
Kid-friendly vacation rentals in Skokie
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Top-rated kid-friendly rentals in Skokie
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Popular amenities for Skokie kid-friendly rentals
Kid-friendly house rentals

Cozy Home in Skokie
Had a great stay at this Airbnb! Check-in was super easy, and Mian was very responsive, which made everything smooth. The location was very convenient, with easy access by car or train to downtown, close to other suburbs, and not too far from the airport. Overall, a great spot, and I’d definitely stay here again!

*King bed *Outdoor Living *Sought-After Area
Beautiful home, clean and worked perfect for our family. Elisabeth always responded quickly and it was a seamless check in and check out process.

Quiet and Cozy Home in Evanston
Absolutely enjoyed our stay. Will definitely rebook here when we visit Evanston again. Apt. Was well set up and extremely comfortable . Shanna is a great host

Chic & cozy 3BR house near all amenities in Skokie
We had a great time. The place was cozy and accessible. Would stay again!

Chicago River House -BBQ Oasis now open!
Even more spacious than in the photos! Well-kept place, with a fully stocked kitchen, projector, BOSE speaker, and great backyard. Double shower in the master bedroom, and strong water pressure. Entry is easy with a code. Finally, the host is VERY accommodating, flexible, and responsive. Recommended!

Larimer Park Carriage House
The moment I walked in, it feels like home! The house is very nicely decorated, and it has everything you need to have a very comfortable stay. The kitchen is well stocked and she even has a basketball for my kid to play with in the court right in front of the house. She even welcomes the guests with a nice bar of chocolate , card and fresh flowers! We will stay here again if we visit Evanston!

Chicago getaway for two!
My boyfriend and I had a fantastic weekend at Gladys’ place. She was super responsive, and check-in was easy with clear instructions. The apartment was cozy and modern, but still felt homey—like our own space for the weekend. It was clean, well-kept, and had thoughtful touches like a Brita pitcher, fresh towels, sheets, and a stocked kitchen. The layout was cute and the decor was simple but perfect—more personality than a hotel room without being cluttered. One of the highlights was the bus stop literally 10 feet from the door, which made getting into southern Chicago (via bus to the Blue Line) super convenient. We also loved walking to Dunkin’ each morning once we realized how close it was. The location felt peaceful but still had a few cute restaurants nearby. We never ran into the hosts, but it felt private even with the shared entry. This stay is in our top 5 Airbnbs—perfect for a couples getaway! Thank you, Gladys, for being such a thoughtful host!

New Chic 6bd 2 bth Ranch Home, Skokie w/basement
So happy with our stay! Sheila was responsive in communicating each step of check in and check out process. There were complimentary pastries upon our arrival which was a nice touch. The location is in a good location and had all the amenities described in the listing. There was an abundance of towels and the basement room was a nice room to gather and play table tennis or corn hole which was available. I would definitely stay again when visiting Chicago! Thank you Sheila!
Kid-friendly apartment rentals

Vintage sunlit 2.5 BR apt. Perfect for families!
I enjoyed my stay at Letitia's place. I was traveling between the city and northern burbs, and Letitia's place provided a nice centralized location with easy access to both. Letitia's place is clean, charming, and comfortable. Letitia responded quickly to any questions. I recommend this as a comfortable place to explore the greater Chicagoland area.

Spacious 3 bdrm apt. near NU + Chicago + lake.
We felt very comfortable at Daniela’s place. The flat is spacious and clean. We had no trouble walking to the train and parking in the dedicated spot. The decor is appealing & stylish. I recommend if in town visiting plus Evanston is the best!

Stylish & Comfy Gem near Downtown~Balcony~Parking
This was one of my best Airbnb experiences. Every little detail was attended to, from the extremely comfortable bedding & coordinated kitchen color scheme to the cleanliness & quiet surroundings.

Basement Efficiency Apartment
Mary is a very good host, she responded quickly and even allowed for early check in!

Ashland Ice Cream House
The house was comfortable and spacious
Clean and Bright Stay 2BRM close NU campus
Tracy's home is clean, comfortable, and feels like a great home to return to when you are visiting Evanston. we didn't get a chance to cook in their fabulous kitchen, but I plan to next time!!

