weekend in chicago

Tyler and I have been dying to go to Chicago for a while now. We use this aviation app called “Foreflight” that helps measure distance of places we can reach in the airplane in under 4 hours (which is a single leg trip: aka: no need to stop to refuel). Chicago was juuuuuust inside that range so we put Chi-Town on top of our list. We’ve also been trying to get Hamilton tickets for the better part of the last year… but have realized it's completely hopeless to think we'll be able to go in NYC. A few weeks ago, my Dad and his wife Karen told us they were going to see Hamilton in Chicago and wanted us to come see it with them! UH DUH! Two birds, one stone. 

We sent a bunch of texts out the night before to some friend groups in hopes of finding a few travel buddies (since we had two empty seats) - luckily, we’ve got some bomb dot com friends who are spontaneous (or crazy?) enough to take us up on the offer. Elna + Mark said they could join us 10 minutes before we ran out the door! They met us out on Long Island at the airport and we all hopped in road trip style: complete with snacks! Flying is half the fun of these weekend trips, especially if we convince new friends to come along. Elna and Mark are some of the best conversationalists and super entertaining to have along. 

The flight to Chicago ended up being two legs (because of insane head winds) so we made one stop for gas, and popped back up for the jump across Lake Michigan. We landed around 9pm, decided to drop off our bags at hotels and head out for dinner + games at Chicago Athletic Association. You guys- I’m not kidding when I say this was my favorite "entertainment venue" I’ve ever seen. It’s this old men’s club gym turned hotel/rooftop bar/games room. All through the 13 floor building you get the vibe of classy gentleman’s club with it’s dark wood and swanky lighting and music. We ate dinner at the Cherry Circle Room (I recommend the 3 dollar pretzel, which we ordered three times ;) We finished out the evening in the billards/games room with foosball & shuffleboard. Wandering around Chicago at 3am afterwards, we had millennium park all to ourselves, walked in the middle of empty avenues, and along a silent boardwalk. I love sleeping cities. 

We stayed at the Cambria Hotel - for an insanely reasonable 80 bucks a night (we couldn’t find an Airbnb for that cheap! We slept in the next morning, and met up with my dad and Karen for brunch. We had a lazy walk down Michigan Avenue stopping for hot cocoa and Chicago style popcorn at Garrett’s. We wound our way to the Bean and joined the hundreds of people trying to find a cool shot! 

We thought it would be cool to visit the planetarium, so we hopped in a cab and drove out to the edge of the water, only to find out it closed early! boo hoo! 

It ended up being alright, because we headed back to the hotel early to get fancied up for Hamilton and go out for dinner. We wanted to take the parents back to the Chicago Athletic Association to eat at the rooftop restaurant Cindy’s. Again, if you’re ever in Chicago - you gotta check this place out. Cindy’s has super interesting cocktails and huge shareable platters of food. We tried their pike, brussels sprouts, pork and ribs, and crunchy potatoes, and clams. We had a crazy amount of food on the table and it was all to die for. 

We headed off to Hamilton after dinner. Check out the pictures and review from the play here.

On Sunday we just had enough time to grab a late and lazy brunch before heading to the airport. We ate at a classic diner West Egg, which was tasty and off the beaten path. We made sure to grab another bag of popcorn before heading out though! The flight back was much quicker and we were able to make it in one leg! Tyler and I kept saying “we should come to Chicago every weekend.” It’s pretty cool to travel from a huge city like NYC to a huge city like Chicago and feel like you just have a massive amount to explore! I know we didn’t even scratch the surface of Chicago this trip! I can’t wait to go back! 

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^ have you had enough Bean pics yet???

^ have you had enough Bean pics yet???

^the Cherry Circle Room

^the Cherry Circle Room

^ view from the roof top of Cindy's

^ view from the roof top of Cindy's

^ the old swimming pool of the Chicago Athletic Association - turned dining room ;)

^ the old swimming pool of the Chicago Athletic Association - turned dining room ;)

^ Garrett's Chicago style popcorn - my new fav

^ Garrett's Chicago style popcorn - my new fav

^ Cindy's rooftop restaurant + bar

^ Cindy's rooftop restaurant + bar

^ This is the prettiest bar I've ever seen

^ This is the prettiest bar I've ever seen

I'm wearing:

This parka from Patagonia

These jeans from AG