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.

5833 W Midway Park

5833 W Midway Park

Chicago, IL
$1,195
Vacation Rentals, Unknown  NEW!
Spacious 2BR TOP floor unit located in a quaint 2 unit building, Chicago/OakPark area. Located in the Historic District of Austin, the neighborhood......

1800 W Ohio Street

1800 W Ohio Street

Chicago, IL
$4,000
Vacation Rentals, Unknown  NEW!
Beautiful Single Family Home with 2 car garage across street from Talcottschool, park and playground. Close to Chicago Ave...great family friendly......

8036 S Lafayette Avenue

8036 S Lafayette Avenue

Chicago, IL
$1,450
Vacation Rentals, Unknown  NEW!
Fully rehabbed and luxury property. 3 bedrooms, 1 bathroom. Section 8 Accepted.Amazing Brick Single family home, close to I-90/94 and close to......

8619 S Lowe Avenue

8619 S Lowe Avenue

Chicago, IL
$1,450
Vacation Rentals, Unknown  NEW!
Brick 3-Bedroom Splltt-Level in the Ashburn Gresham area. Recently fixed up withnew Stainless-Steel Appliances, recessed lights, maple cabinets, granite,......

2443 N Lorel Avenue

2443 N Lorel Avenue

Chicago, IL
$1,350
Vacation Rentals, Unknown
This beautiful total rehabbed apartment located in a very quiet neighborhood ofBelmont Cragin available NOW. Main floor boasts lots of natural light in a......

113 W Chestnut Street

113 W Chestnut Street

Chicago, IL
$15,000
Vacation Rentals, Unknown
The Chestnut Row Homes provide a rare opportunity for single-family living inthe heart of downtown Chicago. The seven row homes match that of the......

3826 N Greenview Avenue

3826 N Greenview Avenue

Chicago, IL
$1,495
Vacation Rentals, Unknown
3815-23 N. Greenview. Great., 1 bedroom apartments in a beautiful courtyardbuilding just off of Southport within walking distance to restaurants,......

11235 S King Drive

11235 S King Drive

Chicago, IL
$1,050
Vacation Rentals, Unknown
Large 2bed+/1bath units. Fully renovated in 2014 with all new plumbing andelectric. Hardwood floors throughout. New stainless steel kitchen......

844 W Ainslie Street

844 W Ainslie Street

Chicago, IL
$1,075
Vacation Rentals, Unknown
Lovely & bright, newly remodeled 1 bedroom/1 bath garden unit located in theUptown neighborhood! Unit features include new appliances, new hardwood......

6171 N Sheridan Road

6171 N Sheridan Road

Chicago, IL
$1,390
Vacation Rentals, Unknown
The Panoramic View, The Beach, The Amenities, The Location, Large One BedroomCondo For Rent This high rise condominium building has its front feet in......

904 W 87th Street

904 W 87th Street

Chicago, IL
$1,650
Vacation Rentals, Unknown
Owner wants 6 bedroom Section 8 voucher" Fully rehabbed and luxury property. 5bedrooms, 2 bathroom. Amazing Brick Single family home, close to I-90/94......

3255 N Kenneth Avenue

3255 N Kenneth Avenue

Chicago, IL
$1,750
Vacation Rentals, Unknown
Great single family home for rent. 1 bedroom down and two up (dormer) with afull bath on each level. In the process of being totally rehabbed. Big......

6738 N Lakewood Avenue

6738 N Lakewood Avenue

Chicago, IL
$1,795
Vacation Rentals, Unknown
Property Id: 138320 Hardwood flooring throughout, modern eat-in kitchen, updatedbathroom, decorative fireplace, sun room, up to 2 cats OK with $50......

4015 N Leclaire Avenue

4015 N Leclaire Avenue

Chicago, IL
$1,185
Vacation Rentals, Unknown
WOW Great 2 bedroom unt on the second floor. Central heat and AC, Hardwoodfloors. Great location, close to public transportation, stores , park and

422 N Noble Street

422 N Noble Street

Chicago, IL
$1,745
Vacation Rentals, Unknown
In-unit laundry! Gorgeous West Town 850 sf 1 bed 1 bath condo with tons ofspace. Unit features hardwood floors throughout, granite and stainless......

4955-57 N Damen Avenue

4955-57 N Damen Avenue

Chicago, IL
$1,425
Vacation Rentals, Unknown
Available September 1st! This cozy second floor 1 Bed/1 Bath is in a greatRavenswood location, within walking distance of the Damen Brown Line and a......

W Leland Avenue

W Leland Avenue

Chicago, IL
$1,950
Vacation Rentals, Unknown
2 bedroom 2 bath ensuite, modern, apt steps from the brownline. Amenitiesinclude: Granite counters, high ceilings (loft), central air, in-unit......

N Monticello Avenue

N Monticello Avenue

Chicago, IL
$1,400
Vacation Rentals, Unknown
Rehabbed 2BR/1BA Apartment in Old Irving Park! Central Heat / Air, StainlessSteel Appl w/ Dishwasher! This Updated 2 Bedroom, 1 Bathroom unit has......

1210 W Waveland Avenue

1210 W Waveland Avenue

Chicago, IL
$1,950
Vacation Rentals, Unknown
Renovated Lakeview 2BD Apt w/ In unit laundry. Close to Red Line! Locatedinbetween the Sheridan Red/Purple Line and the Southport Brown Line -......

4707 S King Drive

4707 S King Drive

Chicago, IL
$2,500
Vacation Rentals, Unknown
Apply Today, Move Tomorrow! If you have been searching Bronzeville for somethingcompletely modern and reasonably priced or if you need to move quickly or if......

