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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.

4253 N Mason Ave

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4253 N Mason Ave

Chicago, IL
(Contact seller for price)
Vacation Rentals, Unknown
MOVE-IN READY! Gorgeous brick bungalow in Portage Park with space to spread out, entertain, and relax! This newly updated home offers 5 bedrooms, 3 full baths, and over 2,500 square feet of......

4552 N Drake Ave #1B

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4552 N Drake Ave #1B

Chicago, IL
(Contact seller for price)
Vacation Rentals, Unknown
HURRY! Completely updated 1 bedroom/1 bath is waiting for you! Spacious bedroom will fit queen size bed and have ample room for a dresser. The living room has tall windows to allow natural lighting......

S Harding Ave

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S Harding Ave

Chicago, IL
(Contact seller for price)
Vacation Rentals, Unknown
Conveniently located in a forest Chicago neighborhood this 4 Bed/2Bath Huge brick Cape Cod home with great curb appeal. This property is 7 minutes from midway airport, easy access to I55, down the......

8730 S Halsted St

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8730 S Halsted St

Chicago, IL
(Contact seller for price)
Vacation Rentals, Unknown
Welcome Home!! This property boasts 4 bedrooms and 1 bathroom located in the Auburn Gresham neighborhood. Large living room, separate dining room, and an updated kitchen. Main level has 2 bedrooms......

4914 W Warwick Ave

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4914 W Warwick Ave

Chicago, IL
(Contact seller for price)
Vacation Rentals, Unknown
Welcome to your new home in the heart of Chicago's charming Portage Park neighborhood! This lovely single-family residence offers a mix of classic charm and modern amenities, making it perfect for......

8405 S Hamilton Ave

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8405 S Hamilton Ave

Chicago, IL
(Contact seller for price)
Vacation Rentals, Unknown
Welcome to this stunning, fully rehabbed home in the sought-after Auburn Gresham neighborhood! Every detail has been meticulously updated, featuring brand-new windows, completely remodeled......

11156 S Parnell Ave

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11156 S Parnell Ave

Chicago, IL
(Contact seller for price)
Vacation Rentals, Unknown
3bed/2bath brick single family home available now. Features include: Hardwood floors. Freshly painted. Updated kitchen with new floor and backsplash. Full dining room. Parking pad in rear of......

9336 S Forest Ave

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9336 S Forest Ave

Chicago, IL
(Contact seller for price)
Vacation Rentals, Unknown
Welcome home! This completely rehabbed house is waiting for the perfect tenant! Updates include new flooring, fresh paint, bathroom and kitchen updates, new light fixtures, and so much more! The......

6351 S Parnell Ave

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6351 S Parnell Ave

Chicago, IL
(Contact seller for price)
Vacation Rentals, Unknown
A totally renovated single family home that features three bedrooms and two bathrooms with modern upgrades and contemporary accents. Open floor plan, high ceilings, large windows, custom lighting,......

1920 W Cermak Rd #3R

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1920 W Cermak Rd #3R

Chicago, IL
(Contact seller for price)
Vacation Rentals, Unknown
One bed + Office. Laundry in building (interior access). Great location with the CTA Pink Line Damen Avenue station less than 3 blocks away. Newly remodeled kitchen with granite countertops and......

1007 N Drake Ave

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1007 N Drake Ave

Chicago, IL
(Contact seller for price)
Vacation Rentals, Unknown
Single family with 2 kitchens. Ideal for a family with parents or share with sibling...

4413 W Iowa St

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4413 W Iowa St

Chicago, IL
(Contact seller for price)
Vacation Rentals, Unknown
Two-bedroom apartment available for rent in December in the West Humboldt Park! This bright and cozy 2nd-floor unit features 1.5 baths, laminate wood flooring throughout, and a modern kitchen with......

4656 N Malden St

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4656 N Malden St

Chicago, IL
(Contact seller for price)
Vacation Rentals, Unknown
Great rental near transportation, the lake, Truman College, amazing restaurants, shopping and more. Unit features: Stainless steel Appliances including dishwasher and microwave -Hardwood Flooring......

9955 S May St

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9955 S May St

Chicago, IL
(Contact seller for price)
Vacation Rentals, Unknown
Welcome Home! This property boasts 4 bedrooms and 1.5 bathrooms, located in the Washington Heights neighborhood. There is a separate living room and dining room, with an updated kitchen. 3 bedrooms......

