How to Spend 3 Days in Chicago: a Chicago Itinerary

A full 3 days in Chicago Itinerary

So you only have 3 days in Chicago? Well, 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 to enjoy. The people are pure gold, the food is *chefs kiss*, and there are ample things to do in Chicago. In this guide, I’m sharing everything to know before visiting so you can truly enjoy all it has to offer!

Best Time to Visit Chicago

They don’t call it the windy city for anything! The temperatures in Chicago can drop below zero in the winter so it’s best to travel to Chicago from May-July and September-November. Where the weather is mild and you’ll be able to enjoy walking around the city without freezing. Finally, St. Patricks Day is the most popular time to visit Chicago. The riverwalk turns green to celebrate the occasion and the entire city takes place in the festivities.

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 its 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.

Mid-range hotels:

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

Millennium Park

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.

Architecture River Cruise

If you’ve seen “My Best Friends Wedding” then you’ll remember when Julia Roberts is dancing with Michael atop the Architecture River Cruise. It’s one of the most popular things to do in Chicago. A must-see for your 3 days in Chicago. There is nothing like admiring architecture from the water. There are ample architecture 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 and tourists alike. 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 is best experienced in the early morning while the city is still sleeping. Furthermore, you’ll recognize this spot from many movies including one of my personal favorites, While you were sleeping.

Lincoln Park

Lincoln Park is Chicago’s largest park bordering the most affluent neighborhoods in the city. It’s an oasis to the locals from the bustling city of Chicago. This park is 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. It’s especially pretty to visit in the fall to witness the changing leaves against the cityscape.

Skydeck Chicago

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.

Visit Milton Lee Olive Park

Located close by to Navy Pier is Milton Lee Olive Park. It’s lesser known spot overlooking Lake Michigan featuring stunning views of the skyline. Finally, it’s a secluded spot to the city often with runners and locals taking their daily walk.

Other things to do in Chicago if you have time:

Visit Navy Pier
Catch a ball game at Wrigley Field
360 Chicago Observation Deck
Garfield Park Conservatory
Admire the architecture at the University of Chicago
Visit North Avenue Beach
Check out the Chicago Water Tower
Check out the Museum of Science
Beautiful views from the Willis Tower

Where to Eat in Chicago

Three Arts Cafe ($$$$): Did you really visit Chicago if you didn’t go to Three Arts Cafe? The prettiest restaurant in Chicago. Located inside the Restoration Hardware store this cafe is heaven. Don’t sleep on the burger, the best one I’ve ever had in my life!
Beatnik on the River ($$$): amazing views of the riverwalk and delicious Mediterranean-inspired foods.
Adorn ($$$$): located in the Four Season Hotel, Chef Jonathon Sawyer is cooking up award-winning dishes featuring global-inspired cuisine. Get the poutine and thank me later!
Pequod’s ($$): the locals love this spot for the most famous Chicago dish, deep-dish pizza. Being from New York, I’m a hard one to judge but this was surprisingly good. Chicago deep dish pizza is not your average pizza and reminds me more of a casserole dish. But nonetheless, still tasty!
Portillo’s ($): when visiting Chicago you NEED to get a famous Chicago dog. Portillos’s is the most famous spot with locations all around the city. What makes Chicago dogs special is its poppy seed bun.
Do-Rite Donuts & Chicken ($)
Girl & The Goat ($$$)

What to Pack for Chicago

While all opinions and recommendations are always my own, the content on this blog post contains affiliate links for products I use and love. This means I get a small commission (at no additional cost to you) if you make a purchase after clicking one of these links. As always, I am so thankful for your support so I can continue to offer free resources!

If you’re traveling during the colder months make sure to have a warm coat. I’m talking about a puffer jacket. We all want to look cute but when walking around Chicago I highly suggest this puffer 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 3 day Chicago itinerary. 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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