Search for vacation rentals in Chicago.

Whether it's vacation home rentals, apartments, condos, or cabins/cottages, we have you covered -- search for rental properties in the entire Chicago area to find the perfect spot for your vacay.

7636 S Eberhart Ave
	7636 S Eberhart Ave Chicago, IL $1,800 Vacation Rentals, Unknown  NEW! Fresh and breezy house with 1bath and 2 bedrooms on the first floor and 2baths and 3 bedrooms on the second floor. Perfect for your living....

10123 S Crandon Ave
	10123 S Crandon Ave Chicago, IL $2,798 Vacation Rentals, Unknown  NEW! Welcome to your new home! Discover 10123 S Crandon, a 3-bedroom, 1.5-bathroom home designed for practical living. The open-concept layout connects a spacious living area to an eat-in kitchen with......

1114 W Grand Ave #3
	1114 W Grand Ave #3 Chicago, IL $2,000 Vacation Rentals, Unknown  NEW! Recently rehabbed the apartment features hard- wood floors, central air conditioning, quartz countertops with huge kitchen island, stainless steel appliances, private deck, high ceilings, walk in......

1928 N Bissell St
	1928 N Bissell St Chicago, IL $6,900 Vacation Rentals, Unknown  NEW! Come see this elegant, turn-of-the-previous century, Victorian home nestled on beautiful & quaint Bissell Street. A rehabbed home with a functional layout; All 3 bedrooms are on one floor; Cook in......

8500 S Rhodes Ave
	8500 S Rhodes Ave Chicago, IL $2,000 Vacation Rentals, Unknown  NEW! Beautiful, spacious single-family house is available for rent. The house has 3 full bathrooms, 4 bedrooms, dining room and a laundry, 2 car garage. The house located on the quite tree lined street......

12741 S Saginaw Ave
	12741 S Saginaw Ave Chicago, IL $1,700 Vacation Rentals, Unknown  NEW! Spacious and sun-filled 3 bedroom, 1 bathroom single family home. Freshly painted walls, brand new flooring, like-new kitchen with open layout to dining area. Water heater and A/C unit newly......

11309 S Stewart Ave
	11309 S Stewart Ave Chicago, IL $1,900 Vacation Rentals, Unknown  NEW! House is a 4 bed, 2 bath. One of the bedrooms is a Master's sweet, with bathroom, and a walk in closet. Freshly painted, new carpet, and appliances. Quite area near school. House has a fenced in......

W 125th St
	W 125th St Chicago, IL $1,500 Vacation Rentals, Unknown  NEW! Beautiful three bedroom home with large fenced backyard. SCHEDULE A SHOWING ONLINE AT: 3 bedroom ranch style home...

12114 S Wallace St
	12114 S Wallace St Chicago, IL $2,500 Vacation Rentals, Unknown  NEW! For more properties like this visit Affordable Housing....

2008 W 80th St
	2008 W 80th St Chicago, IL $1,375 Vacation Rentals, Unknown  NEW! Freshly painted home with beautiful hardwood floors. Two bedrooms with a spacious living room, dining room and eat in kitchen. There are 4 new ceiling fans throughout the home. Finished basement......

3303 S Bell Ave
	3303 S Bell Ave Chicago, IL $2,800 Vacation Rentals, Unknown  NEW! Single family home! This home has been partially updated, bright, & large split-level 3 bedrooms upstairs, 2 bathrooms, basement has been finished and can be used for an additional bedroom or use......

8003 S Marquette Ave
	8003 S Marquette Ave Chicago, IL $1,850 Vacation Rentals, Unknown  NEW! Must see this beautiful 5 bedroom 1.5 bathroom Home in Decatur! Enter into this ample living room, with vinyl floors and wooden details all around! Then step inside this dinner area, which is next......

6141 S Throop St
	6141 S Throop St Chicago, IL $2,900 Vacation Rentals, Unknown  NEW! AVAILABLE NOW IN THE FAST-GROWING WEST ENGLEWOOD COMMUNITY IS A GREAT FRAME BUNGALOW HOME. THIS HOME FEATURES A MODERN OPEN FLOOR CONCEPT, A SPACIOUS BACKYARD, A COVERED FRONT PORCH, AND A FULL......

