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Chicago Holiday Rentals

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49 rentals in Chicago.
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Sonder | The Queen | Stylish Room, holiday rental in Chicago
Sonder | The Queen | Stylish Room, holiday rental in Chicago
Sonder | The Queen | Stylish Room, holiday rental in Chicago

Sonder | The Queen | Stylish Room

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
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Heart of Oak Park, train ride to downtown Chicago.  WIFI & Cable Included!, holiday rental in Chicago
Heart of Oak Park, train ride to downtown Chicago.  WIFI & Cable Included!, holiday rental in Chicago
Heart of Oak Park, train ride to downtown Chicago.  WIFI & Cable Included!, holiday rental in Chicago

Heart of Oak Park, train ride to downtown Chicago. WIFI & Cable Included!

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
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★ Sanitized ★ Home Living ★ Kids & Dogs ★ FREE PARKING ★ Quiet Area ★, holiday rental in Chicago
★ Sanitized ★ Home Living ★ Kids & Dogs ★ FREE PARKING ★ Quiet Area ★, holiday rental in Chicago
★ Sanitized ★ Home Living ★ Kids & Dogs ★ FREE PARKING ★ Quiet Area ★, holiday rental in Chicago

★ Sanitized ★ Home Living ★ Kids & Dogs ★ FREE PARKING ★ Quiet Area ★

Holiday Rental House in Portage Park, Northwest Side
2 bedrooms
1 bathroom
Sleeps 10
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Large, sunny 3 bedroom apartment two blocks from down town Oak Park.

Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 8
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The entire FLAT.  Stay Like You Own! Central AIR.
TWO FULL BATHROOMS. Unique., holiday rental in Chicago
The entire FLAT.  Stay Like You Own! Central AIR.
TWO FULL BATHROOMS. Unique., holiday rental in Chicago
The entire FLAT.  Stay Like You Own! Central AIR.
TWO FULL BATHROOMS. Unique., holiday rental in Chicago

The entire FLAT. Stay Like You Own! Central AIR. TWO FULL BATHROOMS. Unique.

Condo/Apartment in Edgewater, Magnolia Glen, Far North Side
2 bedrooms
2 bathrooms
Sleeps 5
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Cozy Nest in Chicago s Vibrant Lincoln Square. Steps to Western Brown Line., holiday rental in Chicago
Cozy Nest in Chicago s Vibrant Lincoln Square. Steps to Western Brown Line., holiday rental in Chicago
Cozy Nest in Chicago s Vibrant Lincoln Square. Steps to Western Brown Line., holiday rental in Chicago

Cozy Nest in Chicago s Vibrant Lincoln Square. Steps to Western Brown Line.

Condo/Apartment in Lincoln Square, Ravenswood, Far North Side
3 bedrooms
2 bathrooms
Sleeps 5
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Oak Park Home Duplex, holiday rental in Chicago
Oak Park Home Duplex, holiday rental in Chicago
Oak Park Home Duplex, holiday rental in Chicago

Oak Park Home Duplex

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
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Historic Andersonville Coach House, holiday rental in Chicago
Historic Andersonville Coach House, holiday rental in Chicago
Historic Andersonville Coach House, holiday rental in Chicago

Historic Andersonville Coach House

Holiday Rental House in Edgewater, Far North Side
3 bedrooms
1 bathroom
Sleeps 4
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Logan Square 2 BR/1 BA-modern, quality close to Metra, holiday rental in Chicago
Logan Square 2 BR/1 BA-modern, quality close to Metra, holiday rental in Chicago
Logan Square 2 BR/1 BA-modern, quality close to Metra, holiday rental in Chicago

Logan Square 2 BR/1 BA-modern, quality close to Metra

Condo/Apartment in North Side, Logan Square
2 bedrooms
1 bathroom
Sleeps 4
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Cozy, Comfortable and Convenient apartment. Close to everything!, holiday rental in Chicago
Cozy, Comfortable and Convenient apartment. Close to everything!, holiday rental in Chicago
Cozy, Comfortable and Convenient apartment. Close to everything!, holiday rental in Chicago

Cozy, Comfortable and Convenient apartment. Close to everything!

