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, also known as the “Windy City”, is one of the largest and most vibrant cities in the United States. This Midwestern metropolis has something for everyone, from world-class museums and stunning architecture to trendy neighborhoods and delicious food.

It’s 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 “3 Days in Chicago Itinerary”, 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.

While all opinions and recommendations are always my own, my content on this blog post may contain affiliate links for hotels I’ve traveled to, tours I’ve completed, and products I recommend. This means I get a small commission (at no additional cost to you) if you book a stay or purchase a product after clicking one of these links. As always, I am so thankful for your support so I can continue to offer free resources.

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. Experiencing the Langham Club was incredible I think about those stunning views often. Book your stay here!
The Four Seasons: the ultimate 5-star hotel close to all the major shops. This hotel offers incredible service and rooms, beautiful views of the lake, and the tastiest in-house restaurant, Adorn. Book your stay here!

Mid-range hotels:

The Pendry: located right across from Millennium Park this hotel is in a prime location. Book your stay here!
Kimpton Gray Hotel: also located near millennium park this hotel offers packages that include food as well. Book your stay here!

Best Things to Do in Chicago

Millennium Park

Home to the infamous bean (which is properly named the Cloud Gate sculpture), Millennium Park is a must-see for every visitor. Take a stroll through the park and enjoy the public art and green spaces. 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 opportunity.

Another popular feature of Millennium Park is the Jay Pritzker Pavilion, an outdoor concert venue that hosts concerts, festivals, and other events throughout the year. The pavilion is famous for its unique design, which includes a trellis made of stainless steel that curves over the stage and a sound system that provides excellent acoustics.

Millennium Park is open year-round and admission is free. It’s a popular destination for both tourists and locals, and there are always events and activities happening in the park. Whether you’re looking to take in some art, catch a concert, or simply enjoy a sunny day in the city, Millennium Park is a must-visit destination in Chicago. Finally, it’s magical to visit during the fall.

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.

During the 90-minute tour, knowledgeable guides provide insight into the history and design of each building, offering a fascinating look at the city’s rich architectural heritage. Some of the highlights of the tour include the Wrigley Building, the Tribune Tower, the Marina City complex, and the Willis Tower (formerly known as the Sears Tower).

There is nothing like admiring architecture from the water. Overall, the Chicago Architecture Foundation River Cruise and walking tours are a must-do for anyone interested in architecture, history, or just taking in the stunning views of the city. There are ample architecture tours to choose from!

Walk the Chicago Riverwalk

The Chicago Riverwalk is a picturesque pedestrian walkway along the Chicago River that offers stunning views of the city skyline. Visitors can enjoy drinks at one of the waterfront bars, take a boat tour, or simply stroll along the river.

This 1.25-mile path is a treasured natural amenity for residents and tourists alike. 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.

Visit the Art Institute of Chicago

Chicago is also home to several world-renowned museums, such as the Art Institute of Chicago, the Museum of Science and Industry, and the Field Museum. The Art Institute houses an impressive collection of art, including works by famous artists such as Monet, Van Gogh, and Picasso. The Museum of Science and Industry features fascinating exhibits on space exploration, genetics, and other scientific topics. The Field Museum is a natural history museum that has exhibits on dinosaurs, ancient cultures, and much more.

Depending on your preference either of those museums are a great way to spend an afternoon in Chicago. Book your tickets in advance!

Walk around 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. One of the main attractions in Lincoln Park is the Lincoln Park Zoo, which is free to the public and open year-round. The zoo features a wide variety of animals, from big cats and primates to reptiles and birds. It also has a beautiful nature boardwalk that provides stunning views of the Chicago skyline.

Another popular attraction in Lincoln Park is the Honeycomb. This structure is unique and offers unique views of the chicago skyline. When visiting, you’ll be surrounded by nature while admiring the skyline from afar. Make sure to wear your walking shoes when exploring this beautiful part of the city. Finally, it’s especially pretty to visit in the fall to witness the changing leaves against the cityscape.

Willis Tower/Skydeck Chicago

The Skydeck Chicago is an observation deck located on the 103rd floor of the Willis Tower (formerly known as the Sears Tower) in downtown Chicago. It’s one of the city’s most popular attractions, offering stunning views of the city and Lake Michigan.

The Skydeck experience begins with a high-speed elevator ride to the top of the tower, which takes less than a minute. Once you arrive, you can step out onto the glass-floored Ledge, a series of glass boxes that extend out from the side of the building. The Ledge provides a unique and thrilling experience for visitors, as they can see the city from a completely different perspective, with nothing between them and the street below but a layer of glass.

Fun fact, you can see four states from the observation deck. It’s most definitely an experience everyone needs to try when visiting. Because of it’s popularity, it is extremely busy so make sure to book your time slots in advance!

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 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
Visit the Chicago Water Tower

3 Days in Chicago Itinerary

Here’s a summary of a suggested 3-day itinerary for exploring Chicago:

Day 1:

Visit the Sky Deck for panoramic views of the city
Walk the Chicago Riverwalk for waterfront views, drinks, and boat tours
Take an Architecture River Cruise
Dinner at Beatnik on The River

Day 2:

Visit Millennium Park
Explore the Art Institute of Chicago for impressive art collections
Shopping on the Magnificent Mile
Lunch at Three Arts Cafe
Walk around the Gold Coast Neighborhood
Stroll through Lincoln Park and visit the Honeycomb

Third Day:

Breakfast in the trendy River North neighborhood
Explore Navy Pier for entertainment, shopping, and dining
Check out Milton Lee Park for unique views
Have dinner at Pequod’s restaurant and catch a show at The Chicago Theatre

Where to Eat in Chicago

When it comes to food, Chicago is famous for its deep-dish pizza. There are several restaurants throughout the city where you can try this classic dish. However, Chicago is also home to a diverse range of cuisines, from hot dogs and Italian beef sandwiches to Korean BBQ and sushi. I’ve listed the top picks below:

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 ($): when visiting Chicago you NEED to get a famous Chicago dog. Portillos is the most famous spot with locations all around the city. What makes Chicago Dogs special is its poppy seed bun.
Do-Rite Donuts & Chicken ($)
Girl & The Goat ($$$)

What to Pack for Chicago

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. Chicago is a city that has something for everyone. Whether you’re interested in museums, food, architecture, or simply exploring unique neighborhoods, Chicago is a destination worth visiting.

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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