Urban, hip, trendy, cool. These all describe the lifestyle of Chicago. And I am decidedly…not. Haha.

Philip and I recently celebrated our four year (four years?!) anniversary on August 10th and, to celebrate, made the short trip down to Chicago for a mini two-day getaway. We attempted to fit in with the “hip” 20’s- and 30’s-somethings young professionals—and I’d like to say we succeeded—with a $15 drink in hand and all. ;) It’s always fun to pretend sometimes, right? But safe to say, downtown Chicago is not going to be a place we call home anytime soon. But to visit? Oh yes, we’ll be back. Today I’m filling you in on the highlights. I would highly recommend all the places we went and stayed at!

Oh, and while we’re on the topic of our anniversary, if you’re interested or like sappy things like wedding stories, you can read here about how we met, or here about our one year anniversary (ironically enough, also included a trip to the Chicago area) and what we learned in that one year of marriage, or here and here about our two year anniversary. Guess I missed our 3 year! ;)

Accommodations

If you want to be in the heart of the city, the Chicago Athletic Association Hotel is where it’s at! Right on Michigan Avenue and overlooking Millennium Park, this 200+ year old building used to house a men’s club for the who’s who in Chicago back in the day, speakeasy included.

The decor and ambiance was just incredible, plus seeing the original architecture and detailing really felt like you were walking back through history a little bit. Every detail was accounted for, all the way to the design of the pads of paper and room service menu in the rooms.

One of the highlights of our stay there was checking out their Game Room, which was set up for anybody to start up a game of pool, shuffleboard, or even bocce ball. Since Philip and I didn’t really have a strict schedule to follow, we were able to refresh our memory on bocce ball and give billiards our best go. Let’s just say, I was a little rusty when it came to playing pool. :)

Dining

Naturally, the food was an important part of our trip. For dinner, I had heard great things about Cindy’s Rooftop, which was actually on top of our hotel. Talk about convenient. :) It had an airy and hip vibe to it thanks to the open air concept and a balcony overlooking Lake Michigan.

It was casual and approachable while offering some of the best tasting food I’ve had. It seemed to be the spot to meet up with friends after work for happy hour. We probably gave ourselves away by the pictures we were taking, but we tried to play it cool. ;)

I have no pictures of our breakfast stop, but a short walk from our hotel was a lovely bakery called Le Pain Quotidien, French for “daily bread.” Their bread is baked fresh daily (I bet you didn’t guess that one. ;)) and they have a delicious selection of pastries and croissants. I can’t speak for the rest of the menu, but if it’s half as good as the avocado toast I ordered, then you can’t go wrong.

Other places we visited worth mentioning:

Shake Shack for a chocolate shake for a late night treat. Yum!
SweetGreen for a light lunch. Seriously, this is one of my favorite places to eat! I discovered it last year when we were on the East coast. We ate there three times during our short week stay because it was that good. I didn’t think there were any in the Midwest, so this was definitely a great surprise to top off an already amazing trip.

Attractions/Shopping

The whole reason for planning this trip was to see the long awaited musical, Hamilton. And it did not disappoint! The music was fantastic, the storyline was powerful, and the talent was top notch. It certainly made for a very memorable trip and anniversary. Before we checked out of our hotel and lost our wifi service the next day, we quickly bought the soundtrack and listened to it in its entirety the entire trip home. :) So good!

The rest of our trip was pretty open. We toured around Millennium Park together and walked along Lake Michigan after our breakfast at Le Pain Quotidien. #tourists

And the rest of the time we shopped! Before exploring the rest of Michigan Avenue, our first priority was Trunk Club. I mentioned about this personal stylist company in a previous post from the last time we were in Chicago and I guess we just keep going back. :) It’s a loft on the top floor of an older building in downtown Chicago and, talk about hip and trendy, this place definitely has that going for them.

All in all, this was one of my favorite trips to Chicago. From the hotel accommodations and dining experiences to the phenomenal musical, it made for a special four year anniversary celebration for both Philip and me!