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.

205 W 109th Pl
	205 W 109th Pl Chicago, IL $2,300 Vacation Rentals, Unknown  NEW! 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  NEW! 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  NEW! 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......

3457 S Lituanica Ave
	3457 S Lituanica Ave Chicago, IL $4,995 Vacation Rentals, Unknown  NEW! Phenomenal opportunity to rent this massive, gut rehabbed, 5-bedroom single family home, situated on a lot with no buildings on either side in the most desirable sweet spot of Bridgeport. Walking......

10107 S Yates Blvd
	10107 S Yates Blvd Chicago, IL $1,800 Vacation Rentals, Unknown  NEW! 3Bedroom House For Rent Solid 3bedroom all brick home for rent. The house was recently updated and features a full basement, big back and front yard. Updates include; new roof, tuck-pointing,......

1 E Scott St #910
	1 E Scott St #910 Chicago, IL $2,100 Vacation Rentals, Unknown  NEW! AMAZING LOCATION. BRIGHT AND AIRY ONE BEDROOM FEATURES FLOOR TO CEILING WINDOWS, 24 HR. DOORMAN, LAUNDRY, OUTDOOR POOL, SUNDECK. BRAND NEW PAINT AND CARPET BEING INSTALLED!! EASY ACCESS TO......

222 E Pearson St #2104
	222 E Pearson St #2104 Chicago, IL $2,795 Vacation Rentals, Unknown  NEW! Take a look at this incredible 2-bedroom 1-bath space in the heart of Streeterville. This condo is perfectly situated across the street from Lurie Childrens and Northwestern Medical and Law......

2527 S Stark St
	2527 S Stark St Chicago, IL $5,000 Vacation Rentals, Unknown  NEW! GREAT ALL BRICK HOME ON CUL-DE-SAC IN BRIDGEPORT! THE LARGE KITCHEN FEATURES GRANITE COUNTERS AND SS APPLIANCES. GLEAMING HARDWOOD FLOORS THROUGHOUT THE 1ST FLR. PRIMARY BEDROOM SUITE CONTAINS WIC......

538 W Dickens Ave
	538 W Dickens Ave Chicago, IL $6,000 Vacation Rentals, Unknown  NEW! Awesome Designer Home in the heart of Lincoln Park AVAILABLE July 1st Large 3 bedroom, 3 bath single family home, 3800sqft. Fabulously designed home with all luxuries including an elevator & 2 1/2......

4912 S Lamon Ave
	4912 S Lamon Ave Chicago, IL $4,000 Vacation Rentals, Unknown  NEW! Newly renovated. Basement: 1 room and 1 big living room and laundry room and bathroom First floor : Master bedroom opens to backyard deck, kitchen, living room and bathroom Second floor: 2 rooms......

7320 S Bell Ave #HOUSE
	7320 S Bell Ave #HOUSE Chicago, IL $1,700 Vacation Rentals, Unknown Updated house with all new wood floors, new roof , furnance, water heater, paint local landlord...

3618 N Plainfield Ave
	3618 N Plainfield Ave Chicago, IL $2,100 Vacation Rentals, Unknown This one level, updated, freshly painted single family ranch home. Backroom can be used as a 3rd bedroom or office, Living Room dining combo, SS kitchen appliances with brand new cabinets. No......

6732 S Indiana Ave
	6732 S Indiana Ave Chicago, IL $2,200 Vacation Rentals, Unknown UNDER CONSTRUCTION Section 8 welcome No security deposit needed to move in...

4847 N Natchez Ave
	4847 N Natchez Ave Chicago, IL $3,000 Vacation Rentals, Unknown Welcome to this lovely ranch-style home nestled in a the quiet Big Oaks neighborhood of Chicago. With 4 bedrooms and 2 full bathrooms, this residence offers comfortable living and modern......

