From architecture to history and food, the Windy City has it all. If you only have a few days, don't fret! We've compiled the best of the best in a packed-yet-relaxing three-day itinerary for Chicago. You'll see classics like the Bean and Willis Tower, dine at beloved restaurants, and explore world-class museums and parks, all in the span of a long weekend. 

Is 3 Days in Chicago Enough?

You could spend months exploring everything this city has to offer, but three days is perfect for the highlights. Planning a three-day trip to Chicago works out well since many of these activities are close together. Most of Chicago's must-see activities are found in the downtown area, which is near Navy Pier, the Central and South Loops, and Millennium Park and Grant Park. You can cram in a lot of sights each day, and Chicago's central location and excellent public transit system make travel a breeze.

How to See Chicago in 3 Days

Gear up for this historic city with some good walking shoes and our guide on what to do in Chicago in three days:

Day 1: Willis Tower, Millennium Park and Navy Pier

Start your day off right with a trip to Willis Tower. Formerly known as the Sears Tower, it's the third-tallest building in the Western Hemisphere. Head up to the 103rd floor and step out onto an exhilarating glass balcony, from which you can see down into the city from over 1,300 feet in the air. Since you're there in the morning, you should be able to beat most of the crowd.

After that spectacular view, head across the street to Giordano's. There, you can get some classic Chicago-style deep-dish pizza.

Next, you'll work off your lunch by taking in the sights at Millennium Park. There, you'll find:

• The Crown Fountain
• Cloud Gate, AKA “the Bean”
• Lurie Garden
• The Jay Pritzker Pavilion
• The BP Bridge
• Maggie Daley Park
• The Chicago Cultural Center

Of course, you'll have to see the Bean and take a classic warped photo of your reflection in this piece of art. If you're visiting Chicago in the summer, dip your feet in the reflecting pool at the Crown Fountain. If you're there in the winter, look for the free ice rink at the McCormick Tribune Plaza.

Then, take the BP Bridge across to Maggie Daley Park, which has a sprawling expanse of activities and sights, like gardens, a play area and picnic spaces. You can even rent rollerblades and micro scooters or play mini golf. Finish up with a stroll through the beautiful Lurie Garden.

Pop over to Chicago's popular South Loop for dinner from your choice of spectacular restaurants, or head straight to the last stop of the day, Navy Pier. There's something for everyone here, including restaurants and bars, rides and games, public art and shopping. Ride the Centennial Wheel for stunning views, grab a snack from Garrett Popcorn Shops or stop in at the Chicago Children's Museum. Summer visitors should go on a Wednesday or a Saturday night, which is when Navy Pier traditionally holds its can't-miss fireworks shows.

Day 2: Chicago Museums and Nightlife

After all that excitement, it's time for a slower day full of enriching sights and education. Grab a quick breakfast and hop on a Metra train at Union Station. You'll take the Milwaukee District North (MD-N) train up to the Fox Lake station and Volo, Illinois, home to a museum of mechanical marvels and much more. Located just outside the city, the Volo Auto Museum has no shortage of exhibits, including:

• Vintage and antique cars, tractors, trains, boats, planes, bicycles and campers
• TV-famous cars, including the Batmobile collection and the Mystery Machine
• Celebrity cars, like those owned by Elvis, Britney Spears and Princess Diana
• Military gear, including tanks, uniforms, helicopters and weapons
• Antique arcades and kiddie rides
• Seasonal train rides
• The Jurassic Gardens for an immersive, prehistoric experience

After touring your heart out, stop by Showtime Pizzeria and see an animatronic show while you eat. Follow it up with dessert at Grams Central Station Ice Cream and Coffee Parlor. When you've had your fill, get back on the train toward downtown Chicago.

Once you arrive, make your way from Union Station over to Museum Campus, located below Millennium Park and Grant Park. It's home to Shedd Aquarium, the Field Museum and the Adler Planetarium — all highly respected institutions. 

The Field Museum is a massive natural history museum, and the Adler Planetarium was one of the first planetariums in the world, now offering gorgeous exhibits and shows. Shedd Aquarium is a stunning experience that gets you up close and personal with aquatic life from all over the globe.

Pick one or two of these places to tour for the late afternoon, depending on your pace. Next, you'll be going back downtown to the 360 CHICAGO observation deck, formerly known as the John Hancock Observatory. Like Willis Tower, 360 CHICAGO offers a gorgeous view of the city from up high, but this time, you get to see it at night. This attraction has a 360-degree observation deck and a unique thrill ride called TILT that tips you over the city for a top-down view.

