A month ago I spent a weekend in Chicago and I had the best time. I’ve been to Chicago for music festivals and concerts, but I’ve never had the time to properly explore the city. Southwest Airlines had an amazing deal so I grabbed tickets and away I went for a weekend adventure.
If you’re ever in Chicago for a couple of days, here are a couple of things to do, eat, and see while you’re in town!
Before heading to Chicago I knew I wanted to visit the wndr museum. I bought tickets ahead of time after reading that tickets sell out on weekends. wndr museum is Chicago’s new experiential museum located in a warehouse in the West Loop. The museum describes itself as “WHERE BEAUTY & THE IMAGINATION MEET. Step into a space that reveals the wonder of the natural world around us.” Walking in felt like stepping inside an adult fun house. There were 19 exhibits including the Yayoi Kusama Infinity Mirror Room. I spent about an hour and a half wandering and playing throughout the museum. It was a neat experience and a different change to my usual museum spots.
I don’t follow baseball or particularly understand it, but I love attending baseball games. Luckily, I was able to catch a Cubs game! I may not have known what was going on, but I loved the atmosphere. The Cubs were winning and everyone was celebrating. I had some beer, pretzels , a hot dog and I learned the cubs victory song which is so catchy and has been stuck in my head ever since.
Take a boat tour. There are so many to choose from, but I chose an architecture tour on Lake Michigan. It was a relaxing 2 hour cruise through the city and out on Lake Michigan. I learned some interesting tidbits from the tour guide about the city and seeing the entirety of Chicago’s shoreline from Lake Michigan was amazing.
You can’t go to Chicago without having deep dish pizza. I got suggestions from everyone and the two places that were mentioned the most were Giordano’s and Lou Malnati’s. I tried both and they were both delicious, but Lou’s was by far the better of the two. I loved the buttery crispy crust and the whole tomatoes. If you visit either, be patient. It takes about 45 min to an hour to prepare. Totally worth it. Lunch at Portillo’s also came highly recommended. I got a traditional Chicago hot dog , fries and a drink. So simple, but it was so good! And so good I had it twice more on the trip!
Those were all yummy but my favorite meal was from a place I randomly stumbled into. While exploring the West Loop I worked up an appetite and saw a little restaurant with a little goat on the roof. Obviously I had to eat there. I checked for at least 4 stars on yelp and decided to go. The aptly named Little Goat was super chic. A fantastic diner with big open windows and great decor. I’ve found that a lot of places that are super Instagrammable, have “meh” food . Not the case here. I got the Everything is Everything Crumpets (lox, fried egg salad, tzatziki cream cheese, pickles). It was EVERYTHING! I can’t wait to stop by again and try something new
My days were so busy that I was too tired for any big night outs. I went out for live music at Rosa’s, a blues lounge that reminded me so much of a Memphis blues bar, and had cocktails at a couple of spots around the city. My favorite was Delilah’s in Lincoln Park. The bar dive bar vibe and boasts more than 800 whiskeys and a great beer selection.
If you’re into vintage and catch yourself in town when the Randolph Flea Market is on. YOU MUST GO! It’s an indoor/outdoor market with hundreds of vintage vendors, food, and live music. It’s held at the end of the month most of the year. I found so many treasures!
My favorite neighborhoods to explore were Wicker Park and Lincoln Park. Loved the little coffee shops, bookstores and cute shops. Favorite coffee shop was The Wormhole. Great coffee and the shop is 80s themed and completely decked out in stuff I had in my room back in the day! Spent way too much money at Volumes bookstore and of course visited Rotofugi twice. Rotofugi is a toy store and art gallery and I know it will always be a stop whenever I’m in town. They have an entire Tokidoki wall and section. I was in heaven!
I’ll be back Chicago. There’s so much more to explore, eat, do and you’re just a 6 hour drive away! Have you been to Chicago? What is something I must add to my to do list.