Following the ultimate NYC weekend guide Austen and I created, I was inspired to create another weekend post, this time for Chicago. I visited for the first time on a weekend attached to a work trip this month and got to explore the windy city.
Our first stop after dropping our bags off at the hotel was breakfast at Nutella Cafe, the perfect place to have crepes and waffles with a chocolatey filling.
After that we made our way over to Millennium Park to see the bean because it was our one day where it didn’t rain.
My absolute favorite part of the trip came after that. We took an architecture river cruise with Chicago Line Cruises (check out Groupon for discounts) and loved it! The views were fantastic and our guide was knowledgable and entertaining. Joe and I recently read The Devil in the White City, which is about architecture in Chicago, and I would recommend the book regardless of if you have plans to visit (p.s. let’s be friends on Goodreads!). Our hotel, the Swissotel, was pointed out on the tour, which made us feel pretty cool.
We also went to the Chicago Tribune Building that has stones from all over the world incorporated on its exterior. From the Taj Mahal to Washington Landing in New Jersey, there were so many to enjoy.
The next morning we began with another sweet breakfast, this time at Chicago Waffles. A cinnamon apple order was right up my alley. (I forgot to take a picture until I had already eaten half of it because I was so excited).
We took a walk over to the Adler Planetarium in the greatest downpour I have ever experienced. It turned into a hilarious run that ended up with us soaked walking into the planetarium. At the planetarium we listened to a lecture on theories of other beings in the universe, saw a show about a potential ninth planet in our solar system, and got to explore the extensive museum with interactive exhibits.
Next, we had lunch at Lou Malnati’s, a Chicago classic for deep dish pizza. I loved it, but Joe wasn’t completely sold and will be sticking with his New York pizza, thank you very much haha.
After that we met up with some Chicago friends at Andy’s Jazz Club. It was so nice to enjoy the music and excellent food together.
The day after that, we started out at Chicago Bagel Authority where you can get every breakfast sandwich combination under the sun!
From there, we walked to Lincoln Park to check out the Peoples Gas Education Pavilion. I spotted it on Instagram before our trip, but clearly the weather was not making it easy for me to recreate some of the cool photos I saw.
We also checked out the free conservatory in Lincoln Park. Thank goodness I planned indoor activities in anticipation that we might not be able to wander outside much.
Continuing our indoor activities, we went over to Wicker Park to see the Flat Iron Arts Building where artists have studios you can wander around for free. Since it was the weekend, most were closed up because the artists weren’t working, but we still got to see pieces hung in the halls.
After that, we poked around some vintage stores and also went into Myopic Books, a huge used book store. Then it was time for an ice cream break (essential for any vacation) at Jeni’s Splendid Ice Creams. Joe went for chocolate based flavors and I went for vanilla. Both were delicious and the staff was so sweet (sweet, haha, get it)! 
We headed back in to the heart of the city to visit the free cultural center. There are a variety of exhibits, most were centered around architecture, and it was another good place to have fun while avoiding the rain.
We parted ways the next day when Joe headed back to New York and I began my week of training. It was a great, quick trip and I hope this helps you plan your own Chicago weekend. If you want to check out how I plan trips, take a look at this post. And you can see all of my travel posts here.
Have you visited Chicago? What cities do you think are great for a weekend trip?
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