When Anthony found out that his job was sending him to Chicago last weekend, the decision as to whether or not I was going to join him was an easy one. We loved our first trip to Chicago a few years ago, and it was our anniversary weekend, after all!

He flew out first, and I joined him for the weekend. My flight got in super late and I was exhausted, and not particularly excited about the long cab ride to the hotel. As I approached baggage claim, I stumbled upon the most wonderful surprise! Anthony came all the way to the airport as a surprise to greet me and share the ride back with me. What a perfect start to the weekend, and what a wonderful guy.

The next morning, we slept in a bit and checked out of our first hotel (where Anthony had been staying for work), and walked over to the Hard Rock Hotel for the rest of our stay. It wasn’t the fanciest, but it was affordable and in a very beautiful old building. Plus, it was close to the Riverwalk which quickly became a favorite strolling spot for us.

After checking in, we made the trek to lunch at The Chicken Shop. My sweet friend Gabi had recommended it on her blog, By Gabriella, and Anthony’s love for chicken sandwiches (seriously, this guy can find a chicken sandwich on any menu) made it the perfect choice. The cozy and modern decor was the perfect setting for our lunch, and the food was incredible. My only regret is that I didn’t order one of the milkshakes. Next time, I guess! After lunch, we enjoyed exploring the surrounding neighborhood. There were so many fun restaurants to choose from, we can’t wait to go back!

We decided to play tourists for the rest of the afternoon and headed over to the Field Museum of Natural History and even opted into a CityPass to be able to visit other museums during our trip. I’m a sucker for museums, and it’s become a running joke that I always end up getting so emotional when I visit them. Dinosaurs! The Universe! The ocean! How am I supposed to process that all of these things exist(ed), you guys?! The Field Museum was an absolute dream and we had so much fun exploring the exhibits. I could have wandered all day!

Later we headed over to U.S. Cellular Field for a White Sox game. Anthony is a huge baseball fan (hence why we got engaged at the Baseball Hall of Fame) and tries to go to a game in a new city whenever he has the chance. It was a bit rainy, but it was free hat night so that kind of made up for it. The White Sox won and even celebrated with a fireworks display at the end of the game!

The next morning we once again slept later than we meant to (whoops!) and then headed out on our inevitable quest for Deep Dish Pizza. All of the locals (and even the not-so-locals) recommended Lou Malnati’s, so that’s where we went. We ended up stuffed to the brim with pizza, but it was worth every bite.

Another afternoon, another museum. We went to the Shedd Aquarium, and once again I was in awe. Sting rays are weird (we should know – we got to pet them)! Dolphins are amazing! Giant spider crabs are hilarious but also terrifying! The penguins and beluga whales were some favorite exhibits, and the temporary amphibian was a lot more fun than expected. You haven’t really lived until you’ve seen a giant, ugly toad eat a cricket using his tongue from across his tank. Trust me.

For dinner, we headed back across the river to Frontera, which had been recommended to us by a colleague of Anthony’s. I was skeptical, because it was surrounded by so many other fun-looking restaurants and I was hesitant to choose, but I am so glad we stuck with Frontera. The food. Was. Incredible. We decided to order two meals and share, and each bite was more delicious than the last. Tacos galore, a margarita mixed at the table, and some of the best guacamole I’v ever had. What more could we ask for? We left even more full than after our deep dish pizzas, and once again, it was worth every bite.

When we got back to the hotel, it was still a bit early, so we embraced the king sized bed (our queen sized bed at home always feels a bit cramped since we share it with our pup Wally) and just relaxed before ordering cookies and ice cream from room service. We fell asleep feeling pampered and cozy, and still full to the brim.

Sunday was our last day, so we woke up bright and early to make sure we had time to indulge in a Chicago staple: donuts. Firecakes was not far from our hotel, so we stopped there and easily could have ordered one of everything.

Yet another day, yet another museum. We spent Sunday at the Museum of Science and Industry per a recommendation by none other than Anthony’s grandma. We embraced our inner little kids in the Lego exhibit and had lots of fun checking out the whimsical model train exhibit. The mining exhibit was particularly fun (and very involved – it’s practically a ride!). Truly, each exhibit was fun, engaging, and made us feel like little kids again, and we’d definitely visit this museum again.

With a few hours left to spare before heading to the airport, we decided to head over to the Wicker Park neighborhood where we came across a local craft fair. There were so many booths full of unique local goodies, and we enjoyed gourmet hot dogs for lunch at Bangers and Lace before taking a long walk back to the hotel to pack up and head home. 

It was a fun-filled, museum-filled, and food filled trip and we hope to visit Chicago again soon! Until next time, Windy City!

Next stop: White Mountains, NH in October