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 |
|---|---|---|---|
13223 S Buffalo AveChicago, ILWelcome to Hegewisch - a warm, close-knit Chicago neighborhood known for its small-town fe... |
3 beds | 2 baths | 1,100 sq.ft. |
$189,900 |
Airbnb cash on cash: 3.79%
|
5911 N Keating AvenueChicago, ILMeticulously maintained & recently renovated 4 bedroom + family room/3 bath with rarely av... |
4 beds | 3 baths | N/A |
$749,500 |
Airbnb cash on cash: 0.98%
|
12025 S Prairie AveChicago, IL12025 S Prairie Ave, Chicago, IL 60628 | Single Family Residential |
3 beds | 2 baths | 1,295 sq.ft. |
$160,000 |
Airbnb cash on cash: 2.85%
|
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: 3.5%
|
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: 6.49%
|
5701 N Sheridan Rd #3EChicago, ILBright, beautifully maintained 1-bedroom with sweeping lake and skyline views in the highl... |
1 beds | 1 baths | 850 sq.ft. |
$179,000 |
Airbnb cash on cash: 0.75%
|
5455 N Sheridan Rd #1908Chicago, ILBeautiful rehabbed 1 bed/1 bath condo on the 19th floor with views of the Lake and Park! T... |
1 beds | 1 baths | 850 sq.ft. |
$225,000 |
Airbnb cash on cash: -1.7%
|
6631 N Caldwell AveChicago, IL6631 N Caldwell Ave, Chicago, IL 60646 | Single Family Residential |
3 beds | 2 baths | 1,545 sq.ft. |
$649,000 |
Airbnb cash on cash: -0.18%
|
1712 N Albany Avenue #1Chicago, ILThoughtfully updated and meticulously maintained 3-bedroom, 3-bath duplex-down in the hear... |
3 beds | 3 baths | 2,100 sq.ft. |
$599,000 |
Airbnb cash on cash: -0.85%
|
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: 1.53%
|
5801 S Blackstone AveChicago, IL5801 S Blackstone Ave, Chicago, IL 60637 | Single Family Residential |
5 beds | 4 baths | 4,580 sq.ft. |
$1,595,000 |
Airbnb cash on cash: -1.03%
|
5642 N LOCKWOOD AvenueChicago, ILWelcome home to Edgebrook Glen! A private enclave of 64 homes nestled in the heart of Jeff... |
3 beds | 4 baths | 2,273 sq.ft. |
$689,900 |
Airbnb cash on cash: -0.49%
|
1905 N Bissell St #3Chicago, ILOVERSIZED DUPLEX-UP PENTHOUSE WITH PRIVATE ROOF DECK IN PREMIER LINCOLN PARK LOCATION! In... |
4 beds | 3 baths | N/A |
$1,895,000 |
Airbnb cash on cash: -0.58%
|
3726 W Mclean AveChicago, ILCharming, sun-filled Logan Square single-family home! This beauty features hardwood floors... |
4 beds | 3 baths | N/A |
$640,000 |
Airbnb cash on cash: 1.89%
|
780 S Federal St #604Chicago, ILBest value in Printers Row and pet friendly! Huge, corner 1 bedroom in the heart of it all... |
1 beds | 1 baths | 900 sq.ft. |
$212,500 |
Airbnb cash on cash: 0.59%
|
40 E 9th St #1616Chicago, IL40 E 9th St #1616, Chicago, IL 60605 | Condo/Coop |
3 beds | 3 baths | 1,900 sq.ft. |
$375,000 |
Airbnb cash on cash: -1.12%
|
701 S Wells St #804Chicago, IL701 S Wells St #804, Chicago, IL 60607 | Condo/Coop |
2 beds | 2 baths | 1,200 sq.ft. |
$399,999 |
Airbnb cash on cash: -0.55%
|
225 N Columbus Dr #5701Chicago, IL225 N Columbus Dr #5701, Chicago, IL 60601 | Condo/Coop |
1 beds | 1 baths | 1,119 sq.ft. |
$550,000 |
Airbnb cash on cash: -4.03%
|
3640 N Artesian AveChicago, IL3640 N Artesian Ave, Chicago, IL 60618 | Single Family Residential |
4 beds | 3 baths | 2,600 sq.ft. |
$535,000 |
Airbnb cash on cash: 0.63%
|
5602 N Fairview AveChicago, IL5602 N Fairview Ave, Chicago, IL 60631 | Other |
N/A beds | N/A baths | 0 sq.ft. |
$469,000 |
Airbnb cash on cash: -1.64%
|
9913 S Parnell AveChicago, ILWelcome to 9913 S. Parnell! This spacious 4-bedroom, 2-bath home offers a functional layou... |
4 beds | 2 baths | N/A |
$275,000 |
Airbnb cash on cash: 0.14%
|
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: 6.31%
|
4836 S Dorchester AveChicago, ILLooking for a Stunning 3-Flat Georgian Style Multi-Family Building or convert to your Sing... |
7 beds | 3 baths | N/A |
$925,000 |
Airbnb cash on cash: -1.07%
|
1905 W Fullerton AveChicago, IL
|
N/A beds | N/A baths | 777 sq.ft. |
$399,900 |
Airbnb cash on cash: -0.19%
|
1220 N Damen AveChicago, IL1220 N Damen Ave, Chicago, IL 60622 | Single Family Residential |
4 beds | 4 baths | 5,000 sq.ft. |
$2,199,800 |
Airbnb cash on cash: -1.81%
|
3035 N Luna AveChicago, ILClassic Chicago bungalow with 3 full bedroom's on the first floor. Many beautiful intact ... |
6 beds | 2 baths | 1,600 sq.ft. |
$499,500 |
Airbnb cash on cash: 5.87%
|
6816 W 65th St #5Chicago, ILBeautifully up-kept townhouse in the Chicago land area. Home offers natural light througho... |
3 beds | 2 baths | 1,850 sq.ft. |
$369,900 |
Airbnb cash on cash: 0.8%
|
12504 S Lowe AveChicago, IL12504 S Lowe Ave, Chicago, IL 60628 | Single Family Residential |
4 beds | 1 baths | 1,610 sq.ft. |
$154,997 |
Airbnb cash on cash: 0.63%
|
6118 N Sheridan Rd #310Chicago, IL6118 N Sheridan Rd #310, Chicago, IL 60660 | Condo/Coop |
1 beds | 1 baths | 561 sq.ft. |
$149,000 |
Airbnb cash on cash: 0.49%
|
1122 W Catalpa Ave #616Chicago, ILEdgewater 2 bedroom/2 bathroom modern loft featuring panoramic west views. Open floor plan... |
2 beds | 2 baths | N/A |
$324,900 |
Airbnb cash on cash: -1.73%
|
6811 N Olmsted Ave #205Chicago, IL100% OWNER OCCUPIED - ACROSS FROM EDISON PARK METRA . GREAT LOCATION TOP FLOOR IN EXCELLEN... |
2 beds | 1 baths | 1,050 sq.ft. |
$215,000 |
Airbnb cash on cash: -0.95%
|
Real Estate investment in Chicago, IL
There are 7,839 properties for sale in the city of Chicago . The median list price in Chicago is $419,749 and the average price per square foot is $243. In August 2026, the average monthly cash on cash return in Chicago is 2.00%. The average monthly rental income in Chicago is $2,122.