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Chicago Athletic Association


Travel: A Weekend With Friends in Chicago

Cindys Bar Chicago.jpg

A friends weekend away without the kids in Chicago is just what the doctor had ordered. That and tequila shots. This was by no means our first time visiting the Windy City but this trip was full of firsts. Lets talk trip details: 


We booked rooms at the Chicago Athletic Association. It. Was. Excellent. The hotel is an 1893 hotel of a landmark that is a 'living, breathing ode to Chicago.' A space that was once reserved for the rich and privileged is now one of the hottest hotels in in the city. There you'll find a plush lobby/reception area where you can grab drinks, food, coffee (via the Milk Room), meet or do work. It's rich in texture like leather and dark wood and full of warmth. Around the corner is the authentic Game Room with billiards, checkers, darts and more. We caught a late game of shuffle puck on Friday and it was a blast. It's also home to Cindy's which I'll address next and did I mention there is a Shake Shack in on the first floor?! 


So many drinks so little time. We kicked off our weekend away with cocktails at Cindy's located on the rooftop of the Chicago Athletic Association. Talk about views... it over looks Lake Michigan and Millennium Park and it's just as fabulous as it looks in photographs. The drinks were pretty and the place was hop'n - it was the perfect start to our party. 

We eventually made it out of the hotel and found our way to Three Dots and a Dash, a super fun tiki bar just off the beaten path. The waitresses are dressed to the nines and as far as I could tell every single drink had rum in it! We ordered The Conch bowl to share with the table and it did not disappoint... complete with dry ice/fog, neon lights and those childish uber long straws that resemble those giant pixie sticks we ate as kids. It was perfect. 


We were led by our good friend and Chicago local Timm Bloem to Ema, a Mediterranean restaurant showcasing share plates. We were spoiled by both our waiter and Chef CJ Jacobson when they asked if they could take control of our dinner orders for the evening. They did not disappoint and afterwards the group agreed it was a top notch experience. If you go, order all of the hummus!


A friend recently said to me, "Of course there will be mimosas at brunch, without them it's just called breakfast." I'm likely late to the party on that joke, but it's one that should be repeated. On Saturday morning we made reservations at The Lakefront Restaurant at Theatre on the Lake. Located just north of downtown right near Lincoln Park on the waterfront, The Lakefront serves a hefty brunch menu complete with signature mimosas. 

Also, Dove's Luncheonette! So, full disclosure we didn't actually eat here but we certainly did some day drinking here. Located in the heart of Wicker Park you'll find this adorable diner that's straight out of the 1960s. They do counter service all hours of the day and play music from a record player. 


On Friday night we toured the Nike Chicago's House of Go, their latest pop-up shop showcasing their newest running shoe: the Epic React. The pop-up took over the old Cole Haan store front located just next door to the Nike Chicago on Michigan Ave. The first floor was designated to sharing a bit of the Epic React experience where people could test out the shoe and wear them through a guided 'fun-house' of sorts. With the guidance of our buddy Timm who's a crucial part in the Nike Chicago campaign and brand, we meandered our way through the House. Emily and I tested out the shoes on the animated treadmill - a mega two person track with digital wall displays on all sides. I managed just find while on the treadmill and I shit you not, two seconds after stepping off the treadmill I fell flat on my face. I was embarrassed but glad to have provided a solid set of laughs to my friends and strangers alike. 

Saturday night was 100% dedicated to watching Michigan basketball. We snagged a primo spot at Henry's Chicago in front of their 4 screen TV display which was perfect for watching the game. We splurged on nachos and wings for dinner and I wasn't kidding about the tequila shots. After Michigan won we celebrated by dancing like fools at the Rec Room located just below Henrys. We danced hard and enjoyed the heck out of the night. So much so that Jeff actually left the bar with someone else's jacket. We returned it when he realized he couldn't fit his arm into the sleeve. 

And of course, we couldn't make a trip to Chicago without doing some shopping. We skipped the normal spots on the magnificent mile and went local for shops in Wicker Park and Lincoln Park. We wore our walking shoes and made sure to stop along the way as we got thirsty. A super fun spot worth writing home about was the Chubbies Chicago Pop-Up Shop.  Swim suits were purchased. That's all I can say.

Thank you Chicago and thank you Timm for a fantastic weekend away. We love you both! 

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