Colton and I spent Labor Day weekend with some friends in Chicago to celebrate one of them turning thirty. There are a few places I love to escape to on a three-day weekend, and Chicago is one of them. Chicago is a city that has everything- great restaurants, fun nightlife, outdoor activities, and more. Since we have been twice, I put together a list of what to do in Chicago.
Disclaimer: I was in Chicago with three photographers and two videographers, but we chose to be present with one another and took very few photos. All of these were taken with an iPhone, so the quality is not the best.
Getting to and from Chicago
On this trip, we booked the cheapest tickets possible and braved Spirit airlines. Since O’Hare is an international airport, nearly every airline flies in and out of it daily, making it very easy to get to.
I will sum up the Spirit experience for you with a list of positives and negatives.
- Spirit has cool branding
- Cheap flights
- Seats don’t recline (I know this seems like a negative, but I never recline my seat and always end up with a seat in my lap from the person in front of me)
- Don’t depend on being on time (I expect being late with every airline which is why Colton and I typically leave on the earliest flights). Our flight was about 40 minutes late leaving but only about 20 minutes late at the gate.
- You have to pay for everything (carry on luggage, checked luggage, picking your seat, water and sodas on board, snacks)
- No in-flight entertainment, not even wifi
- Very little legroom (unless you upgrade your seat) on the newer planes
- Tiny tables on newer planes that would not hold a laptop
Overall, it was not the worst flight I have ever been on, nor was it the worst flying experience. I would take Spirit again on short flights where the price difference is significant.
Where to stay in Chicago
The most popular area to stay in Chicago is the Magnificent Mile, on or right off Michigan Ave. On our first visit, Colton and I stayed at the Inn of Chicago. It was right in the center of everything, so it was a close walk to all kinds of restaurants, parks, and night life.
This time, our group rented an Airbnb in the South Loop near the Museum District. I highly recommend going the Airbnb route because there are tons of great places to stay. Our town home had 4 stories, a full kitchen, 3 bathrooms, 2 balconies and a terrace. It was perfect for the 6 of us! We took Uber/Lyft, Divvy Bikes, and the L train to get to where we needed to go.
What to do in Chicago
Touristy things to do in Chicago
Visit Millennium Park and take a photo with Cloud Gate or “The Bean”– The bean is one of the most recognizable sculptures in the world. It is found in Chicago’s largest park, Millennium Park, a beautiful spread out park with a lot of green space. Between the sculptures, exhibitions, garden, events and more, you will not run out of things to do.
Wrigleyville– Wrigleyville is home of the Chicago Cubs and their fans are serious about baseball. Wrigley Field is one of the oldest fields in the United States. Wrigleyville is the area surrounding and including Wrigley field, so if you are a Cubs fan you will be in Heaven. There are a ton of great bars and restaurants in the area to catch a game on TV if ticket prices are too expensive at the field.
Navy Pier– The Navy Pier is another Chicago landmark. You can catch a ride on the ferris wheel or any of enjoy any of the attractions. Navy Pier has a Shakespeare theater, children’s museum and more. We enjoyed just strolling down the pier, catching a couple of songs from the live performance and the beer garden, and people watching.
Visit one of Chicago’s beaches– Chicago has a few great beaches to relax, read a book, play sand volleyball, throw a frisbee, and get some sun. It is a great escape from the city life. The water from the Lake is almost as blue as the ocean, so you forget you are in the city.
The Magnificent Mile– Michigan Avenue is full of shops and restaurants, so it is labeled as the Magnificent Mile. You never know what you will see while shopping and strolling the mile. The last time we were there, Colton saw Steve Harvey jump out of a giant, wrapped gift.
iO theater– Chicago has some of the best improvisational theaters in the country. One of the many famous theaters where many favorite SNL cast members were trained and performed at is the iO theater. Our group had a great time catching a $5 late night show and some laughs.
Unique things to do in Chicago
No. 18 karaoke in Chinatown– Our friend Amanda found this hole-in-the-wall gem while looking for places to sing karaoke. For $30 an hour, you can rent a private room and sing the night away. We had a blast belting out all of our favorites, and we never had to wait for anyone else. Many of the songs play the music video during the karaoke session, but a few of them had some hilarious videos to go with. Although we didn’t have a reservation, we were still able to get a room for a couple of hours.
Divvy Bikes– Divvy bikes are a shared bike system that allows people to rent bikes for 24 hours, but in thirty minute increments. This is my absolute favorite way to see the city of Chicago. There are hundreds of drop off and pick up spots throughout the city. Chicago is a bicycle-friendly city, so riding around the streets is safe and convenient.
We rode all over the city, but the best place to ride is along Lake Shore Drive. You can watch the beautiful reverse sunset and enjoy the breeze.
Kayak Chicago– Kayak Chicago offers many different rental and tour options, so it will fit into any itinerary. Our group opted for the Architectural tour of the Chicago River, a three hour, 5-mile kayaking tour. Our tour guides were charming, informative, and attentive. It was a great way to see the buildings, riverwalk, and city. I would highly recommend trying one of their tours while you are there. (Be sure to check Groupon! We were able to get a discounted rate for our group.
Explore neighborhoods– Chicago has a variety of neighborhoods, each with their own style and charm. Along with Wrigleyville and Magnificent Mile, we explored Chinatown, Lakeview, Lincoln Park, Little Italy, the Loop, Wicker Park and Bucktown. We saw several other neighborhoods as we rode around on our Divvy bikes.
What is your favorite thing to do in Chicago? Now that you know what to do in Chicago, the next question is when will you visit? Leave me a comment below!