So you only have 3 days in Chicago? That is the perfect amount of time to explore the windy city. Chicago is one of my favorite cities because it has a little something for everyone. The people are pure gold, the food is *chefs kiss*, and there are ample things to do. In this guide, I’m sharing “How to Spend 3 days in Chicago” so you can enjoy all this city has to offer.
Best Time to Visit Chicago
They don’t call it the windy city for nothing! The temperatures in Chicago can drop below zero in the winter so it’s best to travel to Chicago during May-July and September-November. Where the weather is mild and you’ll be able to enjoy walking around the city without freezing.
Where to Stay in Chicago
Chicago has no shortage of beautiful hotels to choose from. If you’re like me and love a little luxury then I highly recommend these two hotels:
- The Langham Chicago: luxury at it’s finest with the best views of the riverwalk. Make sure to take advantage of their club access when staying it includes breakfast, lunch, and dinner. The food is incredible.
- The Four Seasons: the ultimate 5-star hotel with incredible service and the rooms have beautiful views of the lake.
- The Pendry: located right across from Millennium park this hotel is in a prime location.
- Kimpton Gray Hotel: also located near millennium park this hotel offers packages that include food as well.
Things to Do in Chicago
Home to the infamous bean, Millennium Park is a must-see for every visitor. The bean sculpture is the most famous landmark in this city and with the Chicago skyline in the background, it makes for the perfect photo op. As you can see, it’s magical to visit during the fall. Finally, because of Covid, it doesn’t open until 8 am now.
Riverboat Architecture Tour
If you’ve seen “My Best Friends Wedding” then you’ll remember when Julia Roberts is dancing with Michael atop the riverboat. Well, that is the famous Chicago Architecture Tour boat. Another must-see when visiting Chicago for the first time. There is nothing like admiring architecture from the water. There are ample tours to choose from ranging from 60 minutes to 90 minutes. Linking a popular tour here. Make sure to make reservations in advance.
Walk the Chicago Riverwalk
This 1.25-mile path is located along the river and is a treasured natural amenity for residents. Whether you choose to walk, run, or just sit on a bench and admire you’ll experience the prettiest views of the city. It’s open from 6 am – 11 pm and you can learn more about it here.
Lincoln Park is Chicago’s largest park bordering the most affluent neighborhoods in the city. It’s home to the insta-famous Honeycomb and the Lincoln Park Zoo. When visiting, you’ll be surrounded by nature while admiring the skyline from afar. Grab your walking shoes to explore this beautiful part of the city.
Explore Chicago from above on the 103rd floor of the Sears Tower. With clear observation boxes, you’ll be looking down on the entire city (and be able to see 4 states). It’s most definitely an experience everyone needs to try when visiting.
The Chicago Theatre
An icon! The Chicago Theatre rivals “the bean” for the most photographed part of the city. This legend was built in 1921 and was America’s first large movie palace. Even if you’re not going to a show, you need to visit the famous marquee. Click here for a show schedule.
The Magnificent Mile
If you’re an avid shopper then The Magnificent Mile is the place for you. This street spans one mile of high-end luxury stores, beautiful architecture, and top-notch eateries. It’s the perfect place to spend an afternoon and grab lunch when you only have 3 days in Chicago.
Other things to do in Chicago:
- Navy Pier
- Wrigley Field
- Garfield Park Conservatory
- University of Chicago
- North Avenue Beach
- Museum of Science
Where to Eat in Chicago
- Three Arts Cafe ($$$$): the prettiest restaurant in Chicago. Located inside the Restoration Hardware store this cafe is heaven. Don’t sleep on the burger, the best one I’ve ever had in my life!
- Beatnik on the River ($$$): amazing views of the riverwalk and delicous meditteranean inspired foods.
- Adorn ($$$$): located in the Four Season hotel, Chef Jonathon Sawyer is coooking up award winning dishes featuring global inspired cuisine. Get the poutine and thank me later!
- Pequod’s ($$): the locals love this spot for another famous Chicago dish, deep dish pizza. Being from New York, I’m a hard one to judge but this was surprisingly good. Deep dish pizza is not your average pizza and reminds me more of a casserole dish. But nonetheless, still tasty.
- Portillo’s ($): when visiting Chicago you NEED to get a famous Chicago dog. Portillos’s is the most famous spot with locatuons all around the city. What makes Chicago dogs special is it’s poppy seed bun.
- Do-Rite Donuts & Chicken ($)
- Girl & The Goat ($$$)
What to Pack for Chicago
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- If you’re traveling during the colder months make sure to have a warm coat. I’m talking a puffer jacket. We all want to look cute but when walking around Chicago I highly suggest this coat.
- Warm socks to keep your feet warm
- A comfortable but cute pair of booties. I love these chic ones, they’re comfortable for walking!
- A warm beanie
- A good scarf
- My favorite leather leggings that pair nicely with the booties
Thank you for reading my itinerary on “How to Spend 3 days in Chicago”. I hope you have a fabulous time exploring the windy city. If you need more help packing you don’t want to miss my “22 Travel Essentials for your next trip” post. Enjoy your trip!
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