My Midwestern Adventure – Part 2 – Chicago!

I’ve realized that Chicago has to have one bad quality or else everyone would want to live there — brutally cold weather. Fortunately, the weather was just about perfect while I was there a couple weeks ago. Sunny and 75 (I think that’s a song?).

My friend Kat and I decided to drive to Chicago from Des Moines the day after the wedding, just for fun. I love that city and would never turn down an opportunity to go. So, Monday morning, we hopped in our rental car and began our journey across Iowa and into Illinois. I have to say that this was one of the prettiest drives I’ve been on through all the corn fields. I loved looking out and being able to see for miles, but still seeing rolling hills and farms everywhere. And of course I had to stop and take a picture with the corn!

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We made it to Midway Airport after about 5 hours and dropped off the car. I got a great deal with Hertz. It only cost me $30! Maybe because I picked up the car and dropped it off at airport locations? I also found a promo code. ALWAYS SEARCH FOR PROMO CODES. Anyway, I definitely suggest doing that because it was so easy! We took the shuttle from the rental car drop-off to baggage claim where we met our other friend Jenna, who flew in about an hour earlier. From there, we took the train into the city.

I love the train! It’s kind of weird, but I love the idea of public transportation. Maybe because Atlanta traffic is so bad? Either way, it’s nice not to worry about traffic or driving.

We stayed the night at MileNorth Hotel, located just off Michigan Avenue on E. Superior Street. It was the perfect location and I also found a really good deal on this hotel for only $109! We ended up needing an extra bed because Jenna came last minute, but it was only a $25 upgrade — worth it for sure! It also had a rooftop bar along with a restaurant and bar downstairs, Starbucks, and the room was nice and spacious for the three of us.

The Cubs were playing that day (which we missed the game, unfortunately), but I still thought it would be fun for us to go to Wrigleyville and hang out. [Side note: My brother lived in Chicago for a couple years, so he showed me quite a bit while he lived there!] We stopped by the stadium to take pictures first, and then found a nice patio at Deuce’s and the Diamond Club to get some food. Again, the weather couldn’t have been better! Afterwards, we hopped down to the Alabama bar, Houndstooth Saloon, to get a drink and hang out for a bit.

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After a few hours, we headed back into downtown to get ready and have a drink at the rooftop bar before going out with a friend of Kat’s who lives in Chicago, and is from Bulgaria. We went to some bars about a 15 minute walk away from the hotel in the River North area. It was a great time!

The second day, we woke up kind of early so we could get some time in the city before leaving that afternoon. We left our bags at the hotel and headed out of the hotel down to the river. We had a mini photo shoot there and did all the touristy things like going to The Bean at Millennium Park and taking a million pictures there too. What is it about a giant reflective surface like that? Anyway, of course we had to have some sort of Chicago staple food while we were there, and America’s Dog was our next stop! Probably not the best place in The Windy City to go for hotdogs, but they were still really good!

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We actually just ended up wandering around for a while after that. I took plenty of pictures of the trains. Such a tourist! I try not to be one when I travel sometimes. I like to blend in with my surroundings, but I just can’t help it when it comes to getting a cool train picture in Chicago! I’m pretty happy with the way it turned out…

After dropping Kat off at the train stop, Jenna, Georgi, and I got a drink at a little hole in the wall bar, Pippin’s, to kill some time before going to the airport. It was nice to just sit and enjoy the city for the last hour that we had there.


Twenty-four hours in Chicago is not enough. There’s just something about it that draws me in and I love it and can’t wait to go back.

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