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Plan a day trip to Chicago using this free, ready-to-go itinerary! Show off the beauty of the city and your own neighborhood all in one weekend. This itinerary has the perfect combination of bonding time and activity time. Your guests will feel taken care of, well rested and entertained.

Upon arrival, greet your guests with snacks, beverages and an essentials welcome basket. With a delivery of Chicago’s famous pizza, they will already be in heaven! Then jet off to downtown Chicago to showcase the city life – Millennium Park, State Street, the Chicago Riverwalk and more! But also spend the day in your own part of town, sharing your “every day” life. Top it off with a wine tasting event that comes to your home. Your visitors will be begging to come back soon!

Check out my blog post on the Six Ways to Earn the “Best Host Ever” Title.

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, layers, 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. There are plenty of taxis in the downtown area, but they are over-priced. 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.
  • Include essentials in the guest rooms.
  • Prepare snacks and food ahead of time for in home dining.

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