7532 S Parnell Ave
	7532 S Parnell Ave Chicago, IL $1,300 Vacation Rentals, Unknown  NEW! FURNISHED 3-level 4BD/3 BTH single family home. Within walking distance to public transportation. Private 2- car detached garage parking and always open free street parking directly in front of the......

10924 S Wentworth Ave
	10924 S Wentworth Ave Chicago, IL $2,200 Vacation Rentals, Unknown For more properties like this visit Affordable Housing....

9227 S Yates Blvd
	9227 S Yates Blvd Chicago, IL $2,500 Vacation Rentals, Unknown Welcome to 9227 S Yates Blvd - where luxury living meets unparalleled comfort! This exquisite single-family home boasts 4 bedrooms, 2 bathrooms, and an array of amenities, making it the epitome of......

1306 E 69th St
	1306 E 69th St Chicago, IL $2,490 Vacation Rentals, Unknown Remodeled 5BR/2BTH House! Heat and Cooking Gas Included! No App Fee, No Security Deposit, No Move-in Fee! Remodeled 5-Bedroom Home with 2 Full Baths! New Kitchen with Hardwood Floors and Granite......

5869 N Central Ave
	5869 N Central Ave Chicago, IL $4,250 Vacation Rentals, Unknown Four bedroom three bathroom (plus one bedroom one bathroom in basement) house for rent. The house has spacious rooms with walk-in closet, hardwood floor throughout, quartz countertop, and......

11206 S Bishop St
	11206 S Bishop St Chicago, IL $3,000 Vacation Rentals, Unknown For more properties like this visit Affordable Housing....

1922 W Grace St
	1922 W Grace St Chicago, IL $125 Vacation Rentals, Unknown Welcome to luxury living in the heart of the city! This remarkable residence offers 6 bedrooms and 6 bathrooms on an extra-wide 38' corner lot, ensuring both space and style. The expansive main......

4527 S Drexel Blvd #3N
	4527 S Drexel Blvd #3N Chicago, IL $1,685 Vacation Rentals, Unknown Beautifully renovated 2bed/2bath apartment in vintage courtyard condominium building in Kenwood. Natural stained hardwood floors. Minutes from downtown Chicago. Blocks from Lake Michigan. Close to......

2020 N Tripp Ave
	2020 N Tripp Ave Chicago, IL $15 Vacation Rentals, Unknown Brand new 3 story luxury Home. Perfect for large or small groups.6 large bedrooms. All new furniture & bedding. Lots of natural light. Gorgeous kitchen.2 Family rooms. Rooftop deck & Bar with......

2453 N Richmond St
	2453 N Richmond St Chicago, IL $7,500 Vacation Rentals, Unknown Spacious and bright 4 level home with soaring 12' ceilings and desirable yard in prime Logan Square location steps to the Boulevard, Farmer's Market, Blue Line, and some of the best restaurants in......

8511 S Damen Ave
	8511 S Damen Ave Chicago, IL $2,200 Vacation Rentals, Unknown Beautiful Single Family Brick House. Sec 8 3 bedroom Voucher Holders are welcome. No Security Deposit. Move in fee $550....

6148 S Carpenter St
	6148 S Carpenter St Chicago, IL $2,500 Vacation Rentals, Unknown Beautiful Updated 4 Bed 2 Bath In Englewood $1,800 AVAILABLE NOW KEY FEATURES Bedrooms: 4 Beds Bathrooms: 1 Bath Lease Duration: 1 Year Pet Policy: Pets Negotiable Laundry: In Unit Floors: Redone......

5524 W Roscoe St
	5524 W Roscoe St Chicago, IL $3,300 Vacation Rentals, Unknown Imagine that a perfect peaceful place with a precious green yard is waiting for you after a long day. Imagine that once you enter, you will find a cozy fireplace, with hardwood floors which make it......

4184 S Wallace St
	4184 S Wallace St Chicago, IL $2,525 Vacation Rentals, Unknown GREAT LOCATION AND NICE 3 BEDROOM 1 1/2 BATH SINGLE HOUSE BEAUTIFUL APARTMENT IN THE HEART OF CHICAGO BRIDGEPORT. FEATURES 3 NICE SPACIOUS BEDROOMS WITH 1 & 1/2 BATH, LARGE LIVING ROOM/DINNER ROOM......

