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Plan a Summer Staycation in Chicago

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Chicago shines in the summertime. Beach days at Lake Michigan, patio dining, music festivals, Cubs games, and blue skies are just a few of my family’s favorite summer in Chicago things. It’s a spectacular season, but it’s also fleeting — so make the most of it with a few days off in the city.

Our city’s most coveted season calls for a staycation so you can maximize the fun. Luckily, there’s a family-friendly hotel and activity pairing for every kind of family under the summer sun. Here’s my guide to a spectacular family staycation in Chicago

Beach staycation

See: 31st Street Beach
Stay: Hyatt Regency McCormick Place

It’s not summer in Chicago without a trip to the beach. Get some fun in the sun at 31st Street Beach, where you’ll find sandy shores and incredible skyline views. If your family’s feeling adventurous, you can rent kayaks, paddleboards, jet skis, and boats at the nearby harbor. For lunch, grill out or grab something from the nearby concession stands.

Hyatt Regency McCormick Place keeps the summer fun going with lake-facing rooms, an indoor pool, and an outdoor deck. Nestled in the scenic and historic Prairie District, the hotel has easy access to the lakefront and other downtown attractions.

Chicago-centric staycation

Architecture cruise
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See: Architecture Cruise and Riverwalk 
Stay: Palmer House

An architecture cruise down the scenic Chicago River is one of the most popular family-friendly attractions in the city. Enjoy the sunshine while your marvel at architectural gems on the Chicago Architecture Foundation Center River Cruise aboard Chicago’s First Lady, where an experienced docent will share fascinating stories behind more than fifty buildings along the water.

After your cruise, spend some time exploring Chicago’s Riverwalk. The 1.25-mile pedestrian stretch runs along the south bank of the Chicago River from Lake Shore Drive to Lake Street and is dotted with public art, splashing fountains, kayak rentals, and tons of patio dining options. O’Brien’s has a kids menu for picky eaters and cocktails for parents.

Live a bit of Chicago history at the Palmer House, one of the city’s most iconic hotels. The original Palmer House was built just 13 days before the Great Chicago Fire and was promptly destroyed. Reopened in 1873, the ornate lobby has welcomed everyone from U.S. presidents to Frank Sinatra to movie stars. Your kids (and you) will feel like you’re staying in a palace.

Museum staycation 

Bugs exhibit at Field Museum
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See: Museum campus
Stay: Hilton Chicago

You could spend your whole staycation exploring the lakefront Museum Campus and still not see everything. Located just south of Grant Park, the Museum Campus is home to three of the city’s most family-friendly museums — the Adler Planetarium, the Shedd Aquarium, and the Field Museum

Get up close and personal with Earth’s smallest superheroes at Fantastic Bug Encounters, one of the newest Field Museum’s exhibits. Don’t forget to say hi to Máximo, the biggest dinosaur ever discovered. At the country’s oldest planetarium, little ones will love the Planet Explorers Playspace while bigger kids will enjoy launching a stomp rocket and racing to save the crew of Apollo 13 in the Mission Moon exhibit. And the Shedd Aquarium is home to many magical marine creatures, from beluga whales to tiny tropical frogs.

After a long day exploring, stay at the Hilton Chicago, which overlooks Grant Park and is within easy walking distance of the Museum Campus. Kids will love the hotel’s sun-filled atrium, indoor swimming pool, and the seasonal sundeck with unbeatable views of the city. Ask about their family fun packages.

Animal adventures staycation

Penguin observation at the Lincoln Park Zoo
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See: Lincoln Park Zoo and Imagination Station
Stay: Hotel Lincoln

The always-free Lincoln Park Zoo is a long-time local family favorite. Over 1,100 animals call the zoo home. Plan your visit around the many daily animal encounters that give kids a chance to meet the animals and their trainers. 

Bring the safari indoors at Bixbee Imagination Station. Just a few minutes away, this kid-friendly pop-up is super hands-on and perfect for kids with wild imaginations. They’ll meet a polka-dotted elephant, technicolor monkeys, a friendly shark, a taco-loving dinosaur, and more.

End the day at the Hotel Lincoln, located right on the park. Check out the wacky art and sculptures throughout the lobby, then head to the rooftop for a birds eye view of Lincoln Park and the water. And take advantage of the complimentary bike rentals for a spin around the scenic lakefront.

Historic staycation 

Hamilton: The Exhibition
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See: Hamilton: The Exhibition 
Stay: The Blackstone

History buffs of all ages will be captivated by Hamilton: The Exhibition. The 360-degree immersive mini-museum was designed by the creators of the revolutionary musical (now playing in Chicago at the CIBC Theatre). Located on Northerly Island, the exhibit’s interactive games and lifelike projections showcase the life of Alexander Hamilton and his fascinating role as one of the most influential founding fathers. Don’t forget to grab an audio guide, narrated by Lin-Manuel Miranda.

Extend your immersion into Chicago’s cultural history with a stay at the Blackstone Hotel. Located on Michigan Avenue’s “Cultural Mile”, this historic Chicago hotel has long been a celebrity hot spot: Lena Horne, Nat King Cole, and Rudolph Valentino were all frequent visitors. The hotel is close to Northerly Island and tons of other downtown attractions. Stick around for live music entertainment in the lobby, hosted every Wednesday and Saturday evening. 

Save 50% on premium admission to Chicago’s top attractions with CityPASS tickets. Includes prepaid admission to 5 must-see attractions:

Valid for 9 consecutive days, Chicago CityPASS tickets cost $108 for adults (value $214) and $89 for children ages 3-11. Buy online at CityPASS.com or at any CityPASS attraction. Spend less, experience more.

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