A Weekend Getaway in Chicago

Chicago is a really special city, it’s sophisticated and charming and it totally stole our hearts last weekend. Matt and I really hadn’t been away together since before Millie was born so when Matt suggested a weekend trip to Chicago I was mentally already packing my bags. I had traveled to Chicago last year for work and really fell in love with the city. The architecture, the food, and the people impressed me so much. There’s so much to do in Chicago and it was tough packing everything we wanted to do in a weekend and our itinerary isn’t for the faint at heart because we hardcharged the whole weekend but if you’ve only got a weekend, you fit it all in. Here’s a recap of our weekend getaway in Chicago.

A Weekend in Chicago – What to see, do, and eat

Where we stayed in Chicago
We stayed at the LondonHouse Hotel right in downtown Chicago. The hotel is situated right on the Chicago River. We had the most amazing view of the Chicago River and the Wrigley Building from our hotel from. I had stayed at this same hotel last year so I knew it was the perfect location for us as a home base as we explored the city. It’s walking distance to tons of amazing restaurants, attractions, and of course shopping.

The other perk to staying at the LondonHouse was the access to the beautiful rooftop bar. From the rooftop of the LondonHouse, you get the most incredible views of the city. We tried to visit as early as possible because it gets packed in the evenings. Every night there was a long line to get upstairs, although as a guest you don’t have to wait, it was a very popular evening destination.

What we wore in Chicago

What we did in Chicago
Funny story, our top reason for choosing Chicago as our getaway destination was because we wanted to see Hamilton. Matt surprised me with the tickets to the show and it did not disappoint.

We arrived in Chicago at 9 am on Friday morning. We dropped our bags at the hotel, grabbed a quick bite to eat at the hotel restaurant and then headed out to explore the city. We did all the tourist things. We checked out Navy Pier, Millenium Park, The Chicago Cultural Center, and The Magnificent Mile before we headed back to our hotel to get ready for the Cubs game.

While the Bean is the most well-known attraction at Millenium Park, the park grounds themselves are stunning and the views from the park are incredible. We also really enjoyed the Chicago Cultural Center.

It was once Chicago’s first public library, it now features amazing art and cultural exhibits. I was excited to see StoryCorps as one of the featured exhibits.

They were recording the day we visited so we didn’t get to go in but I love the message of humanity and compassion that StoryCorps represents.

We didn’t spend a ton of time at Navy Pier but I’d love to bring the girls back there one day. They had what looked like a pretty incredible Children’s Museum and splash park in addition to the giant Ferris wheel.

The Cubs Game
If you want to really get a feel of Chicago, go to a Cubs game. This was recommended to us by readers and friends and it was an amazing experience. We headed over to Wrigleyville a couple hours before the game and grabbed a couple of drinks at The Cubby Bear bar which is iconic.

Then, we headed to the stadium. Wrigley Field is impressive on its own and the fans are DIEHARD. I just imagine them being generations of Cubs fans with lots of memories to share. Matt is a big baseball fan, we’re Washington Nationals fans actually, so he did some research ahead of time and got us great seats in the shade. Chicago was experiencing a heat wave the weekend we were there so shade felt like a luxury.

We had to eat a true Chicago style hot dog and it was literally, the best hot dog of my life. I mean, I can’t stop thinking about it.

After the game (by the way – Cubs won), we headed back to our hotel to cool off and rest for a bit before dinner and the Second City show. We decided to eat at a trendy little spot called Union Sushi + Barbeque. We didn’t have a reservation so we sat at the bar and I was happy we did. The restaurant was obviously a hot place to be on a Friday night in the city.

We got a couple of their signature drinks which were incredible but even better than the drinks was the sushi. I’m a bit of a sushi snob and it’s very hard to find delicious sushi here in Jacksonville so I didn’t have very high expectations for midwest Chicago but oh boy, I was impressed.

