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 withHilton so you can stay close to the action. Plus, Hilton offers their guestsspecial 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 atKitty O’Sheas in theHilton Chicago. Once fueled up, set off to the nearbyMillennium Park for selfies with Cloud Gate, better known as “The Bean”, and winter skating at theMcCormick Tribune Ice Rink (Hilton provides free skate rental for two when you show your confirmation email for that day). Or walk over to theMuseum Campus, where you can explore theField Museum,Shedd Aquarium (show your Hilton key card and get 10% off the Behind-the-Scenes Tour), andAdler Planetarium.

Combine lunch with a Chicago history lesson during theHistory is Hott!! tour at the Loop’s historicPalmer House, a Hilton Hotel. The tour begins with a luncheon at the hotel’sLockwood 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 toSkydeck 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 atVu Skyward, a year-round rooftop restaurant and bar located 22 stories above the tri-brandHiltons at McCormick Place, encompassing a Hilton Garden Inn,Hampton Inn, andHome2 Suites. Or, in the summer, dine atNoyane, an acclaimed rooftop Japanese-Peruvian restaurant atop theConrad Chicago.

Step out for the evening and catch a hitBroadway 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 atThe Magic Parlour.

Day 2

Begin the day with a Parisian-inspired breakfast atMargeaux Brasserie in theWaldorf Astoria Chicago, helmed by James Beard Award-winning chef Michael Mina. Then, walk over to the nearbyMuseum of Contemporary Art and view works by modern masters. Or head to theChicago Architecture Center, where you’ll find fascinating interactive exhibits and a huge selection oftours (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 beautifulPalm Court in the historicDrake, a Hilton Hotel. Then spend the afternoon shopping alongThe Magnificent Mile, where you’ll find everything from popular name brand stores to high-end fashion. Don’t miss neighboringOak Street, home to designer boutiques like Prada and Hermès.

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

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

Hilton Hotel Savings

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