Real Estate Investment Properties for Sale in Chicago, IL
Looking for investment property in Chicago, IL with high ROI ?
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 |
|---|---|---|---|
2610 W 80th StChicago, IL2610 W 80th St, Chicago, IL 60652 | Single Family Residential |
2 beds | 1 baths | 855 sq.ft. |
$250,000 |
Airbnb cash on cash: N/A
|
7801 S Ada StChicago, ILWelcome to this stunning, fully remodeled solid-brick single-family home in Auburn Gresham... |
4 beds | 3 baths | 1,200 sq.ft. |
$259,999 |
Airbnb cash on cash: N/A
|
3219 N Richmond StChicago, IL3219 N Richmond St, Chicago, IL 60618 | Single Family Residential |
4 beds | 3 baths | 1,920 sq.ft. |
$875,000 |
Airbnb cash on cash: N/A
|
5918 S Albany AvenueChicago, ILGREAT OPPORTUNITY TO OWN IN THIS FAST APPRECIATING AREA !!! REAR OF THE LOT !!BRICK SINGLE... |
2 beds | 2 baths | 832 sq.ft. |
$175,000 |
Airbnb cash on cash: N/A
|
1722 N Keeler AveChicago, ILHot Hermosa location! Updated single family home on a great block. House went through exte... |
3 beds | 1 baths | 842 sq.ft. |
$279,900 |
Airbnb cash on cash: N/A
|
1750 N Clybourn Avenue unit: 202 #202Chicago, ILThis boutique elevator building presents a RARE opportunity to own a luxury condo that sea... |
2 beds | 2 baths | N/A |
$649,950 |
Airbnb cash on cash: N/A
|
1938 N Hudson AveChicago, IL1938 N Hudson Ave, Chicago, IL 60614 | Single Family Residential |
5 beds | 5 baths | 5,849 sq.ft. |
$2,995,000 |
Airbnb cash on cash: N/A
|
60 E Monroe St #2001Chicago, IL60 E Monroe St #2001, Chicago, IL 60603 | Condo/Coop |
3 beds | 2 baths | 1,750 sq.ft. |
$1,000,000 |
Airbnb cash on cash: N/A
|
7228 N Rogers AveChicago, ILThis is a 3 Bedroom, 1.5 Bath, 2 story, frame farm house with 1 Deeded Parking Space. It i... |
3 beds | 1 baths | 1,600 sq.ft. |
$399,000 |
Airbnb cash on cash: N/A
|
4343 N Clarendon Avenue #707Chicago, ILInvestors! Welcome to Buena Park. This incredible unit is a large one bedroom one bath wit... |
1 beds | 1 baths | 790 sq.ft. |
$139,900 |
Airbnb cash on cash: N/A
|
4004 N Clarendon Avenue #1Chicago, ILWelcome to this stunning home featuring beautiful vintage details and millwork with modern... |
4 beds | 2 baths | 2,750 sq.ft. |
$639,000 |
Airbnb cash on cash: N/A
|
9100 S Wallace StChicago, ILWelcome to 9100 S Wallace - a beautifully renovated 3-bedroom, 3-bathroom home offering mo... |
3 beds | 3 baths | 1,312 sq.ft. |
$299,000 |
Airbnb cash on cash: N/A
|
7205 S HAMLIN AvenueChicago, ILMaintenance free 4 bedroom ranch with finished basement. 3 bedrooms on the main and one in... |
3 beds | 2 baths | 1,080 sq.ft. |
$359,900 |
Airbnb cash on cash: N/A
|
2854 S Central Park AveChicago, IL2854 S Central Park Ave, Chicago, IL 60623 | Single Family Residential |
5 beds | 2 baths | 896 sq.ft. |
$348,500 |
Airbnb cash on cash: N/A
|
4836 S Dorchester AveChicago, ILStunning 3-Flat Georgian Style Multi-Family Building in the Hyde Park/Kenwood Community, w... |
7 beds | 3 baths | N/A |
$975,000 |
Airbnb cash on cash: N/A
|
1613 S Ruble StChicago, ILCompletely renovated modern single-family home in East Pilsen featuring 4 bedrooms, 3.5 ba... |
4 beds | 3 baths | 2,400 sq.ft. |
$750,000 |
Airbnb cash on cash: N/A
