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Check prices for these dates

Next weekend
2 May - 4 May
In two weeks
9 May - 11 May
In one month
23 May - 25 May
In two months
20 Jun - 22 Jun

Compare 203 Vacation Homes in Flossmoor with updated reviews, rates, and availability.

Cozy Home Sweet Homewood.
Fridge, microwave, oven, stovetop

Cozy Home Sweet Homewood.

9.8 out of 10, Exceptional, (22)
"Liked very much"
Cozy Home Sweet Homewood.
Private Home Awaits
Fridge, microwave, oven, stovetop

Private Home Awaits

10.0 out of 10, Exceptional, (2)
"Very convenient to all my activities for my 55th Birthday "
Private Home Awaits
House with garage, outdoor dining and basement bar
Fridge, microwave, oven, dishwasher

House with garage, outdoor dining and basement bar

House with garage, outdoor dining and basement bar
Comfy 4 bedroom Apartment in the center of CHICAGO! 15 mins from Downtown!
Exterior

Comfy 4 bedroom Apartment in the center of CHICAGO! 15 mins from Downtown!

7.8 out of 10, Good, (7)
"I would stay again and the communication was on point. Thank you for having us."
Comfy 4 bedroom Apartment in the center of CHICAGO! 15 mins from Downtown!
Renovated 6 Bedroom 5 Bathroom Home 10 Minutes from Downtown Chicago
Fridge, microwave, oven, stovetop

Renovated 6 Bedroom 5 Bathroom Home 10 Minutes from Downtown Chicago

9.0 out of 10, Wonderful, (7)
"To say we enjoyed our stay, is an understatement. My sister was able you bring in her 21st birthday properly along with her close friends. It was so spacious, everyone had their own area to hang out. The master bedroom is gorgeous, a real selling point. My only regret is that it is winter && we were unable to enjoy the backyard. Our host was amazing and very helpful during the whole process, any question was promptly answered. If you’re looking for a nice place in a quiet area, don’t hesitate to...
Renovated 6 Bedroom 5 Bathroom Home 10 Minutes from Downtown Chicago
Charming 3-bedroom house in serene and lovely Evergreen Park. WiFi/ AC
Interior

Charming 3-bedroom house in serene and lovely Evergreen Park. WiFi/ AC

9.0 out of 10, Wonderful, (2)
"Lovely new (or well remodeled?) house in a nice neighborhood. Host was nice and communicative. Kitchen is well stocked. There’s only one shower but we had no problem sharing. "
Charming 3-bedroom house in serene and lovely Evergreen Park. WiFi/ AC
Gorgeous historic mansion on UChicago campus. Renovation with original detail.
Fridge, microwave, oven, stovetop

Gorgeous historic mansion on UChicago campus. Renovation with original detail.

10.0 out of 10, Exceptional, (8)
"We had a fabulous time visiting our college aged child. The house is centrally located between the university and the commercial area. It is impeccably clean and tastefully furnished. We look forward to returning!"
Gorgeous historic mansion on UChicago campus. Renovation with original detail.
The Comfy King Ranch - King Bed/Spacious Home/Fast WiFi/Free Parking
Fridge, microwave, oven, stovetop

The Comfy King Ranch - King Bed/Spacious Home/Fast WiFi/Free Parking

9.6 out of 10, Exceptional, (47)
"Nice property with 3 bedrooms & a fenced in back yard. Great communication with owner. "
The price is AED 675
AED 1,398 total
includes taxes & fees
27 Apr - 28 Apr
The Comfy King Ranch - King Bed/Spacious Home/Fast WiFi/Free Parking
Spacious Family Glenwood Estates Home w/ Hot Tub!
Indoor spa tub

Spacious Family Glenwood Estates Home w/ Hot Tub!

9.4 out of 10, Exceptional, (14)
"Place was perfect! I grew up in the suburbs of Chicago and wanted to come back to honor my grandmother's 90th birthday. This place was perfect. It had a piano and the pastor was able to serinate her in playing church hymnals. Of course, her famiy, fch family, family and friends were all able to show"
Spacious Family Glenwood Estates Home w/ Hot Tub!
Beautiful and updated place to stay in a quiet neighborhood of Munster Indiana.
Fridge, microwave, oven, stovetop

Beautiful and updated place to stay in a quiet neighborhood of Munster Indiana.