8341 S Constance Ave
	8341 S Constance Ave Chicago, IL $2,700 Vacation Rentals, Unknown CHARMING!! It's the only way to describe this awesome 1.5 Story home. Exceptionally rehabbed from top to bottom and ready for you to call home. The interior features 4 bedrooms and 2 full baths and......

4820 W Iowa St
	4820 W Iowa St Chicago, IL $1,999 Vacation Rentals, Unknown Nice and quiet neighborhood. Owner pays for trash and water and sewage, Tenant pays for Gas and Electricity, move in fees applicable. Cat owners are welcome!...

2614 W Fitch Ave
	2614 W Fitch Ave Chicago, IL $1,350 Vacation Rentals, Unknown This spacious condo is located at 2614 W Fitch Ave #GN, Chicago, IL in the West Rogers Park neighborhood in Chicago comes with 1 Bed with lots of natural light and a bath which is recently......

8205 S California Ave
	8205 S California Ave Chicago, IL $2,300 Vacation Rentals, Unknown We are currently making final preparations for this home to be available. We make Pre-Leasing easy! Apply now and, once you're approved, take this home off the market by paying a Pre-Lease Hold......

7215 S Yates Blvd #2A
	7215 S Yates Blvd #2A Chicago, IL $1,095 Vacation Rentals, Unknown Introducing a charming 1-bedroom, 1-bathroom gem nestled in South Shore! This delightful residence boasts a seamless fusion of style and functionality. Step into an inviting open kitchen/living......

460 N Noble St
	460 N Noble St Chicago, IL $4,500 Vacation Rentals, Unknown With 4 beds and 2.5 baths, this residence offers a seamless blend of comfort and modern design. The first floor connects the living, dining, kitchen, and main floor bedroom. Featuring a......

S Indiana Ave
	S Indiana Ave Chicago, IL $1,950 Vacation Rentals, Unknown Beautiful newly remodel 4 bedroom, 2 bathroom home with a two car garage. This home is located on nice and quiet block in the Chicago area, Section 8 welcome with qualifications! Please call Ms.......

12249 S Normal Ave
	12249 S Normal Ave Chicago, IL $2,250 Vacation Rentals, Unknown Introducing a charming single-family home in West Pullman, IL. This recently rehabbed property boasts new everything, including a modern kitchen with granite counters, gas stove/oven, and......

9732 S Peoria St
	9732 S Peoria St Chicago, IL $2,500 Vacation Rentals, Unknown Furnished 4 Beds 2 baths home $1,500 move-in fee. Renter's insurance required. 620+ credit. Must have 3+ voucher size and amount. Property Coming soon in May. For more properties like this visit......

3234 N Osceola Ave
	3234 N Osceola Ave Chicago, IL $3,000 Vacation Rentals, Unknown Lovely home with 2 living spaces New appliances Large back yard. Wonderful neighbors...

2327 N Halsted St
	2327 N Halsted St Chicago, IL $4,650 Vacation Rentals, Unknown Renovated Lincoln Park row home with extra wide & bright interior. The large living room has a wood-burning fireplace with a vintage mantle. Updated kitchen with SS appliances & granite countertops......

654 N Talman Ave
	654 N Talman Ave Chicago, IL $2,900 Vacation Rentals, Unknown Brand new 2nd floor complete rehab luxury rental in Ukrainian Village neighborhood, one block walk to smith park. Spacious 2bed/1bath for $2900/month. Brand new Black Stainless Steel appliances,......

4378 W 25th Pl
	4378 W 25th Pl Chicago, IL $1,500 Vacation Rentals, Unknown 3B 1B no refrigerator nor stove included.Little Village community very accessible to restaurants and commercial centers. Close by to public transportation and highways....

1523 W Altgeld St
	1523 W Altgeld St Chicago, IL $9,800 Vacation Rentals, Unknown Stunning 4 bedroom home with phenomenal open floor plan. Large living and dining room greet you upon entry with lovely, dark hardwood floors. Gorgeous kitchen opens to large family room that has......

