Holiday Homes in Chicago

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Check prices for these dates

In two weeks
24 Oct - 26 Oct
In two months
5 Dec - 7 Dec
In three months
2 Jan - 4 Jan
In four months
30 Jan - 1 Feb

Featured Holiday Homes in Chicago and around

Classic Forest Park Foursquare < 1 Mi to Blue Line
Private kitchen

Classic Forest Park Foursquare < 1 Mi to Blue Line

2.0 star property
The price is €353
includes taxes & fees
11 Nov - 12 Nov
Classic Forest Park Foursquare < 1 Mi to Blue Line
Getaway Near ORD With Great Local Amenities
Fridge, microwave, oven, stovetop

Getaway Near ORD With Great Local Amenities

8.8 out of 10, Excellent, (3)
"Very nice and clean place to stay at. Great communication from property manager. I would absolutely stay here again!"
The price is €239
includes taxes & fees
15 Oct - 16 Oct
Getaway Near ORD With Great Local Amenities
A quiet stay while you are away
Exterior

A quiet stay while you are away

9.8 out of 10, Exceptional, (32)
"We stayed a few nights and everything was nice and clean. Thank you!"
The price is €170
includes taxes & fees
14 Oct - 15 Oct
A quiet stay while you are away
Quaint Bungalow, near Great Lakes Naval Base
Dining

Quaint Bungalow, near Great Lakes Naval Base

10.0 out of 10, Exceptional, (64)
"Wonderfully charming home in a great location!"
The price is €293
includes taxes & fees
19 Oct - 20 Oct
Quaint Bungalow, near Great Lakes Naval Base
Guesthouse Gem 2BR, Smart TVs, W/D, & Parking
Private kitchen

Guesthouse Gem 2BR, Smart TVs, W/D, & Parking

10.0 out of 10, Exceptional, (1)
"Very quiet and private and cl9se to alot of things "
The price is €245
includes taxes & fees
15 Oct - 16 Oct
Guesthouse Gem 2BR, Smart TVs, W/D, & Parking
PROMO 15% MONTHLY DISCOUNT! Cozy House, Close to Benedictine & North Central
Outdoor dining

PROMO 15% MONTHLY DISCOUNT! Cozy House, Close to Benedictine & North Central

9.4 out of 10, Exceptional, (16)
"Convenient location to family that lives in the area"
PROMO 15% MONTHLY DISCOUNT! Cozy House, Close to Benedictine & North Central
Ideal Spot Just Minutes from O’Hare Airport | LCP Collection
Fridge, microwave, oven, stovetop

Ideal Spot Just Minutes from O’Hare Airport | LCP Collection

Ideal Spot Just Minutes from O’Hare Airport | LCP Collection
Master qtr close to nature & easy urban facilities
Exterior detail

Master qtr close to nature & easy urban facilities

9.8 out of 10, Exceptional, (67)
"Beautiful, quiet space."
The price is €172
includes taxes & fees
3 Nov - 4 Nov
Master qtr close to nature & easy urban facilities
Chic 4BR Escape w/ Game Room – LCP Collection
Private kitchen

Chic 4BR Escape w/ Game Room – LCP Collection

2.0 star property
Chic 4BR Escape w/ Game Room – LCP Collection
*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi
Fridge, microwave, oven, stovetop

*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi

9.6 out of 10, Exceptional, (51)
"Perfect place for an 8 person golf trip! "
The price is €294
includes taxes & fees
21 Oct - 22 Oct
*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi
Cozy Home near O'Hare & fun Hubs with AC
Fridge, microwave, oven, stovetop

Cozy Home near O'Hare & fun Hubs with AC

Cozy Home near O'Hare & fun Hubs with AC
Modern Farmhouse | Yard + Pets OK | LCP Collection
Fridge, microwave, oven, stovetop

Modern Farmhouse | Yard + Pets OK | LCP Collection

Modern Farmhouse | Yard + Pets OK | LCP Collection
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
Microwave, oven, stovetop, dishwasher

Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed

7.8 out of 10, Good, (11)
"Very nice place "
The price is €207
includes taxes & fees
13 Oct - 14 Oct
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
Townhome with Game Zone, Big Beds, & Smart TVs
Living area

Townhome with Game Zone, Big Beds, & Smart TVs

The price is €414
includes taxes & fees
15 Oct - 16 Oct
Townhome with Game Zone, Big Beds, & Smart TVs
Updated Spacious Home -Near NWU- Hospitals+More
Fridge, microwave, oven, stovetop

Updated Spacious Home -Near NWU- Hospitals+More

10.0 out of 10, Exceptional, (2)
"We had a great stay, nice neighborhood, nice home & clean home, fantastic communication with the host. Would stay here again!"
The price is €402
includes taxes & fees
15 Oct - 16 Oct
Updated Spacious Home -Near NWU- Hospitals+More
Sleeps 24+ Luxury house Near Chicago 12 king beds
Fridge, microwave, oven, stovetop

Sleeps 24+ Luxury house Near Chicago 12 king beds

The price is €4,093
includes taxes & fees
10 Nov - 11 Nov
Sleeps 24+ Luxury house Near Chicago 12 king beds
Cozy Westchester Retreat Near Chicago & Parks | LCP Collection
Fridge, microwave, oven, stovetop

Cozy Westchester Retreat Near Chicago & Parks | LCP Collection

Cozy Westchester Retreat Near Chicago & Parks | LCP Collection
Lovely 3-bedroom house in Villa Park with WiFi and AC
3 bedrooms, iron/ironing board, WiFi, bed sheets

Lovely 3-bedroom house in Villa Park with WiFi and AC

Lovely 3-bedroom house in Villa Park with WiFi and AC
Enamored in Elmhurst
Smart TV

Enamored in Elmhurst

2.0 star property
10.0 out of 10, Exceptional, (12)
"Great stay"
The price is €438
includes taxes & fees
13 Oct - 14 Oct
Enamored in Elmhurst
Cicer3bdrm w Pool Table & Shufflle Board
Fridge, microwave, oven, stovetop

Cicer3bdrm w Pool Table & Shufflle Board

10.0 out of 10, Exceptional, (2)
"Was perfect location to get to and from downtown Chicago, just 30 min with Lyft/Uber. Our 2 dogs did great and had a fenced backyard for them to run. Garage was nice to put our vehicle in. "
The price is €470
includes taxes & fees
13 Oct - 14 Oct
Cicer3bdrm w Pool Table & Shufflle Board
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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Top Chicago Hotel Reviews

Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG

10/10 Excellent
"Great location"
Patricia 3-night trip
Posted 2 days ago
Crowne Plaza Chicago West Loop by IHG

Find out more about Chicago

Chicago Holiday Homes information

Number of reviews
63,453
Accommodation
842 Holiday Homes
Lowest Price
€97
Highest Price
€264