After breaking a sweat with this nerve-wracking ride, grab a drink at 360 CHICAGO's CloudBar or head up one floor for dinner at the Signature Room at the 95th. One more floor up is the Signature Lounge at 96th, another great spot to get some drinks amidst the clouds. Relax and unwind as you close out Day 2.

Day 3: Shopping and Tours

The last day of your Chicago three-day itinerary starts about a thousand feet below 360 CHICAGO, at the Magnificent Mile. This stretch of North Michigan Avenue is packed with upscale shopping and sightseeing opportunities. You can window shop and gaze at architectural wonders, like the Chicago Water Tower, Tribune Tower and the Wrigley Building Skyscraper. The Magnificent Mile is also the departure point for many tours, whether you're exploring by foot, bus or boat. 

Wrap up your morning with a tour that interests you. One great option is to hit the water for architectural, history or lunch cruises that take you down the Chicago River. You can learn about the rich past of the city from the relaxing deck of a boat. Other options include:

• Gangster tours to visit landmarks related to prohibition and Al Capone
• Food tours, with tastings for deep-dish pizza, hot dogs and other Chicago classics
• Hop-on, hop-off bus tours for exploring the city's best attractions at your own pace
• Craft brewery and drink tours to try out the Windy City's best brews

If you're visiting in the summer and you like sports, you have to catch a game at Wrigley Field. Savor the trip through Wrigleyville and stop in at the sports bars and shops leading up to the stadium. If you're not a sports fan, pick up another tour, wander down the Chicago Riverwalk or stop at a rooftop restaurant like Cindy's or The J. Parker.

And with that, your trip to Chicago comes to a close! Now that you know what to see in Chicago in three days, you can start making plans and gear up for this Midwest gem.

Where to Stay for Your 3 Days in Chicago

Chicago is full of amazing accommodations and places to stay. There are loads of fantastic options to check out, no matter what your budget range might be. From affordable hotels and hostels to the most luxurious spots in the city, these are popular places you should look into for your visit. These are some recommended places to stay during your 3-day Chicago itinerary:

Hostels

Hostels offer dormitory-like facilities to sleep in and communal living and common areas. For backpackers, adventurers and visitors who love communal living, here are some places to add to your 3-day itinerary Chicago adventure.

HI Chicago Hostel 

If you're looking for a comfortable hostel that offers great facilities and is near a lot of landmarks, then consider HI Chicago Hostel during your stay. HI Chicago is only a short walk away from Buckingham Fountain, the Skydeck at Willis Tower, the Bean and Millennium Park. If your main goal is to take in the sights, this central location is exactly what you're looking for.

Amenities include free breakfast and Wi-Fi, staff around the clock, luggage storage, private bathrooms, free towels and free bed sheets. It's situated close to public transit and has a guest kitchen and an onsite café to cover all of your food and transport needs. Additionally, there is a games room, guest laundry facilities and plenty of power and USB outlets.

Getaway Hostel

Looking for a high-quality hostel experience? Then, you should take a look at what the Getaway Hostel can offer you. This modern hostel is equipped with a key card access system, a state-of-the-art kitchen and air conditioning for the ultimate experience in safety, dining and comfort. Plates and dishes are provided for guest cooking, as is all bedroom linen. Food storage pins and on-site vending are also available. The hostel is also equipped with an elevator, and each floor has a guest bathroom. 

There is a lot to do in the Getaway Hostel during your spare time. A pool table, foosball table, Wi-Fi, business center, guitars, weekly social events and more. There is more than enough to keep you going and entertained during your stay. Extended stays, single bookings and group booking options are available to make your reservation process as easy as possible.

Wrigley Hostel

Wrigley Hostel, not to be confused with Wrigley Field, offers private rooms, rooms with four beds, rooms with eight beds and female-only dorms to provide the privacy and comfort that best suits your preferences. This modern, self-catering hostel has a well-equipped kitchen and a BBQ deck. 

A BYOB bar, flat-screen TV, pool table and shuffleboard are located in the common room. Enjoy the free Wi-Fi and computer room to keep up with your emails and online activities during your visit. The Wrigley Hostel has everything you need to make your stay in Chicago great.

