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“Hey, Chicago! What do you say??” Well, you know what I say… book that trip! You haven’t experienced Chicago unless you’ve watched the Cubs at Wrigley Field. Yes, there is another baseball team in the city, but I am biased. Here is an itinerary consisting of baseball, hot dogs, tacos, margaritas, brunch and more. Spend time in Lakeview and Lincoln Park walking the bustling shopping districts or endless amount of restaurants and bars. Beyond sports, Chicago is known for an amazing food scene. I suggest you hit up as many food stops as possible; therefore, you’ll find a taco crawl and bar crawl schedule. If you have the means to spend each day in the stadium… go for it! And cheer hard for the W!

My itineraries are made with a focus on doing, eating & drinking, which leads to seeing! Make plans easier — the editable excel 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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