The only time I haven’t been to Chicago is during the harsh winter. Otherwise, I have been in the summer, fall, and now Christmas. It is and will always be one of my favorite cities in the United States. There’s something about the mix of old and new buildings, food, and the Midwest people that make my heart happy. Chicago is a city that has everything- great restaurants, fun nightlife, outdoor activities, and more.
Getting to and from Chicago
Typically, I go for the cheapest tickets and brave 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)
- Not always on time (although what airline is now?)
- You have to pay for everything (carry on luggage, checked luggage, picking your seat, water and sodas on board, snacks)
- No in-flight entertainment, but paid wifi is coming
- Very little legroom (unless you upgrade your seat) on the newer planes
- Tiny tables on newer planes that would not hold a laptop
Where to stay in Chicago
The most popular area to stay in Chicago is the Magnificent Mile, on or right off Michigan Ave. A cool spot is 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.
Most recently, I stayed in Lincoln Park at Hotel Lincoln and absolutely would go back. They have a couple of restaurants, including a beautiful rooftop bar, and the decor is a dream.
Another great option in Chicago is to rent an Airbnb . A few years ago, I went with a group and stayed in a 4-story townhome on the South Loop near the Museum District. 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. During the holidays, there is even an ice skating rink.
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 since several shows are filmed in Chicago.
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.
Unique things to do in Chicago
Gangster and Ghosts Tour- Take a walking tour through Chicago’s Loop Vice District and learn about Chicago’s haunted past. It’s the best way to learn more about the city and some of the famous haunts.
Eat a brownie at the Palmer House– Bertha Palmer led the creation of the first brownie at the Columbian Exposition World’s Fair in 1893. Over 100 years later, this famous hotel serves the same recipe and it’s delicious. The hotel is gorgeous and full of gold.
Go to a Bears game– Chicago is a sports-centric city, so grab tickets to a Bears game and go experience the oldest stadium in the NFL. The tailgating parties alone are worth checking out
No. 18 karaoke in Chinatown– Looking for a hole-in-the-wall gem while to sing karaoke? For $30 an hour, you can rent a private room and sing the night away.
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.
One of the most scenic areas to 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. The three hour, 5-mile Architectural Tour is a great way to see the city. (Be sure to check Groupon!)
Explore neighborhoods– Chicago has a variety of neighborhoods, each with their own style and charm. Along with Wrigleyville and Magnificent Mile, soak up Chinatown, Lakeview, Lincoln Park, Little Italy, the Loop, Wicker Park and Bucktown.
Visit the Lincoln Park Zoo- The Lincoln Park Zoo is one of the oldest zoos in North America. It’s also free, so it’s the perfect place for a date or to take the family. During the holidays, they have Zoo Lights and the zoo becomes a magical wonderland in the evening. The zoo is open 365 days a year, so check it out any day of the week!
What is your favorite thing to do in Chicago? me a comment below!