunch, to compare later with Lou Malnati’s.
  5. Take a stroll through Millennium Park to see Cloud Gate aka “The Bean,” and other sculptures, and Buckingham Fountain (11 minute walk from Millennium Park). Can be moved to day two if preferred.
  6. End your night with a drink or dessert at The Signature Room
Chicago Itinerary Map: Day One

Day 2:

  1. Climb up to the 360 Chicago Observation Deck.
  2. Eat an Italian Beef sandwich at one of the many locations of Portillos.
  3. Visit the Willis Tower to learn all about the building’s history.
  4. Purchase tickets for the Chicago Pizza and Cocktail Tour.
Chicago Itinerary Map: Day Two

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