Luxury Vacation Rentals with a Private Pool in Chicago

Luxury Vacation Rentals with a Private Pool 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 1 private pool vacation rentals – enter your dates for availability.

Top-rated private pool vacation rentals in Chicago

Luxury Suite w/Gym and Balcony property photo 1

Luxury Suite w/Gym and Balcony

3 bedrooms•2.5 baths
742 US dollars for 3 nights•
New

~$60 less than other sites

Welcome to private poolside luxury in Chicago

Welcome to private poolside luxury in Chicago

Explore our collection of luxury private pool vacation rentals in Chicago, where the polish of a five-star stay meets the privacy of a well-appointed home. Every Wander is beautiful, expertly operated, and exactly as pictured, so you can relax the moment you step through the door.
Take a quiet swim in your own pool whenever the mood strikes, then settle into plush linens, dedicated workspaces, and ultra fast WiFi. With pristine cleaning, inspiring views, and 24/7 concierge service, your Chicago stay is as effortless as it is elevated. This is city living, perfected.

Available soon in Chicago

Luxury Suite w/Gym and Balcony property photo 1

Luxury Suite w/Gym and Balcony

3 bedrooms•2.5 baths
742 US dollars for 3 nights•
New

~$60 less than other sites

All homes in Chicago

Luxury Suite w/Gym and Balcony property photo 1

Luxury Suite w/Gym and Balcony

3 bedrooms•2.5 baths
742 US dollars for 3 nights•
New

~$60 less than other sites

View all homes

Highlights in Chicago

Discover world-class museums, iconic architecture, and vibrant public parks in the heart of the Windy City.
Millennium Park
Art Institute of Chicago
Navy Pier
Willis Tower Skydeck
Shedd Aquarium
Wrigley Field

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 private pool vacation rentals in Chicago

Outdoor pool (1)
Pool table (1)
Bbq area (1)
Garden (1)
Dryer (1)
Washer (1)
Oven (1)
Tv (1)
Kitchen (1)
Wifi (1)
Microwave (1)
Dishwasher (1)
Heating (1)
Toys (1)
Coffee maker (1)
Dedicated workspace (1)

Other popular amenities & vacation types in Chicago

Family vacation rentals in Chicago
Large group vacation rentals in Chicago
Discover more beyond the pool in Chicago

Discover more beyond the pool in Chicago

Chicago rewards every season with energy and style. Summer brings sunlit days along Lake Michigan, afternoons on the Riverwalk, and open air concerts in Millennium Park. Fall paints the boulevards in gold. Winter twinkles with holiday markets and ice skating ribbons. Spring returns with gardens and patio culture as the skyline gleams above it all.
World-class arts, iconic architecture tours, championship sports, and destination shopping create an itinerary that writes itself. Two major airports and efficient transit keep plans easy. That is why Wander's luxury private pool vacation rentals in Chicago are the perfect choice, whether you're traveling for work or leisure.

FAQs: Vacation Rentals in Chicago

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

Wander offers a level of consistency and quality you won’t find with most private pool 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 private pool vacation rentals in Chicago?

Some of our most popular private pool vacation rentals in Chicago include 3BR Luxury Suite w/Gym and Balcony and 3BR Luxury Suite w/Gym and Balcony. 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 private pool vacation rentals does Wander have available in Chicago?

Wander offers 1 private pool 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 private pool vacation rentals in Chicago?

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

Do Wander’s private pool 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.