Luxury Vacation Rentals 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 35 vacation rentals – enter your dates for availability.

Top-rated vacation rentals in Chicago

Modern 1 King City Escape

1 bedroom•1 bath

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New

~$35 less than other sites

ENVITAE Hotel, Luxury Modern Apartments

4 bedrooms•3 baths

•

~$45 less than other sites

Sophisticated Suite - Walk to Shops, Dining & Transit

4 bedrooms•3 baths

•

New

~$40 less than other sites

Designer Suite in City Center w/ Skyline Views

2 bedrooms•2 baths

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New

~$35 less than other sites

Stylish Cozy Boho, 10 Min to Downtown

1 bedroom•1 bath

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~$20 less than other sites

City Loft Sweeping Glass Views

2 bedrooms•2 baths

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New

~$30 less than other sites

The Gilean

3 bedrooms•2 baths

•

~$35 less than other sites

Chic with Skyline Views, Firepit and Gym

4 bedrooms•3 baths

•

New

~$45 less than other sites

Welcome to Chicago

Find your next city escape with Wander’s luxury vacation rentals in Chicago. Our collection merges five-star polish with the privacy of a beautifully designed home, so every stay feels effortless.

Arrive to spotless spaces that look like the photos, with ultra fast WiFi, plush bedding, and dedicated workstations for getting things done. Sleek kitchens make hosting easy, and many homes include access to gyms or pools. From roomy layouts ideal for groups to refined retreats for two, Chicago stays with Wander deliver hotel-grade comfort and a stress-free experience backed by 24/7 concierge.

Available soon in Chicago

Modern 1 King City Escape

1 bedroom•1 bath

•

New

~$35 less than other sites

ENVITAE Hotel, Luxury Modern Apartments

4 bedrooms•3 baths

•

~$45 less than other sites

Designer Suite in City Center w/ Skyline Views

2 bedrooms•2 baths

•

New

~$35 less than other sites

Stylish Cozy Boho, 10 Min to Downtown

1 bedroom•1 bath

•

~$20 less than other sites

City Loft Sweeping Glass Views

2 bedrooms•2 baths

•

New

~$30 less than other sites

The Gilean

3 bedrooms•2 baths

•

~$35 less than other sites

Chic with Skyline Views, Firepit and Gym

4 bedrooms•3 baths

•

New

~$45 less than other sites

Gilean Haven: Paradise Retreat

3 bedrooms•2 baths

•

~$45 less than other sites

All homes in Chicago

Modern 1 King City Escape

1 bedroom•1 bath

•

New

~$35 less than other sites

ENVITAE Hotel, Luxury Modern Apartments

4 bedrooms•3 baths

•

~$45 less than other sites

Sophisticated Suite - Walk to Shops, Dining & Transit

4 bedrooms•3 baths

•

New

~$40 less than other sites

Designer Suite in City Center w/ Skyline Views

2 bedrooms•2 baths

•

New

~$35 less than other sites

Stylish Cozy Boho, 10 Min to Downtown

1 bedroom•1 bath

•

~$20 less than other sites

City Loft Sweeping Glass Views

2 bedrooms•2 baths

•

New

~$30 less than other sites

The Gilean

3 bedrooms•2 baths

•

~$35 less than other sites

Chic with Skyline Views, Firepit and Gym

4 bedrooms•3 baths

•

New

~$45 less than other sites

View all homes

Highlights in Chicago

Discover iconic architecture, world-class museums, and stunning lakefront parks in the vibrant and welcoming heart of the Midwest.

Millennium Park

Navy Pier

The Art Institute of Chicago

Willis Tower

Field Museum

Shedd Aquarium

The Magnificent Mile

Chicago Riverwalk

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 vacation rentals in Chicago

Other popular amenities & vacation types in Chicago

Family vacation rentals in Chicago

Large group vacation rentals in Chicago

Hot tub vacation rentals in Chicago

Discover more of Chicago

Chicago rewards every visit with fresh perspective. The skyline shimmers along Lake Michigan, mirrored in the river, and miles of waterfront paths frame sunrises you will not forget. Architectural icons sit beside bold new builds, creating a cityscape that feels both classic and forward-looking.

Culture here runs deep, from acclaimed theater and live blues to powerhouse sports and a dining scene that leads the conversation. Summer brings festivals and breezes, autumn warms the city in gold, winter sparkles with rinks and markets, and spring wakes the parks with color. It all adds up to a vibrant, year-round destination, which is why Wander’s luxury 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 vacation rentals?

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

Some of our most popular vacation rentals in Chicago include Modern 1 King City Escape, ENVITAE Hotel, 4BR Luxury Modern Apartments, and Sophisticated 4BR Suite - Walk to Shops, Dining & Transit. 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 Chicago?

Wander offers 35 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 vacation rentals in Chicago?

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

Do Wander’s 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.