3 Days in Chicago: Everything You Should Know

Published by: Bounce12 September, 2022

The cultural diversity, renowned architecture, outstanding museums, and top-notch dining makes a trip to Chicago well worth it. Places like the Tribune Tower, John Hancock Observatory, and the Buckingham Fountain are a huge draw. And some people come to the city just to try the Chicago deep dish pizza!

Since you only have 3 days in Chicago, there are many things you will want to pack into your itinerary. Try to include a little bit of everything when you plan your 3-day schedule. Remember, if you are visiting over a long weekend, things will be packed with locals and tourists. Book tickets for main attractions in advance.

Visit anytime throughout the year, but remember, Chicago winters can be rather brutal. You may want to forgo any outdoor activities unless you are a huge fan of biting winds and frigid temps. You can easily look for indoor rainy day activities to add to your itinerary instead of outdoor activities if you run into days with snow or rain.

Do a hop-on-hop-off bus tour to see several of the top landmarks, visit the Shedd Aquarium with over 32,000 aquatic animals, check out the two observation decks (the SkyDeck and 360 Chicago), or take a stroll along the Magnificent Mile. Don’t forget the Art Institute of Chicago for a little bit of culture and then sign up for a river cruise to learn more about the architecture of the city.

Rushing through the city and finding your shopping bags and large items weighing you down? Leave your bags with Bounce luggage storage so you are not lugging bags with you through Chicago. You will not find many places that allow larger bags inside for safety reasons, so leave all big items in storage for the day. Then get ready to make the most of your Chicago three day itinerary!

Chicago itinerary – Day 1 

Morning: Hop-On-Hop-Off Bus Tour

The Big Bus Chicago tour is one of the best ways to get a quick introduction to Chicago and learn about the top landmarks and attractions. It really is a good way to pack a lot of sightseeing into a short trip. The friendly tour guides will make your bus adventure fun and informative as well as share tips and insider info on where the best shops, restaurants, and clubs are located.

The bus stops at most of the landmarks and you can get off to walk around and get photos. Expect to see the Navy Pier, Museum Campus, Willis Tower, Water Tower Place Mall and so much more. Most tours last about two hours and you can see quite a bit of the city. Purchase a Go Chicago pass and the hop-on-hop-off bus tour tickets are included. 

Afternoon: Chicago’s Museum Campus

There is an area known as Museum Campus where you will find several interesting and fun attractions including the Shedd Aquarium, Field Museum, and Adler Planetarium. Why not spend the afternoon here?

Shedd Aquarium

The Shedd Aquarium is one of the most fascinating aquariums in the United States, as well as the biggest. With about 32,000 diverse and rather interesting aquatic animals, you could spend an entire day exploring all the aquarium has to offer. Check out the beluga whale, watch the penguins waddle around, and laugh at the sea otters.

There are several popular exhibits included with admission including “Amazon Rising”, “Waters of the World”, “Abbott Oceanarium”, “Caribbean Reef”, “Polar Play Zone”, and “Wild Reef”.  Reach your hand in the touch pools and feel a stingray as it swims past.

Field Museum

This natural history museum is a wonderful place to hang out in the afternoon to learn more about our history. The biggest attraction at the Field Museum is Sue, the most complete T-Rex skeleton in the world. You cannot miss Sue as soon as you enter the museum. The Tsavo Lions are another popular attraction that is very impressive in person.

The museum has been gathering artifacts and putting together impressive collections for over 100 years. Look for the extensive ancient Egyptian collection and the natural gemstones collection.

Adler Planetarium

A visit to the planetarium will round out your time on the Museum Campus. There are nine exhibits to explore, several different theaters, and the Atwood Sphere. It is one of the best family-friendly attractions where you and your kids will spend a few hours learning more about space.

Several of the popular attractions include “Planet Explorers”, “Our Solar System”, “Imagine the Moon”, and “Chicago’s Night Sky”. The Go Chicago pass includes tickets to the planetarium.

Evening: Miller Light Beer Garden

Depending on the time of year you visit Chicago, taking the time to check out the Miller Lite Beer Garden on Navy Pier is a fun choice. Spend the evening enjoying views of the city skyline. Live outdoor music is fabulous entertainment and will get you to celebrate your quick getaway.

Open from May to October, the beer garden is a place to have a bite to eat while sampling refreshing cocktails and ale.

Chicago itinerary – Day 2 

Morning: Architecture River Cruise

Head out for a morning cruise along the Chicago River, as long as you are visiting during the warmer months. River cruises are not available during the winter months. Make your reservations in advance to ensure you have a seat on the day and time you would like. While on the cruise, you will listen to your guide discuss the history of some of the most iconic landmarks in Chicago.

Most of these landmarks make up much of the beautiful Chicago skyline. You will learn about the architects and designers behind many of the buildings. You will know more about Helmut Jahn, Mies van der Rohe, and Skidmore Owings Merrill. Discover why the Sears Tower was renamed the Willis Tower and the history of the Old Post Office Building.

