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This is one of my favorite itineraries for Chicago. The Gold Coast/Old Town area is chic and happening. This, to me, screams girls weekend! Start off with tacos, ice cream and late night pizza in Old Town. Enjoy a posh brunch at RH, stroll through Lincoln Park, hit up a hip rooftop overlooking it, then get your laugh on at Second City. Sweat out those cocktails before shopping til you drop near Rush Street, pop in to get a Sprinkles Cupcake, and indulge in an upscale dinner followed by a speakeasy piano bar. Top it off with a visit to the 95th floor of the John Hancock for a goodbye cocktail. If that didn’t get you to book your ladies’ trip, I don’t know what will!

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.