12725 S Saginaw Ave

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12725 S Saginaw Ave

Chicago, IL
(Contact seller for price)
Vacation Rentals, Unknown
Welcome to this inviting 3-bedroom, 1-bathroom pet-friendly home offering 986 sq ft of comfortable living space. The kitchen is equipped with essential appliances, including a refrigerator and......

1000 W Washington Blvd #127

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1000 W Washington Blvd #127

Chicago, IL
(Contact seller for price)
Vacation Rentals, Unknown
West Loop Timber Duplex Loft - Features include: 20' timber ceilings, beams and columns. Lofted master bedroom with two walk-in closets, dual vanities and soaking tub. Hardwood floors throughout on......

6139 W Byron St

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6139 W Byron St

Chicago, IL
(Contact seller for price)
Vacation Rentals, Unknown
A very nice room with big closet with mirrors doors available now for rent for nonsmoking working man. Monthly price is $800 plus one month deposit. All utilities are included to rent price....

2010 W 115th St

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2010 W 115th St

Chicago, IL
(Contact seller for price)
Vacation Rentals, Unknown
Amazing 4 beds one bath house for rent Location 115 and longwood Dr Good and quiet neighbor Huge kitchen and living room with high ceilings Great for short term and long term rental...

11221 S Avenue H

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11221 S Avenue H

Chicago, IL
(Contact seller for price)
Vacation Rentals, Unknown
This 5 bedroom 2 bath completely remodeled Brick Ranch is move in ready. The first floor boasts bamboo hardwood floors throughout with the exception of the beautiful tile on the bathroom floor.......

12549 S Yale Ave

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12549 S Yale Ave

Chicago, IL
(Contact seller for price)
Vacation Rentals, Unknown
THIS IS A MUST-SEE! 4 bed - 1 and 3/4 bath raised brick ranch with a finished basement in the West Pullman Area. Updates include refreshed hardwood flooring on the main level, new flooring in the......

N Ashland Ave

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N Ashland Ave

Chicago, IL
(Contact seller for price)
Vacation Rentals, Unknown
Enjoy a FULLY FURNISHED classic Chicago Greystone built in 1893 and renovated in 2023, a true mix of old charm with modern touches of art deco and Scandinavian design. Available for monthly......

713 E 88th Pl

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713 E 88th Pl

Chicago, IL
(Contact seller for price)
Vacation Rentals, Unknown
Beautifully maintained spacious 4 Bedroom, 2 Bath with a classic brick exterior and an inviting cozy front porch, with an excellent curb appeal, and a welcoming entrance in the Auburn Greshman......

3525 W Walnut St

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3525 W Walnut St

Chicago, IL
(Contact seller for price)
Vacation Rentals, Unknown
Beautifully designed rowhouse right across the street from the Garfield Park Conservatory. 3 bedrooms and 2.5 baths including gorgeous en suite with huge stand up shower. Open livingroom/dining......

12325 S Parnell Ave

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12325 S Parnell Ave

Chicago, IL
(Contact seller for price)
Vacation Rentals, Unknown
COMING SOON! Discover this spacious 5 bedroom, 2 bathroom home nestled in the heart of Chicago's West Pullman neighborhood. With ample room for comfortable living, this home offers a bright and......

1833 N Milwaukee Ave

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1833 N Milwaukee Ave

Chicago, IL
(Contact seller for price)
Vacation Rentals, Unknown
Charming Single-Family Home in the Heart of Bucktown Spacious, Convenient, and Pet-Friendly! Nestled right on Milwaukee Ave, this charming 3-bedroom, 2-bath single-family home in Bucktown is just......

3646 N Wilton Ave

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3646 N Wilton Ave

Chicago, IL
(Contact seller for price)
Vacation Rentals, Unknown
Discover timeless elegance and modern luxury in this rare Greystone with breathtaking Wrigley Field views. This 4-bedroom, 2.1-bath home spans three meticulously restored levels, showcasing......

W 114th St

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W 114th St

Chicago, IL
(Contact seller for price)
Vacation Rentals, Unknown
Three level home, 3 bedrooms and full baths with a bonus room. Finished basement. Appliances To prequalify or apply, download the RentRedi app from Google Play or the App Store. For applying......

