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Chicago Holiday Rentals

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5 mi
49 rentals in Chicago.
The following properties within 32 kms of Chicago match all your filters:
Brand new private 2 bedroom unit, holiday rental in Chicago
Brand new private 2 bedroom unit, holiday rental in Chicago
Brand new private 2 bedroom unit, holiday rental in Chicago

Brand new private 2 bedroom unit

Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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N Ridgeway · Logan Square Cozy Apartment - Games+Arcade - Patio, holiday rental in Chicago
N Ridgeway · Logan Square Cozy Apartment - Games+Arcade - Patio, holiday rental in Chicago
N Ridgeway · Logan Square Cozy Apartment - Games+Arcade - Patio, holiday rental in Chicago

N Ridgeway · Logan Square Cozy Apartment - Games+Arcade - Patio

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
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Family-friendly, stylish Chicago Apartment in Logan Square, holiday rental in Chicago
Family-friendly, stylish Chicago Apartment in Logan Square, holiday rental in Chicago
Family-friendly, stylish Chicago Apartment in Logan Square, holiday rental in Chicago

Family-friendly, stylish Chicago Apartment in Logan Square

Condo/Apartment in North Side, Logan Square
3 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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Home away from home. Perfect for remote workers., holiday rental in Chicago
Home away from home. Perfect for remote workers., holiday rental in Chicago
Home away from home. Perfect for remote workers., holiday rental in Chicago

Home away from home. Perfect for remote workers.

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Cozy 2 Bedroom on a Quite Street, holiday rental in Chicago
Cozy 2 Bedroom on a Quite Street, holiday rental in Chicago
Cozy 2 Bedroom on a Quite Street, holiday rental in Chicago

Cozy 2 Bedroom on a Quite Street

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Clean & Cozy entire 3 bedroom unit 7 miles from downtown, holiday rental in Chicago
Clean & Cozy entire 3 bedroom unit 7 miles from downtown, holiday rental in Chicago
Clean & Cozy entire 3 bedroom unit 7 miles from downtown, holiday rental in Chicago

Clean & Cozy entire 3 bedroom unit 7 miles from downtown

Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Charming Chicago Retreat with Modern Comforts - Spa Bath, holiday rental in Chicago
Charming Chicago Retreat with Modern Comforts - Spa Bath, holiday rental in Chicago
Charming Chicago Retreat with Modern Comforts - Spa Bath, holiday rental in Chicago

Charming Chicago Retreat with Modern Comforts - Spa Bath

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Amazing, sunny and spacious 3BD/ 1BA-minutes from Downtown, holiday rental in Chicago
Amazing, sunny and spacious 3BD/ 1BA-minutes from Downtown, holiday rental in Chicago
Amazing, sunny and spacious 3BD/ 1BA-minutes from Downtown, holiday rental in Chicago

Amazing, sunny and spacious 3BD/ 1BA-minutes from Downtown

Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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CPS3 Logan Square Corner 3BR Apt Walkable to Highlights, holiday rental in Chicago
CPS3 Logan Square Corner 3BR Apt Walkable to Highlights, holiday rental in Chicago
CPS3 Logan Square Corner 3BR Apt Walkable to Highlights, holiday rental in Chicago

CPS3 Logan Square Corner 3BR Apt Walkable to Highlights

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful Chicago 2BD 1BA, minutes from Downtown!, holiday rental in Chicago
Beautiful Chicago 2BD 1BA, minutes from Downtown!, holiday rental in Chicago
Beautiful Chicago 2BD 1BA, minutes from Downtown!, holiday rental in Chicago

Beautiful Chicago 2BD 1BA, minutes from Downtown!