|
1647 W Sherwin Ave #1Chicago, IL1647 W Sherwin Ave #1, Chicago, IL 60626 | Condo/Coop |
3 beds | 2 baths | 1,039 sq.ft. |
$264,000 |
Airbnb cash on cash: N/A
|
3214 S Canal StChicago, IL3214 S Canal St, Chicago, IL 60616 | Single Family Residential |
5 beds | 5 baths | 8,800 sq.ft. |
$1,849,999 |
Airbnb cash on cash: N/A
|
124 W Polk St #905Chicago, IL124 W Polk St #905, Chicago, IL 60605 | Condo/Coop |
2 beds | 1 baths | 1,200 sq.ft. |
$315,000 |
Airbnb cash on cash: N/A
|
175 E Delaware Pl #7204Chicago, ILWelcome to your home in the sky, offering breathtaking North-facing views from the 72nd fl... |
2 beds | 2 baths | 1,470 sq.ft. |
$720,000 |
Airbnb cash on cash: N/A
|
4852 N Sacramento Ave #3Chicago, IL4852 N Sacramento Ave #3, Chicago, IL 60625 | Condo/Coop |
2 beds | 1 baths | 1,000 sq.ft. |
$265,000 |
Airbnb cash on cash: N/A
|
544 E 46th PlChicago, IL544 E 46th Pl, Chicago, IL 60653 | Single Family Residential |
5 beds | 3 baths | 3,000 sq.ft. |
$760,000 |
Airbnb cash on cash: N/A
|
3916 W Grand AvenueChicago, ILMove in ready! This cozy single-family home has a lot to offer with three full bathrooms, ... |
3 beds | 3 baths | 900 sq.ft. |
$320,000 |
Airbnb cash on cash: N/A
|
3740 N Pacific AveChicago, ILStep into this beautifully updated 5-bedroom, 3-bath raised ranch, offering nearly new-con... |
5 beds | 3 baths | 3,000 sq.ft. |
$600,000 |
Airbnb cash on cash: N/A
|
545 N Dearborn St #3601Chicago, IL545 N Dearborn St #3601, Chicago, IL 60654 | Condo/Coop |
3 beds | 2 baths | 2,500 sq.ft. |
$1,149,000 |
Airbnb cash on cash: N/A
|
1112 N Dearborn St #1Chicago, IL1112 N Dearborn St #1, Chicago, IL 60610 | Condo/Coop |
2 beds | 2 baths | 2,255 sq.ft. |
$1,395,000 |
Airbnb cash on cash: N/A
|
950 N Michigan Ave #4904Chicago, ILWelcome to the stunning Michigan Ave Penthouse, located at Magnificent Mile building. This... |
3 beds | 4 baths | 5,400 sq.ft. |
$2,699,000 |
Airbnb cash on cash: N/A
|
401 E Ontario St #809Chicago, ILLOCATION, LOCATION, LOCATION! This OVERSIZED CORNER unit with gorgeous city and lake views... |
2 beds | 2 baths | 1,200 sq.ft. |
$397,000 |
Airbnb cash on cash: N/A
|
405 N Wabash Ave #4308Chicago, IL405 N Wabash Ave #4308, Chicago, IL 60611 | Condo/Coop |
4 beds | 4 baths | 3,100 sq.ft. |
$1,195,000 |
Airbnb cash on cash: N/A
|
9021 S Exchange AveChicago, ILSingle Family 4 bedrooms, 1 bath home. Updates in 2019 include kitchen, baths, - ceramic t... |
4 beds | 1 baths | 1,298 sq.ft. |
$125,000 |
Airbnb cash on cash: N/A
|
7927 S Burnham AveChicago, ILPossible FHA/VA Financing * We are in the area covered by the Cook County DP Assistance Pr... |
4 beds | 2 baths | 1,124 sq.ft. |
$190,000 |
Airbnb cash on cash: N/A
|
8434 S Yates BlvdChicago, IL8434 S Yates Blvd, Chicago, IL 60617 | Single Family Residential |
4 beds | 3 baths | 1,700 sq.ft. |
$305,000 |
Airbnb cash on cash: N/A
|
Real Estate investment in Chicago, IL
There are 5,257 properties for sale in the city of Chicago . The median list price in Chicago is $325,000 and the average price per square foot is $185. In January 2026, the average monthly cash on cash return in Chicago is 3.00%. The average monthly rental income in Chicago is $2,123.