4718 W McLean Ave

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4718 W McLean Ave

Chicago, IL
(Contact seller for price)
Vacation Rentals, Unknown
A big home for rent for a big group/family. Includes the first and second floor, with 4 bedrooms, 3 baths, and a garage space. You will feel right at home. It is located in a family-oriented......

3518 W Huron St

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3518 W Huron St

Chicago, IL
(Contact seller for price)
Vacation Rentals, Unknown
Newly remodeling home with a large living room and dining room, new appliances and a large back yard....

6300 W Bryn Mawr Ave

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6300 W Bryn Mawr Ave

Chicago, IL
(Contact seller for price)
Vacation Rentals, Unknown
Great location in Norwood Park. This 4 bedroom English Tudor home has recently been updated. Freshly painted throughout, hardwood floors sealed, updated kitchen with stainless appliances and white......

10312 S Claremont Ave

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10312 S Claremont Ave

Chicago, IL
(Contact seller for price)
Vacation Rentals, Unknown
The application fee is $20 per household. **long-term and short-term (minimum 30days)** Make this charming 3 bedroom 2.5 bathroom house your new home! This home features a bright and spacious......

5602-04 N Saint Louis Ave #5604

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5602-04 N Saint Louis Ave #5604

Chicago, IL
(Contact seller for price)
Vacation Rentals, Unknown
Spacious multi-level + basement townhouse in Hollywood Park. 3 bedrooms + 4th bedroom (or office/den) on the 1st floor, 2 baths, a large basement. Townhouse is newly updated. Kitchen has new......

5449 N Lynch Ave

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5449 N Lynch Ave

Chicago, IL
(Contact seller for price)
Vacation Rentals, Unknown
Lease this home and get more from Invitation Homes professional property management. This home comes fully loaded with quality amenities, must-have services, high-end tech and 24/7 emergency......

9210 S Bennett Ave

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9210 S Bennett Ave

Chicago, IL
(Contact seller for price)
Vacation Rentals, Unknown
**Join Us for the First Open House: Sunday, November 3rd, 4:00 PM - 5:00 PM. All applicant types are welcome, including voucher holders.** Welcome to 9210 S Bennett Ave, a rare rental opportunity......

635 E 90th Pl

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635 E 90th Pl

Chicago, IL
(Contact seller for price)
Vacation Rentals, Unknown
Step into this stylish 3-bed, 1-bath haven with gleaming hardwood floors, a modern kitchen featuring new appliances, and a private gated backyard. Perfect for both relaxation and entertaining, this......

10118 S May St

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10118 S May St

Chicago, IL
(Contact seller for price)
Vacation Rentals, Unknown
Spacious 5-bedroom, 1.5-bathroom home available in Washington Heights! This bright, welcoming house features a large living area, well-equipped kitchen, and generously sized bedrooms. Enjoy the......

3006 N Lowell Ave

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3006 N Lowell Ave

Chicago, IL
(Contact seller for price)
Vacation Rentals, Unknown
This house has 2 full bathrooms, 4 large bedrooms kitchen and living room. Central heat and air conditioning. Walking distance from several parks, close to shopping....

4746 S Kenwood Ave

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4746 S Kenwood Ave

Chicago, IL
(Contact seller for price)
Vacation Rentals, Unknown
VERY LOVELY HOME WITH SPACIOUS FLOOR PLAN AND FANTASTIC NATURAL LIGHTING. PRIVATE LIVING ROOM SIZE PATIO PLUS GRASSY COURT YARD. PARKING...

7245 S Paulina St

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7245 S Paulina St

Chicago, IL
(Contact seller for price)
Vacation Rentals, Unknown
BEAUTIFUL ALL BRICK HOUSE WITH 3 BEDROOMS 1 BATHROOM, FULL UNFINISHED BASEMENT, AND MUCH MORE. AGENT OWNED. CALL TODAY...

3817 W Maypole Ave

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3817 W Maypole Ave

Chicago, IL
(Contact seller for price)
Vacation Rentals, Unknown
*House is being repainted and fixed. Will be ready for 11/15 move in. Beautiful and spacious 5 bedroom/1.5 bathroom single family home located next to Garfield Park. House features include full......

Chicago, IL

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