1530 W Adams St
	1530 W Adams St Chicago, IL $4,500 Vacation Rentals, Unknown ONE OF A KIND! AVAILABLE NOW WITH A 30 DAY MOVE. WEST LOOP Loft--Extraordinary Live/Work. This is an amazing stand alone live-work loft in the West Loop. A large private space in the rear is a......

700 W Van Buren St #910
	700 W Van Buren St #910 Chicago, IL $2,050 Vacation Rentals, Unknown 6/1/2024 Available! Beautiful 1Bd/1Ba Concrete Loft conveniently located in West Loop! Walking distance to office buildings in the loop, Union Station, Greek Town, trendy restaurants and......

1321 N Bosworth Ave #2N
	1321 N Bosworth Ave #2N Chicago, IL $3,895 Vacation Rentals, Unknown Amazing unit! Great location! Duplex down, by Wicker Park/Bucktown/Noble Square area. 3 bedrooms, 2 baths, jacuzzi, double vanity, Beautiful open layout, living room, fireplace, gourmet kitchen,......

9339 S Eberhart Ave
	9339 S Eberhart Ave Chicago, IL $2,550 Vacation Rentals, Unknown Welcome to this charming 3-bedroom, 2-bathroom Brick Bungalow nestled in the heart of Chicago. Step into the updated kitchen, boasting modern amenities and style. With sleek stainless steel......

136 E 119th St
	136 E 119th St Chicago, IL $2,250 Vacation Rentals, Unknown HUGE HOUSE!! HUGE AND BEAUTIFUL TWO STORY HOUSE!! FORMAL LIVING, DINNING ROOM, LARGE KITCHEN, HUGE MASTER BEDROOM ON THE 2ND FLOOR WITH WALKING CLOSET GREAT FOR A LARGE FAMILY, GATED, HARDWOOD......

10024 S Campbell Ave
	10024 S Campbell Ave Chicago, IL $2,800 Vacation Rentals, Unknown This home for rent is a 3 bedroom, 2 bathroom raised ranch in the heart of West Beverly, Chicago, Illinois. Built in 1949, this 2,200 sq ft house has undergone extensive renovations in the past 4......

10237 S La Salle St
	10237 S La Salle St Chicago, IL $1,850 Vacation Rentals, Unknown **Huge house on nice block Formal living room, dinning room house with 5 bedrooms and 3baths First floor with huge formal living, dinning area. Lovely kitchen and 2 bedrooms with bath 2nd floor......

17 E 120th St
	17 E 120th St Chicago, IL $2,300 Vacation Rentals, Unknown Come to see this sensational experience! Don't miss out the opportunity to get this cozy home for rent, which is in a good location,and a pretty neighborhood too! Feel at home with it's classic......

209 N La Crosse Ave
	209 N La Crosse Ave Chicago, IL $2,500 Vacation Rentals, Unknown Newly converted brick home located in the heart of the Austin community. Ceramic and hardwood floors, granite countertops, 4 bedroom, 2 bath, vaulted ceilings. Quit block with friendly neighbors......

9252 S Merrill Ave
	9252 S Merrill Ave Chicago, IL $1,175 Vacation Rentals, Unknown 2 BEDROOMS / 1 BATH / APPLIANCES INCLUDED / COIN LAUNDRY ON SITE Welcome to your new cozy abode! This delightful unit features 2 bedrooms and 1 bath, complete with appliances for your convenience.......

205 W 109th Pl
	205 W 109th Pl Chicago, IL $2,300 Vacation Rentals, Unknown Single Family Home Single family home for rent. 5 bedrooms, 2 full bathrooms. In good condition. Fence yard, 2 car garage and central air conditioning. For more properties like this visit......

9710 S Dobson Ave
	9710 S Dobson Ave Chicago, IL $1,895 Vacation Rentals, Unknown Many upgrades. Freshly painted, recessed lights, refreshed baths, refinished hardwood floors, new kitchen with new appliances and granite countertops. Full finished walk-out basement. No pets and......

1758 N Whipple St
	1758 N Whipple St Chicago, IL $3,750 Vacation Rentals, Unknown Single family with massive yard right next to the 606 in Logan Square! 4 bedrooms 2.5 bathrooms, with many updates including newer roof, newer central heat and air, new windows, side by side washer......