Planning a weekend getaway to Chicago? There’s a lot to cover in 48 hours, so Hilton has created an itinerary to help you hit the highlights. And with more than 90 hotels in the Chicagoland area, representing 12 different brands, you’ll want to book a room with Hilton so you can stay close to the action. Plus, Hilton offers their guests special savings at some of the city’s biggest attractions. Get ready to explore Chicago.

Day 1

Start your morning with a weekend brunch of Irish fare at Kitty O’Sheas in the Hilton Chicago. Once fueled up, set off to the nearby Millennium Park for selfies with Cloud Gate, better known as “The Bean”, and winter skating at the McCormick Tribune Ice Rink (Hilton provides free skate rental for two when you show your confirmation email for that day). Or walk over to the Museum Campus, where you can explore the Field Museum, Shedd Aquarium (show your Hilton key card and get 10% off the Behind-the-Scenes Tour), and Adler Planetarium.

Combine lunch with a Chicago history lesson during the History is Hott!! tour at the Loop’s historic Palmer House, a Hilton Hotel. The tour begins with a luncheon at the hotel’s Lockwood Restaurant & Bar, followed by a guided exploration of the glorious Art Deco lobby and ballrooms, along with spaces not normally open to the public.

In the afternoon, make your way 103 floors up to Skydeck Chicago, the highest observation deck in the United States, perched atop the Willis Tower. For truly jaw-dropping views step out onto The Ledge, a series of glass boxes hovering 1,353 feet up in the air.

For dinner, enjoy even more breathtaking views at Vu Skyward, a year-round rooftop restaurant and bar located 22 stories above the tri-brand Hiltons at McCormick Place, encompassing a Hilton Garden Inn, Hampton Inn, and Home2 Suites. Or, in the summer, dine at Noyane, an acclaimed rooftop Japanese-Peruvian restaurant atop the Conrad Chicago.

Step out for the evening and catch a hit Broadway in Chicago play at a historic downtown theatre. Or head back to the Palmer House and be wowed by the sleight of hand and mind reading of magician Dennis Watkins at The Magic Parlour.

Day 2

Begin the day with a Parisian-inspired breakfast at Margeaux Brasserie in the Waldorf Astoria Chicago, helmed by James Beard Award-winning chef Michael Mina. Then, walk over to the nearby Museum of Contemporary Art and view works by modern masters. Or head to the Chicago Architecture Center, where you’ll find fascinating interactive exhibits and a huge selection of tours (from walks to seasonal boat cruises) that let you experience Chicago architecture up close.

Stop for a proper afternoon tea, accompanied by the music of a live harpist, at the beautiful Palm Court in the historic Drake, a Hilton Hotel. Then spend the afternoon shopping along The Magnificent Mile, where you’ll find everything from popular name brand stores to high-end fashion. Don’t miss neighboring Oak Street, home to designer boutiques like Prada and Hermès.

For dinner, indulge in seafood and steak at Ocean Prime in LondonHouse Chicago, Curio Collection by Hilton. During warm-weather months, have dinner and drinks with a stunning Chicago River view at LH, LondonHouse’s dramatic tri-level rooftop.

In the evening, see a rising comedy star at The Second City. Or watch a concert at the landmark Chicago Theatre (and enjoy a free drink or snack courtesy of Hilton). End the night with a cocktail and glittering city panorama at the ROOF on theWit, a year-round rooftop on the 27th floor of theWit Chicago  – A DoubleTree by Hilton Hotel.

Hilton Hotel Savings

Book your stay today at any Chicagoland Hilton hotel and save at local attractions like Millennium Park, the Shedd Aquarium, The Chicago Theatre, and more.