Best price vacation rentals in Chicago, IL, USA • 150 Listings
Chicago, IL, USA Vacation Rentals |
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Home w/ Office + Yard: 25 Mi to Downtown Chicago!
Home w/ Office + Yard: 25 Mi to Downtown Chicago!
Up to 10 Guests
$350
$386
Not listed
3rd-Floor Chicago Condo: Walk to CTA Stations!
3rd-Floor Chicago Condo: Walk to CTA Stations!
Up to 3 Guests
$225
$334
Not listed
Chicago Local Vibe Residential 1BR Roscoe Village
Chicago Local Vibe Residential 1BR Roscoe Village
Up to 2 Guests
$54
$165
Not listed
Griffin Mansion w/ Yard, 5 Mi to Dtwn Chicago!
Griffin Mansion w/ Yard, 5 Mi to Dtwn Chicago!
Up to 5 Guests
$183
$256
Not listed
Urban Chicago Escape ~ 1 Mi to Local Beaches!
Urban Chicago Escape ~ 1 Mi to Local Beaches!
Up to 6 Guests
$191
$314
Not listed
Lakefront Family Retreat w/ Grill: Steps to Beach!
Lakefront Family Retreat w/ Grill: Steps to Beach!
Up to 8 Guests
$368
$578
Not listed
Sonder The Opal | Studio Apartment
Sonder The Opal | Studio Apartment
Up to 2 Guests
$128
$205
Not listed
Lakefront Portage Home: 3 Mi to Lake Michigan!
Lakefront Portage Home: 3 Mi to Lake Michigan!
Up to 10 Guests
$281
$347
Not listed
Classic Oak Park Home, 11 Mi to Dtwn Chicago!
Classic Oak Park Home, 11 Mi to Dtwn Chicago!
Up to 8 Guests
$250
$630
Not listed
2BR Live in Style Designer Apt in Festive Boystown
2BR Live in Style Designer Apt in Festive Boystown
Up to 4 Guests
$54
$151
Not listed
Sonder The Plymouth | Spacious 3BR Apt
Sonder The Plymouth | Spacious 3BR Apt
Up to 6 Guests
$192
$343
Not listed
Glendale Heights Home with Office and Backyard!
Glendale Heights Home with Office and Backyard!
Up to 6 Guests
$160
$184
Not listed
Serene Garden-Level Apt: 30 Miles to Chicago!
Serene Garden-Level Apt: 30 Miles to Chicago!
Up to 4 Guests
$129
$148
Not listed
Cozy 3 bedroom Apt Andersonville Neighborhood
Cozy 3 bedroom Apt Andersonville Neighborhood
Up to 4 Guests
$164
Not listed
Classic Lake House Retreat: BOOK NOW!
Classic Lake House Retreat: BOOK NOW!
Up to 12 Guests
$850
Not listed
Beautifully decorated ranch near beach & shops
Beautifully decorated ranch near beach & shops
Up to 6 Guests
$350
Not listed
Best Location! LUX 2/2 Condo 51st fl Amazing Views
Best Location! LUX 2/2 Condo 51st fl Amazing Views
Up to 4 Guests
$225
Not listed
Stunning Lake Views, Huge Deck, Water Fun!
Stunning Lake Views, Huge Deck, Water Fun!
Up to 12 Guests
$350
Not listed
Soft Suede and Warm Bricks at a Stylish Rogers Park Home
Soft Suede and Warm Bricks at a Stylish Rogers Park Home
Up to 5 Guests
$125
Not listed
Professionally Sanitized - Dome Away From Home
Professionally Sanitized - Dome Away From Home
Up to 8 Guests
$279
Not listed
Remodeled, Near Loyola, Beach and Subway
Remodeled, Near Loyola, Beach and Subway
Up to 6 Guests
$600
Not listed
Staycation Nautical 4/3 Waterfront w/ Bonus Room
Staycation Nautical 4/3 Waterfront w/ Bonus Room
Up to 9 Guests
$349
Not listed
HOT TUB w/ Views; Winter Getaway 12 Mins to Wilmot
HOT TUB w/ Views; Winter Getaway 12 Mins to Wilmot
Up to 14 Guests
$499
Not listed
Best Lincoln Square location. Spacious 2 bedroom
Best Lincoln Square location. Spacious 2 bedroom
Up to 4 Guests
$189
Not listed