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 |
|---|---|---|---|
11616 S Harvard AveChicago, ILBe the first to move into this fully renovated home, on a DOUBLE lot, located on a quiet b... |
3 beds | 2 baths | 1,200 sq.ft. |
$229,900 |
Airbnb cash on cash: N/A
|
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. |
$240,000 |
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. |
$829,900 |
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
|
5130 S Menard AveChicago, IL5130 S Menard Ave, Chicago, IL 60638 | Single Family Residential |
3 beds | 1 baths | 945 sq.ft. |
$290,000 |
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
|
2710 W Chicago Ave #4Chicago, ILYou don't want to miss this absolutely stunning 3 bedroom, 2 bathroom home providing luxur... |
3 beds | 2 baths | 1,700 sq.ft. |
$525,000 |
Airbnb cash on cash: N/A
|
5801 S Blackstone AveChicago, IL5801 S Blackstone Ave, Chicago, IL 60637 | Single Family Residential |
5 beds | 4 baths | 3,919 sq.ft. |
$1,975,000 |
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
|
222 N Columbus Dr #3103Chicago, ILStunning 31st-floor 2-bedroom, 2-bath residence at Park Millennium, offering breathtaking ... |
2 beds | 2 baths | 1,225 sq.ft. |
$399,000 |
Airbnb cash on cash: N/A
|
130 N Garland Ct #3702Chicago, ILStunning high-floor condo with awesome views of city & sunsets from floor-to-ceiling windo... |
3 beds | 2 baths | 1,653 sq.ft. |
$745,000 |
Airbnb cash on cash: N/A
|
10922 S Peoria StChicago, IL10922 S Peoria St, Chicago, IL 60643 | Single Family Residential |
4 beds | 1 baths | 1,578 sq.ft. |
$220,000 |
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
|
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. |
$289,000 |
Airbnb cash on cash: N/A
|
9020 S Carpenter StChicago, ILCOME TAKE A LOOK AT THIS BEAUTIFUL NEWLY REMODELED 4 BEDROOM 2 BATH HOME IN WASHINGTON HEI... |
3 beds | 2 baths | 1,400 sq.ft. |
$225,000 |
Airbnb cash on cash: N/A
|
6813 S Keeler AveChicago, IL6813 S Keeler Ave, Chicago, IL 60629 | Single Family Residential |
4 beds | 3 baths | 2,000 sq.ft. |
$390,000 |
Airbnb cash on cash: N/A
|
7216 S Central Park AveChicago, ILWell-maintained brick ranch in move-in condition! Features gleaming hardwood floors, origi... |
4 beds | 2 baths | 1,080 sq.ft. |
$290,000 |
Airbnb cash on cash: N/A
|
7205 S Hamlin AveChicago, ILMaintenance free 4 bedroom ranch with finished basement. 3 bedrooms on the main and one in... |
5 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
|
3103 W Wilson Ave #1Chicago, IL3103 W Wilson Ave #1, Chicago, IL 60625 | Condo/Coop |
2 beds | 1 baths | N/A |
$250,000 |
Airbnb cash on cash: N/A
|
3553 W Sunnyside Ave #1Chicago, IL3553 W Sunnyside Ave #1, Chicago, IL 60625 | Condo/Coop |
1 beds | 1 baths | 725 sq.ft. |
$164,900 |
Airbnb cash on cash: N/A
|
1134 W Granville Ave #820Chicago, IL1134 W Granville Ave #820, Chicago, IL 60660 | Condo/Coop |
2 beds | 1 baths | N/A |
$335,000 |
Airbnb cash on cash: N/A
|
5814 S Massasoit AveChicago, IL5814 S Massasoit Ave, Chicago, IL 60638 | Single Family Residential |
3 beds | 1 baths | 1,017 sq.ft. |
$359,000 |
Airbnb cash on cash: N/A
|
2645 W Haddon Ave #2Chicago, IL2645 W Haddon Ave #2, Chicago, IL 60622 | Condo/Coop |
2 beds | 2 baths | 1,200 sq.ft. |
$439,900 |
Airbnb cash on cash: N/A
|
2947 W Belden Ave #1Chicago, IL2947 W Belden Ave #1, Chicago, IL 60647 | Condo/Coop |
1 beds | 1 baths | 1,034 sq.ft. |
$250,000 |
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
|
1449 W Walton St #2Chicago, ILUpgraded 2 bed/2 bath in a 3-unit building on a tree-lined street in the heart of West Tow... |
2 beds | 2 baths | N/A |
$450,000 |
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. |
$1,849,998 |
Airbnb cash on cash: N/A
|
845 N May StChicago, ILThis spacious and well-designed 4 level townhome is nestled in the highly sought-after and... |
3 beds | 2 baths | 2,283 sq.ft. |
$799,000 |
Airbnb cash on cash: N/A
|
2105 W Concord Pl #5Chicago, ILBoutique loft building in the heart of Bucktown! Dramatic top floor loft unit has it all -... |
2 beds | 2 baths | N/A |
$675,000 |
Airbnb cash on cash: -2.61%
|
1219 N Cleaver St #2Chicago, ILLuxury 4 Bedroom Penthouse unit in a solid brick building offers over 3000 sf of living sp... |
4 beds | 3 baths | 3,000 sq.ft. |
$1,000,000 |
Airbnb cash on cash: N/A
|
2005 N Albany Ave #2005Chicago, IL2005 N Albany Ave #2005, Chicago, IL 60647 | Condo/Coop |
3 beds | 2 baths | 1,988 sq.ft. |
$739,900 |
Airbnb cash on cash: N/A
|
2730 N Magnolia AveChicago, IL2730 N Magnolia Ave, Chicago, IL 60614 | Single Family Residential |
6 beds | 6 baths | 6,200 sq.ft. |
$4,250,000 |
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. |
$710,000 |
Airbnb cash on cash: N/A
|
401 E Ontario St #707Chicago, ILDiscover this spacious and sun-filled one-bedroom in the heart of Streeterville-complete w... |
1 beds | 1 baths | 800 sq.ft. |
$315,000 |
Airbnb cash on cash: N/A
|
3558 W Belle Plaine Avenue unit: 3 #3Chicago, ILBright and full of personality, this two-bedroom Irving Park condo offers stylish comfort ... |
2 beds | 1 baths | 1,000 sq.ft. |
$255,000 |
Airbnb cash on cash: N/A
|
1060 W Hollywood Ave #502Chicago, IL1060 W Hollywood Ave #502, Chicago, IL 60660 | Condo/Coop |
1 beds | 1 baths | 700 sq.ft. |
$195,000 |
Airbnb cash on cash: N/A
|
Real Estate investment in Chicago, IL
There are 5,191 properties for sale in the city of Chicago . The median list price in Chicago is $339,700 and the average price per square foot is $193. In February 2026, the average monthly cash on cash return in Chicago is 3.00%. The average monthly rental income in Chicago is $2,098.