A Weekend in Chicago!

-Our cozy airBnB in the Avondale neighborhood-

Greg and I drove to Chicago this past weekend and it was amazing! I loved Chicago and being in a big city again was exactly what I needed. We left early on Friday morning (it’s about a 5 hour drive from Columbus) and arrived around 1pm. The first thing we did was stop at a Cuban restaurant., 90 Miles Café.  I ‘m half Cuban so naturally I grew up eating the food (If you ask me, there is no better cuisine).  Greg loves it too, which is a good thing because whenever we travel, if there is a Cuban restaurant near our destination, we stop!

After lunch we weren’t sure what to do so we figured we’d drop our stuff off at our AirBnB, hop back in the car and head downtown. It turns out that you don’t just hop in the car and head downtown on a Friday night in Chicago (traffic sucks). We were staying about 8 minutes from downtown, but it took 25 to get there. Then another 15 to find parking, but it all worked out because we parked a little further from where we intended and found a wine bar! The place was called Acanto and the happy hour was pretty great.  The bartender, Chris, was very helpful and gave us some tips on where we could go salsa dancing. The salsa dancing was totally unplanned and I didn’t pack anything for it, but we love to dance so we were in.

Top is from J.Crew Factory (it’s linked here), skirt is from Loft (linked here) it’s on sale and an extra 40% off, and the custom engraved pendant (mine says steph & greg 07.06.18) in gold is from Gilda Lane Jewelry on Etsy (linked shop here

After Acanto we walked around a bit, went to Kilwin’s and got some delicious chocolate, then headed back to the AirBnB to get ready for salsa dancing! Like I said, I didn’t come prepared for salsa so my outfit was a little more casual then I wanted but it worked.

We headed out to Nacional 27, had some mojitos and hit the dance floor. Greg is really fun to dance with. He doesn’t care who’s around and he just lets lose (it’s awesome) and he’s actually a pretty great salsa dancer.  After an hour of salsa dancing we were beat.

We left Nacional 27 and headed across the street. I can’t for the life of me remember the name of this bar, but we walked over and the bouncer instructed us to walk through the upstairs bar toward the jukebox, turn left, head down the stairs and stop at the shelf. When we got down the stair, we were greeted by a guy who handed us tarot cards (how you order drinks there) and showed us to our seats.  We learned that we were in a speakeasy, the same speakeasy (The Drifter) that Al Capone’s gang hung out in apparently (not sure how much I believe that, but there is a sign inside with bullet holes in it that his gang shot up and stole to hang in the bar).  It was a neat experience. We both ordered the B.B. Gun. I was too tired to finish it and so I drank half and we headed back to our AirBnB.

The famous ‘Rose all day’ sign at The Hampton Social

On Saturday, we had brunch at The Hampton Social (whatever you do, order the hash browns and the pineapple mimosa). They’re Instagram ‘famous’ for their ‘Rosé All Day’ sign. It’s a very “instaworthy” (lol). The food was good and the service was great!

After that, we walked for a bit and decided to check out Eataly. There are two locations in NYC, one in Chicago, Boston, Vegas, and Hollywood. If you’re in any of those places, GO TO EATALY. I have never had pasta that good.

Pretty much everything in this place is from imported from Italy or made fresh in-house daily. We basically spent the whole day there. We ate at a pizza at BAITA and had pasta at Ravioli & Co. We ordered Rosé at the wine cart and ate hazelnut-chocolate gelato at Gelato Bar. It was the BEST day.

Saturday night was rather uneventful. We were super full from Eataly, but decided we still had to try the Chicago Deep Dish pizza. We ordered one small pie from Pequod’s and one from Lou Milnati’s. I have to say, so far, no one does pizza like NY/NJ. Honestly, I’ve had Uno’s pizza so I was expecting all Chicago deep dish to be amazing. Peqoud’s and Lou Milnati’s both came highly recommended and they both have really great reviews, it just wasn’t for us.

Sunday morning we packed up the car and headed back to Columbus. Naturally, we stopped at two wineries in Indiana on our way home and we took home two great bottles of wine (Chambourcin and Traminette) from Wildcat Winery.

Overall, it was an awesome trip and another great experience with Greg. Seeing new places together is something we both enjoy so much. It helps when you can figure out how to do it on a budget!      

Drop a comment and let me know what your favorite city is and some must-sees!

With love & gratitude,



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