3032 N Halsted Unit Ig1-b

3032 N Halsted Unit Ig1-b

Chicago, IL
$1,115
Vacation Rentals, Unknown
Vintage rehabbed one bedroom, one bath in Lakeview features updated kitchen,updated ceramic tile bath, on-site laundry, cats welcome, convenient to

1255 N Sandburg Terrace

1255 N Sandburg Terrace

Chicago, IL
$1,800
Vacation Rentals, Unknown
Great 1 bd, 1 ba condo for rent in the heart of the city. Pool and parkingavailable. Steps from transportation, brand new Jewel, Lake Michigan,......

519 W Brompton Avenue

519 W Brompton Avenue

Chicago, IL
$995
Vacation Rentals, Unknown
Affordable East Lakeview studio steps from Lake Shore Drive and Belmont Harbor.Easy commute to downtown with express bus stop right on the corner.......

3038 N Halsted Unit Ig1-a

3038 N Halsted Unit Ig1-a

Chicago, IL
$975
Vacation Rentals, Unknown
Fantastic studio in a well maintained courtyard building in Lakeview atWellington and Halsted features heat, water, and cooking gas included,......

3038 N Halsted Street

3038 N Halsted Street

Chicago, IL
$1,650
Vacation Rentals, Unknown
Affordable vintage 2bed/2bath in perfect East Lakeview location walking distancefrom Red/Brown/Purple line trains and all the entertainment options......

520 W Stratford Unit C103

520 W Stratford Unit C103

Chicago, IL
$995
Vacation Rentals, Unknown
Fabulous studio in East Lakeview features heat and cooking gas included, updatedeat in kitchen, spacious living area, amazing closet space, newer......

3028 N Halsted Unit Three-c

3028 N Halsted Unit Three-c

Chicago, IL
$1,125
Vacation Rentals, Unknown
Appealing and affordable one bedroom, one bath in Lakeview offers large queensize bedroom, refinished hardwood floors throughout, built-in breakfast......

3034 N Halsted Unit Ig1-c

3034 N Halsted Unit Ig1-c

Chicago, IL
$1,125
Vacation Rentals, Unknown
Spacious one bedroom, one bath in Lakeview offers large queen size bedroom,hardwood floors throughout, built-in breakfast bar, on-site laundry,......

1460 N Sandburg Terrace

1460 N Sandburg Terrace

Chicago, IL
$3,699
Vacation Rentals, Unknown
Best designer rehab in Sandburg!. High end kitchen with Stainless steelappliances, range hood, granite, 42 in cabinets. dishwasher, microwave, LG......

429 W Belden Avenue

429 W Belden Avenue

Chicago, IL
$1,050
Vacation Rentals, Unknown
Lincoln Park studio one bathroom rehab with newer kitchen, plenty of closetspace, and hardwood floors throughout. Building features on-site laundry and......

3720 N Pine Grove Avenue

3720 N Pine Grove Avenue

Chicago, IL
$1,350
Vacation Rentals, Unknown
Renovated One bed in Lakeview w/ No Security Deposit. Walk to lake & Red Line!Walk to everything - the lake is two blocks away, the Red Line is four......

9020 S Carpenter Street

9020 S Carpenter Street

Chicago, IL
$1,500
Vacation Rentals, Unknown
com/lt/5a53e5308a 4 BDRMS / 2 BTHS - CENTRAL AIR - GRANITE - GARAGE Great SFHwith 4 large bedrooms, garage, central air, recessed cans, open floor......

2022 N Wolcott Avenue

2022 N Wolcott Avenue

Chicago, IL
$9,000
Vacation Rentals, Unknown
Spectacular Bucktown home with three levels, soaring ceilings, skylights, lotsof windows and high-level finishes. Luxurious, design-forward retreat......

545 N Dearborn Street #904

545 N Dearborn Street #904

Chicago, IL
$2,600
Vacation Rentals, Unknown
Live the dream in this one of a kind heart of River North large one bed withYOUR OWN secluded 850 sf deck with grill, hammock, patio furniture,......

545 N Dearborn Street

545 N Dearborn Street

Chicago, IL
$3,000
Vacation Rentals, Unknown
Located in desirable River North neighborhood within walking distance of: RedLine Train Metra Stations Bus Lines Lake Michigan Northwestern Hospital......

S King Drive

S King Drive

Chicago, IL
$1,500
Vacation Rentals, Unknown
Available now! 3-Bed|2-BATHS CONDO IN HYDE PARK AREA. 3 BEDROOM SECTION 8VOUCHER ACCEPTED. ALL CASH TENANTS ACCEPTED. ALL CREDIT ACCEPTED.......

N Milwaukee Avenue

N Milwaukee Avenue

Chicago, IL
$1,300
Vacation Rentals, Unknown
New gut rehab with granite, stainless, dishwasher, central HVAC and hardwood!Parking included! "Look and Lease": $250 off 2nd month's rent if prospect......

932 W Dakin Street

932 W Dakin Street

Chicago, IL
$2,400
Vacation Rentals, Unknown
Please TEXT for FASTER response!! 312-857-8306 De' Xeunxom Gut Rehabbed Duplex 2bedroom / 2 bathroom in Wrigleyville area just steps to CTA "L" Red Line......

W Chestnut Street

W Chestnut Street

Chicago, IL
$3,607
Vacation Rentals, Unknown
PERFECT GOLD COAST LOCATION! NEWLY UPDATED 2BED, 2BATH! Spacious layout Largewindows Stainless steel apps Dark-colored cabinetry Granite countertops......

N Elston Avenue

N Elston Avenue

Chicago, IL
$1,500
Vacation Rentals, Unknown
Condo Quality 2BR in Irving Park - Hardwood Floors - Granite Countertops -Stainless Steel Appliances - Dishwasher - In-Unit Laundry - 2 Blocks for......

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Chicago, IL

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