Luxury Vacation Rentals for Families in Illinois
Never book a bad vacation home again. Every Wander comes with hotel-grade amenities, inspiring views, pristine cleaning and 24/7 concierge service.
We found 6 family vacation rentals – enter your dates for availability.
Terre Haute, Indiana
Wander Terre Haute Escape
Next avail.
Dec 5 - Dec 7
59
McHenry, Illinois
Wander Illinois Highwood
Next avail.
Dec 11 - Dec 13
512
Innsbrook, Missouri
Wander Innsbrook Woods
Next avail.
Dec 7 - Dec 8
516
4.5
Chicago, Illinois
Wander Chicago Sky
Next avail.
Dec 10 - Dec 12
516
Chicago, Illinois
Wander Chicago Modern
Next avail.
Dec 7 - Dec 9
516
Rockford, Illinois
Wander Rockford Vista
Next avail.
Dec 2 - Dec 4
616
Welcome to family adventures in Illinois
Bring the whole crew to Illinois with Wander. Our luxury family-friendly vacation rentals in Illinois make room for every generation, with multi-bedroom layouts, generous living areas, and full kitchens for easy mornings.
In Chicago, our modern retreats pair inspiring views with hotel-grade polish. Count on ultra fast WiFi for remote work and streaming, plush bedding, pristine cleaning, and 24/7 concierge support. Select homes include gyms or pools for on-site fun, so downtime is effortless and bedtimes are easy. Settle in and enjoy a smoother family getaway from the moment you arrive.
Innsbrook, Missouri
Wander Innsbrook Woods
Next avail.
Dec 7 - Dec 8
516
4.5
Chicago, Illinois
Wander Chicago Modern
Next avail.
Dec 7 - Dec 9
516
Terre Haute, Indiana
Wander Terre Haute Escape
Next avail.
Dec 5 - Dec 7
59
McHenry, Illinois
Wander Illinois Highwood
Next avail.
Dec 11 - Dec 13
512
Chicago, Illinois
Wander Chicago Sky
Next avail.
Dec 10 - Dec 12
516
Rockford, Illinois
Wander Rockford Vista
Next avail.
Dec 2 - Dec 4
616
IT'S A VACATION HOME, BUT BETTER
The Wander difference
Wander is different because we combine the quality of a luxury hotel with the comfort of a private vacation home. Your best trip ever is just a few clicks away.
All homes in Illinois
Terre Haute, Indiana
Wander Terre Haute Escape
Next avail.
Dec 5 - Dec 7
59
McHenry, Illinois
Wander Illinois Highwood
Next avail.
Dec 11 - Dec 13
512
Innsbrook, Missouri
Wander Innsbrook Woods
Next avail.
Dec 7 - Dec 8
516
4.5
Chicago, Illinois
Wander Chicago Sky
Next avail.
Dec 10 - Dec 12
516
Chicago, Illinois
Wander Chicago Modern
Next avail.
Dec 7 - Dec 9
516
Rockford, Illinois
Wander Rockford Vista
Next avail.
Dec 2 - Dec 4
616
Discover more family fun in Illinois
Illinois rewards families with variety. Chicago’s lakefront parks, sandy beaches, acclaimed museums, and iconic sports experiences keep every age engaged, while architecture cruises and theater add a sense of occasion.
Beyond the city, day trips to Starved Rock State Park reveal waterfalls and canyons, and nearby towns host festivals and farmers markets across the seasons. Summer brings fireworks over Lake Michigan, autumn glows with fall color, and winter sparkles with skating rinks and holiday displays. With convenient airports and simple transit, planning is easy. This is why Wander’s luxury family-friendly vacation rentals in Illinois are the perfect choice, whether you are traveling for work or leisure.