Cool Airbnb Rentals for Chicago Families

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Editor’s note: We’re making every effort to provide you with the most up-to-date information. However, the situation with COVID-19 is fluid and ever-changing. Please be sure to check with these Airbnb listings directly for any pandemic-specific safety protocols, rules and procedures before booking a visit. Stay safe!

Looking to plan family travel? Ditch the headache of airport travel and opt for the ease of a staycation instead. From a rustic cabin to a converted church and cozy dwellings to spacious party-worthy spaces, we’ve scoured Airbnb listings for the unique and special primed for memory-making. Read on and plan on.

The Draw: It's a Treehouse!

The specs: 3 guests; 2 beds, 1 private RV-type bath (not in the treehouse)
The neighborhood: Schaumburg
Parking situation: on-premises
Laundry access: no

What kid wouldn't love to spend the night in a treehouse? It's straight out of dreamland for most kids. Glamp the night away in this cedar treehouse set 15-feet above a waterfall, koi pond and fire table outfitted with a fireplace, air conditioning, private deck, kitchenette, Wi-Fi, hi-def cable TV with premium channels and a new Wi-Fi TV for Netflix, fireman's pole, private outdoor RV-type toilet and private outdoor shower. They even offer full-color gift certificates if you want to gift this experience to your favorite tree lover.

You could easily just spend a weekend in the treehouse, unplugged from the world or add LEGOLAND Discovery Center to the adventure. Sounds like a journal-worthy birthday weekend for some special little one!

The Draw: Converted Church

The specs: Sleeps 12; 3 bedrooms, 3 beds, 2 couches and 4 air mattresses, 2 baths
The neighborhood: Logan Square
Parking situation: garage
Laundry access: on-premises

While this spot teeming with history is a bit of a splurge, it can accommodate a larger group looking to split the tab. Construction on this former church began in 1888 and it functioned in a religious capacity until private owners began the conversion in 1990. Since then, it's been featured in Chicago Tribune Home Design Magazine, on the first season of HGTV's Extreme Homes and is regularly tapped for not-for-profit house tours, including the Art Institute, the Museum of Contemporary Art, the Lyric Opera Guild and more.

Logan Square is home to the only weekly, year-round farmers market in Chicago, held indoors during winter months and outdoors in the summer. It's a low-key spot to grab an inexpensive breakfast or lunch or stock up on fresh ingredients for a meal prepared back at your home-away-from-home. If you want a break from cooking, Revolution Brewery is just down the way and is great for grub and a cold beer. Be sure to try their parmesan bacon popcorn! A fun resource nearby is Four Star Family Cyclery, which rents swoon-worthy cargo bikes you'll want to take home.

The Draw: More Fun Than Home for Kids

The specs: Sleeps 8; 4 bedrooms, 3 beds, 1 crib, 1 floor mattress, 1 air mattress, 3.5 baths
The neighborhood: Wrigleyville
Parking situation: on-premises
Laundry access: on-premises

When the baseball is back to allowing fans, this two-story coach house should do the trick to watch the Cubbies fly the "W". In the meantime, be nearby to cheer them on in spirit and keep busy on nearby lakepaths and Lincoln Park Zoo. It's home to 4 kids and it's telling with the abundance of toys, art supplies, large library of children's books, kid-proof dinnerware, retractable safety gates and indoor infant swing . . . just to name a few. There's even a playroom accessible by ladder for kids ages 4 and up.

A family favorite for dining in Lakeview is Crosby's Kitchen on Southport. There's always a slew of strollers, a good sign that it's kid-approved, and outdoor seating in the warmer weather months is an added bonus. Try their skillet chocolate chip cookie or save some room for their neighbor, Jeni's Ice Cream, a Columbus, OH import offering some of the best ice cream you'll ever taste using only the finest, natural ingredients.

The Draw: Sidelined Pullman Train Car

The specs: 6 guests; 3 bedrooms, 3 beds, 3 baths
The neighborhood: Plano
Parking situation: on-premises
Laundry access: no

Oh, the stories this Pullman Train car, the Constitution, could tell. Built in 1905, it was basically Air Force One for Presidents Harding and Wilson and when the president of the Illinois Railway Museum visited, he said it was the most well-preserved Pullman train car in the U.S. A large living room with fireplaces, a master bedroom and bathroom have been added to the original car, which consisted of 4 staterooms, an observation deck, a dining room and a galley. This is all set atop a bluff overlooking Big Rock Creek and a floodplain full of 200-year old oak trees where you might see an Eagle or two. During the summer months, there's even a pool onsite to enjoy.

We recommend bringing along a few groceries to utilize the kitchen facilities and make this a true staycation, where you unplug and fully immerse yourself in a getaway with a country feel.

The Draw: Rustic Charm

The specs: 10 guests; 1 bedroom, 5 beds, 2 baths
The neighborhood: Oregon, IL
Parking situation: on premises
Laundry access: no

If you're looking for a rustic getaway, we've got you covered. You'll find this early-1900-era cabin less than 2 hours west of Chicago on Rock River, where you can spend a weekend hiking, boating, BBQing and porch-sitting where Sauk and Fox Indians used to call home. Venture within a few miles from the cabin and you may just spot wild bison grazing. 

If you're looking to get out on the water, nearby White Pelican, Inc. offers canoes and kayaks, as well as shuttle service, and Lowden-Miller State Park is the perfect spot for families looking to take a hike. 

The Draw: An Outdoor Pool . . . in the City!

The specs: 16 guests, 6 bedrooms, 6 beds, 5.5 beds
The neighborhood: Wrigleyville
Parking situation: on-premises and street parking
Laundry access: on-premises

Take your family . . . and maybe a couple of other families for that matter . . . to this mansion with a heated outdoor pool (a rarity in the city confines). You'll enjoy country club-style living right smack dab in the middle of the city with 2,000-square-feet of decks and patio and an outdoor music system and TV to go along with a cool-down in the pool during summer months. When you're not soaking up the sun, you'll find the fun continues on the inside in the game room with a bar, ping pong, foosball, arcade games, darts, a blackjack table and more.  

While you're in the neighborhood, check out Gallagher Way. When restrictions are lifted it's a great destination for farmer's markets, community events, festivals, dining and a fantastic spot to be in the middle of the action during Chicago Cubs game days, even if you don't have tickets. 

The Draw: Views for Days

The specs: 7 guests; 3 bedrooms, 4 beds, 3 baths, pack 'n play travel crib available upon request
The neighborhood: Streeterville
Parking situation: paid parking on and off-premises
Laundry access: on-premises

You'd be hard-pressed to find a better location in the city for a family staycation. You're within a stone's throw of Navy Pier, Museum Campus with Shedd, The Field and Adler, Millennium Park, beaches and Mag Mile. During the summer months, you can enjoy the Wednesday and Saturday evening fireworks displays, courtesy of Navy Pier. When you're not out and about enjoying the city, hang at the rooftop lounge with cabanas, grills and a fire pit or take a dip in the indoor and outdoor pools.

Post-COVID-19 suggestion: If you're looking for a unique family dining experience, check out SafeHouse Chicago, a spy-themed restaurant that requires a password, or a willingness to complete silly tasks, to gain entrance. They have a great kids menu and more activities to keep the interest of little diners than they can even handle in one visit.

—Maria Chambers


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