Affordable Hotels

You can experience the best of Chicago in three days without breaking your budget. There are loads of affordable hotels to choose from that will give you a lot of value for your money. Explore Chicago in comfort with these affordable hotel options.

Chicago River Hotel

Stay in the hub of downtown Chicago in The Chicago River Hotel. With a wide range of rooms and suites to choose from, you can find the room you want, from luxurious stays to affordable rooms that are both stylish and comfortable. View the city from the inside and explore all of Chicago's biggest attractions easily by staying in the epicenter of the city.

The hotel has a top-notch restaurant and delicious in-room dining options. It specializes in making deep-dish pizza for those who want the authentic Chicago pizza dish. If you've wanted to visit Chicago and get the most out of your time there, this centrally located hotel is a great way to finish everything in your three-day Chicago itinerary.

The Congress Plaza Hotel

Located in the heart of Chicago, The Congress Plaza Hotel is a piece of living history on Michigan Avenue. This city icon was established in 1893 and has hosted countless celebrities and U.S. presidents for decades. Experience a part of Chicago's history with all the modern conveniences, including free Wi-Fi and flat-screen TVs. The best part is you can book a room for under $100 and experience all this charming spot has to offer. 

Mid-Range Hotels

For those who want a bit more from their accommodation, these mid-range hotel recommendations will give you the visit to Chicago you've always wanted.

Chicago Suites Hotel

One of Chicago's trendiest boutique hotels is as affordable as it is unique. Located in the Northalsted neighborhood, Chicago City Suites Hotel is a few short steps from the L Train stop, several bus lines and is within walking distance from Belmont. You can fast-track your exploration of the city in this prime location. With 45 guest rooms, each with its own Art Deco styling and modern comforts, this hotel is a great place for you if you're an art lover and want to tour Chicago in style.

Majestic Hotel Chicago

From standard rooms to large suites, the Majestic Hotel in Chicago is the ultimate place to stay if you're a sports fan. Enjoy a high-end room with all the amenities and comforts at a great price. With regular deals and offers, you can enjoy everything this hotel has to offer at even better rates. It is great for the family and great for visitors who want to see, experience and enjoy Chicago's many wonders.

Hotel Versey

Immerse yourself in all that Chicago offers at a great price by staying at Hotel Versey. Located near iconic attractions like Lake Michigan and Lincoln Park Zoo. Adding a stay at Hotel Versey to your three days in Chicago itinerary will make it easier to fit in a lot more of the great Windy City's secrets into your agenda. You'll also find yourself close to comedy clubs, restaurants and other hidden gems this city has to offer those who explore it.

Sentral Michigan Avenue

For an affordable yet luxurious place to stay near the Field Museum and Shedd Aquarium, Sentral Michigan Avenue hotel is exactly what you're looking for. Featuring resort-style pools, an entertainment lounge, a fully-equipped fitness center and optimized workstations, this hotel has all the greatest amenities and more. You can find what you need in this grand hotel and get everything you want outside, as this hotel is near some of the best venues in the whole city.

Luxury Hotels

Chicago is home to a myriad of luxurious hotels. These recommendations are how to see Chicago in three days in style.

The Peninsula Chicago

This five-star hotel brings far-Eastern graciousness and hospitality to Chicago. With immaculate rooms and suites, The Peninsula exclusively offers excellence to the guests who stay there. With award-winning restaurants, guests will be able to partake in delicious dishes for every meal during their stay and enjoy the wellness services on offer as well.

The “Our Chicago” services offered by The Peninsula give you the best insights and travel tips to help you find everything you are looking for and more out of your visit. Fill your Chicago itinerary for three days in no time with expert recommendations on museums, nightlife, entertainment, shopping, events and so much more provided by The Peninsula.

Pendry

This gorgeous 4-star hotel was built in the 1929 Art Deco Carbide & Carbon Building located in Chicago's Loop neighborhood. Paying homage to the past and present of Chicago, the luxurious Pendry Hotel celebrates the entire city's artistic passions and merits. 

While the building is an artistic icon from the past, it has been updated and equipped with modern interiors and inspirational gathering spaces. It serves signature culinary concepts to all who dine and stay in this beautiful hotel. Art lovers and those with fine tastes will adore their stay at the Pendry.

The Langham Chicago

Luxurious rooms, excellent facilities and world-class service await you at The Langham Hotel Chicago. With deluxe rooms and suites with enchanted views of the city and lake, you will feel immersed in the best views and scenery Chicago offers. 

