For as long as I can remember, I have loved Chicago. I’d never been there, but I just had this feeling we would vibe. Living in Austin + traveling to other US cities taught me that you can love a city but not have it be a great fit. Chicago, I imagined, was I city that I could love + would fit. Last month I put that theory to the test + went with some friends to visit. It. Was. Amazing.
I spent several weeks planning this trip. I poured over Pinterest, blogs, and crowdsourced on social media to plan the perfect trip. Like every trip, plans can change. Even though I didn’t get to go everywhere I wanted, I had an amazing time with friends discovering the tourist spots + hidden gems of the city. Whether you’re planning a birthday, bachelorette or girls trip, this guide is for you!
Where to go in Chicago
There is SO much to do in Chicago. Unless you’re there for a while, you’ll never fit it all in. You have to decide on your priorities + do the things you know you wouldn’t want to miss. I wasn’t able to get to everything on my list, but the things I did get to were awesome! Something I did + that everyone suggested was to take the Wendella Boats Architecture Tour. It’s a great way to see the city + get to know it a little. You also *have* to hit some touristy spots – I don’t make the rules. Go to Millennium Park to check out the Bean + Lurie Gardens. There is also an outdoor amphitheater where you may be able to catch a show.
Speaking of shows, if there is a good one in town, hit up the Chicago Theater. You’ll also want to go to a Cubs game if they’re in town (they weren’t when I was there ?). If you’re not totally afraid of heights, go to Chicago 360 or the Skydeck to get a one-of-a-kind view of Chicago. You can also get a great view riding the Ferris wheel at Navy Pier. After checking out the pier, my friends + I headed to the beach – which was maybe my favorite activity of the entire trip. We hit up the North Avenue beach which was full of other tourists, locals, and parties.
Don’t forget to enjoy a little mural tour! I was only able to make it to a couple of the murals I wanted to see, but the city is full of them. I went to the Love mural, but when I go back you can bet you’ll be seeing pictures of me at The Green Bean Nursery, Bernie’s Lunch and Supper, the Flamingo mural, and more! Next time I make it to the city, I also hope to make it to the Lincoln Park Zoo, a show at The Second City, and do more shopping on the Magnificent Mile.
Where to eat in Chicago
All those activities are going to make you hungry + Chicago is a city that loves food. Hot dogs + deep dish pizza are their staples, but we had plenty of other amazing dishes. We got our deep dish from Lou Malnati’s + while it was good, it wasn’t the best Italian food on the trip. That came from Ceres’ Table. Not only was the food incredible, but so was the service. S/o to Brian for being the best waiter we had all weekend (you won’t regret making a reservation).
Speaking of reservations, that is a sure-fire way to get the best seat in the house at The Hampton Social. This restaurant is insta-worthy from the front door to the view out the windows. Come for the iconic “Rosé all day” sign, stay for the frosé + delicious food. Pro-tip: If it’s your birthday, you can also count on a slice of carrot cake. Owned by the same people, we also checked out The Beach Social. Formerly Mahola, this beach-themed spot doesn’t have a brunch menu yet but the food was really good – I got the fried chicken sandwich. My only qualm with The Beach Social is that between making my reservation + actually going there, they rebranded + changed the menu without so much as a heads up. The atmosphere was great, though.
Our first stop in the Windy City after an 11-hour train ride (more on that to come) was Bombobar. This little window shop makes delicious doughnuts, breakfast sandwiches, and drinks sure to put you in a sugar coma. It’s a very cute place to grab-and-go or catch up with a friend. The last stop on our tour of Chicago (and a repeat location) was Timothy O’Tooles. This may be a “tourist trap” but I don’t even care. The Chicago Fire Burger (sans fire) is THE best burger I have ever had in my life. Ever. I don’t know what they’re secret is, but as someone who loves burgers, let me tell you, I do not bestow this honor lightly. They also have bomb spinach dip which I may or may not have taken as leftovers on the train. #sorrynotsorry
Where to drink in Chicago
When we weren’t touring or eating, we were drinking. It was a birthday/girls’ trip after all! If you can’t tell by my pictures, Chicago is gorgeous. The river, the city views, it can’t be beaten. The city really takes advantage of this by having bars that allow you to soak in Chicago in all its glory. The first place we stopped was Chicago City Winery on the Riverwalk. They have a bigger location that allows reservations, but if you’re willing to wait (or go on a rainy Friday afternoon) you can enjoy drinks right beside the river. Nearby, we enjoyed drinks at Raised Rooftop Bar. It’s a little expensive, but the view is great + the patio is amazing. Places I didn’t make it but heard rave reviews for were Dot Dot Dash, Cindy’s Rooftop at the top of the Chicago Athletic Club, Joy District, Celeste, and the bar at RPM Italian.
As you can see, I have so many things left to check off my Chicago list, that I’ll be back soon! I’m even more excited for my second trip now that I have a couple of must-do tourist items checked off. I can’t wait to explore the neighborhoods more deeply + spend an entire day on Lake Michigan. If you’re wondering where to have your next girls’ trip, I 10/10 recommend Chicago! Send me your favorite discoveries after you go.