Travel Guide: A Weekend in Chicago

Chicago is one of my favorites cities - however, I think it’s seriously underrated. I’d rather spend a weekend there than in New York City. It’s cleaner, it’s located right on Lake Michigan so it has an awesome beachfront, and it’s more spread out and not nearly as congested! And, it’s easier to get to if you live in the Midwest. There is so much to see and do that it can become slightly overwhelming, especially if you’re only there for a short time. The last thing you want is to waste time trying to decide where to go. That’s why I’ve created this guide. It includes my favorite things. Whether you want to follow this list exactly or just pick a few, here are some awesome ideas to jumpstart your planning. And, tried and true, you can pack everything on this list into one short weekend!

The Bean and Millennium Park: This is the first thing I think of when I think Chicago. We went to The Bean at night which was really cool. Usually, when I see pictures it’s during the day, but I liked going at night because the reflection of the city lights on the bean is beautiful. This is definitely a must see if you’re in Chicago.

Navy Pier: We went around sunset, which perfect time to go. We got tons of great pictures. The inside of Navy Pier is this interesting building that seems like it goes on forever. There are plenty of restaurants to choose from, so even the pickiest eater will find something they like. I feel like there was so much more we could’ve explored if we spent more time walking around. Going at sunset is the perfect time to grab a late lunch or early dinner. We had a late lunch at DMK Burger and Fish Bar. I ordered the bison burger and a milkshake. Definitely the right move. We watched the sunset over the water while enjoying our meal.

Brunch: We went to a place for brunch that was literally called “Brunch,” and it was amazing. The décor was absolutely adorable. The service was just ok. It took them three times to get the coffee order right but the food made up for it. Also, the portions were huge! You could definitely split an entrée here. We tried the chicken and waffle bites and the chilaquiles. There were two of us, and splitting both was more than enough food. Be sure to make a reservation in advance if you choose to go. It was insanely busy when we went, and I can’t imagine how long we would have waited without a reservation.

Wndr Museum: This place was SO. FREAKING. COOL. I wanted to stay there forever. It’s an experiential museum designed to engage all five senses. These are popping up all over because they’re the perfect place to get cool pictures for social media. This was, by far, my favorite thing I did in Chicago. Not only is it a great place to get pictures, but every exhibit was so intricate that I felt like I was dreaming the whole time I was there. The best experience was the poet. You give them a topic and they write a poem for you. My topic was travel, and the poem she wrote definitely hit the mark.

Stan’s Donuts: Yum! I’m such a sucker for a good donut shop, and this one was right up my alley. With more than 50 different flavors to choose from, as well as gluten-free options, you literally can’t go wrong here. Not a donut person? They also serve coffee and ice cream!

Sawada Coffee (West Loop): This place was really unique. It was a coffee shop, bar, and barbeque restaurant. I just got a coffee but it was the perfect mid-day pick-me-up while exploring the city. Definitely stop in here if you’re looking for a cool place to sit down for a little a while.

Bar Roma: This is a trendy, Italian restaurant in Andersonville. The meatballs were to die for! I’m not a huge fan of meatballs, and I couldn’t pass these up. They were huge; perfect for sharing! If you go, you HAVE to try them. This restaurant is a little pricey, so I would recommend getting a few appetizers and splitting them. The portion sizes are big enough so it should be plenty of food. I highly recommend this place for dinner, especially for a date.

Giordano’s Pizza: It’s a must to get classic Chicago-style pizza while you’re in Chicago, and Giordano’s is the place to go. This deep-dish pizza is absolutely delicious. I recommend going in and placing your order early since the pizza takes a while to cook. We placed our order, walked around the city for a little bit, and then came back. We didn’t have to wait near as long for our pizza to come out, and the people next to us were definitely jealous when we got our food first. 

Transportation: Chicago is a huge city, and the hardest thing to plan was the transportation. There are three main ways to get from one place to the next: The EL (train), the bus, or Uber. We ubered most of the time but it started to add up. Ubering is the way to go if you’re crunched for time, but if you’re not, try to take the train. A one-day pass is only $10, which would be about the cost of one Uber ride. They also offer a student discount which is great for all my college ladies out there!

Safe travels!

Want to keep up with Her Campus OSU? Make sure to like us on Facebook, follow us on Instagram, check out our Pinterest board and read our latest Tweets