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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La Villita - Gateway to Chicago (2 bedroom apartment 10 mins from downtown), holiday rental in Chicago
La Villita - Gateway to Chicago (2 bedroom apartment 10 mins from downtown), holiday rental in Chicago
La Villita - Gateway to Chicago (2 bedroom apartment 10 mins from downtown), holiday rental in Chicago

La Villita - Gateway to Chicago (2 bedroom apartment 10 mins from downtown)

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Affiliated with FlipKey
Private 1 BR 1 BA Guest Suite, holiday rental in Chicago
Private 1 BR 1 BA Guest Suite, holiday rental in Chicago
Private 1 BR 1 BA Guest Suite, holiday rental in Chicago

Private 1 BR 1 BA Guest Suite

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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In the Heart of Little Mexico! Shared Stylish Apartment in Chicago, holiday rental in Chicago
In the Heart of Little Mexico! Shared Stylish Apartment in Chicago, holiday rental in Chicago
In the Heart of Little Mexico! Shared Stylish Apartment in Chicago, holiday rental in Chicago

In the Heart of Little Mexico! Shared Stylish Apartment in Chicago

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Airy Avondale Getaway with King Bed, holiday rental in Chicago
Airy Avondale Getaway with King Bed, holiday rental in Chicago
Airy Avondale Getaway with King Bed, holiday rental in Chicago

Airy Avondale Getaway with King Bed

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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North-Side of Chicago near Wrigley + 90/94 + CTA Addison Blue Line Station, holiday rental in Chicago
North-Side of Chicago near Wrigley + 90/94 + CTA Addison Blue Line Station, holiday rental in Chicago
North-Side of Chicago near Wrigley + 90/94 + CTA Addison Blue Line Station, holiday rental in Chicago

North-Side of Chicago near Wrigley + 90/94 + CTA Addison Blue Line Station

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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✨Rustic Studio Apartment Heart of Lincoln Square✨, holiday rental in Chicago
✨Rustic Studio Apartment Heart of Lincoln Square✨, holiday rental in Chicago
✨Rustic Studio Apartment Heart of Lincoln Square✨, holiday rental in Chicago

✨Rustic Studio Apartment Heart of Lincoln Square✨

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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KING LOVELY SPACE, holiday rental in Chicago
KING LOVELY SPACE, holiday rental in Chicago
KING LOVELY SPACE, holiday rental in Chicago

KING LOVELY SPACE

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Cozy Private Bedroom and bathroom with full kitchen, holiday rental in Chicago
Cozy Private Bedroom and bathroom with full kitchen, holiday rental in Chicago
Cozy Private Bedroom and bathroom with full kitchen, holiday rental in Chicago

Cozy Private Bedroom and bathroom with full kitchen

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Retro 2 bedroom bungalow in Chicago's Avondale neighborhood, holiday rental in Chicago
Retro 2 bedroom bungalow in Chicago's Avondale neighborhood, holiday rental in Chicago
Retro 2 bedroom bungalow in Chicago's Avondale neighborhood, holiday rental in Chicago

Retro 2 bedroom bungalow in Chicago's Avondale neighborhood

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Chicago Modern Condo- Perfect for family time or a good time in Chicago., holiday rental in Chicago
Chicago Modern Condo- Perfect for family time or a good time in Chicago., holiday rental in Chicago
Chicago Modern Condo- Perfect for family time or a good time in Chicago., holiday rental in Chicago

Chicago Modern Condo- Perfect for family time or a good time in Chicago.

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Bedroom 2 Comfy Pvt - Shared BA - Living Room - Washer Dryer - Pet & Family Fr., holiday rental in Chicago
Bedroom 2 Comfy Pvt - Shared BA - Living Room - Washer Dryer - Pet & Family Fr., holiday rental in Chicago
Bedroom 2 Comfy Pvt - Shared BA - Living Room - Washer Dryer - Pet & Family Fr., holiday rental in Chicago

Bedroom 2 Comfy Pvt - Shared BA - Living Room - Washer Dryer - Pet & Family Fr.

Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
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Warm|Cozy|Lovely|1BR|Lincoln Sq.|, holiday rental in Chicago
Warm|Cozy|Lovely|1BR|Lincoln Sq.|, holiday rental in Chicago
Warm|Cozy|Lovely|1BR|Lincoln Sq.|, holiday rental in Chicago

Warm|Cozy|Lovely|1BR|Lincoln Sq.|

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Pvt Rm Bdrm 4 Comfy Pvt Rm - Shared Bath/Liv, holiday rental in Chicago
Pvt Rm Bdrm 4 Comfy Pvt Rm - Shared Bath/Liv, holiday rental in Chicago
Pvt Rm Bdrm 4 Comfy Pvt Rm - Shared Bath/Liv, holiday rental in Chicago

Pvt Rm Bdrm 4 Comfy Pvt Rm - Shared Bath/Liv

Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
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Bdrm 1 Comfy Pvt Rm - Shared Bath/Liv, holiday rental in Chicago
Bdrm 1 Comfy Pvt Rm - Shared Bath/Liv, holiday rental in Chicago
Bdrm 1 Comfy Pvt Rm - Shared Bath/Liv, holiday rental in Chicago

Bdrm 1 Comfy Pvt Rm - Shared Bath/Liv

Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
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Pvt Rm Bdrm 3 Comfy Pvt Rm - Shared Bath/Liv, holiday rental in Chicago
Pvt Rm Bdrm 3 Comfy Pvt Rm - Shared Bath/Liv, holiday rental in Chicago
Pvt Rm Bdrm 3 Comfy Pvt Rm - Shared Bath/Liv, holiday rental in Chicago

Pvt Rm Bdrm 3 Comfy Pvt Rm - Shared Bath/Liv

Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
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Quiet Chicago Townhome - 7 Mi to Downtown!, holiday rental in Chicago
Quiet Chicago Townhome - 7 Mi to Downtown!, holiday rental in Chicago
Quiet Chicago Townhome - 7 Mi to Downtown!, holiday rental in Chicago

Quiet Chicago Townhome - 7 Mi to Downtown!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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LOGAN SQUARE: Chic, Comfy 1st Floor 2 BDRM APT! Parking Incld!, holiday rental in Chicago
LOGAN SQUARE: Chic, Comfy 1st Floor 2 BDRM APT! Parking Incld!, holiday rental in Chicago
LOGAN SQUARE: Chic, Comfy 1st Floor 2 BDRM APT! Parking Incld!, holiday rental in Chicago

LOGAN SQUARE: Chic, Comfy 1st Floor 2 BDRM APT! Parking Incld!

Holiday Rental House in North Side, Logan Square
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Great Chicago getaway, holiday rental in Chicago
Great Chicago getaway, holiday rental in Chicago
Great Chicago getaway, holiday rental in Chicago

Great Chicago getaway

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Vintage/Modern Hideaway in Logan Square, holiday rental in Chicago
Vintage/Modern Hideaway in Logan Square, holiday rental in Chicago
Vintage/Modern Hideaway in Logan Square, holiday rental in Chicago

Vintage/Modern Hideaway in Logan Square

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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FREE PARKING! Desirable Logan Square Location with Modern Touches and Beautiful, holiday rental in Chicago
FREE PARKING! Desirable Logan Square Location with Modern Touches and Beautiful, holiday rental in Chicago
FREE PARKING! Desirable Logan Square Location with Modern Touches and Beautiful, holiday rental in Chicago

FREE PARKING! Desirable Logan Square Location with Modern Touches and Beautiful

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Minutes from Downtown Gorgeous ,spacious 2BD/ 1BA w/ Parking, holiday rental in Chicago
Minutes from Downtown Gorgeous ,spacious 2BD/ 1BA w/ Parking, holiday rental in Chicago
Minutes from Downtown Gorgeous ,spacious 2BD/ 1BA w/ Parking, holiday rental in Chicago

Minutes from Downtown Gorgeous ,spacious 2BD/ 1BA w/ Parking

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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home sweet home chicago - garage parking & downtown in 20m, holiday rental in Chicago
home sweet home chicago - garage parking & downtown in 20m, holiday rental in Chicago
home sweet home chicago - garage parking & downtown in 20m, holiday rental in Chicago

home sweet home chicago - garage parking & downtown in 20m

Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Perfectly Located, Bright 2B/1BA Urban Oasis, holiday rental in Chicago
Perfectly Located, Bright 2B/1BA Urban Oasis, holiday rental in Chicago
Perfectly Located, Bright 2B/1BA Urban Oasis, holiday rental in Chicago

Perfectly Located, Bright 2B/1BA Urban Oasis

Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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1,400 SqFt Stylish Top Floor.15min Dr to S. Loop or Med District., holiday rental in Chicago
1,400 SqFt Stylish Top Floor.15min Dr to S. Loop or Med District., holiday rental in Chicago
1,400 SqFt Stylish Top Floor.15min Dr to S. Loop or Med District., holiday rental in Chicago

1,400 SqFt Stylish Top Floor.15min Dr to S. Loop or Med District.

