Skip to Main Content.
Download the app button
Download the app button with download icon
Get the app
United States
Trip Boards
List your property
Help
My trips
Sign in
Vrbo just got better
Earn rewards across our family of brands with One Key™
Sign in
Sign in as an owner
Learn about One Key
Feedback
Going to
Going to
Dates
Travelers
Adults
Adults
Decrease the number of adults
Increase the number of adults
Children
Ages 0 to 17
Decrease the number of children
Increase the number of children
I am traveling with pets
If checked, only properties that allow pets will be shown
Done
Search
Filters
Popular
Price
Rooms & spaces
Sort by recommended
300+ properties
How our sort order works
Opens in a new window
Search results showing properties in Chicago, IL, United States of America (CHI-All Airports). May 12, 2024 through May 15, 2024
Google map showing 500 properties
Chicago is popular!
Only 25% of properties are available on our site for your dates.
Photo gallery for Bright Garden Studio
Property grounds
Show previous image for Bright Garden Studio
Show next image for Bright Garden Studio
Premier Host
Apartment · 9 min drive to the beach
Bright Garden Studio
Sleeps 4 · 1 bedroom · 1 bathroom
9.4/10
Exceptional
(3 reviews)
9.4 out of 10 Exceptional (3 reviews)
The price is $110
$110
$506 total
$506 total
More information about Bright Garden Studio, opens in a new tab
Photo gallery for Riverfront cabin on Rock River
Property grounds
Show previous image for Riverfront cabin on Rock River
Show next image for Riverfront cabin on Rock River
Premier Host
House · 6.8 mi (11 km) to Rockford center
Riverfront cabin on Rock River
Sleeps 4 · 2 bedrooms · 1 bathroom
10/10
Exceptional
(155 reviews)
10 out of 10 Exceptional (155 reviews)
The price is $170
$170
$638 total
$638 total
More information about Riverfront cabin on Rock River, opens in a new tab
Photo gallery for Found Chicago powered by Sonder | Bunk Room
Room
Show previous image for Found Chicago powered by Sonder | Bunk Room
Show next image for Found Chicago powered by Sonder | Bunk Room
Premier Host
Apartment · 10 min drive to the beach
Found Chicago powered by Sonder | Bunk Room
Sleeps 2 · 1 bathroom
8.8/10
Excellent
(8 reviews)
8.8 out of 10 Excellent (8 reviews)
The price is $118
$118
$354 total
$354 total
More information about Found Chicago powered by Sonder | Bunk Room, opens in a new tab
Apartment · Within Downtown Chicago
Sonder Market Hall | Studio Apartment w/ City View
Sleeps 2 · 1 bathroom
8.4/10
Very Good
(15 reviews)
8.4 out of 10 Very Good (15 reviews)
The price is $213
$213
$640 total
$640 total
More information about Sonder Market Hall | Studio Apartment w/ City View, opens in a new tab
House
Country Guesthouse at Wind Ridge Herb Farm
Sleeps 6 · 3 bedrooms · 1 bathroom
9.8/10
Exceptional
(58 reviews)
9.8 out of 10 Exceptional (58 reviews)
The price is $129
$129
$520 total
$520 total
More information about Country Guesthouse at Wind Ridge Herb Farm, opens in a new tab
Apartment · Within North Center
Roscoe Village Inn | Guesthouse | Walk to Chicago's Wrigley Field
Sleeps 4 · 2 bedrooms
10/10
Exceptional
(144 reviews)
10 out of 10 Exceptional (144 reviews)
The price is $172
$172
$698 total
$698 total
More information about Roscoe Village Inn | Guesthouse | Walk to Chicago's Wrigley Field, opens in a new tab
House · 3.6 mi (5.7 km) to Byron center
The Rock River Cabin
Sleeps 4 · 2 bedrooms · 1 bathroom
9.8/10
Exceptional
(19 reviews)
9.8 out of 10 Exceptional (19 reviews)
The price is $140
$140
$584 total
$584 total
More information about The Rock River Cabin, opens in a new tab
Apartment · Within Avondale
Beaming & Roomy 2BR Apartment near Shops
Sleeps 4 · 2 bedrooms · 1 bathroom
9.0/10
Wonderful
(2 reviews)
9.0 out of 10 Wonderful (2 reviews)
The price is $92
$92
$406 total
$406 total
More information about Beaming & Roomy 2BR Apartment near Shops, opens in a new tab
Condo · 15 min walk to Montrose Beach
Steps to the Lakefront! This Uptown Beauty is Everything You Need for a Perfect Chicago Getaway by RedAwning
Sleeps 4 · 1 bedroom · 1 bathroom
10/10
Exceptional
(13 reviews)
10 out of 10 Exceptional (13 reviews)
The price is $127
$127
$519 total
$519 total
More information about Steps to the Lakefront! This Uptown Beauty is Everything You Need for a Perfect Chicago Getaway by RedAwning, opens in a new tab
Condo · 8 min drive to the beach
Walking distance to restaurants, shops and Lake Michigan,
Sleeps 6 · 2 bedrooms · 2 bathrooms
9.6/10
Exceptional
(155 reviews)
9.6 out of 10 Exceptional (155 reviews)
The price is $197
$197
$879 total
$879 total
More information about Walking distance to restaurants, shops and Lake Michigan,, opens in a new tab
House · 12 min walk to Oak Street Beach
Explore Chicago! Free Breakfast, Fully-equipped Kitchen, Pet-friendly Property!
