Search Villas in Chicago

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
15 Aug - 17 Aug
In two weeks
22 Aug - 24 Aug
In one month
5 Sept - 7 Sept
In two months
3 Oct - 5 Oct
HUGE! 3BR Private Home+Garage+360° Roof Deck+Hot Tub+EV+Sleeps 12
Outdoor dining

HUGE! 3BR Private Home+Garage+360° Roof Deck+Hot Tub+EV+Sleeps 12

10.0 out of 10, Exceptional, (8)
"Great property and very kind and responsive hosts. I would be happy to stay here again. "
HUGE! 3BR Private Home+Garage+360° Roof Deck+Hot Tub+EV+Sleeps 12
Hot Tub & Sauna: Hoffman Estates Villa in Elgin!
Enjoy cooking in this well-equipped kitchen with a sink, microwave, and dishwasher.

Hot Tub & Sauna: Hoffman Estates Villa in Elgin!

10.0 out of 10, Exceptional, (4)
"Amazing property and perfect for our large family! "
Hot Tub & Sauna: Hoffman Estates Villa in Elgin!
Charming Retreat in the Heart of Des Plaines by RedAwning
Relax in this spacious living area with a sofa, side table, and ceiling fan, offering a comfortable space to unwind.

Charming Retreat in the Heart of Des Plaines by RedAwning

8.0 out of 10, Very good, (12)
"Location was great and house was clean."
Charming Retreat in the Heart of Des Plaines by RedAwning
Hot Tub & Sauna: Hoffman Estates Villa in Elgin!
Enjoy cooking in this well-lit kitchen with a large window, stainless steel appliances, and modern cabinetry.

Hot Tub & Sauna: Hoffman Estates Villa in Elgin!

3.0 star property
Hot Tub & Sauna: Hoffman Estates Villa in Elgin!
Elegant Riverwoods Escape w/ Private Sauna!
Interior

Elegant Riverwoods Escape w/ Private Sauna!

3.0 star property
Elegant Riverwoods Escape w/ Private Sauna!
▌360° City Skyline Chicago ▌
Enjoy the city view from this room's spacious balcony with a table and chairs.

▌360° City Skyline Chicago ▌

▌360° City Skyline Chicago ▌
★★★Charming 2BR near downtown, +FREE parking★★★
Enjoy the city view from this balcony with a table and two chairs.

★★★Charming 2BR near downtown, +FREE parking★★★

★★★Charming 2BR near downtown, +FREE parking★★★
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chicago Hotel Reviews

Hyatt Regency Chicago

Hyatt Regency Chicago

10/10 Excellent
"Highly recommended "
Claudia 1-night trip
Posted 17 hours ago
Hyatt Regency Chicago