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Looking for a unique twist on a Chicago date weekend? Enter Wicker Park, Bucktown and Logan Square, a hub for the creative types which leaves room for exploring and adventuring through coffee shops, book stores and boutiques. These active neighborhoods have blossomed over the past ten years being officially invaded by young professionals and families. Here you’ll find recommendations for a cooking class, carefully crafted cocktail spots, mind blowing tacos, local coffee shops and enjoyable walking paths. To complete your special weekend, book a romantic experience at Aire Ancient Baths Chicago to soak in a salt, cold or hot bath topped off by a calming massage. With this in mind, I am about to block off a weekend right now for us to go!

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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