How to have the ultimate weekend in Chicago

There’s nothing quite like a summer getaway to Chicago—and we’ve found a way you can squeeze even more out of your experience, saving big on major attractions as you go
Navy Pier Chicago
Written by Time Out. Paid for by Hilton
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With a packed lineup of festivals, fabulous spots to drink outdoors, gorgeous beaches and a long list of world-class attractions, Chicago in summer really is the perfect spot for a weekend city break. There’s so much to do in Chicago that it can be hard to decide what to do—but that’s where Hilton comes in. Hilton’s ‘Experience Chicago’ package offers exclusive discounts and perks at more than 20 great local attractions, from breweries and theaters to zoos and boat tours. Naturally, the package includes a room at a fabulous Chicagoland Hilton hotel. It’s a no-brainer, really: you’ll save money on things you were already planning to do, plus you’re guaranteed great accommodation at one of more than 50 hotels in downtown Chicago and the surrounding suburbs.

To kick things off, we’ve picked out seven of our favorite offers included in Hilton’s Experience Chicago’ package. Happy travels!

Feeling brave enough to take a long look down at Chicago’s streets from more than 1000 feet above the Magnificent Mile? With the ‘Experience Chicago’ package, you’ll get a complimentary ticket to TILT at 360 CHICAGO, an attraction which places guests on a platform that gradually extends to a 30-degree angle over the side of 875 North Michigan Avenue (formerly known as the John Hancock Center). If you don’t feel like confronting the height head-on, you can redeem a free drink upgrade at 360 CHICAGO’s BAR94 instead.

2. iO Theater and Second City

Before Stephen Colbert, Tina Fey, Bill Hader and Amy Poehler became titans of comedy, they trained and tread the boards at world-famous comedy hotspots iO Theater and The Second City. Both theaters are known for their insanely funny improv performances; you can catch shows that poke fun at the week’s news, witness songs being made up on the spot or see tales of past relationships provided by members of the audience turned into hilarious scenes. With the ‘Experience Chicago’ package you’ll score deals at both theaters that may make you laugh out loud (in joy and disbelief!): two tickets for the price of one to nearly any iO Theater show, and 25% off Tuesday, Wednesday and Thursday performances at The Second City.

As the home to one of the organizations that brought about Prohibition, Evanston was a booze-less city for nearly a century, much to the delight of bar owners in nearby Rogers Park. In 2011, FEW Spirits managed to become the Chicago suburb’s first distillery, transforming a former mechanic’s garage into a space where award-winning whiskey and gin is made. You can enjoy a complimentary tour of the facility and taste some FEW Spirits creations by taking advantage of the ‘Experience Chicago’ package.

Gino’s East of Chicago
Gino’s East of Chicago

If you’re visiting Chicago, a slice (maybe two, depending on your appetite) of deep dish pizza is probably on your list of must-try local delicacies. Gino’s East of Chicago has been cooking pies loaded with gooey cheese and topped with savory sauce since 1966, expanding from its original location on the Magnificent Mile to neighborhoods throughout Chicago as well as nearby Wheaton, Rosemont and Barrington. Save some dough on a few hearty slices with a coupon for $10 off your dine-in meal at any Gino’s East Chicagoland location, included in the ‘Experience Chicago’ package.

Brookfield Zoo
Brookfield Zoo

Housing more than 2,000 animals, ranging from clouded leopards to naked mole rats, you can easily spend an afternoon exploring the hundreds of acres of displays and habitats at the Brookfield Zoo. Hilton’s ‘Experience Chicago’ package includes 10% off the price of online general admission to the zoo—you can spend the money you save on additional experiences like daily giraffe feedings and up-close penguin encounters.

If you’re already planning a trip to Navy Pier to board a lake cruise or enjoy a Rainbow Cone on the waterfront, you need to add a spin on the Centennial Wheel to your itinerary. Soaring nearly 200 feet into the air, the rotating attraction allows riders to snap amazing photos of the skyline from inside a climate-controlled gondola (no need to let rain or cold temperatures stop you from getting the ‘gram). Anyone who books the ‘Experience Chicago’ package can get up to $4 off a Centennial Wheel ticket, with dates stretching through Labor Day.

Vertiport Chicago
Vertiport Chicago

Even if you’ve flown to one of Chicago’s airports, seeing the city from aboard a helicopter tour presents an entirely different perspective than a tiny airplane window can provide. Vertiport Chicago offers a variety of flights that take off from its heliport on the city’s southwest side, including short 15-minute tours, late-evening fireworks excursions and the opportunity to help pilot a copter (with the assistance of a trained professional, naturally). Book Hilton’s ‘Experience Chicago’ package and you’ll receive 10% off the price of any Vertiport Chicago helicopter tour.

Whether you’re looking for the perfect weekend family vacation spot, a getaway with friends or a romantic holiday, the ‘Experience Chicago’ package has something for you. Book now!

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