A Perfect 3-Day Weekend in Chicago

I’ve always wanted to be the kind of person who spontaneously decides to take a vacation to a random city just because they found a cheap flight. Well, that dream finally came true a couple weeks ago when I found a flight to Chicago ($65 roundtrip, thanks to booking during the off-season) and decided that a three day weekend would be the perfect opportunity to get acquainted with the windy city.

I’m going to share all that we did during our time in the city, but first, a few disclaimers:

1. As far as I’ve heard, flying Spirit Airlines, while it’s usually very cheap, comes at its own risk. I was actually very nervous about one of our flights getting delayed because I’ve heard some horror stories... But thankfully, our flights were both on time. I did see another flight to Texas delayed at O’Hare though. So, it happens. If it’s a risk you’re willing to take, go for it. I personally had no problems with Spirit and actually enjoyed both flights because the flight attendants were very friendly and attentive.

2. I paid the same amount ($70) for my hotel for both nights that I did for my flights because 1) I split the cost with my mom and sister and 2) I did my research and used the best hotel discount website I could find. We wanted a hotel within walking distance to Magnificent Mile and were able to get one by purchasing a blind deal on Hotwire, which basically means that you pay before you know the actual name of the hotel you’ll be staying at (with a guarantee that it’ll be a 4-star hotel). For such a short stay, I can’t imagine a better deal. Our hotel was The Ambassador, which had a beautiful lobby, a great shower (this is honestly the most important thing to me about hotels because I love my hot showers, ha) and was only a short walk from the Magnificent Mile.

Day One

We traveled with as little luggage as possible to avoid having to pay for carry-ons, which ended up being perfect because our hotel check-in time wasn’t until 3pm. Since we arrived pretty early on Sunday, we decided to check out a church in the area, which is one of my favorite things to do when visiting a new city. We opted for a bit of a splurge on a Lyft ride to the church (meaning we paid $18 total) because we had just arrived and wanted to save our energy.

After church, we took the bus and the L (Chicago’s above ground subway, $2.50 per ride) straight to the Jane Addams Hull House museum by the University of Illinois in Chicago. I’d actually heard about Jane Addams in a social work class in college, but didn’t remember she had done her work in Chicago until I noticed the museum on Google maps while planning our itinerary. A good lesson to keep in mind that as many great "things to do in X city" articles you find on Pinterest, it's still easy to miss something you'd love if you don't do research based on your personal interests.

just me in my absolute element.

I loved that we got to visit this museum because it gave us quite a bit of history on the city of Chicago, not to mention I got to learn all about Jane Addams and other social reformers, which if you know me you'll know I'm fascinated by. This experience taught me something else: visiting a history museum is one of the best ways to start your vacation in a new city, because it will help put everything that you see throughout your stay in context and make your trip even more interesting.

We ended the first day by having classic Chicago deep dish pizza at Giordano's. Apparently, the two most popular deep-dish restaurants in Chicago and Lou Malnati's and Giordano's, and there seems to be no consensus on which is actually better. We went for Giordano's just because it was on the Magnificent Mile, which we started to explore that night. The pizza was definitely amazing, but we got very full very fast (keep in mind these pizzas are much thicker so they fill you up more) with just one medium pie for the three of us. Another note: the wait time for a table wasn't long for us on Sunday night, but you do have to wait on average 40 minutes for the pizza.

tastes so much better than it looks, especially if you love lots of cheese on your pizza

Day Two

This was our only full day in Chicago, which is why we decided to make it our most packed day. We took a bus tour so we wouldn't have to waste time figuring out how to get from one place to another, and also to see buildings and landmarks we otherwise wouldn't have seen. It was a bit pricey ($40 per person), but I think if you're only spending a couple days in a new city, bus tours are worth it. This was a hop-on, hop-off tour, so after getting picked us up from Millenium Park (which we walked to in the morning because it was close enough to our hotel), we rode until the Shedd Aquarium.

the best view of the Bean is before 9am, when it's much less crowded.

the view at the Chicago riverwalk was one of my favorites. It's the perfect photo-op.

the iconic Chicago water tower will forever remind me of Rapunzel's tower.

the Chicago theatre, which we got a perfect view of from our double-decker tour bus.

