chicago vacations

Spending a long weekend in Chicago soon? Here are our top things to do, to see and to eat in the Windy City.

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.

TIP! If you’re an HGV Club Member and have points leftover, consider using them on urban attractions such as Leisure Pass Group Go City Cards or Explorer Passes, through ClubPartnerPerks.


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 also 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 along the Lake Michigan lakefront. You can also ride a Segway or a Divvy Bike Share. Even if it’s a chilly day, make sure to dip your toes in the water! And on the way back to your resort, sit in the sand at Ohio State Beach, also accessible from the Lakefront Trail.

Chicago, Illinois: Horizontal view of two people riding bicycles by the Lake Michigan, with Chicago skyline in the background, North Ave Beach

Night: Laugh it Up at the Second City Comedy Club

Grab an early dinner so you can enjoy a core workout 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.


Spend today in 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, you can also calm your body and mind with a yoga class, held outdoors during the summer months so you can take in stunning city and lakeside views, and indoors during autumn and winter month when it’s much too chilly to be outside! 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 destination for spectacular fireworks synchronized to music over Lake Michigan. These biweekly firework shows occur on Wednesdays and Saturdays from Memorial Day through Labor Day.


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

Grab your pick-me-up cup of coffee and 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”and, if it’s summer, feel the spray of the Buckingham Fountain, the facial images of Crown Fountain, and take a photo with the Art Institute lions.

chicago vacations visiting the bean

Late Afternoon: Get craft 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, Monet, and so many more.

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 4:00 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 you take. 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 Skydeckfor spectacular city views. Offering spectacular 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.

Leave a Comment