Learn how the Great Chicago Fire of 1871 changed the downtown skyline and how the city rebounded after such a devasting event. Purchase a Go Chicago pass, tickets for the Chicago Architecture Boat Tour are included. 

Afternoon: Magnificent Mile

The Magnificent Mile is really a section of Michigan Avenue that stretches from Lake Shore Drive to the Chicago River and is one of the best shopping districts in Chicago. Stroll along and check out high-end boutiques, artisan jewelry and handbags, affordable fashions, and souvenirs.

There are also several amazing restaurants and cafes to choose from for a quick lunch before you head over to the next thing on your list. Grab lunch at one of the cafes. Don’t be afraid to check out the side streets, you will find great little shops, smaller art galleries, and adorable boutiques.

The Water Tower Place Mall is nearby so after you are finished exploring the Magnificent Mile, head over for more shopping or check out the entertainment options when you need a break. This mall is located near the Chicago Water Tower which amazingly survived the Great Chicago Fire of 1871.

Night: 360 Chicago

One of two observation decks open to the public, 360 Chicago is located at the top of the John Hancock Tower, on the 94th floor. You are over 1000 feet above the city and have unparalleled views of downtown Chicago and Lake Michigan. You can lean against the tilted glass for an even better view of the streets below.

Step onto one of the fastest elevators in Chicago and be zipped right to the 94th floor in just under a minute. Bring your camera for some of the best social-media-worthy panoramic views of the Chicago skyline. 360 Chicago is located just minutes from Michigan Avenue so you can walk over after exploring the Magnificent Mile. The Go Chicago pass has your 360 Chicago tickets or you can pick them up when you get there.

Chicago itinerary – Day 3 

Morning: Millennium Park and The Art Institute of Chicago

One of the best urban spaces in Chicago, Millennium Park is home to the Bean or the Cloud Gate Sculpture. Sit by the refreshing Crown Fountain or take a stroll through Lurie Garden. The Pritzker Pavilion is an architectural wonder and should not be missed.

There is almost always something fun and exciting happening at Millennium Park from the beginning of spring through the end of fall. You will find anything from carnivals to festivals to yoga classes. Live music is common when you visit Millennium Park.

The park is located in the Loop just to the north of the Art Institute of Chicago. It is free to go explore Millennium Park, but there may be fees for activities held in the park such as admission fees for festivals or art exhibits.

After you have thoroughly explored Millennium Park, you can walk to the Art Institute of Chicago, which is one of the most prestigious art museums in the United States. View modern and contemporary art, design, photography, and architecture. Enjoy Impressionist paintings and decorative arts. Use your Go Chicago pass, tickets for the Art Institute are included with the pass.

Some of the more well-known pieces on display include the Chagall stained glass windows, Matisse’s Bathers by a River, Georgia O’Keeffe’s Black Cross, New Mexico, and Grant Wood’s American Gothic.

Afternoon: Navy Pier Centennial Wheel and Bike Rental

This will give you the chance to explore some of the Navy Pier while you are in Chicago. It is one of the most-visited attractions in the city. The pier is home to the Chicago Shakespeare Theater and the Children’s Museum, as well as the Centennial Wheel, an impressive observational wheel that you have to make time to ride.

This Ferris wheel is super-sized and is visible throughout the city. Book tickets in advance to make sure you get to ride the wheel. There are also a few other rides nearby that you may find to be wonderful fun. If you have a Go Chicago pass, tickets for the wheel are included.

After you have ridden the Centennial Wheel, head over and rent a bike for an easy way to fully explore the pier. Chicago has 26 miles of fabulous lakefront trails for you to explore. Bike rentals are generally valid for four hours, but you are on a time crunch so you will want to limit your ride to about an hour.

Night: Skydeck Chicago

Before you wrap up your 3 days in Chicago, check out the second observation deck, the Skydeck which is located in Willis Tower on the 103rd floor. The Willis Tower was formerly called the Sears Tower and the Skydeck sits 1353 feet above street level.

Be sure to step out onto the glass box that extends out from the side of Willis Tower for even better views of the city. You will see everything from the Museum Campus and Soldier Field to Navy Pier and the Centennial Wheel. Tickets for the Skydeck are included with a Go Chicago pass or you can get your tickets on the ground floor of the Willis Tower.

Deep dish pizza and more

Your Chicago itinerary will definitely want to include all the things listed above, but a side trip to the Lincoln Park Zoo would be fun if you have time. The same goes for visiting Lake Michigan. While you are on the go, grab a slice of deep dish pizza or a couple of Chicago style hot dogs and stroll through Grant Park or along North Avenue Beach.

The Chicago Riverwalk is another great thing to see during a 3 day trip to Chicago. Visiting Chicago should be great fun so be sure you check out a few of the Chicago attractions without wearing yourself out. Make sure you have plenty of time to rest during your trip, and maybe take in a Cubs game at Wrigley Park!

Still planning your visit to Chicago? Check out these guides for more ideas!

Things To Do In Chicago With Kids
Where To Stay In Chicago: The Ultimate Neighborhood Guide
Where To Find The Best Street Food In Chicago

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