How to spend 12 hours in Chicago
3 pm arrival:
This hotel was a perfect first time for us, second stay for our besties. Right in the heart of the magnificent mile, it is well within walking distance of a full day of activities. Valet parking is available on site and we used Uber for the remainder of our stay. The rooms were spotless, spacious, and the beds were cozy. Upgrade to the king corner room for some pretty spectacular views (and I believe it was maybe $17 extra but worth the skyline)
After check in we hit up Timothy O'Toole's Pub:
Just a block away from the hotel you can find one of the best sports bars in the city. Featured on Man v Food: home of the Big Timmy Burger Challenge. Really wanted to come back the next morning to try their mammoth meal sized blood marys but we unfortunately didn't make it back this trip. Next time!
4:45 pm Dinner Reservations:
Grab an uber from O'Tooles and head West to the Gilt Bar if you are looking for the perfect date night. This place was phenomenal!! Everything about it - the vibes, the drinks, the food omgosh the food!!! There's a fun photo booth / hall in the basement too so be sure to check that out. It sounds corny but it was actually so cute. Tack your photo on the wall of nostalgia. They do have a speakeasy downstairs too but was closed on our visit for a special event. Reva & Colby have visited the speakeasy before though and we will be back here again!
Game day tickets or just want to hit up a sports bar lined with TVs and hyped up patrons, then head over to the Barn Hockey Bar. Don't expect to find a table though on game days unless you plan to arrive early. Luckily for us, Colby broke his foot so the manager noticed him struggling to get to the bar for a drink and put us in one of the reserved tables. We didn't stay long, just one drink before walking over to United Center, but the place definitely vibes on game night!
7:30 pm Blackhawks Game:
Of course we came for the hockey action and thoroughly enjoyed the Blackhawks game, but you could also catch the Bull's play, a concert, comedy show, or even Disney on Ice. The perfect date night options!
"Richard’s Bar is a classic tin-ceiling bar with budget beers, hard-boiled eggs & a jukebox filled with rat-pack classics located in Chicago at 491 N Milwaukee Ave."
My husband actually told me about this classic little tavern after a local told him about it. We hit this up after the game and I am a sucker for a place full of history, this bar met my expectations!
If you want a nostalgic feel, history fueled, no fuss, dirt cheap drinks with jukebox classics this is the joint for you. With many of its original pieces still in place, like the cash register and fee boards, the trap door at the front, and much of the decor, you can almost feel the essence of the infamous mafia days in this place. Possibly past and present...
Another recommendation from our buddies and the highlight of my trip!
"In 1872, following the Great Chicago Fire of 1871, the Green Door Tavern opened its doors. A lot has changed since then, but the Green Door has always remained true to its historic Chicago roots." The building actually began leaning shortly after being built and is quite obvious to the naked eye.
8 am Sunday:
We stayed up way too late the night before so vanilla lattes and Packzy's were in order. Saw this place on our way to O'Tooles the night before and knew I had to try it before we left (only a minute walk from the hotel). If you are boring and prefer overpriced subpar Starbucks, the hotel has one of those too
9 am Sunday brunch:
It doesn't look like much from the street but she was worth the 12 minute Uber to brunch. This place popped up on a dozen reddit threads so we opted to check the hype and it sure exceeded my expectations! Three of us ordered the Little Piggy based on an instagram video we saw, confirmed by the waiter's rec and my gosh it was so goooood. Colby ordered the breakfast burger and reported it was also 10/10. Make sure you ask for their homemade hot sauce!
We ended our day back at the hotel around 10 am and explored the area on foot for about an hour and a half. It was a little chillier than I cared for, and we were also regretting staying out until 2 am so we didn't have much energy left for more than a walk. We checked out the Starbucks Roastery which is also the largest Starbucks in the world! Be sure to hit the rooftop from some city views.
Not to be confused as anti-starbucks because I thought this place was pretty cool and I do drink it from time to time. I just don't choose a Starbucks over a cute local find on vacation ;)
We walked down Michigan Ave and turned around at the Chicago River. There are dozens of shops and sites along the way. On our way back, we hit up Dollop Coffee Co to get Reva refueled for the drive home.
Check out at the Hyatt is at noon, which was really nice to not have to worry about our things all morning. We returned to pack up around 11:30 before making our way back home to Indiana.
It was our intention to grab a slice of pizza on our way out of town, but the first two places on our route were both closed and we really weren't too hungry yet after our huge breakfast so we made our way south. Funny enough, we ended up ordering Lou Malnati's which just opened up down the street from our house (a Chicago staple).
We definitely plan to return to the windy city for some warmer weather exploring, thinking a baseball game is in the cards! Might have to find us some baseball romance novels next...
Til next time Chicago!
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