Luxury Vacation Rentals 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 31 vacation rentals – enter your dates for availability.

Top-rated vacation rentals in Illinois

Home in McHenry

5 bedrooms•3.5 baths

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Luxury

Home in Rockford

6 bedrooms•6.5 baths

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Property in Chicago

4 bedrooms•3 baths

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New

Apartment in Chicago

4 bedrooms•3 baths

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New

Property in Chicago

4 bedrooms•3 baths

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New

Apartment in Chicago

1 bedroom•1 bath

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New

Property in Chicago

4 bedrooms•3 baths

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New

Property in Chicago

3 bedrooms•2 baths

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New

Welcome to Illinois

Elevate your stay in the heart of the Midwest with Wander’s luxury vacation rentals in Illinois. Centered in Chicago, our portfolio pairs the polish of a five-star hotel with the privacy of a refined city home, so you can arrive confident and relax completely.

Expect inspiring skyline views, generous living spaces, dedicated work setups with ultra fast WiFi, and meticulous housekeeping, all backed by 24/7 concierge support. Hotel-grade amenities like gyms and pools make it effortless to balance productivity and downtime. Thoughtful design and reliable operations mean every detail is dialed, from plush linens to smart home comforts.

Destinations in Illinois

Chicago

Available soon in Illinois

Home in McHenry

5 bedrooms•3.5 baths

•

Apartment in Chicago

4 bedrooms•3 baths

•

New

Property in Chicago

4 bedrooms•3 baths

•

New

Property in Chicago

4 bedrooms•3 baths

•

New

Apartment in Chicago

1 bedroom•1 bath

•

New

Apartment in Chicago

3 bedrooms•2 baths

•

New

Apartment in Chicago

2 bedrooms•2 baths

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New

Apartment in Chicago

2 bedrooms•2 baths

•

New

Featured vacation rentals in Illinois

Home in McHenry

5 bedrooms•3.5 baths

•

Luxury

Home in Rockford

6 bedrooms•6.5 baths

•

Highlights in Illinois

From Chicago's iconic skyline and world-class museums to the historic heartland where Abraham Lincoln's legacy lives on.

Millennium Park

Navy Pier

Willis Tower

The Art Institute of Chicago

Abraham Lincoln Presidential Library and Museum

Lincoln Home National Historic Site

Starved Rock State Park

The Magnificent Mile

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.

All homes in Illinois

Home in McHenry

5 bedrooms•3.5 baths

•

Luxury

Home in Rockford

6 bedrooms•6.5 baths

•

Property in Chicago

4 bedrooms•3 baths

•

New

Apartment in Chicago

4 bedrooms•3 baths

•

New

Property in Chicago

4 bedrooms•3 baths

•

New

Apartment in Chicago

1 bedroom•1 bath

•

New

Property in Chicago

4 bedrooms•3 baths

•

New

Property in Chicago

3 bedrooms•2 baths

•

New

View all homes

Most popular amenities for vacation rentals in Illinois

More popular destinations in Illinois

Other popular amenities & vacation types in Illinois

Family vacation rentals in Illinois

Large group vacation rentals in Illinois

Pet-friendly vacation rentals in Illinois

Hot tub vacation rentals in Illinois

Private pool vacation rentals in Illinois

Discover more of Illinois

Illinois blends urban edge with Midwestern ease. In Chicago, lakefront beaches meet striking architecture, celebrated galleries and theaters, and a dining scene that never slows. Sports, live music, and a packed calendar of cultural events keep the city buzzing year round.

Beyond the skyline, scenic escapes sit within easy reach, from the sandstone canyons of Starved Rock to the historic streets of Galena. Farther south, the Shawnee hills and Garden of the Gods reveal dramatic rock formations and quiet trails. This is why Wander’s luxury vacation rentals in Illinois are the perfect choice, whether you are traveling for work or leisure.

FAQs: Vacation Rentals in Illinois

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

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

Every home in Illinois 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 vacation rentals in Illinois?

Some of our most popular vacation rentals in Illinois include Wander Illinois Highwood, Wander Rockford Vista, and Envitae Hotel, 4BR Modern Sleek Apartment. 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 vacation rentals does Wander have available in Illinois?

Wander offers 31 vacation rentals in Illinois, 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 vacation rentals in Illinois?

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

Do Wander’s vacation rentals in Illinois have WiFi access?

Yes. Every Wander home in Illinois 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.