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 |
|---|---|---|---|
5019 N Kostner AvenueChicago, ILCharming and Spacious North Mayfair Brick Bungalow A rare oversized bungalow with 8 bedroo... |
5 beds | 3 baths | 3,837 sq.ft. |
$670,000 |
Airbnb cash on cash: N/A
|
7801 S Ada StreetChicago, ILWelcome to this stunning, fully remodeled solid-brick single-family home in Auburn Gresham... |
3 beds | 3 baths | 1,200 sq.ft. |
$240,000 |
Airbnb cash on cash: 1.13%
|
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: 4.14%
|
3149 W Lexington St #5Chicago, IL3149 W Lexington St #5, Chicago, IL 60612 | Townhouse |
3 beds | 2 baths | 1,500 sq.ft. |
$175,000 |
Airbnb cash on cash: 5.22%
|
5701 N Sheridan Road #3EChicago, ILBright, beautifully maintained 1-bedroom with sweeping lake and skyline views in the highl... |
1 beds | 1 baths | 850 sq.ft. |
$189,000 |
Airbnb cash on cash: 0.97%
|
5728 S Stony Island Ave #2Chicago, IL5728 S Stony Island Ave #2, Chicago, IL 60637 | Condo/Coop |
1 beds | 1 baths | 900 sq.ft. |
$95,000 |
Airbnb cash on cash: 2.26%
|
5801 S Blackstone AveChicago, IL5801 S Blackstone Ave, Chicago, IL 60637 | Single Family Residential |
5 beds | 4 baths | 3,919 sq.ft. |
$1,745,000 |
Airbnb cash on cash: N/A
|
1905 N Bissell Street #2Chicago, ILImpeccably designed resale from critically acclaimed PLD Development. This highly upgraded... |
3 beds | 2 baths | N/A |
$950,000 |
Airbnb cash on cash: -0.81%
|
3726 W Mclean AvenueChicago, ILCharming, sun-filled Logan Square single-family home! This beauty features hardwood floors... |
3 beds | 3 baths | N/A |
$660,000 |
Airbnb cash on cash: 0.32%
|
40 E 9th St #1616Chicago, IL40 E 9th St #1616, Chicago, IL 60605 | Condo/Coop |
3 beds | 3 baths | 1,900 sq.ft. |
$389,000 |
Airbnb cash on cash: -1.29%
|
8 W MONROE Street #1209Chicago, ILUnbeatable location in the heart of the Loop, with the Red and Blue train lines on the sam... |
2 beds | 2 baths | 990 sq.ft. |
$315,000 |
Airbnb cash on cash: 2.32%
|
225 N Columbus Dr #5701Chicago, IL225 N Columbus Dr #5701, Chicago, IL 60601 | Condo/Coop |
1 beds | 1 baths | 1,119 sq.ft. |
$599,000 |
Airbnb cash on cash: -3.17%
|
10736 S Church StChicago, IL10736 S Church St, Chicago, IL 60643 | Single Family Residential |
4 beds | 3 baths | 2,250 sq.ft. |
$399,999 |
Airbnb cash on cash: -1.36%
|
5602 N Fairview AveChicago, IL5602 N Fairview Ave, Chicago, IL 60631 | Other |
N/A beds | N/A baths | 0 sq.ft. |
$474,900 |
Airbnb cash on cash: -1.67%
|
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: 5.6%
|
4836 S Dorchester AvenueChicago, ILLooking for a Stunning 3-Flat Georgian Style Multi-Family Building or convert to your Sing... |
6 beds | 5 baths | N/A |
$925,000 |
Airbnb cash on cash: 0.9%
|
1905 W Fullerton AveChicago, IL
|
N/A beds | N/A baths | 777 sq.ft. |
$399,900 |
Airbnb cash on cash: 0.08%
|
1220 N Damen AveChicago, IL1220 N Damen Ave, Chicago, IL 60622 | Single Family Residential |
4 beds | 4 baths | 5,000 sq.ft. |
$2,300,000 |
Airbnb cash on cash: -1.99%
|
6816 W 65th Street #5Chicago, ILBeautifully up-kept townhouse in the Chicago land area. Home offers natural light througho... |
3 beds | 3 baths | 1,850 sq.ft. |
$379,900 |
Airbnb cash on cash: -0.16%
|
5054 W Berwyn AveChicago, IL5054 W Berwyn Ave, Chicago, IL 60630 | Single Family Residential |
4 beds | 4 baths | 3,402 sq.ft. |
$1,100,000 |
Airbnb cash on cash: N/A
|
12504 S Lowe AveChicago, IL12504 S Lowe Ave, Chicago, IL 60628 | Single Family Residential |
4 beds | 1 baths | 1,610 sq.ft. |
$158,497 |
Airbnb cash on cash: -0.94%
|
2645 W Haddon Ave #2Chicago, IL2645 W Haddon Ave #2, Chicago, IL 60622 | Condo/Coop |
2 beds | 2 baths | 1,200 sq.ft. |
$409,000 |
Airbnb cash on cash: -0.31%
|
832 N Washtenaw Avenue #3Chicago, ILPerched up above the neighborhood with privacy and natural light in every direction, welco... |
2 beds | 2 baths | N/A |
$550,000 |
Airbnb cash on cash: -0.12%
|
2447 W Winona StreetChicago, IL5-bedroom, 3.5-bath home on one of Lincoln Square's quietest tree-lined streets. Three lev... |
5 beds | 4 baths | 3,600 sq.ft. |
$1,250,000 |
Airbnb cash on cash: -0.73%
|
40 E 9th St #1601Chicago, IL40 E 9th St #1601, Chicago, IL 60605 | Condo/Coop |
2 beds | 2 baths | 1,500 sq.ft. |
$325,000 |
Airbnb cash on cash: 0.47%
|
910 S Michigan Avenue #1009Chicago, IL
|
1 beds | 1 baths | N/A |
$245,000 |
Airbnb cash on cash: 3.45%
|
840 N Lake Shore Drive #201Chicago, ILEnjoy the unobstructed views of the lakefront and the park in the world class Lucian Lagra... |
3 beds | 4 baths | 3,985 sq.ft. |
$2,695,000 |
Airbnb cash on cash: -4.06%
|
Real Estate investment in Chicago, IL
There are 6,071 properties for sale in the city of Chicago . The median list price in Chicago is $408,789 and the average price per square foot is $231. In June 2026, the average monthly cash on cash return in Chicago is 2.00%. The average monthly rental income in Chicago is $2,182.