Fresh off my first Babes That Wander trip, I decided to put all of my thoughts and memories about traveling to Chicago in a blogpost! During our stay in Chi-Town, we slept over at the 21c Museum hotel. This Downtown Chicago hotel is unique in the fact that it has a free museum with contemporary works on the first two floors below rooms! From our hotel, we could walk to many of the locations we had plans to visit. Below are some of the experiences I’d recommend while visiting The Second City over a weekend. I’ve provided a downloadable three-day itinerary for you to use on your next trip:
Easy Ways to Explore and Learn About Chicago
Chicago Greeter
In my humble opinion, one of the coolest ways to explore the city it with a local expert! Luckily, Chicago Greeter matches visitors with a resident knowledgeable about the city to take them on tours. They match you with someone from your language and interests. The best part is that it is free! The local guides volunteer their time, and often study about Chicago, in order to conduct excursions with tourists. We went with Sherry Wolf, who you can request to be your guide as well. Sherry mentioned that the local experts get together monthly for pub crawls to share their new city findings and stay up-to-date with all things Chicago. I loved that by having an escort around the town, we were able to get insider knowledge, and even insider views, of places that make Chicago special.
Chicago Architecture Foundation River Cruise
During our trip, Babes That Wander hopped on a 90 min Chicago Architecture Foundation River Cruise aboard Chicago’s First Lady Cruises. While riding down the river, the crew shares stories on over 50 buildings & architecture along the water. Besides hearing cool history, they taught us about how Downtown Chicago became one of the world’s largest cities in less than 100 years!
I’d definitely recommend this boat ride for anyone wanting to bask in the soft evening light, looking for a relaxing ride, or eager to learn mega interesting Chicago facts. Tickets are about $50, not including concessions. PRO TIP: The cruise goes out rain or shine, so don’t miss your boat if it begins to sprinkle!
Where to Find Art and Culture in Chicago
Pilsen Neighborhood
We visited the Pilsen neighborhood during our Chicago Greeter tour and I now hold it close to my heart. It is an area rich with culture, often the landing place for many immigrant families. I have Czech ancestors, and it used to be the first place many of them arrived when they came to America, creating an entire Bohemian community. Pilsen is now heavily influenced by Latinx culture, and you can see this in the small businesses thad local restaurants that line the streets.
There are many beautiful murals in this neighborhood, some even painted right onto personal homes! The creative and diverse community have a lot of street art as part of the Resurrection Project. This project was born out of a need to keep youth off the streets and channeling their energy into the arts. While here, I was told that professional muralists come and outline a wall, and kids are invited to help paint the street art to finish the projects. PRO TIP: head to this neighborhood with a Chicago Greeter so they can share the 150 years of history that make it an offbeat and creative center.
Art Institute of Chicago
No trip is complete without seeing the Art Institute of Chicago. There are a variety of pieces to look at; I could have spent an entire day there. My favorite artists’s work to see was Bisa Butler. She created unique art pieces out of quilting, using her heritage to to tell stories in the quilted portraits. I also loved seeing the Obama portraits and walking through the exhibit at AIC. The walk-up to the two famous paintings had history about the Obamas and how they dedicated their lives to their country. Unfortunately, this was closed on August 15th. General admission to the museum includes seeing all the collections they have to offer and is $25, unless given a resident or student discount.
PRO TIP: For popular exhibits, there is a waitlist! Simply head to the desk and scan the QR code to be put into a virtual line. You can then explore other ares of the museum and will be notified by text when it’s your turn to head back to the portrait exhibit.
Iconic Sightseeing in Chicago
Lake Michigan Beach
I’d often heard from Chicago natives about the shoreline of Lake Michigan and how it was a happening place to be. However, I was still pleasantly surprised at how much it felt like being on a coastal beach! The lake is so big that it almost seems as endless as the ocean. Along with that, the beaches are sandy and you’ll find sunbathers and beachcombers lounging out on summer days. It honestly took me out of the city and felt like I was enjoying a seaside vacation. 20+ of these beaches are free, so this is a great activity for the whole family on a budget!
Millennium Park, Cloud Gate, and Lurie Garden
Did you know that Chicago has a secret garden inside Millennium Park? Tucked away behind a wall of hedges, you’ll find Lurie Garden that is open all four seasons! It’s home to many plants and wildlife; I was amazed by all the bees buzzing around. It’s a quiet area away from the bustling city and busy park area. Most people don’t know about this peaceful place, so it’s worth it to check the garden out to meditate or take gorgeous photos of the cityscape mixed with greenery. Visiting the Lurie Garden is free, as are most of the experiences located in the park.
Besides having a concert venue, ice rink, many water fountains, and kids recreation areas, Millennium has amazing art installations! I went to see Cloud Gate (a.k.a. The Bean) during midday and the crowds were wild! Although some of the Babes That Wander crew went around 7:00 am to capture a photo at this iconic Chicago sculpture, I opted to sleep in until breakfast. While I got my beauty rest, they got the shots! PRO TIP: If you want to see this public work of art & capture photos without other human “beans”, head out early.
Skydeck Chicago and The Ledge
The Skydeck Chicago is in the eighth-tallest building in the world called Willis Tower. At the immersive experience there, called The Ledge, the tower glass boxes at the 103 floor that extend 4.3 feet out, giving you a thrill of the entire Chicago skyline & cityscape. Before entering the elevator to get up to the tower, patrons walk through an interactive museum of Chicago’s history, including many fun photo opportunities! Tickets are $28 and need to be bough in advance.
PRO TIP: When going into the glass boxes on The Ledge, you only get about 30 seconds per person to take photos (less time if your group size is bigger). Plan ahead by splitting into groups of 2-3, know your preferred poses, and have your camera settings ready! I think I broke out in more of a sweat worrying about getting the perfect photo than I did about the height.
Chicago Theatre
Although Marquee Tours of the Chicago Theatre are currently closed, it’s now open as a venue for shows again! Inside the historical building it is gorgeous, but the theatre front is also a sight worth seeing! We went to visit playhouse later at night (around 9 pm) to catch the dazzling lights and capture photos emblematic of our first trip to the City of Big Shoulders.
PRO TIP: if you want to capture a night photo like the one shown here, be sure to flash on your camera or bring extra light sources!
Places to Eat in Chicago That You Must Try
In case you missed it, I put together a list of 7 Chicago restaurants and bars that you should check out the next time you visit The Second City. With many families immigrating to the area, Chi-Town has a variety of tastes and cultural flavor fusions. You often hear about deep dish pizza and Chicago-style hot dogs, there’s a lot more food to explore when visiting. I plan on heading back in the winter to visit the Christkindlmarket Chicago and try even more of the delicious eats. Be sure to arrive hungry!
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Be sure to check out these other Chicago Travel Guides written by my friends and Babes That Wander group members:
Greta Hollar
Living Lesh
Lauryncakes sometimes receives compensation and/or hosted travel and sample products related to blog posts. This Chicago story may include affiliate links for which I receive a small commission at no extra cost to consumers. Be sure to check with businesses and locations regarding travel restrictions and safety precautions before visiting.
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