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PERFECT ITINERARY FOR 2 DAYS IN CHICAGO

  • Writer: Cameron Cooper
    Cameron Cooper
  • Apr 9, 2020
  • 2 min read

Updated: Apr 14, 2020

I don't know about you, but these bitches have full-time jobs so we do a lot of our traveling over the weekend. So if you're in the same boat, we put together an itinerary for a weekend trip to Chicago, IL - arriving Friday night and leaving Sunday afternoon.


Saturday

  • I know you probably got in late Friday night for a post-work flight, but be sure to get ready to rise and shine for an early Saturday morning!

  • We recommend starting off your day with a trip to the Willis Tower - SkyDeck (used to be Sears Tower) - get the earliest time slot available so you can avoid too long of a wait. This will take you to the 103rd floor so you can get photos on a glass floor and will provide you an amazing view of 4 states.


  • Once you're done with your photo session, walk over to the iconic Bean. Spend some time here getting some fun pictures. And if you're in Chicago during winter time, hit up the McCormick Tribune Ice Rink right out front of the Bean.


  • By now, you're probably hungry and ready for lunch. So walk across the street to Cindy's Rooftop so you can enjoy food and drinks with a beautiful rooftop view overlooking the Bean.

  • After this, take some time to walk around the city and fully take it all in. And if you're like us, you were ready for a midday nap ;)

  • Once the sun starts to go down, it's time for a fun evening activity and we HIGHLY recommend getting tickets to the underground Chicago Magic Lounge (get tickets as early as you can!). This is a fun place to get dinner and drinks, plus see a MIND BLOWING magic show. It was such a fun and unique experience.

  • If you're feeling up to it, now it's time to hit up the Chicago nightlife before you head back to the hotel. We didn't really know a lot about it but we were recommended to go to Tao Nightclub and WOW, what an experience. Expect to wait outside in line for awhile and then for an absolutely jam-packed inside, but it was such a fun time, especially if you're a dancer.


Sunday

  • After a wild night, it's time to make that early morning sacrifice one last time before you head home. First stop we recommend is heading to Navy Pier where you can shop, eat, and ride the ferris wheel!

  • Before you head back to the airport, we recommend getting stopping for lunch to grab a yummy Chicago-style pizza at the famous Lou Malnati's. There are multiple around the city, so be sure to find the closest one to you.


XOXO, Cam

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