This last November I signed up for the Southwest credit card because they were giving away a companion pass and 40,000 points. SO Brock and I are doing our damndest to make our way around the US and see this beautiful country of ours!

So where was our first stop? Chicago, Illinois. We have an awesome friend out there and me being the snow/cold weather craving person I am I was eager to get both in my life as soon as possible. Where can you count on to always have cold and snow in January? Chicago… right? WRONG (insert palm to face emoji). It was a whopping 32 degrees during the day and the air was so dang dry. BUUUUT we still had a freaking blast!!

It was a quick trip so we crammed as much into it as we could! We started with brunch at Highline Bar + Lounge. On the weekends they have bottomless brunch AND bottomless mimosas soooo we got a little tipsy. There were donuts, and waffles, and candy galore. Oh, and a Bloody Mary bar with tons of awesome toppings.

After brunch we made our way to the sky deck but the wait was too long for our short trip so we went straight to the famous BEAN! It was crowded but so awesome! And there’s a rooftop bar, Cindy’s, that overlooks Millennium Park right around the corner! We enjoyed some drinks by the fire and watched the sunset on Lake Michigan. It was one of my favorite parts of the trip.

We were pretty exhausted so we went back to our hotel after that and took an hour nap before going out for the night. THIS was the most fun we had the entire weekend (even though the whole thing was a blast). We went to Three Dots and a Dash, Bub City, and a few others. This next part’s gonna get ya. Or at least it got me. We were talking about going to Bub City and how it was a country bar. I started to tell a story of the time we went to Moonshine Beach and there was an artist there (Chris Shrader) who was freakin awesome. The most fun we’d had like ever. What do you know?! CHRIS SHRADER WAS PERFORMING AT BUB CITY IN FREAKIN CHICAGO. Smallest freakin world ever. I literally almost knocked a girl over running to tell everyone it was the same guy I was just talking about. 

I stopped drinking after Bub’s and just enjoyed the next few stops because I knew I wanted to get up early and go see the Bean with no people in front of it. I knew if I kept going that most likely wouldn’t happen. We got home around 4am and I got up at 8am. Safe to say there was a Starbucks stop on the way that morning. After the bean we made our way to the pier, walked it end to end, just about died because it’s the longest freakin pier EVER. So pretty though!! 

Our last meal was at Mott St. THE BEST BRUNCH BURGER ON THE PLANET. I mean it. If you’re in Chicago, GO! In my book, any burger with an egg on it is gonna be pretty dang good but this one was over the top amazing! Theres a picture in here somewhere so keep scrolling for some mouthwatering goodness.

Last but not least, Wrigleyville. We hit some balls at sluggers in the batting cages upstairs and then watched a little bit of the pro bowl downstairs at the bar. Yeah you heard that right. Batting cages… in a bar. AWESOMEEEEE.

This trip was short but SO dang good. We explored another beautiful city and got to spend two days laughing and loving life. I hope these photos let you see a little glimpse of our trip!