Real Estate Investments for Sale in Chicago, IL With High ROI
Are you looking for a vacation rental in Chicago, IL? Look no further! We have a wide variety of vacation available for sale, including beachfront condos, mountain single-family homes, townhouses, vacation homes and everything in between.
Explore a variety of short-term homes & houses in Chicago, IL. Invest wisely with VRBO & Chicago, IL Airbnb properties available for purchase. Find your ideal investment property among our curated listings for a rewarding real estate venture.
Investment Property for Sale in Chicago, IL
| PROPERTY | DETAILS | SALE PRICE | INVESTMENT PERFORMANCE |
|---|---|---|---|
9215 S Greenwood AvenueChicago, ILCome and view this huge 4 bedroom 3 bathroom Chicago Style Bungalow ready for a new family... |
4 beds | 3 baths | 3,000 sq.ft. |
$245,000 |
Airbnb cash on cash: 9.26%
|
13217 S Buffalo AvenueChicago, ILCOMPLETE REHABBED Brick Bungalow in Hegewisch!. New kitchen cabinets with granite counter ... |
3 beds | 2 baths | 955 sq.ft. |
$227,500 |
Airbnb cash on cash: 5.79%
|
11930 S Calumet AvenueChicago, IL5 bed 2 bath home. New HVAC, water heater, plumbing, updated electric, rehabbed in rent c... |
2 beds | 2 baths | 1,000 sq.ft. |
$149,900 |
Airbnb cash on cash: 6.57%
|
11725 S Wentworth AvenueChicago, ILMove-in ready 4BR/2BA house on a quiet block in West Pullman. Main floor features new prem... |
2 beds | 2 baths | N/A |
$160,000 |
Airbnb cash on cash: 5.74%
|
12147 S Ashland AvenueChicago, ILSolid brick tri-level in a prime location is waiting to be yours. 3 bedrooms, 2 bathrooms,... |
3 beds | 2 baths | 1,224 sq.ft. |
$185,000 |
Airbnb cash on cash: 9%
|
4654 N Spaulding Avenue #2Chicago, ILAmazing 2 bed/2 bath condo steps from brown line stop on quiet tree lined street in Albany... |
2 beds | 2 baths | N/A |
$255,000 |
Airbnb cash on cash: 4.04%
|
5245 S KOLMAR AvenueChicago, ILBeautifully maintained charming brick raised ranch boasts four bedrooms and two baths, cre... |
3 beds | 2 baths | 1,730 sq.ft. |
$329,900 |
Airbnb cash on cash: 3.69%
|
8021 S Loomis BoulevardChicago, ILWelcome to this charming Raised Ranch nestled in the heart of the Auburn Gresham area. The... |
3 beds | 2 baths | 1,312 sq.ft. |
$259,900 |
Airbnb cash on cash: 3.71%
|
6918 S Artesian AvenueChicago, ILWelcome to this captivating bungalow, offering 6 bedrooms, 3 baths, and 2 parking spaces. ... |
4 beds | 3 baths | 3,019 sq.ft. |
$350,000 |
Airbnb cash on cash: 4.55%
|
6615 S Richmond StreetChicago, ILLarge 4 bedroom 2 bath home built in 1924 with all of the old world charm to go with it. T... |
3 beds | 2 baths | 1,124 sq.ft. |
$230,000 |
Airbnb cash on cash: 6.05%
|
1407 W Rascher Avenue #1Chicago, ILDiscover the charm of Andersonville with this beautifully updated 2BR/1BA condo, perfectly... |
2 beds | 1 baths | 770 sq.ft. |
$349,000 |
Airbnb cash on cash: 3.57%
|
5117 S Normandy AvenueChicago, ILThis well-maintained Garfield Ridge home overlooking Normandy Park offers a comfortable an... |
3 beds | 4 baths | 2,290 sq.ft. |
$589,000 |
Airbnb cash on cash: 0.82%
|
512 W Barry Avenue #202Chicago, ILWelcome to this cozy 1 bedroom + den/ office located in the highly coveted Lakeview East n... |
1 beds | 1 baths | N/A |
$309,900 |
Airbnb cash on cash: 2.46%
|
2626 N Lakeview Avenue #1701Chicago, ILThis updated and spacious 2 bedroom, 2 bath condo is located in the perfect nook in East L... |
2 beds | 2 baths | 1,200 sq.ft. |
$345,000 |
Airbnb cash on cash: 3.83%
|
2734 N Marshfield AvenueChicago, ILIntroducing one of the most incredible homes to ever hit the Lincoln Park luxury marketpla... |
5 beds | 5 baths | N/A |
$1,725,000 |
Airbnb cash on cash: 1.75%
|
1803 N Kedzie Avenue #202Chicago, ILWelcome to Logan Square! This oversized 2 bed, 2 bath condo overlooks the 606 Trail and i... |
2 beds | 2 baths | 1,400 sq.ft. |
$450,000 |
Airbnb cash on cash: 2.13%
|
3021 W Armitage Avenue #408Chicago, ILDon't miss this top floor 2 bedroom, 1 bath condo in a highly sought-after Logan Square bo... |
2 beds | 1 baths | 959 sq.ft. |
$350,000 |
Airbnb cash on cash: 3.76%
|
360 E Randolph St #402Chicago, IL360 E Randolph St #402, Chicago, IL 60601 | Condo/Coop |
1 beds | 1 baths | 1,000 sq.ft. |
$399,000 |
Airbnb cash on cash: 2.28%
|
1000 W Washington Blvd #128Chicago, IL1000 W Washington Blvd #128, Chicago, IL 60607 | Condo/Coop |
