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America (Midwest)

Itinerary: A Long Weekend in Chicago

on March 30, 2017

So Matt and I wanted to plan a big trip for April/May of this year, but we made the decision to purchase a home instead, which meant we had to put trip plans on hold. But we knew we wouldn’t be able to make it without some kind of getaway to satisfy our wanderlust. We decided a long weekend in Chicago would be the perfect solution!

We flew in early on a Saturday and flew out on Tuesday afternoon, giving us about 3.5 days to explore this amazing city. Here’s how we spent our time.

Sidenote: Once again, I won’t bombard you with photos. But if you’d like to see all of our photos from the trip, you can view them here.


Day One

We took a 6am flight out of Houston and arrived in Chicago around 8:30. After dropping our suitcase off at our Airbnb, we set out to explore the city. We stopped by Portillo’s for some lunch, then walked the Magnificent Mile. There was a lot of amazing architecture and cool history to gawk at. And I was pleasantly surprised at how much knowledge Matt has about the city!

Our first big stop of the day was the Hancock Center to check out 360 Chicago. We purchased the CityPass a few weeks before our trip, and redeemed it at 360 since it was our first stop. (The CityPass ended up being the best decision of this trip! We got VIP and fast pass access to five amazing attractions around the city. Those attractions are noted with a * on this post.) From the 94th floor we got a great view of the city! We paid $7 extra each to the do the “Tilt,” which was actually pretty thrilling!

Next we headed over to visit the Shedd Aquarium, another CityPass attraction. There was a loooooong line to get in, but luckily we got to bypass that with the VIP entry from our CityPass. The aquarium was pretty crowded, but it wasn’t too bad. I’m pretty spoiled because I grew up going to the best aquarium in the world (Monterey Bay), but I still really enjoyed the Shedd. I nearly missed seeing the belugas, so make sure you don’t miss them either! Included with our CityPass was a ticket to a 4D film in their theatre. This was a hilarious experience, but that’s a story for another time.

For dinner we stopped at a bar called Flo & Santos for dinner because I loooove me some pub food! I tried pirogis for the first time and now I’m obsessed.

Day Two

We walked the city for most of the morning, got some delicious pastries at Stan’s Donuts, explored Grant Park, ventured into some interesting buildings to admire the architecture, then went to see Cloud Gate. I was excited to cross “the Bean” off of my travel to-do list!

Next we used our CityPass to get into the Art Institute of Chicago. I had wanted to visit this museum for as long as I can remember. It has one of the best Impressionist collections, which is my absolute favorite art movement. Matt had fun spotting the pieces featured in Ferris Bueller’s Day Off, and we had a Cameron Frye moment while looking upon A Sunday on La Grande Jatte.

As the museum was closing, we made our way to the Willis Tower. We took the long way around because we stopped for food at the Flat Top Grill (pick your own stir fry ingredients! SO COOL!) and ended up getting distracted by the Trump Tower. We decided to walk over to get a closer look at the building. During this walk, we ended up on the Irv Kupcinet Bridge, where we got an amazing view of the river and some of the coolest skyscrapers in the city.

Our CityPass really came in handy when going to the Skydeck! We got to skip a huge line, saving us about 45 minutes of waiting time. But then we just stood in line for about 45 minutes to get out onto The Ledge. Which, in my honest opinion, was so overrated and not worth the wait.

We got to see the sun going down over the city from the Skydeck, and as it began to get dark outside, we decided to explore the city some more. We went to see the famous Chicago sign, and on the way we stumbled upon the PrivateBank Theatre AKA the home of Hamilton in Chicago. It took me great amounts of strength to keep from bawling my eyes out because we couldn’t get decently priced tickets to see Hamilton during our trip. Or ever.

One day I will see you, Hamilton. One day.

Day Three

We spent almost an entire day at the Field Museum nerding out over rocks, minerals, ancient artifacts, totem poles, and taxidermy. This museum was by far the least crowded of all the CityPass attractions. With the CityPass we had access to all the special exhibits and tickets to one of their 3D films (which was a much better experience than at Shedd). This was definitely in the top 5 museums I’ve ever visited.

After the museum, we went to Devil Dawgs for dinner (another one of Matt’s favorites) and binged on sliders and milkshakes. We needed to walk it off after, so we took a stroll down the street and happened upon the Chicago Public Library. We went in to look around and somehow ended up participating in one of their free classes in the Maker Lab. We learned how to make designs to be cut on vinyl, which we then made into bookmarks of our own!

When the class was over, we went to check out the Chicago Jazz scene. We visited a bar where some local college musicians were playing. The Jazz was a little too “avant-garde” for us, so we didn’t end up staying long, but it was still an interesting experience.

Day Four

  • Exploring the Pilsen neighborhood
  • National Museum of Mexican Art

Our last day in Chicago was really more like a half day, so we decided to stay around the neighborhood where we had been staying. I really loved this part of town. There were a lot of Mexican cultural influences in this area. The National Museum of Mexican Art was actually just down the road, and entry is always free, so we decided to visit. We got to see lots of the Pilsen neighborhood as we walked to the museum, it reminded me a lot of the Mexican neighborhoods where my grandparents live. It felt almost like a version of home. The museum was nice, and was filled with lots of thought provoking pieces. I love the way their exhibits explore the evolution Mexican-American identity.

We stopped into La Catrina Cafe for some food and coffee, and I fell in love with decor. I love anything and everything catrina or calaca.

At the recommendation of our Airbnb host, we visited Pilsen Community Books. It was the most amazing bookstore I’ve ever seen. The walls were lined with books from floor to ceiling, throughout the entire store. And the best part? Nearly all the books were under $10! I had to fight the urge to throw out everything I brought in my suitcase to make room for books instead. I settled for one book. But maybe one day I’ll be back for more…


There are many more attractions I would have loved to visit during this trip, but just didn’t have the time for. No worries though, it leaves plenty for my next trip to Chicago!