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City Escapes

3 Days in Chicago

Hilton Grand Vacations picks some of its favorite Windy City activities

The Vacationeer

If you're spending a long weekend in Chicago soon, check out Hilton Grand Vacations favorite things to do, see and eat in the Windy City.

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.

Morning: Take a Downtown Architecture River Cruise

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.

Afternoon: Hike the 606 

Modeled after New York City’s High Line, the 606 urban hiking trail is the best way to see some of Chicago’s neighborhoods.

This 2.7-mile elevated pathway along an old railway line stretches through neighborhoods like Bucktown, Logan Square, and Humboldt Park.

There are plenty of bars, restaurants and coffee shops along the way where you can stop for a little break.

Early Evening: Stroll Along the Lakefront 

Continue your outdoor exploration with a walk, Segway ride or Divvy Bike Share along the Lake Michigan lakefront.

Even if it’s a chilly day, make sure to dip your toes in the water and sit in the sand at Ohio State Beach, also accessible from the Lakefront Trail.

Night: Laugh it Up at the Second City Comedy Club

Grab an early dinner so you can enjoy an evening filled with belly laughs at the famous Second City Comedy Club. Names like Tina Fey, Chris Farley, and so many other greats in comedy have shown off their talents behind the microphone here.

Day Two

Spend the day in the South Loop and Grant Park exploring some of the most famous museums and exhibits Chicago has to offer.

Morning: Visit the Shedd Aquarium

There is so much to see at Shedd, so consider planning your time here around its special experiences.

Touch a sturgeon, attend an animal chat with penguins, sharks and sea lions, and watch a presentation on how beluga whales are cared for.

Before Shedd opens for the day, calm your body and mind with a yoga class, held outdoors during the summer months. After class, enjoy an up-close animal encounter or behind-the-scenes experience.

Afternoon: Explore the Field Museum

Your Chicago three-day itinerary isn’t complete without a visit to the Field Museum.

Browse the ancient Egypt exhibit, visit Sue the T-Rex, and admire the shine in the Grainger Hall of Gems.

Evening: Have Some Fun on the Navy Pier

Take a photo by the famous “Captain on the Helm” statue and enjoy a fun-filled evening on the lively Navy Pier.

Navy Pier is home to many of the most beloved Chicago attractions, including the Chicago Shakespeare Theater, an IMAX theater, the Chicago Children’s Museum, the Centennial Ferris Wheel, and more.

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.

Day Three

Enjoy more time outside and a hearty meal to end your visit.

Morning: Walk Down Magnificent Mile

Spend the last morning of your Chicago stay window shopping and admiring the architectural wonders along Miracle Mile.

Afternoon: Coffee and Art in Grant Park

Spend the early afternoon exploring Grant Park, which is like one enormous art gallery.

Snap a selfie at “The Bean,” but don’t stop there.

Walk among the giant headless sculptures that make up the “Agora.” If it’s summer, feel the spray of the Buckingham Fountain, enjoy the facial images of Crown Fountain, and take a photo with the Art Institute lions.

Late Afternoon: Get crafty at the Art Institute of Chicago

Marvel at the galleries of Greek, Roman, and Byzantine art along with major works by Seurat, Picasso, Van Gogh and Monet.

Early Evening: Happy Hour at the Palmer House 

Walk across the street to the iconic Palmer House by Hilton and enjoy a cocktail at the bar or high tea, served until 4 p.m.

Evening: It’s Time for Deep Dish

You can’t leave Chicago without tucking into a famous deep-dish pizza.

Head to Giordano’s where you’ll remember every bite.

Order a bigger pie so you can take leftovers home on the plane or ship a fresh one to your house to enjoy after you return from your vacation. 

Late Evening: Hit the Skydeck

Stay up a little later on your last night to climb to the top of the Skydeck for spectacular city views. At 1,353 feet in the air, The Ledge at the Skydeck 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, Hilton Grand Vacations Club Chicago Downtown/Magnificent Mile, located just steps from the city’s best attractions, including Magnificent Mile, Navy Pier, Millennium Park, Grant Park, and the Chicago Theater. 

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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