Planning a road trip to Chicago? There’s a lot to see this fall and winter, so we’ve created a weekend itinerary full of the city’s top must-do’s. And you’ll want to reserve a hotel room with Hilton so you can stay close to the action. Get ready to experience Chicago!
Day 1
Begin the day with the city literally at your feet on The Ledge at Skydeck Chicago. You’ll hover in a dramatic glass box 1,353 feet above the Loop on the highest observation deck in the U.S., perched 103 floors atop Willis Tower.
Next, head to downtown Millennium Park to see the spectacular fall colors and snap the quintessential Chicago selfie in front of the popular Cloud Gate sculpture (also known as “The Bean”). When the winter snow falls, lace up a pair of skates and do your best figure eights at Millennium Park’s McCormick Tribune Ice Rink. Also check out nearby Maggie Daley Park, where you can rent ice skates and glide along the picturesque Skating Ribbon.
Spend the afternoon at the Art Institute of Chicago and view one of the world’s largest collections of Impressionist paintings by masters like Monet. Or walk over to the Museum Campus and discover Egyptian tombs at the Field Museum, see leaping dolphins at the Shedd Aquarium, and explore the galaxies at the Adler Planetarium.
Enjoy shared plates and creative cocktails at The Lobby Bar at Lockwood, located within the historic Palmer House, a Hilton Hotel. Afterwards, catch a show at The Magic Parlour, also at the Palmer House, where you’ll be wowed by the sleight of hand and mind reading of magician Dennis Watkins.
Day 2
Start your morning with a weekend brunch of Irish farm-to-fork fare at Kitty O’Sheas in the Hilton Chicago. Then, head to the Chicago Architecture Center (CAC), where you’ll find fun interactive exhibits and a huge selection of tours. Don’t miss the free Open House Chicago, hosted by the CAC from Oct. 16-17, which includes self-guided tours of architectural treasures not normally open to the public. Or hop on the popular Chicago Architecture Foundation Center River Cruise Aboard Chicago’s First Lady (running through Nov. 21), that points out some of the city’s most notable design gems along the Chicago River.
Through October, explore the Chicago Riverwalk, where you’ll find everything from restaurants with waterside dining to the Community Marketplace selling locally made goods to fascinating attractions like the McCormick Bridgehouse & Chicago River Museum.
Then, stroll along nearby North Michigan Avenue and do some holiday shopping on The Magnificent Mile, where you can browse name brand stores, upscale malls, and designer boutiques. Don’t miss the BMO Harris Bank Magnificent Mile Lights Festival, which kicks off the holidays on Nov. 20 with the illumination of one million twinkling lights along the busy boulevard.
Before you know it, you’ll have made your way to the lakefront Navy Pier, one of the city’s top attractions (Hilton is the official hotel partner of Navy Pier). Spend the afternoon at Navy Pier, home to the Chicago Shakespeare Theater, Chicago Children’s Museum, 200-foot-tall Centennial Wheel, and plenty of restaurants that offer dockside dining and drinking.
Have dinner with a waterfront view at the Latin-inspired Lirica in the stunning new Sable at Navy Pier Chicago, a Curio Collection by Hilton hotel. Be sure to head upstairs for an after-dinner cocktail at Offshore, the nation’s largest rooftop bar, which boasts sweeping views of the city skyline and Lake Michigan all year-round.
Cap off your night with a turn on TILT at 360 CHICAGO, a thrill ride that tilts you over the edge of the sky-high observation deck, 1,030 feet above The Magnificent Mile. Or head back to the Chicago Riverwalk to view the nighttime Art on theMART, the largest digital art installation in the world, featuring spectacular images projected onto the Chicago River-facing facade of theMART.
Plan your Chicago getaway and book your Hilton stay today! Check out all Chicago Hilton hotels here.