Charming one bedroom apartment
My stay with Donald was extremely pleasant. A beautiful apartment with great attention to detail and very comfortably furnished. Donald and his wife were very nice and helpful. When I'm back in Chicago, I will definitely want to stay there again.

Stunning, Sunny Flat with Beautiful Backyard
Julie and Sebastian are warm and welcoming hosts and their home is perfect. Great location, quiet, and a lovely space for us to spend time visiting our local family. Kitchen is well equipped with a great Wolf range, dining room is also super. We will definitely stay again.
Kid-friendly condo rentals

Soft Suede and Warm Bricks at a Stylish Rogers Park Home
The renovated classic Chicago greystone is spectacular. This is an amazing update of an architectural gem. The space has all modern amenities but the character and charm are thoroughly maintained. The spaces are spotless. Rogers Park is a wonderful lakeside neighborhood and is a melting pot of ethnicities and cultures. There are great restaurants within walking distance as well as close by in Evanston, Andersonville, etc. The Metra and the El are an easy walk. Lillian was so accommodating and proactive. We loved this stay and will be back.

Lovely top floor 2BR/2BA, steps from everything!
When we were first looking for a place to stay, none of the available AirB&Bs looked great. A week later, we looked again, and suddenly Julia's place popped up. It was so much better looking, and with a fairer price, than any others I could find in the list. A two-bedroom that is a *real* two-bedroom, for the price that others were charging for a pull-out bed in the living room. It was just as beautiful in-person. We felt immediately at-home and comfortable. I'm someone who has insomnia, especially while traveling, but there, I had no problem sleeping somehow. Also, it truly is a short walk to the Blue Line, or even a just few steps from the 77 bus route, which goes to the Blue Line, or all the way right into downtown Chicago.

Picture Perfect 3Bed Steps from Train and FLW
Great stay at Anne’s place. She was very communicative and went out of her way to ensure we were comfortable. We would definitely recommend to anyone coming to the Chicago area!

The Ramblers Inn, Northside NEW Reno w/parking!
Easy check in and close to LUC which is what we needed. Clean and comfortable. Bonus that it included parking.

3D Tour! Designer Condo near Logan Square
I had an amazing stay! Place was very accurate to the post on Airbnb and the host was very polite with clear instructions, and check in! Thank you for providing such an amazing Chicago experience for me and my husband!

Newly updated 1BD/1B in Old Irving Chicago!
The time spent here was wonderful. This place has everything you need to feel at home away from home. Everything was clean and comfortable. The area was also really nice with tons of food and drinks within walking distance. The blue line is a short walk away and the busses run on the corner. I would definitely stay here again when coming back to Chicago.

Cozy 3BR on Chicago's North Side & Free Parking
Planned a weekend trip with our daughters and their partners to Chicago. Loved this location being outside of the city but very conveniently located to public transit. The house itself was beautiful and comfortable, with plenty of room for 6 adults. A perk was the driveway parking space for our car. Would definitely recommend to others and stay again when visiting Chicago!

Cozy 1bdr Rogers Park, Loyola, Northwestern.
This is a WONDERFUL one bedroom apartment that is both private and spacious! The owner/host has the space fabulously decorated with an eclectic mix of original contemporary artwork and antiques. Nothing is generic about the space and it has been outfitted for guests with loving care. The host, Kaye, clearly puts much trust in her guests with her charming decor and furnishings. The amount of space, the privacy and the home-y feel make it a place we'd love to return to.
Quick stats about vacation rentals that are kid-friendly in Skokie
Total rentals
20 properties
Nightly prices starting at
G$16,719 GYD before taxes and fees
Total number of reviews
700 reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace
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- Millennium Park
- Wrigley Field
- Navy Pier
- United Center
- Oak Street Beach
- Shedd Aquarium
- Six Flags Great America
- Humboldt Park
- Guaranteed Rate Field
- 875 North Michigan Avenue
- The Field Museum
- Frank Lloyd Wright Home and Studio
- Museum of Science and Industry
- Lincoln Park
- Lincoln Park Zoo
- Garfield Park Conservatory
- Illinois Beach State Park
- Willis Tower
- Wicker Park
- Washington Park Zoo
- Brookfield Zoo
- The 606
- Moraine Hills State Park
- Richard Bong State Recreation Area