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Chicago
4 Days  •  ​December 2022

Weekend getaway. Are there any better sounding 2 words? 

Ok, Happy Hour is probably at the top of the list….Merry Christmas for sure, Not Guilty…

Despite my slight exaggeration I contend “Weekend Getaway” is top 5 anyway. There is just something about getting away for a couple days that brings a smile to my face. The combination of leaving the norm and arriving someplace different is a tonic that when delivered at the right time is unbeatable. 

Now, there are 2 rules of thought around Weekend Getaways. You should either use them as 1) an adventure where you cram as much excitement into it as possible or, 2) an opportunity to reset and recharge.  For me, it’s the latter. Vacations are for that adrenaline pumping, white knuckle activity you’ve been dreaming about. A Weekend Getaway is the pause button of life. It doesn’t mean you won’t have fun, it just means you’ll hopefully gain more energy than expend.

This past summer, I had the opportunity to do just that. Get out of town for a little bit with the family and exhale. Our destination of choice? Chicago.  Far enough away from Kansas City to feel like you’ve left, but not far enough away to dread the trip.

What did our perfect Chicago Weekend Getaway look like? I’m glad you asked.

Day 1, Friday
  • Arrive late afternoon and check into the quaint and artsy 21c Museum Hotel in the heart of downtown
  • Enjoy a beverage in the hotel lounge, and walk down to Navy Pier.
  • Late night dinner at La Pizza & La Pasta - Eataly

Day 2, Saturday 
  • Explore the city starting at Starbucks Reserve Roastery
  • Riverwalk
  • Panoramic views at Willis Tower
  • Cool off a bit at Jeni’s Splendid Ice Creams
  • Visit Ohio Street Beach at Lincoln Park
  • Get our art fix with “The Devil Wears Prada” at the James N. Nederlander Theatre
  • Cap it off with a late night dinner of Chinese food at Chi Cafe

Day 3, Sunday
  • Sleep in and start the day with brunch at The Hampton Social
  • Shop along the Miracle Mile...every inch of it
  • Feel fancy at the Drake Bar & Lounge 
  • Carbo load with some Deep dish pizza at Gino’s East

Day 4, Monday
  • Get a caffeine fix at Big Shoulders Coffee - the marshmallow latte is a must try
  • Fight the crowds in and around Millennium Park to get a photo of “Cloud Gate” (the Bean)!
  • Checkout the Chicago Cultural Center (old Public Library building). It’s no New York public library, but kind of cool
  • Something for the parents; Crushed by Giants brewery - highly recommend the beer tasting flight
  • Finally, a Cubs game at Wrigley Field - the perfect ending to the perfect weekend​
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Day 4
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