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Chic Chicago Getaway w/ Deck, 7 Mi to Downtown!, holiday rental in Chicago
Chic Chicago Getaway w/ Deck, 7 Mi to Downtown!, holiday rental in Chicago
Chic Chicago Getaway w/ Deck, 7 Mi to Downtown!, holiday rental in Chicago

Chic Chicago Getaway w/ Deck, 7 Mi to Downtown!

Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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Bright & Clean Apt in Front of Lovely Park!, holiday rental in Chicago
Bright & Clean Apt in Front of Lovely Park!, holiday rental in Chicago
Bright & Clean Apt in Front of Lovely Park!, holiday rental in Chicago

Bright & Clean Apt in Front of Lovely Park!

Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Chicago Vacation Rental ~ 7 Miles to Downtown, holiday rental in Chicago
Chicago Vacation Rental ~ 7 Miles to Downtown, holiday rental in Chicago
Chicago Vacation Rental ~ 7 Miles to Downtown, holiday rental in Chicago

Chicago Vacation Rental ~ 7 Miles to Downtown

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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North-Side of Chicago near Wrigley, holiday rental in Chicago
North-Side of Chicago near Wrigley, holiday rental in Chicago
North-Side of Chicago near Wrigley, holiday rental in Chicago

North-Side of Chicago near Wrigley

Condo/Apartment in Irving Park, Northwest Side
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Tranquil newly remodeled 3BR APT w-PKG near bus routes., holiday rental in Chicago
Tranquil newly remodeled 3BR APT w-PKG near bus routes., holiday rental in Chicago
Tranquil newly remodeled 3BR APT w-PKG near bus routes., holiday rental in Chicago

Tranquil newly remodeled 3BR APT w-PKG near bus routes.

Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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BoHo House - Hip hangout spot near local bars+eats, holiday rental in Chicago
BoHo House - Hip hangout spot near local bars+eats, holiday rental in Chicago
BoHo House - Hip hangout spot near local bars+eats, holiday rental in Chicago

BoHo House - Hip hangout spot near local bars+eats

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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LA3 3BR Comfy Apartment in Logan Square, holiday rental in Chicago
LA3 3BR Comfy Apartment in Logan Square, holiday rental in Chicago
LA3 3BR Comfy Apartment in Logan Square, holiday rental in Chicago

LA3 3BR Comfy Apartment in Logan Square

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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LA2 Relaxing 3BR Logan Square with King Beds & Washer, holiday rental in Chicago
LA2 Relaxing 3BR Logan Square with King Beds & Washer, holiday rental in Chicago
LA2 Relaxing 3BR Logan Square with King Beds & Washer, holiday rental in Chicago

LA2 Relaxing 3BR Logan Square with King Beds & Washer

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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LA1 3-BR Gem with Parking and In-Unit Laundry, holiday rental in Chicago
LA1 3-BR Gem with Parking and In-Unit Laundry, holiday rental in Chicago
LA1 3-BR Gem with Parking and In-Unit Laundry, holiday rental in Chicago

LA1 3-BR Gem with Parking and In-Unit Laundry

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Perfect 4 Bedroom + 2 Bath unit on 2 separate floors, Free parking, CUBS, holiday rental in Chicago
Perfect 4 Bedroom + 2 Bath unit on 2 separate floors, Free parking, CUBS, holiday rental in Chicago
Perfect 4 Bedroom + 2 Bath unit on 2 separate floors, Free parking, CUBS, holiday rental in Chicago

Perfect 4 Bedroom + 2 Bath unit on 2 separate floors, Free parking, CUBS

Condo/Apartment
4 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Family Friendly - Wonderful Neighborhood - Perfect Layout for all Groups - Even, holiday rental in Chicago
Family Friendly - Wonderful Neighborhood - Perfect Layout for all Groups - Even, holiday rental in Chicago
Family Friendly - Wonderful Neighborhood - Perfect Layout for all Groups - Even, holiday rental in Chicago

