Chicago · Illinois · USA

Chicago, Chicago I will show you around

Dear world travelers,

A few weeks ago, we decided to escape from Florida and go to Chicago. What was supposed to be a great fun weekend ended up being a nightmare in terms of travel. C’s suitcase got lost and it only got to the hotel by the time we did the check-out on Sunday. It kind of killed the mood a bit but we tried to put that aside to enjoy the city as much as possible.

We started our Friday evening at Giordano’s to try the best deep dish pizza in town (and some people even consider it the best in the U.S.). It was indeed delicious! Also, it was the last meal our waiter was serving as he got promoted, so we had to celebrate with him and of course we made goofy videos.

After dinner we went to check out Moe’s Cantina. The venue has a really groovy open concept and some hip decor and art on the walls. The crowd was lame that night though. We felt that there’s a lot of potential but we picked the wrong time or night to enjoy it fully.

We then moved on to Sub 51, a basement under Hub 51. The dance floor wasn’t huge but more than enough for our moves. The music was great. That DJ was really something! They serve some local brews as well, which made the whole experience even more enjoyable.

By the end of the night we stopped by Hubbard Inn just to check the venue and realized there’s a common trait shared by all the places we had been to thus far. (This also proved to be true for every single place we would visit afterwards.) All venues function as a restaurant, bar and, possibly, as a club. It’s definitely a different concept but we thought the versatility brought more charisma to the city.

On Saturday morning we had breakfast at Sunny Side Up & Coffee. Small place but super hipster, which also meant a huge line. In order not to wait in line, we went to the Coffee Shop downstairs and ordered the food there so that we could be served faster. We got a Croque Madame and Eggs Bennedict.

Both really good and gave us the perfect amount of energy to walk all the way to Grant Park.

We had to go take a picture in front of the Cloud Gate, a.k.a., the Bean. The bean was surrounded by a ton of tourists of course! It was a real struggle to find a decent spot. We recommend going really early in the morning for the perfect shot.

After a 30-minute walk around the park, a friend suggested that we checked the Chicago Athletic Association. Cindy’s is the rooftop bar and apparently a must go when you’re in town. Needless to say, there was a line to go up. We thought to ourselves this really must be the place to be… and indeed it was! The view to Grant Park and the Michigan Lake is sooooo worth it! We stopped and stared at it for a while. Just enjoying the beauty of it. In addition to the view, the craft cocktails were fantastic! The food they were serving for brunch also looked and smelled delicious but unfortunately we were still full from our late breakfast!

We walked a few blocks around town and C’s friend showed us the ROOF bar on theWit hotel. The venue looked amazing and the cocktails were delicious, just like the city got us used to. And again… the views!!! Impressive!

After a couple of hours, we decided to try what is claimed to be the best burger in the US. So we headed to Au Cheval. We got there and the hostess told us in the most natural way possible that there was a 4-hour wait. Like when you tell your friends you’re 2 minutes away. Yeah, that’s exactly how she sounded. We obviously didn’t stay there, so we went to their second location called Small Cheval. We waited less than 10 minutes. The concept is a bit different from the first location but really cool and definitely more relaxed. OMG! Hands down to that burger!!! It is absolutely phenomenal. Even C who doesn’t care about burgers vouches for this one. Totally worth the trip!

After this mouthwatering tasting, we headed to the Goose Island Brewery in Clybourn to try some of their flavors. There are plenty of options so it was hard to pick. Fortunately, the staff was very friendly and knowledgeable and that helped us out with our choices.

As the sunset was approaching we rushed to the John Hancock Building to see the view from the The Signature bar on the 96th floor. The line was completely insane but we had made a reservation so we got upstairs in about 5 minutes. Definitely the best move! The view was absolutely spectacular and breathtaking.

After that gorgeous sunset, it was time for dinner! We had a reservation for Guilt Bar and we were delighted with our choice. The restaurant had a dark but super elegant ambiance. Our waiter was very knowledgeable and recommended the Truffle Pasta and the Risotto. It was funny because those were the two exact dishes we were thinking about sharing. Both of them were quite delectable and utterly recommendable. And don’t tell anyone… but there’s a hidden speakeasy bar downstairs on the way to the restrooms! Shhhh…

Following this delightful meal, it was time for some dance moves. We started our night at Untitled Supper Club, where we had a couple of drinks and danced for a while. The dance floor was completely packed but we had a decent experience.

Subsequently, we checked Three Dots and a Dash. The concept of a tiki bar in the middle of Chicago is pretty ironic but for some reason it works and it’s super trendy. All the tables were full so C decided to ask some group of guys if we could sit with them. Of course it was a bachelor party. Seriously! It was the third one that weekend. Somehow C always gets in the middle of bachelor parties. Funny but not funny! Oh well, at least we had a table.

Later on, we went for some real moves at Fremont. Amazing venue, with great music. The real party was happening there! We couldn’t wait for brunch the following day.

Lastly, we went to check the club right in front of Fremont. We can’t remember or find the name but it’s literally on the other side of the street. We danced for quite a while until we were completely exhausted and headed back to the hotel because Sunday was about to be a very special day.

As you guys might have noticed, C is die hard soccer fan. But more than that, she’s crazy about Benfica. K supports Benfica too but she’s definitely more moderate haha. That Sunday it was the last round of the Portuguese league and Benfica needed one more win to conquer its 35th League trophy. Well, imagine having brunch and watching the game at the same time. Especially because brunch happened at Fremont, which is massive. Huge buffet, lots of variety, even more people, a great DJ and, of course, bottomless mimosas! We stayed there for about 4 hours and we would have stayed longer if we could. We celebrated like champions, met some really nice people, got to speak Portuguese with some crazy but super fun Brazilian ladies, danced, danced and… completely lost track of time.

Things then got a little… out of hand lol K that the brilliant idea to start talking to bartender and telling him he had to marry C and he didn’t have an option. We literally could not stop laughing when he made a ring out of a straw cover and proposed to her. We were all freaking out and screaming like high school girls.. Let’s just say Steve.. you will never be forgotten hahaha when we were leaving.. things got a little.. heated ; ) We’ll leave that up to your imagination haha


It was time to run to the airport!!!!

When we got to there, the TSA line was over 4 hours long and we got there less than 2 hours before our flights. K had TSA pre-check and it still took her more than an hour. C would be stuck in that line forever. There was no point in gently asking to cut the line, because every single person was in the same situation. We actually read some news that 4,000 people lost their flight from O’Hare that day. It really looked like there wasn’t much C could do. Until she had the craziest idea ever and started “proposing” to random guys in line and just making small talk with them. People around her were enjoying and laughing as everyone had accepted the fact that they had lost their flight. Somehow, in 1h30 she got through TSA and luckily her flight was 10 min delayed which was exactly what she needed to make it right before the gate closed.

So yeah, travel wise this trip was a complete nightmare!!! But CHICAGO is absolutely GORGEOUS and EXTREMELY FUN! We could totally picture ourselves living up there. Well, at least during the summer. During the freezing winters we are not so sure!

Safe travels!

– K & C


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