How to Spend a Weekend In Chicago

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I had been wanting to spend a weekend in Chicago for quite some time. Chicago is one of the top cities for travel as it boasts stunning architecture, delicious food, and world-class museums. I FINALLY had the chance to go with a friend who also loves fast paced travel, so off we went! On my first trip to the Windy City, I found that two days in Chicago left me wanting more time to see all that the city had to offer.

We made our way through the airport and followed the signs for the trains to the city. When we reached our destination, we were met with a Chicago sign and the massive Trump Tower in the distance.

I chose to stay at the Fairmont Chicago Millennium Park as it is within walking distance to many of the city’s attractions. We quickly put our belongings in our room and made our way to the concierge for a quick run down of things to do in the area.

We chose a 75-minute architectural boat tour and a hop on hop off bus so that we could get a good feel for the city. The hop on hop off bus is a great way to get a feel for the city for first timers because it hits the highlights in about 2 hours if you chose to stay on. Plus, there are live guides on board that point out the landmarks and tell the history of the area. I have always enjoyed the bus tours. 🙂

Whether you want to people watch, bird watch, stroll along the river bank, or kayak, the Riverwalk has a lot to offer. There’s so much history along this scenic portion of Chicago. You must check this area out for sure.

Formerly known as the Sears Tower, the Skydeck at Willis Tower allows those brave enough to stand on the Ledge. It is a glass box that extends 4 feet out from the skyscraper and 1,300 feet above ground level. The clear glass without any obstruction allows for great photos. I have to admit I didn’t want to look down!

If you want to skip the line and buy your tickets now from GetYourGuide, they offer a free cancellation up to 24 hours before your scheduled activity. (Read the rules of the activity.) You can get Chicago Skydeck and the Ledge Experience tickets by clicking the link.

The main attraction here is the Cloud Gate, aka the Bean. This piece of work by Anish Kapoor is made of nearly 200 stainless steel plates that makes for the perfect place to take photos of the reflecting Chicago skyline. Pro-tip: Get here very early in the morning and you will hopefully have the place to yourself to avoid the crowd.

Navy Pier is fun for all ages. It has food and entertainment and the BEST ice cream that you just HAVE to try called rainbow ice cream. If you are lucky, the best time to visit the Navy Pier is between Memorial Day and Labor Day on Wednesdays and Saturdays. A spectacular fireworks show is displayed over Lake Michigan and its perfectly synchronized to music. I timed it just right to explore the Navy Pier, eat a rainbow cone, and then watch the fireworks. 🙂

For those looking for an adrenaline rush, head to the Tilt at 360 Chicago, formerly in the John Hancock Tower. You will find panoramic views of the city here but if you are wild like me, try the Tilt ride. This thrill ride tilts you out 1,030 feet over the Magnificent Mile and the famous Chicago skyline.

If you want to skip the line and buy your tickets now from GetYourGuide, they offer a free cancellation up to 24 hours before your scheduled activity. (Read the rules of the activity.) You can get 360 Chicago Observation Deck tickets by clicking the link.

When visiting Chicago, you MUST sample some of Chicago’s classic foods. Despite trying to take in as many of the sites possible in just 2 days in the Windy City, we still ate a lot!

Chicago is known for it’s deep dish pizza and Lou Malnati’s was mentioned over and over my several of the locals so we chose it. I decided on a cheese and a sausage and both were very delicious. It was so delicious that I googled how to have it delivered to my home in Tennessee and found a website that actually delivers Lou Malnati’s deep dish pizza and other Chicago classic foods! I bought some for my family and friends so they could enjoy some back home. 🙂

Portillo’s was the fix for the Chicago style hot dogs. Boy, talk about a hot dog! I wish I had one right now. YUM!!! For dessert, I had some delicious chocolate cake.

Some other foods that everyone should try are Garrett’s popcorn and Eli’s cheesecakes. Don’t forget to try the original brownie created in 1893 for the Chicago’s World Fair sold at the Palmer House (the longest continuously running hotel in America).

It’s no secret that since the 1800s that Chicago has been the candy capital of the world. Grab some Tootsie Rolls or M&Ms as you stroll the streets as they were created in Chicago. Stop in Ferrara Bakery located in the Little Italy area to taste pastries and specialty cannoli at it’s original location.

One of the most recommended things to do in Chicago is to take the 75 minute architectural boat tour. It’s a great way to learn about the city’s history and see the the beautiful architecture in the Windy City via a relaxing cruise. Did you know that Chicago was the birthplace for the skyscraper? I think everyone who does this recommends this to another first timer.

There’s always something happening in Chicago. Chicago is known for having great shows and if you would like tickets for a last minute performance you can try buying tickets at Hot Tix. Also, there are several sports teams you may be interested in catching a home game for such as the White Sox, Cubs, Bears, Blackhawks, and Bulls. One day I hope to catch a baseball game at Wrigley field!

Maybe visiting the zoo is your thing. I’m not sure WHAT I was thinking but this was on my list of things to do but I didn’t quite fit it in my busy schedule. 🙂 Did you know its free to enter and it has one of the best views of Chicago? There are over 200 different species of animals at Lincoln Park Zoo and I wanted to do a quick walk around the park just to check them out. But, I didn’t have time. 🙁 I will have to wait for a longer visit!

If visiting a museum is something you want to do, then go to the Adler Planetarium. It was the first planetarium in the United States where you will get a better understating of our solar system with the interactive exhibits such as touching a piece of the moon or Mars. There are active research projects going on here that you are welcome to watch in you want as well. I’m a big fan of anything space related so this is a museum I could really get into!

If you don’t want to visit the museum, definitely make a trip here to take in the views of the Chicago skyline. It has one of the best views of the city! When I was there girls were taking their prom pictures there (so you KNOW it must be one of the best views!).

I know I mentioned this before, but it’s worth repeating! The hop on hop off tours are worth it for first time visitors. You really get a feel for the city and learn things you wouldn’t know otherwise. I will be honest, you will like some guides more than others. But you will always learn something. For example, I learned that one of my favorite actresses, Julia Roberts, played a scene at the Fourth Presbyterian Church in My Best Friends Wedding. That is one of my favorite movies so I had to get a photo!

I also learned the story of William Wrigley, Jr and his chewing gum. You will just have to take the tour to hear it, too. 🙂 Let’s just say he sold it better than he did soap! But, the building below will forever be known as the Wrigley Building in Chicago.

Remember: You can buy your tickets now from GetYourGuide, they offer a free cancellation up to 24 hours before your scheduled activity. (Read the rules of the activity.) You can get Chicago hop on hop off tickets by clicking the link. Then, just show up at the meeting point like we did.

If you are looking for some great hotel deals in Chicago, I suggest looking at Booking.com and comparing rates directly with the hotel you want to stay at. Sometimes I have found a better rate or perks by booking either way. You just have to compare! I do most of my hotels through Booking.com.

Tip: I use tour search engine GetYourGuide to find affordable organized tours to see different parts of Chicago. It’s also great for finding tickets to skip the line so you can walk right past the big crowds. Most of the tours you can cancel up to 24 hours before your scheduled activity which is great if you have to cancel for some reason (like rain).

If you are like me, you will find that having only 2 days in Chicago will have you desiring more time in the Windy City! There’s just SO much to do and SO much food to try. 🙂 What’s your favorite thing to do or something you wish you had done? Let me know in the comments below.

See more photos from my Chicago trip and other vacations on Smugmug here.