Luxury Vacation Rentals for Families in Chicago

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 31 family vacation rentals – enter your dates for availability.

Top-rated family vacation rentals in Chicago

The Gilean

3 bedrooms•2 baths

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~$45 less than other sites

Luxe Gilean: Elegance Awaits

3 bedrooms•2 baths

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~$30 less than other sites

Modern Stay Near DT CHI

3 bedrooms•2 baths

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~$30 less than other sites

Gilean Haven: Paradise Retreat

3 bedrooms•2 baths

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~$50 less than other sites

Chicago Skyline View Pilsen Apt + Parking Spot

3 bedrooms•1 bath

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~$30 less than other sites

Envitae Hotel, Modern Sleek Apartment

4 bedrooms•3 baths

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New

~$70 less than other sites

ENVITAE Hotel, Luxury Modern Apartments

4 bedrooms•3 baths

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New

~$45 less than other sites

Premium 4 King Apartment w/ City Views

4 bedrooms•3 baths

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New

~$55 less than other sites

Welcome to family adventures in Chicago

Make your next getaway with Wander’s collection of luxury family vacation rentals in Chicago, Illinois. Each residence blends the polish of a five-star stay with the comfort and privacy of a real home, giving parents and kids space to recharge without compromise.

Choose from sleek skyline-view condos, expansive townhomes with generous living areas, and contemporary homes crafted for gathering. Expect fully equipped kitchens, multiple bedrooms, ultra fast WiFi, meticulous cleaning, and 24/7 concierge support. Many homes feature media lounges, play-friendly layouts, or fitness areas, so balancing calls, nap times, and movie nights is simple.

Available soon in Chicago

City Retreat, Great for Business & Family

4 bedrooms•3 baths

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New

~$45 less than other sites

Luxury Suite w/Gym and Balcony

3 bedrooms•2.5 baths

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New

~$55 less than other sites

Luxury Glass Apartment, Amazing Views

2 bedrooms•2 baths

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New

~$50 less than other sites

Designer Suite in City Center w/ Skyline Views

2 bedrooms•2 baths

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New

~$45 less than other sites

City Suite w/ Amazing Glass Views

2 bedrooms•2 baths

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New

~$35 less than other sites

City Loft Sweeping Glass Views

2 bedrooms•2 baths

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New

~$45 less than other sites

Sophisticated Suite - Walk to Shops, Dining & Transit

4 bedrooms•3 baths

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New

~$55 less than other sites

South Loop, 3 Kings, Steps from McCormick Place

3 bedrooms•2 baths

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New

~$40 less than other sites

All homes in Chicago

The Gilean

3 bedrooms•2 baths

•

~$45 less than other sites

Luxe Gilean: Elegance Awaits

3 bedrooms•2 baths

•

~$30 less than other sites

Modern Stay Near DT CHI

3 bedrooms•2 baths

•

~$30 less than other sites

Gilean Haven: Paradise Retreat

3 bedrooms•2 baths

•

~$50 less than other sites

Chicago Skyline View Pilsen Apt + Parking Spot

3 bedrooms•1 bath

•

~$30 less than other sites

Envitae Hotel, Modern Sleek Apartment

4 bedrooms•3 baths

•

New

~$70 less than other sites

ENVITAE Hotel, Luxury Modern Apartments

4 bedrooms•3 baths

•

New

~$45 less than other sites

Premium 4 King Apartment w/ City Views

4 bedrooms•3 baths

•

New

~$55 less than other sites

View all homes

Highlights in Chicago

Discover world-class museums, sprawling parks, and iconic architecture that will delight and entertain every member of your family.

Millennium Park

Navy Pier

Shedd Aquarium

Field Museum

Lincoln Park Zoo

Museum of Science and Industry, Chicago

Adler Planetarium

360 CHICAGO Observation Deck

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.

Only the best homes

We’ll never not look like the pictures. Every Wander is beautiful and expertly operated, so you can leave any stress at the door.

Hotel-grade amenities

We’ll never leave you with nothing to do. From ultra fast WiFi to gyms and pools, our homes make it easy to blend work and play.

24/7 concierge service

We’ll never leave you hanging. Our chat-based Concierge is always available to help – from trip questions to special requests.

Inspiring and stunning views

We’ll never leave you uninspired. Every Wander has stunning views to refresh and inspire your soul. Adventure awaits.

Meticulous cleaning

We’ll never have you check in to a dirty house. Our cleaning teams are meticulous, and there are no chores at checkout.

Safety and security

We’ll never pass you off to a stranger. Every Wander location meets our industry-leading safety standards to give you peace of mind.

Most popular amenities for family vacation rentals in Chicago

Other popular amenities & vacation types in Chicago

Large group vacation rentals in Chicago

Hot tub vacation rentals in Chicago

Discover more family fun in Chicago

Set on Lake Michigan, Chicago offers year-round family appeal. Sunny days bring the Lakefront Trail, sandy stretches like Oak Street and North Avenue Beach, and leisurely strolls along the Riverwalk. Kids love the Centennial Wheel at Navy Pier and the climbing walls and play gardens at Maggie Daley Park.

Rain or shine, the Museum Campus delivers favorites like the Shedd Aquarium and the Field Museum, while the Museum of Science and Industry wows with hands-on exhibits. Winter adds ice skating on the Ribbon and festive markets. With world-class culture, green space, and easy transit, this is why Wander’s luxury family vacation rentals in Chicago are the perfect choice, whether you are traveling for work or leisure.

FAQs: Vacation Rentals in Chicago

Why should I book a Wander in Chicago over other family vacation rentals?

Wander offers a level of consistency and quality you won’t find with most family vacation rentals.

Every home in Chicago delivers the quality of a luxury hotel, paired with the comfort and space of a private vacation home. You get hotel-grade amenities, meticulous cleaning, stunning views, and 24/7 concierge support in every stay. Why would you want to stay anywhere else?

Which are Wander’s most popular family vacation rentals in Chicago?

Some of our most popular family vacation rentals in Chicago include The Gilean, Luxe Gilean: Elegance Awaits, and Modern 3BR Stay Near DT CHI. Guests love the quality of a luxury hotel, the comfort of a private vacation home, and the consistently exceptional experience Wander is known for. Explore the full collection to find the perfect home for your next stay.

How many different family vacation rentals does Wander have available in Chicago?

Wander offers 31 family vacation rentals in Chicago, each carefully designed and expertly operated. Browse the full collection to see what’s available for your trip.

What time is check-in and check-out at Wander’s family vacation rentals in Chicago?

You can check-in to Wander family vacation rentals in Chicago after 4.00pm and check-out before 10.00am.

Do Wander’s family vacation rentals in Chicago have WiFi access?

Yes. Every Wander home in Chicago has ultra fast, reliable WiFi so you can stay connected throughout your stay.

What is Wander’s cancellation policy?

You can cancel your reservation within 24 hours of booking for a full refund.

For stays of less than 15 nights, you can cancel or reschedule up to 14 days before check-in for a full refund. For stays of 15 nights or longer, the cancellation window is 60 days.

For some homes, a 30-day deadline applies; this will be clearly shown before you book.