10.0 out of 10, Exceptional, (20)
"Nice sice fenced in yard. Dog park within a short walk. Nice smaller home with 3 good size bedrooms. Kitchen was convenient for cooking meals."
Beautiful and updated place to stay in a quiet neighborhood of Munster Indiana.
Charming 3-bedroom house with AC and WiFi in serene Bridgeview
Private kitchen

Charming 3-bedroom house with AC and WiFi in serene Bridgeview

10.0 out of 10, Exceptional, (1)
"Great area to stay close to everything "
Charming 3-bedroom house with AC and WiFi in serene Bridgeview
Lux Home in Chicago 7mins Downtown
Fridge, microwave, oven, stovetop

Lux Home in Chicago 7mins Downtown

9.8 out of 10, Exceptional, (16)
"Beautiful stay and super nice host would recommend every time "
Lux Home in Chicago 7mins Downtown
Modern Historic Greystone - Near Lake - Free Prkg
Fridge, microwave, oven, stovetop

Modern Historic Greystone - Near Lake - Free Prkg

6.4 out of 10, (5)
"Great property in a quiet neighborhood. Not far from downtown and other tourist attractions. 10/10 would recommend. "
Modern Historic Greystone - Near Lake - Free Prkg
Home w/ Yard & Patio ~ 30 Mi to Downtown Chicago
Fridge, microwave, stovetop, dishwasher

Home w/ Yard & Patio ~ 30 Mi to Downtown Chicago

8.2 out of 10, Very Good, (20)
"We really love the home and the setup."
Home w/ Yard & Patio ~ 30 Mi to Downtown Chicago
Dreamsville Gateway to Indiana Dunes National Park
Exterior

Dreamsville Gateway to Indiana Dunes National Park

6.0 out of 10, (1)
"Listed as private home , once you get there and read the house rules it states shared refrigerator with owner. Owner comes in while you are gone and turns off all lights and the Ac, even goes into your locked room to turn off ac."
Dreamsville Gateway to Indiana Dunes National Park
LakeHouse
Fridge, microwave, oven, stovetop

LakeHouse

10.0 out of 10, Exceptional, (16)
"Host was perfect an house was perfect!!! It's my second time renting an I will be back again!!"
LakeHouse
Charming and spacious 3-bedroom townhome with WiFi and amenities in Gary
Beach

Charming and spacious 3-bedroom townhome with WiFi and amenities in Gary

5.4 out of 10, (3)
"The property itself was ver clean just an older house. Very clean! The neighborhood was a little questionable for families who have never travelex to that area from a rural area. The stay was good and worked for what we needed!"
The price is AED 367
AED 1,045 total
includes taxes & fees
30 Apr - 1 May
Charming and spacious 3-bedroom townhome with WiFi and amenities in Gary
Woodlawn Oasis...10 Minutes to Dining & Downtown
Smart TV

Woodlawn Oasis...10 Minutes to Dining & Downtown

9.6 out of 10, Exceptional, (10)
"The property has lots of space and a game room, ideal for a fun getaway with a large group. Close to bus stops and Metra station (different from metro station, we learned this the hard way). Walking distance from the U of Chicago."
Woodlawn Oasis...10 Minutes to Dining & Downtown
Cozy house in the city
Outdoor dining

Cozy house in the city

2.0 star property
10.0 out of 10, Exceptional, (1)
"Very nice house and host was very thoughtful. Will definitely stay again when coming back to Chicago. "
Cozy house in the city
Spacious 3br home near Chicago, fenced yard for pets
Fridge, microwave, oven, stovetop

Spacious 3br home near Chicago, fenced yard for pets

2.0 star property
9.0 out of 10, Wonderful, (8)
"Nice property easy check in. Experience was amazing. Thank you again "
The price is AED 738
AED 1,469 total
includes taxes & fees
4 May - 5 May
Spacious 3br home near Chicago, fenced yard for pets
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Flossmoor

Comfort Inn Chicago Wind Creek Casino
Comfort Double Room | Desk, laptop workspace, blackout drapes, free WiFi

Comfort Inn Chicago Wind Creek Casino

2.5 star property
3.8 out of 10, (20)
"Lower level had a smell"
The price is AED 328
AED 371 total
includes taxes & fees
1 May - 2 May
Comfort Inn Chicago Wind Creek Casino
Comfy 4 bedroom Apartment in the center of CHICAGO! 15 mins from Downtown!
Exterior

Comfy 4 bedroom Apartment in the center of CHICAGO! 15 mins from Downtown!

7.8 out of 10, Good, (7)
"I would stay again and the communication was on point. Thank you for having us."
Comfy 4 bedroom Apartment in the center of CHICAGO! 15 mins from Downtown!
LakeHouse
Fridge, microwave, oven, stovetop

LakeHouse

10.0 out of 10, Exceptional, (16)
"Host was perfect an house was perfect!!! It's my second time renting an I will be back again!!"
LakeHouse
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.