Nearly three million people live and commute in Chicago’s winter and if there’s one thing we know deep in our bones, it’s that the prolonged gray skies can feel obtrusive and everlasting. One way to bring a little light and joy into a long winter is to enjoy a staycation with the family at one of Chicago’s most brilliant hotels. We’ve rounded up five properties that not only cater to families, but also stave off the dreaded winter blues.

photo: Wendy Altschuler

Robots and Bookish Delights

The first thing you’ll notice when you shake off the snow and walk through the doors of Streeterville’s Hotel EMC2 are all of the books—under the staircases, stacked on top of metal storage cases, lining the shelves in the hallways and filling the Albert, a restaurant clearly inspired by Albert Einstein. 12,000 books in total decorate this magical space. The fun doesn’t stop in the common areas. Once you’ve reached your room and realize that you’ve forgotten your toothbrush—or have pretended to forget it—you can call for a robot to deliver your items. Yes, you’ve read that right. Theo or Leo, the hotel’s on-call robot butlers will autonomously show up at your door and ring the bell, give you the items that you’ve requested, and then roll off to catch the elevator. Your kids can even challenge the robot to bring a “surprise” item.

Nearby Fun: Stroll through the Museum of Contemporary Art, see a show at The Chicago Shakespeare Theater, visit the Chicago Children’s Theatre, bowl at Kings Lincoln Park or listen and laugh at Blue Man Group—a show that should be on every Chicago family’s bucket-list.

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photo: Wendy Altschuler

Swiss Comfort in Chi-Town

Let the warm and cozy-yet-contemporary Swiss design envelop you while your family relaxes at the four-diamond Swissotel Chicago, a tall glass triangle-shaped building located on the Chicago River. You’ll be throwing distance from The Magnificent Mile and you’ll be able to see Navy Pier, Lake Michigan, Millennium Park and grand skyscraper views from the windows. Book a Kids Suite and surprise your littles with amenities tailored to them: bathrobes, games, books, stuffed animals, thematic decorated rooms, special bath toiletries, DVDs and treats. You can even order a hot chocolate amenity that comes with different flavored syrups, marshmallows, sprinkles, and cookies.

Nearby Fun: Visit the Harris Theater for Music and Dance and enjoy a family-friendly production of ballet, opera, modern dance, chamber music, classical Indian dance and more.

photo: Wendy Altschuler

Location, Location, Location

Most families are desperate for a little getaway midway through a Chicago winter. Book a connecting room at Fairmont Chicago, Millennium Park or a hypoallergenic, allergy-friendly Fairmont PURE room, and take advantage of the hotel’s discounted dining for kids—ages five and under eat free from the children’s menu and kids ages six to eleven eat for half price on the regular menu. Parents can schedule a Candlelight Couple’s Massage and Suite Soak at the hotel’s mySpa and enjoy an adults-only dinner at gastropub Columbus Tap, while kids watch movies, decorate cookies and design their own personalized hot cocoa mug in the Kids’ Club.

Nearby Fun: Maggie Daley Park, with its awesome playground, ice skating ribbon, and architecture, is close by. Also, Lincoln Park Zoo, open every day of the year, is free to visit. Ride the carousel, the 65-foot Ferris wheel, the Lionel Train Adventure, or go deep on a virtual submarine ride—the Sea Explorer 5D.

photo: Rose Hotel

Pops of Pink

Whether you’re a working parent with vacation days to burn, or you just need a different view during the long midwestern winter, consider the visual delights of the brand-new The Rose Hotel Chicago O’Hare. Pink flowers, rugs, wall art, and even perfectly positioned exterior lighting brighten up this newly opened winter-y treasure. Elevate your sleeping experience by selecting from the pillow menu at this ultra-modern hotel, with interesting avant-garde art. The hotel, located in the heart of Rosemont’s recently developed Pearl District, gives your family direct access to Fashion Outlets of Chicago, Kings Rosemont, the Rosemont Theatre, iFLY Chicago-Rosemont, Dave and Buster’s and more. Plus, The Rose Hotel offers complimentary shuttles for guests. To learn more about what the Rosemont area has to offer families, read our story Howdy, Hello! Let’s Get to Know: Rosemont!.

photo: Wendy Altschuler

Embrace the Flakes

Perhaps you’ve played tourist enough in your own city and want a weekend family getaway that’s within three hours from Chicago—Madison, Wisconsin might just hit the mark. The UW-Madison Arboretum leads educational winter walks, you can bring the family ice fishing on one of Madison’s five lakes, go sledding at one of the parks, or see what fat biking is all about. One of the best places to stay while in Madison is The Edgewater Hotel in Madison, part of the Historic Hotels of America, reopened in 2014. You’ll be within walking distance to Capital Square and downtown but if you choose to hunker down and enjoy the hotel, you can go ice skating at the hotel’s rink, which overlooks Lake Mendota. Perhaps mom can enjoy a spa treatment at The Edgewater Spa while dad treats the kids to hot cocoa. On Fridays The Edgewater Hotel hosts an Ice House Friday Night Fish Fry and a Family Skate Night. The dining here is also noteworthy—enjoy belly-waring entrées at The Statehouse, Clock Shadow Cheese Curds at Augie’s Tavern, or grab-and-go bites at The Icehouse.

Good to Know: The Edgewater has hosted: Elvis Presley, Elton John, Bob Hope, Bob Marley, Johnny Cash, Sammy Davis Jr., Bob Dylan, John Mellencamp, Carrie Underwood, The Weeknd, Dave Chappelle and even the Dalai Lama. Be sure to view the 3D interactive media wall while staying at the hotel.

—Wendy Altschuler