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how to spend 12 hours in Chicago: date night edition

Chicago magnificent mile, date night

I am going to tell you exactly how I spent the perfect 12 (ish) hour date night in Chicago with my husband and our two best friends; Colby & Reva.

Reva, my fire wife and book bestie, and I have recently entered our hockey romance era (didn’t know that was actually a thing but here we are). After reading a few hockey smut novels we found ourselves booking a trip to the windy city to enjoy a Chicago Blackhawks game…since it was Valentines day the following week, we invited our hubbies to join us too 😉

In case you need some good hockey smut reads feel free to jump on the bandwagon: The Off Campus Series here, my favorite: The Fake Out, or Icebreaker are all great places to start!

It ended up being the absolute perfect evening beyond fulfilling our hearts’ hockey desires. Colby led us to the last standing prohibition era speakeasy, in the basement of the oldest building in Chicago. We shared a second hand smoke fueled visit to one of the mob boss locales as well. Foodie finds on this trip were a solid 10 out of 10! Our hotel was just the right amount of classy yet affordable and we plan to return in the summer to spend some more time exploring the area on foot here too!

If you enjoy this guide please do me a solid and leave me a comment below 😀

Follow me on instagram for all my real time travel finds and as always: take the trip!

3 pm arrival: Check-in at Hyatt Centric Magnificent Mile hotel

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). At right around $180 for the night, this was an affordable option without skipping on a luxury feel.

Shortly after check-in we walked over to Timothy O’Tooles Pub to grab some drinks and pickle fries while waiting for our friends to meet up with us. Located just a block away from the hotel, you will find one of the best sports bars in the city. The atmosphere here was spot on for an Irish pub. This place was 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 mary but we unfortunately didn’t make it back this trip. Next time though for sure!

4:45 pm: dinner at The Gilt Bar

date night: gilt bar, chicago

From O’Tooles we grabbed an Uber and headed 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 and get your photo booth pics up on the hall of fame. It sounds corny but it was actually so cute. They do have a speakeasy downstairs too but this was closed on our visit for a special event. Reva & Colby have visited the speakeasy before though and we will be back here again!

I enjoyed the Wagyu burger and Jordan loved the french dip. The apps were amazing but the menu does rotate. If you get the chance to snag the brussel sprouts, that’s a must. Also the mushrooms were superb and though Jordan gave me a hard time about insisting we try the bone marrow because honestly when do you ever see that on a menu, I still say it was worth it if you’ve never tried it!

If you come for 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 the weekend before our trip and was in a boot, 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: gametime – Chicago Blackhawks

date night: chicago blackhawks, chicago, hockey

Finally time for our main attraction: my first ever NHL game!! While our husbands were existing hockey fans, Reva and I may have enjoyed this one more than the guys did 😀

United Center is host to other events as well. You could also catch the Bull’s play, a concert, comedy show, or even Disney on Ice. The perfect date night options or plan for the whole family too!

post game: Richard’s Bar

richards bar, chicago

My husband told me about this little gem after visiting here a few years ago while waiting for a last minute passport. We hit this place up after the game and I am a sucker for a place full of history, this bar met my expectations!

“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.”

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…

the last standing prohibition era speakeasy: The Green Door Tavern

green door tavern, chicago, speakeasy, date night

Another recommendation from our buddies and the highlight of my trip was visiting The Green Door Tavern!

“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.

The most exciting part of this tavern is the hidden speakeasy in the basement. Called The Drifter, this is the LAST remaining prohibition era speakeasy in all of Chicago. Much of the original structures remain; including several bullet holes in the cement wall. I promise you the wait is worth it to get in. You’ll even be met with a surprise show. Imagine yourself in an entirely different era inside. Fun fact: it is said that if a tavern had a green painted door during the prohibition that a speakeasy was located inside. If you have a chance to chat with the door staff you will find him very eager to share all the history of this bar with you.

Pick your drink at random using the cards given to you in the Drifter for a fun twist. I loved everything about this place and will absolute be returning here again.

8 am sunday: coffee at Stan’s Donuts

chicago coffee, donuts, stans donuts

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 but if you’re like me and refuse to go to places that are readily available in every town then head over to Stan’s and you won’t be disappointed.

9 am: brunch at Little Goat Diner

📷: Little Goat Diner Instagram page

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 to the canal and back. 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 while you’re there.

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 large 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 in Greenwood (a Chicago staple).  It was decent, but I will be eager to return for some authentic small shop pizza on our next visit.

We definitely plan to return to the windy city for some warmer weather exploring; thinking a baseball game is in the cards! May have to find us some baseball romance novels next…

Til next time Chicago!

Check out these Viator tour options in the windy city below:

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