City Escapes

How To Spend 3 Fun Days In Chicago

Including things to do and where to eat in Chicago

The Vacationeer
Chicago skyline on a sunny day

Chicago is known for its soaring skyscrapers, neighborhoods full of shopping and restaurants and iconic food like deep-dish pizza. Whether you’re heading out for a foodie’s long weekend or stopping in The Windy City on a leaf-peeping road trip, here’s how you can spend your time in Chicago.

A yellow tour boat on the river in downtown Chicago, surrounded by skyscrapers 

Day One 

Instead of the typical hop-on-hop-off bus tour, spend your first day exploring Chicago by boat, taking a beachfront walk or hiking along an old rail line turned garden trail.


Take in Chicago’s iconic architecture by boat. The Chicago Architecture Center runs an excellent 90-minute river cruise aboard comfortable tour boats. Volunteers talk you through the architectural styles, historic landmarks and stand-out developments that create Chicago’s sparkling riverfront and skyline.


Hike the 606, a 2.7-mile elevated pathway along an old railway line stretches through neighborhoods like Bucktown, Logan Square and Humboldt Park. The trail is a great way to see Chicago’s neighborhoods and offers plenty of bars, restaurants and coffee shops along the way. Try a Chicago-style hot dog on a poppy seed bun at George’s, a neighborhood staple.


Continue your outdoor exploration with a stroll along the Lake Michigan lakefront. Make sure to dip your toes in the water and sit in the sand at Ohio State Beach, accessible from the Lakefront Trail.

Then grab an early dinner so you can enjoy an evening filled with belly laughs at the famous Second City Comedy Club. Tina Fey, Steve Carell, Chris Farley and many other comedians have shown off their talents behind the microphone here, so keep an eye out for rising stars and emergent talent.

Grass, flowers and hedges at Grant Park in Chicago 

Day Two

Spend the day in the South Loop and Grant Park exploring some of Chicago’s famous museums and exhibits.


Start the day at Millennium Park with a free yoga class and stop to take a selfie at “The Bean” after. Then visit Shedd Aquarium and touch a stingray, encounter a beluga, meet a penguin and learn extraordinary facts about marine wildlife.


Any stay in Chicago is incomplete without a visit to the city’s natural history museum, the Field Museum. Browse the ancient Egypt exhibit, visit Sue the T-Rex and admire the shine in the Grainger Hall of Gems.


Enjoy a lively evening at Navy Pier, home to many of Chicago’s most beloved attractions, including the Chicago Shakespeare Theater, the Chicago Children’s Museum and the Centennial Ferris Wheel.

Navy Pier is also the spot for spectacular fireworks synchronized to music over Lake Michigan. These biweekly firework shows occur on Wednesdays and Saturdays from Memorial Day through Labor Day.

An aerial view of a cross section along Magnificent Mile in downtown Chicago in autumn 

Day Three

End your visit on a high night with delicious eats, stunning art and amazing city views.


Spend the last morning of your Chicago stay window shopping and admiring the architectural wonders along the Magnificent Mile. Stop by Do-Rite Donuts & Chicken for freshly made donuts, chicken sandwiches and coffee.


Take your coffee to-go and explore Grant Park’s outdoor art. While “The Bean” is the most well-known, check out the giant headless sculptures of the “Agora,” cool off by Buckingham Fountain and pose with the lions outside of the Art Institute of Chicago. Then head inside and marvel at the galleries of Greek, Roman and Byzantine art along with major works by Seurat, Picasso, Van Gogh and Monet.


You can’t leave Chicago without tucking into a famous deep-dish pizza. Try Giordano’s or Lou Malnati’s (or both) and decide where you land on the great Chicago-style pizza debate.

The pool at Chicago Magnificent Mile, a Hilton Grand Vacations Club in view of downtown Chicago skyscrapers 

Stay up a little later on your last night to climb to the top of the Skydeck for spectacular city views. The Ledge, a glass balcony at 1,353 feet high, is a must for those without a fear of heights. You can find this unique viewpoint on the 103rd floor of the Willis Tower.

Where to Stay 

Book a Studio or Suite at our new resort, Chicago Magnificent Mile, a Hilton Grand Vacations Club, located just steps from the city’s top attractions, including Magnificent Mile, Navy Pier, Millennium Park, Grant Park and the Chicago Theater. 

Read “How To Plan A Perfect Vacation, According To The Experts” for travel planning tips that will make your Chicago getaway even more memorable.



The Vacationeer

The Vacationeer is a collective of Hilton Grand Vacations storytellers whose goal is to inspire travelers to go further. We're always on the lookout for new destinations to explore, useful travel tips, and unique ideas to help you plan the most memorable vacations possible.

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