I love visiting aquariums, so the steep $40 price tag for this one (the second largest in the country) was worth it to me. If you're considering stopping by the aquarium, you may want to start off on the lower floor, where you can see the dolphins, beluga whales, penguins, otters and more. It took us awhile to figure that out so for the first hour we were just looking at a bunch of fish lol. Which is nice too, but it might have been best to start with the larger animals. In total, we spent about 2.5 hours here, which was a good pace because we didn't feel rushed, and we even had time to enjoy a quick treat at their cafe. You can buy lunch at one of the shops inside the aquarium, or at a hot dog cart right outside (ordering a Chicago style hot dog is a must)! If you don't want to stop inside the aquarium, at least swing by for the incredible view of Lake Michigan and the entire Chicago skyline, which you can see between the aquarium and planetarium.

I mean, look at that skyline...

We hopped back on the bus around 3pm and rode it the rest of the way to the Willis Tower, to see the infamous skydeck. My only regret about this is that the line took way longer than I expected. We were standing for at least 45 minutes, and there's nothing to do but stand and talk/look at your phone. Eventually, we made it to the top just before the sky started darkening. The night view is beautiful too, of course, but if you want to get good day shots, you should probably arrive sometime before 2pm in the winter.

confession: It took me a couple minutes to step onto this thing

and I was too nervous to look down because I hate heights haha.

By the time we were done with the Skydeck, the bus tours had ended for the day, so we took the L back to Magnificent Mile. This was the night we really explored all the shops we wanted to see, like the American Girl store, the Disney store, Garrett's popcorn (get the chocolate dipped strawberry flavor, it's incredible) and more. There are so many shops on the Magnificent Mile, and many of which you can only find in Chicago and New York, so if you love to shop, take advantage of it. We were so hungry and tired that night that we honestly didn't care where we ate, but there was a Velvet Taco (which we also have in Houston) right by our hotel, so we stopped there and had a great meal before heading back.

Day Three

It snowed on our last day in Chicago! My sister and I were so excited because we'd been watching the forecast for literally weeks to see if it would snow when we were there. Sure enough, we woke up to a thin blanket of snow covering the trees, and light flurries that continued to come down as we walked through Magnificent Mile. This was the only day of our trip that we didn't really have any specific plans because we just wanted to relax, take photos, and enjoy the snow. So after stopping into a couple spots on Magnificent Mile, we headed to Millenium Park for breakfast.

Wildberry Pancakes is another spot that I never read about in all the Chicago guides I found on Pinterest! We were looking for breakfast near the park and I knew this place must be incredible because it had over 4000 reviews and an average 4.5 stars rating on Yelp. And I was not wrong. The wild berry pancakes from this place are the best pancakes I've ever had, and the breakfast skillets are incredible. Their cinammon roll panckaes are also so, so good.

After breakfast we walked through Millenium Park to take pictures in the snow and see the Bean once more. We then walked into the Chicago Cultural Center across from the park, which used to be the public library. There's not a lot to do here, but the ceilings and architecture are beautiful and worth the visit. Our next stop was Magnolia bakery. My sister and I wanted to stop here because we loved it in New York. But the Chicago version was honestly a different story haha... Let's just say I'm glad the place is adorable because otherwise I would've regretted going there just for the food. That's just my experience though, maybe I just ordered the wrong thing...

After a bit of souvenir shopping and a stop by Argo Tea (which I wish so badly we had in Texas) for a delicious chocolate mint tea, we took the L back straight to the airport and headed home.

Chicago definitely left an impression on me, and I loved it so much more than I thought I would. The architecture is incredible, the parks are beautiful, and there always seems to be something new to do. Next time I visit I definitely plan to branch out beyond the typical tourist activities, but for a first-time visit, I'm glad we got to knock off the most iconic stops from our bucket list. :)

Check out a short vlog of our trip below:

#travel