2 beds | 2 baths | N/A |
$549,000 |
Airbnb cash on cash: 1.76%
|
1800 W Grace St #421Chicago, IL1800 W Grace St #421, Chicago, IL 60613 | Condo/Coop |
1 beds | 1 baths | 933 sq.ft. |
$382,000 |
Airbnb cash on cash: -0.33%
|
1440 W Carmen Avenue #2Chicago, ILIdeally located in Andersonville, Spacious 2 bedroom plus den, 1 Bath condo in a charming... |
2 beds | 1 baths | 1,000 sq.ft. |
$315,000 |
Airbnb cash on cash: 3.88%
|
4004 N Clarendon Avenue #1Chicago, ILClick the Virtual Tour link to access a 3D Walkthrough Tour. Walk to the Lake, parks, reta... |
4 beds | 2 baths | 2,750 sq.ft. |
$624,500 |
Airbnb cash on cash: N/A
|
10032 S May StreetChicago, ILHUNNY STOP THE CAR! Check out this newly remodeled Tri-level rehab, its move in ready for ... |
4 beds | 2 baths | 1,045 sq.ft. |
$229,000 |
Airbnb cash on cash: 8.04%
|
1439 N Elk Grove AvenueChicago, ILWatch the video for a curated walk-through or walk through yourself with our 3D Tour befor... |
3 beds | 5 baths | N/A |
$1,900,000 |
Airbnb cash on cash: -0.43%
|
4027 W 25TH StreetChicago, ILDiscover this recently rehabbed home in the Little Village Neighborhood with 3 beds, 2 bat... |
3 beds | 2 baths | 1,530 sq.ft. |
$295,000 |
Airbnb cash on cash: 5.77%
|
6933 N Kedzie Ave #805Chicago, IL6933 N Kedzie Ave #805, Chicago, IL 60645 | Condo/Coop |
2 beds | 2 baths | 1,200 sq.ft. |
$218,000 |
Airbnb cash on cash: 2.51%
|
1831 N Marshfield AveChicago, IL1831 N Marshfield Ave, Chicago, IL 60622 | Single Family Residential |
4 beds | 3 baths | 3,900 sq.ft. |
$1,649,000 |
Airbnb cash on cash: 0.07%
|
1620 N Wolcott AveChicago, IL1620 N Wolcott Ave, Chicago, IL 60622 | Single Family Residential |
5 beds | 3 baths | N/A |
$1,499,900 |
Airbnb cash on cash: 1.26%
|
1373 N Milwaukee Avenue #2Chicago, ILStunning 3 bedroom + den in prime Wicker Park/ Bucktown location! This expansive and metic... |
3 beds | 3 baths | 1,700 sq.ft. |
$689,000 |
Airbnb cash on cash: 2.68%
|
5202 W Schubert Avenue #2Chicago, ILINVESTORS!! Buy this single unit or package of 2 units in the building. Affordable 1 bedro... |
1 beds | 1 baths | 700 sq.ft. |
$99,900 |
Airbnb cash on cash: 4.46%
|
3904 N Oak Park AvenueChicago, ILBeautiful brick bungalow in great location. 3 bedrooms, formal dinning room, newer roof, w... |
3 beds | 2 baths | 1,307 sq.ft. |
$369,750 |
Airbnb cash on cash: 3.82%
|
8349 S Constance AvenueChicago, ILBuyers Pre-approval letter is required prior to access confirmation. Tenant occupied with... |
3 beds | 4 baths | 2,150 sq.ft. |
$295,900 |
Airbnb cash on cash: 2.43%
|
1133 E 83rd StChicago, IL1133 E 83rd St, Chicago, IL 60619 | Single Family Residential |
4 beds | 4 baths | 2,500 sq.ft. |
$345,000 |
Airbnb cash on cash: 4.11%
|
5026 N Moody AvenueChicago, ILCheck out this Jefferson Park bungalow featuring 4 bedrooms & 3 full bathrooms! Living roo... |
3 beds | 3 baths | 1,780 sq.ft. |
$499,000 |
Airbnb cash on cash: 2.32%
|
1224 W Van Buren Street #621Chicago, ILWelcome to this wonderful unit at Van Buren Lofts, located in the highly sought-after West... |
2 beds | 1 baths | 1,067 sq.ft. |
$355,000 |
Airbnb cash on cash: 6.55%
|
1318 W Huron StreetChicago, ILDiscover the epitome of urban living in this immaculate 4 bed, 3.5 bath single family home... |
4 beds | 4 baths | 3,300 sq.ft. |
$915,000 |
Airbnb cash on cash: 5.59%
|
425 N Clinton StreetChicago, ILChicago's only gated community, including guard house, private neighborhood on the river w... |
3 beds | 4 baths | 2,416 sq.ft. |
$1,050,000 |
Airbnb cash on cash: 1.27%
|
1160 S Michigan Avenue #3205Chicago, ILDramatic Northwest corner 2 bedroom, 2 bath at The Columbian! Here is a home with well tho... |
2 beds | 2 baths | 1,525 sq.ft. |
$525,900 |
Airbnb cash on cash: 2.45%
|
780 S Federal Street #304Chicago, ILBig industrial-chic studio in beautiful and historic Printers Row! This Unit features a fu... |
N/A beds | 1 baths | 600 sq.ft. |
$175,000 |
Airbnb cash on cash: 1.11%
|
Real Estate investment in Chicago, IL
There are 5,145 properties for sale in the city of Chicago . The median list price in Chicago is $379,000 and the average price per square foot is $209. In April 2024, the average monthly cash on cash return in Chicago is 3.00%. The average monthly rental income in Chicago is $2,353.