The Langham Hotel provides an array of activities and pastimes to make your stay even more memorable. Events include afternoon teas, private screenings in their contemporary cinema suite, gallery tours on the Langham art gallery and many more spectacular events. This resort in the city only aims to impress and exceed expectations.

Where to Eat During Your 3 Days in Chicago

No Chicago travel guide is complete without recommending some of the best and most unique restaurants that truly capture the city's tastes. Chicago is well known for its cuisine and for its signature dish, the deep-dish pizza. This guide will explore different dining options, including delicious takeaways, locally renowned food stands, and luxurious restaurants hidden within the city.

Eating is an important part of traveling, and dining at the right places will greatly enhance your three days in Chicago. Itinerary makers and holiday planners need to cover these restaurants located close to and within the city hub.

Milly's Pizza in the Pan

Starting up during the pandemic, Milly's Pizza in the Pan is a trendy place to experience the deliciousness of Chicago's iconic pizza variant. This small but dedicated operation is run by a passionate man, Robert Maleski, who gives his all to every artisanal pie to which he puts his name. A strong spirit and deep-dish pizza are two of the things Chicago is known for, so putting them together makes sense.

Duck Sel

Hidden in the Edgewater locale, Duck Sel is a culinary experience to behold and immerse yourself in. The owner, Don Young, is the holder of the impressive title “youngest chef to preside over a Michelin-starred kitchen.” This pop-up dining experience is the perfect setting for this culinary virtuoso to showcase his creativity and playfulness. 

This contemporary American venue hosts multiple course events. Keep an eye on when the next one will take place, and count yourself among the lucky people who get to try this outstanding dining experience.

Superdawg Drive-In

If you're looking for a novel treat, the giant hotdogs at Superdawg Drive-in are worth trying. This restaurant offers a truly retro experience where cars park outside and order their food by talking to staff through crackling speakers. Food is delivered on trays by carhops to go the extra mile to recreate the glory days of eating in your car. Enjoy traditional Chicago-style dogs — sans ketchup, of course — in a fun and creative setting.

Alinea

Alinea has three Michelin stars and is the city's only restaurant to hold that rank. It's regarded as one of the world's best restaurants and frequently finds itself on Chicago's bucket list and on the itinerary of most who come to visit. This restaurant delivers a sensory overload and is the perfect way to end a busy day of exploring areas near Lincoln Park. Dishes are presented as works of art and their flavor reinforces that notion.

The Fat Shallot

While the Fat Shallot may have three permanent restaurant locations, it started as a food truck. Food trucks are a staple of Chicago street dining, and The Fat Shallot food truck continues this tradition. You can still catch the red truck roaming the streets of Chicago. They have been regarded as one of the city's best food trucks for years and have grown into a booming success because of their delicious food.

Superkhana International

Unique flavors and a memorable dining experience await those who eat at the Superkhana International restaurant. This restaurant embraces Indian cooking but understands that there is more than just spice that makes it such a unique and beloved cuisine. Mixing the familiar with Indian delights, Superkhana International is a fusion restaurant that has mastered its own style of making authentic Indian food.

Lula Cafe

Jason Hammel, the chef and proud owner of Lula Cafe since 1999, keeps the community at the forefront of this operation. What makes Lula Cafe so special is the freshly baked pastries and menu that change from a delicious breakfast feast to a stunning dinner selection. Enjoy the variety of meals on the menu and feel like you're a part of the community that Hammel takes such care to serve.

Ever Restaurant

Last but not least is the famous Ever Restaurant. Ever is a two Michelin star-rated restaurant founded by the world-famous chef Curtis Daffy and his business partner, Michael Muser. The restaurant known as “Forks” from season two of the popular series The Bear was filmed on location in Ever. This restaurant is famous for its appearance and for its world-class two-and-a-half-hour dining experience.

Make the Most of Your 3-Day Chicago Itinerary

Chicago's exceptional public transit system means it's fast and easy to fit nearby attractions into your trip. The Volo Auto Museum is just a short train ride away from the heart of the city. There's also a cab service available from the train station in Volo. A trip here is a can't-miss experience with over 10,000 mechanical wonders and a jungle of Jurassic proportions. It's perfect for families, gearheads, budding archeologists, pop culture fans, history buffs and, well, just about anyone!

Learn more about planning your visit to the Volo Auto Museum. We can't wait to see you!