At this point, we were completely exhausted from being parents of two up and out past 10 pm but we grabbed a Starbucks and pressed on, heading to the Second City for our 11 pm show. The comedy show wasn’t something that had been on my radar until it was recommended by a friend and I would have been so disappointed if we would have missed it. Matt and I both laughed so hard we had tears streaming down our faces.

The cast was incredible, the jokes were hysterical, and the ambiance was perfect. This should absolutely be a MUST see on your Chicago itinerary.

The view from our room was stunning.

Saturday morning we headed to grab donuts Do-Rite donuts, again, at the recommendation of a reader (thank you guys for giving me the best places to see and eat on this trip). It was this adorable tiny little donut shop that doesn’t have a large menu but you can tell they have perfected the small menu they do have. We got a half dozen and sampled a little bit of each one. My favorite was the cheese danish donut. So good.

After our sugary breakfast, we met our boat for the Chicago architectural river tour. Before we boarded the boat, we got a unique display of the Chicago fire department attempting to the cool off one of the drawbridges. A sailboat headed to Lake Michigan was stuck between two bridges. Apparently, the over 100-year-old bridges can get stuck on really hot days. The heat causes the metal to expand and the bridges don’t go up as usual.

On this day, the fire department was on the water hosing the bridge down to cool it enough for it open. By the time we were heading back for our tour we saw the sail boat heading out.

I opted for the 90-minute tour that takes you out onto Lake Michigan so we could get a really great view of the Chicago skyline, which in my opinion is one of the absolute best.

Bob, our guide was born and raised in Chicago and had so much knowledge about the city.

We ate lunch at the famous Lou Malnati’s. I’ll say, Chicagoans are passionate about their pizza so I didn’t want to mess this up. My best friend is from Chicago and recommended this place over the other popular Giordano’s. It was incredible. We went to the downtown location and it was absolutely packed even at 2 o’clock in the afternoon.

We ordered the Malnati Classic which was sausage, tomato, extra cheese on the famous butter crust. One thing I can say for the food in Chicago is that it didn’t disappoint. Everything was amazing.

Saturday evening was the night of our big show, Hamilton at the CIBC Theatre. I was so excited to get dressed up! Both Matt and I had been so excited about this show but I really had no expectations. We are both lovers of history and knew this would be something enjoyable for us.

 I had heard amazing things about the original Broadway show and our experience at the Chicago show blew us away. I was literally on the edge of my seat the entire show, I love every song, every word, every performer. If you ever get a chance to see this show around the world, GO see it!

What we wore in Chicago

We finished our night at Portillo’s, the iconic Chicago hot dog spot and ate another delicious Chicago style hot dog. I’m embarrassed to admit how much I truly love these dogs. But not embarrassed enough to quit them.

Sunday was our final day in Chicago. We had packed our first two days full of stuff so we took it easy on Sunday. I took in this amazing view one last time, and then we headed out for breakfast at Wildberry Pancakes. From there, we got an Uber to the Chicago History Museum. Our driver gave us an unofficial tour of the city on the way there which was so interesting. If you are ever in a city and have the opportunity to get a quick tour from an Uber driver, take them up on it! They always know way more than you’d think. He gave us some great recommendations for our final eats as well. The museum was great! It was so fascinating learning about the Great Chicago Fire and how the city rebuilt after over a third of it had burned to the ground. We also loved learning about the great American businesses that all started right in Chicago like the Wrigley Company.

I know that was a lot but we really had the best time in Chicago – it was a trip to remember! And we’ve already started thinking about our next trip! I’d love to hear what vacation you’ve absolutely loved!

I’ve written about traveling a few other times here on the blog. You might like reading about our family vacation to Jekyll Island or How to Vacation in Hawaii like a Local.

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One Comment

  1. What a great trip! Chicago is one of my favorite cities. So clean too!
    The boat tour sounds amazing! I’d really like to do that. Plus, the fire department boat was so interesting! I had no idea.