5822 W Catalpa Ave
	5822 W Catalpa Ave Chicago, IL $3,500 Vacation Rentals, Unknown Open living space w/ new hardwood floors, cathedral/vaulted ceilings! 42" new costume cabinets /granite/ New SS appliances/skylight opens to a deck. Finished basement w/ huge family room/fireplace.......

2434 W 47th Pl
	2434 W 47th Pl Chicago, IL $1,450 Vacation Rentals, Unknown Cozy fully rehab home available in Brighton Park. 2 blocks from the Western Orange Line stops. Available for whole home rental or individual rooms. Wash and Dryer available...

11641 S Campbell Ave
	11641 S Campbell Ave Chicago, IL $3,500 Vacation Rentals, Unknown Beverly Woods 4 bdrm 1 1/2 brick house 4 bedroom 1 1/2 bath full basement brick home located in Beverly Woods (mobility) area near Western 115th street For more properties like this visit......

10330 S Walden Pkwy
	10330 S Walden Pkwy Chicago, IL $5,000 Vacation Rentals, Unknown Beautiful 5 bedroom 2 bath house located in the Beverly District. The home is close to the Metra line, coffee shops, dining, shopping, and public transportation....

1621 S Komensky Ave #1A
	1621 S Komensky Ave #1A Chicago, IL $975 Vacation Rentals, Unknown Welcome to 1621 S Komensky Ave Apt 1A in Chicago, IL! This modern 1-bedroom, 1-bathroom apartment features hardwood flooring throughout, stainless steel appliances, and sleek modern finishes.......

8622 S Justine St
	8622 S Justine St Chicago, IL $2,425 Vacation Rentals, Unknown ASK ABOUT OUR CASHLESS SECURITY DEPOSIT OPTION! Gorgeous home in a beautiful neighborhood! This spacious 3 bedroom, 2 bathroom single-family home in Chicago features: Keyless Locks, Smart......

1920 W Cermak Rd #1R
	1920 W Cermak Rd #1R Chicago, IL $1,295 Vacation Rentals, Unknown Studio with den. Laundry in building (interior access). Great location with the CTA Pink Line Damen Avenue station less than 3 blocks away. Newly remodeled kitchen with espresso cabinets and......

3806 N Wilton Ave
	3806 N Wilton Ave Chicago, IL $4,200 Vacation Rentals, Unknown ENTIRE SINGLE FAMILY HOME! - 4 BDRS| FULL BASEMENT | 2-CAR GARAGE INCL. - Available June 1. Recently rehabbed greystone SINGLE FAMILY HOME features new Kitchen-maple cabinets, granite counters & SS......

2342 N Hamlin Ave
	2342 N Hamlin Ave Chicago, IL $5,250 Vacation Rentals, Unknown Impeccable 4 bed, 3.1 bath single family home on a 30 ft lot. Contemporary facade with fenced in front yard. Spacious, open concept main level floor plan with hardwood flooring, great natural......

3010 N Troy St
	3010 N Troy St Chicago, IL $850 Vacation Rentals, Unknown A single room for rent in a family house in the basement at Avondale/ Logan Square. The bathroom is shared with one person . With central AC, kitchen and laundry in the basement. $850per month all......

2140 N Oakley Ave #HOUSE
	2140 N Oakley Ave #HOUSE Chicago, IL $15 Vacation Rentals, Unknown This is a truly stunning 3 bedroom 3.5 bath single family on a double-wide 48 foot lot in the heart of Chicago's vibrant Bucktown neighborhood. This luxurious home offers a spacious and......

2342 W 91st St
	2342 W 91st St Chicago, IL $2,600 Vacation Rentals, Unknown Freshly painted home with all appliances. Easy walking to public transport and a great quiet neighborhood in the Beverly area on 91st western. 2 car street parking in front of the house. Home is......