Sleeps 3 · 1 bedroom · 1 bathroom
10/10
Exceptional
(2 reviews)
10 out of 10 Exceptional (2 reviews)
The price is $170
$170
$580 total
$580 total
More information about Explore Chicago! Free Breakfast, Fully-equipped Kitchen, Pet-friendly Property!, opens in a new tab
House · 1.4 mi (2.3 km) to Oak Park center
A quiet stay while you are away
Sleeps 4 · 2 bedrooms
9.8/10
Exceptional
(26 reviews)
9.8 out of 10 Exceptional (26 reviews)
The price is $95
$95
$525 total
$525 total
More information about A quiet stay while you are away, opens in a new tab
Apartment · 7 min drive to the beach
Enjoy Evanston! Slow Down After a Busy Day Sight Seeing - Walking Distance from Public Transportation by RedAwning
Sleeps 4 · 2 bedrooms · 1 bathroom
8.4/10
Very Good
(11 reviews)
8.4 out of 10 Very Good (11 reviews)
The price is $93
$93
$474 total
$474 total
More information about Enjoy Evanston! Slow Down After a Busy Day Sight Seeing - Walking Distance from Public Transportation by RedAwning, opens in a new tab
Apartment · Within Near West Side
Vintage Graystone in Little Italy near the loop UIC United Ct & McCormick Place
Sleeps 8 · 4 bedrooms · 2 bathrooms
10/10
Exceptional
(175 reviews)
10 out of 10 Exceptional (175 reviews)
The price is $150
$150
$624 total
$624 total
More information about Vintage Graystone in Little Italy near the loop UIC United Ct & McCormick Place , opens in a new tab
Apartment · 14 min walk to Belmont Harbor Dog Beach
All Complete 2BR Apt in Lakeview
Sleeps 4 · 2 bedrooms · 1 bathroom
8.0/10
Very Good
(14 reviews)
8.0 out of 10 Very Good (14 reviews)
The price is $97
$97
$423 total
$423 total
More information about All Complete 2BR Apt in Lakeview, opens in a new tab
House · 1.5 mi (2.4 km) to Schaumburg center
Home Away from Home! Budget-friendly Accommodation! Pets Allowed, Pool, Parking
Sleeps 5 · 2 bedrooms · 2 bathrooms
9.0/10
Wonderful
(8 reviews)
9.0 out of 10 Wonderful (8 reviews)
The price is $174
$174
$574 total
$574 total
More information about Home Away from Home! Budget-friendly Accommodation! Pets Allowed, Pool, Parking, opens in a new tab
Apartment · 0.7 mi (1 km) to Oak Park center
Peaceful 2 Bed w FirePit Free Parking 15 mins to Downtown Chicago
Sleeps 5 · 2 bedrooms · 1 bathroom
9.4/10
Exceptional
(8 reviews)
9.4 out of 10 Exceptional (8 reviews)
The price is $124
$124
$510 total
$510 total
More information about Peaceful 2 Bed w FirePit Free Parking 15 mins to Downtown Chicago, opens in a new tab
Tell us how we can improve our site
Share feedback