Family Friendly - Wonderful Neighborhood - Perfect Layout for all Groups - Even

Condo/Apartment
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Logan Square Cozy 4BR/2BA, Free Parking, W/D, holiday rental in Chicago
Logan Square Cozy 4BR/2BA, Free Parking, W/D, holiday rental in Chicago
Logan Square Cozy 4BR/2BA, Free Parking, W/D, holiday rental in Chicago

Logan Square Cozy 4BR/2BA, Free Parking, W/D

Condo/Apartment
4 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Historic Hermosa - 20 min to Downtown - 3000 sqft, holiday rental in Chicago
Historic Hermosa - 20 min to Downtown - 3000 sqft, holiday rental in Chicago
Historic Hermosa - 20 min to Downtown - 3000 sqft, holiday rental in Chicago

Historic Hermosa - 20 min to Downtown - 3000 sqft

Holiday Rental House
6 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Lux Chicago Home-  6 bd 4 ba- 2 car garage.  25 mins to downtown., holiday rental in Chicago
Lux Chicago Home-  6 bd 4 ba- 2 car garage.  25 mins to downtown., holiday rental in Chicago
Lux Chicago Home-  6 bd 4 ba- 2 car garage.  25 mins to downtown., holiday rental in Chicago

Lux Chicago Home- 6 bd 4 ba- 2 car garage. 25 mins to downtown.

Holiday Rental House
6 bedrooms
4 bathrooms
Sleeps 2
Match: Sleeps
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Spacious Apartment in Hermosa Park, holiday rental in Chicago
Spacious Apartment in Hermosa Park, holiday rental in Chicago
Spacious Apartment in Hermosa Park, holiday rental in Chicago

Spacious Apartment in Hermosa Park

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Showing results 1-49 of 49

Chicago Holiday Rentals
Located on the shores of Lake Michigan, Chicago is a stunning city bursting with attractions. Accommodation can be pricey, but choosing a rental property rather than a hotel is the ideal way to save money. Whether you prefer a spacious apartment in the city centre or a family house in a quieter area, you will feel relaxed and be able to organise your schedule as it suits you. You will of course find a host of restaurants catering to all tastes, but when you are tired of eating out, you can prepare your own food in a fully equipped kitchen.
Chicago attractions
You might not know where to begin seeing the sights of Chicago, so take a trolley tour to give you and your family an overview. A Wellenda Boat tour along the Chicago River and Lake Michigan is another wonderful way to see the city's architecture. Don't miss the Magnificent Mile, where the John Hancock Observatory offers spectacular views of the skyscrapers and Lake Michigan beyond. Art lovers should make a beeline for the Art Institute of Chicago, with its world-class collections of French and American Impressionists and Dutch Masters. The whole family will enjoy a visit to Millennium Park, where the star attractions are the Crown Fountain and the Chicago Bean, an enormous silver sculpture. You can try out the restaurant there, and you might be lucky enough to catch a music festival as well.
Chicago holiday rentals for families
Animal lovers must find time to visit Lincoln Park Zoo, where the Regenstein African Ape Centre, the Kovler Lion House and the Primate House will impress. The youngest members of the family will find the sea lions and penguins especially entertaining to watch. Before you leave Lincoln Park, children will love a visit to Adams Playground. If the weather calls for an indoor activity, head for Chicago Children's Museum at Navy Pier with its interactive exhibits. When you feel like a break from the city, spend some time on one of Lake Michigan's beaches, where you can swim, sunbathe, or go kayaking or canoeing.
Budget holiday rentals in Chicago
For a holiday in a vibrant city, Chicago is hard to beat. Hotels can be expensive, but renting your accommodation is the ideal low-cost alternative. Decide whether you would rather be in the city centre within walking distance of the attractions or in the quieter suburbs. Then have a look at our range of apartments and houses and choose the one that suits you best. It's worth reading through our unbiased customer reviews to help you. After that, you can look forward to what promises to be a holiday to remember in Chicago.