There’s nothing like summer in Chicago. It’s when the city truly comes alive. After months and months of winter weather, Chicagoans are all too eager to ditch their bulky jackets and head outside to soak up the sun—preferably at the beach or on a patio somewhere.

Whether you’re visiting Chicago for the weekend or looking to take a staycation after being bundled up inside for so long, there are so many ways to experience everything the Windy City has to offer. Luckily for you, we’ve gathered some of the top destinations to explore and even save on with our Experience Chicago package.


The Mag Mile

The Magnificent Mile is the premier shopping strip in the city. In fact, people come from all around the world to stroll along the mile of shops down Michigan Avenue. You can find all your favorite stores plus flagship stores like Uniqlo and Gucci, specialties like NikeLab and Starbucks Reserve Roastery (the world’s largest Starbucks), and even mini-malls like The Shops at North Bridge.

One of our favorite stops on the Mag Mile is the 360 Chicago Observation Deck at the John Hancock. While it may not be a shop, it is one of the highest points in Chicago so you can get absolutely stunning views and photos of the city.

Navy Pier

If you’re looking for a day of family-friendly adventures, definitely head over to Navy Pier. Between the Children’s Museum, iconic Centennial Wheel and gorgeous views of the river, you can pass a whole day just cruising down the length of the pier. Just be prepared because Navy Pier is a top tourist destination—after all, that Ferris wheel is pretty amazing.

Brookfield Zoo

Staying on the topic of family-friendly, the Brookfield Zoo in Brookfield, IL is a great stop for any animal lover. Say hello to their newest wombat joey, get inspired by life-size LEGO® animals and see animals from around the world. You can even sign up for an animal encounter to get up close to the Humboldt penguins or meet pandas, llamas and more.

Summer Festivals

Looking for free activities? Chicago summers are filled with free festivals every weekend. From cultural fests to food, art, music and more, there is a festival for everyone. Check out all the fests going on when you’re in town or plan around one of the big ones like Lollapalooza or the Taste of Chicago.


Millennium Park

One of the most iconic spots in Chicago for photos is the Bean. This mirrored structural design is perfect for selfies. Our favorite game is to actually take a photo from afar and try to find yourself! While you’re by the Bean, take advantage of all the exhibitions, cultural events, musical performances and landscape designs nearby. Over summer, there is always something going on at Millennium Park.

Chicago Tours

If it’s your first time coming to Chicago or you’d like to rediscover this amazing city, then look no further than Chicago Detours. These fun walking tours go off the beaten path to explore the city like a local. Choose from architecture (Chicago has a rich history in it), history, food and drinks or different neighborhoods.

The Second City

You can’t come to the Second City and not go to The Second City comedy club. While it may only be for the adults, it’s well worth a stop. After all, the likes of Tina Fey, Chris Farley, John Belushi and so many other greats in comedy have waltzed in and out of those doors.



Deep Dish

No visit to Chicago is complete without lots and lots of food, especially deep dish pizza. Gino’s East is a classic spot for the city’s signature pie. Try some of their specialties like the Chicago Fire or build your own—and bring your appetite.

Fine Dining

For the foodies of the world, Chicago does not disappoint. In fact, there’s a handy dandy map full of the 22 Michelin-starred restaurants in the city. Even if you don’t plan on booking a table, the list is worth a peek.


For any beer lovers out there, check out some of Chicago’s local breweries throughout the neighborhoods. You may even recognize some brewery names like Goose Island, Half Acre or Lagunitas. Another cool one to stop by is the Moody Tongue brewery, re-opening soon at their new location in the South Loop.

Now that you know all the places to see and things to do, the only part left is to plan where you’ll stay. From a romantic weekend at the Conrad Chicago to a downtown stay at the Palmer House to great family-friendly options in River North, we have plenty of hotels to make your stay perfect. And when you book with Hilton this summer, you can save big on Chicago attractions, restaurants and shows. What’re you waiting for, come and experience Chicago today!

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