A few weeks ago Warren and I flew to Chicago for a whirlwind weekend for our friend’s wedding. Warren had never been to Chicago and the last time I was in this city was when I was 8 years old and going to the American Girl Store with my mom! So we were both very excited to explore this new-to-us city. We got in very late Thursday night so we could have a full day on Friday. Luckily we were so beyond blessed with gorgeous weather - I’m talking sunny and in the mid seventies! So glad we got to visit Chicago during the summer :) I’m sharing our itinerary below of what we did and ate for our quick 48 hours in the city!
We slept in a little as we didn’t get into our hotel room until about 2am.
10am: Out the door and went straight to The Bean!
11:15am: Brunch at Beatnik on the River (HIGHLY recommend this place! Great vibes and great food.)
1pm: Met up with friends at Murphy’s Bleachers before the Cubs Game
2pm: Cubs Game
4pm: We tried to go check out Navy Pier after the game but Warren fell asleep in the Uber so we decided to go back to the hotel and take a nap before dinner instead haha.
6pm: Cocktails at London House
7:30pm: Dinner at RPM Italian (SO YUMMY!)
9pm: We then went back to our hotel as the Bride and Groom planned a welcome cocktail hour at 9pm.
11:30pm: Met up with friend’s who had a table at Bodega, which is a super cool speakeasy with an entrance behind a Kitchen in a restaurant!
We had a littleeee bit of a slow start to Sunday as we stayed out late the night before and maybe, just maybe were a tad hungover haha.
9:30am - Room service in bed (I literally LIVE for room service! It’s just the best and worth the $$$ for at least one day)
11am - Shopped along Michigan Ave/The Magnificent Mile for my birthday! We had so much fun walking around.
1pm - Met up with friends at the restaurant where Deep Dish was invented: UNO’s. It was SO good. And even our Uber driver was impressed we went there as he said most tourists go to Giordano’s which apparently is not the best pizza and more of a tourist trap. Another deep dish place that came highly recommended was Lou Malnati’s.
2:30pm - We tried to go to Cindy’s Rooftop bar to grab a drink after lunch as it’s supposed to have amazing views of the city but unfortunately the line to go up was way too long and we decided to just cut our losses and head back to the hotel to get ready for the wedding.
4:30pm - off to the wedding of a century!
We wanted to fit in so much more but sadly were a little limited with time so we will just have to come back! Here’s what we didn’t get a chance to do or eat so saving it for our next trip :)
Duck Duck Goat
Paradise Park (brunch/lunch spot)
Original Billy Goats (Burgers)
The Aviary (world famous cocktails)
Cindy’s Rooftop Bar
Three Dots and a Dash (Tiki Cocktail Bar)
Lost Idol Tiki
Architecture River Cruise
Sky Deck at Willis Tower
Original Crate and Barrel