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
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Only Urban Beach House in Chicago, holiday rental in Chicago
Only Urban Beach House in Chicago, holiday rental in Chicago
Only Urban Beach House in Chicago, holiday rental in Chicago

Only Urban Beach House in Chicago

Holiday Rental House in Rogers Park, Far North Side
4 bedrooms
3 bathrooms
Sleeps 8
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Chicago Bungalow 'get away' in the City, holiday rental in Chicago
Chicago Bungalow 'get away' in the City, holiday rental in Chicago
Chicago Bungalow 'get away' in the City, holiday rental in Chicago

Chicago Bungalow 'get away' in the City

Holiday Rental House in Albany Park, Far North Side
3 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
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Quiet suite in Oak Park, holiday rental in Chicago
Quiet suite in Oak Park, holiday rental in Chicago
Quiet suite in Oak Park, holiday rental in Chicago

Quiet suite in Oak Park

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
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Retro-Chic Urban Oasis, holiday rental in Chicago
Retro-Chic Urban Oasis, holiday rental in Chicago
Retro-Chic Urban Oasis, holiday rental in Chicago

Retro-Chic Urban Oasis

Condo/Apartment in West Ridge (West Rogers Park), Far North Side
2 bedrooms
1 bathroom
Sleeps 4
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ENTIRE GUEST SUITE - Cozy Home Close to all what Logan Square Offers!, holiday rental in Chicago
ENTIRE GUEST SUITE - Cozy Home Close to all what Logan Square Offers!, holiday rental in Chicago
ENTIRE GUEST SUITE - Cozy Home Close to all what Logan Square Offers!, holiday rental in Chicago

ENTIRE GUEST SUITE - Cozy Home Close to all what Logan Square Offers!

Condo/Apartment in Avondale, North Side, Logan Square
1 bedroom
1 bathroom
Sleeps 3
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Sunny Jumbo Studio in the Heart of Oak Park, holiday rental in Chicago
Sunny Jumbo Studio in the Heart of Oak Park, holiday rental in Chicago
Sunny Jumbo Studio in the Heart of Oak Park, holiday rental in Chicago

Sunny Jumbo Studio in the Heart of Oak Park

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
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Beautiful 2-bedroom apt. on a quiet tree-lined rstreet close to downtown Chicago, holiday rental in Chicago
Beautiful 2-bedroom apt. on a quiet tree-lined rstreet close to downtown Chicago, holiday rental in Chicago
Beautiful 2-bedroom apt. on a quiet tree-lined rstreet close to downtown Chicago, holiday rental in Chicago

Beautiful 2-bedroom apt. on a quiet tree-lined rstreet close to downtown Chicago

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
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Comfortable home in historic Oak Park- open For Thanksgiving and Christmas!!!, holiday rental in Chicago
Comfortable home in historic Oak Park- open For Thanksgiving and Christmas!!!, holiday rental in Chicago
Comfortable home in historic Oak Park- open For Thanksgiving and Christmas!!!, holiday rental in Chicago

Comfortable home in historic Oak Park- open For Thanksgiving and Christmas!!!

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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You'll love! Spacious, clean, remodeled, 2 bedroom, parking, coin W/D, linens, holiday rental in Chicago
You'll love! Spacious, clean, remodeled, 2 bedroom, parking, coin W/D, linens, holiday rental in Chicago
You'll love! Spacious, clean, remodeled, 2 bedroom, parking, coin W/D, linens, holiday rental in Chicago

You'll love! Spacious, clean, remodeled, 2 bedroom, parking, coin W/D, linens

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Fully Furnished and rehabbed townhouse with off-street parking and yard, holiday rental in Chicago
Fully Furnished and rehabbed townhouse with off-street parking and yard, holiday rental in Chicago
Fully Furnished and rehabbed townhouse with off-street parking and yard, holiday rental in Chicago

Fully Furnished and rehabbed townhouse with off-street parking and yard

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
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Charming apartment, fantastic location! Spacious 4 bedroom, a rare find!, holiday rental in Chicago
Charming apartment, fantastic location! Spacious 4 bedroom, a rare find!, holiday rental in Chicago
Charming apartment, fantastic location! Spacious 4 bedroom, a rare find!, holiday rental in Chicago

Charming apartment, fantastic location! Spacious 4 bedroom, a rare find!

Condo/Apartment
4 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Oak Park Beauty Sleeps 1 to 8 Guests, holiday rental in Chicago
Oak Park Beauty Sleeps 1 to 8 Guests, holiday rental in Chicago
Oak Park Beauty Sleeps 1 to 8 Guests, holiday rental in Chicago

Oak Park Beauty Sleeps 1 to 8 Guests

Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 6
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Quiet, family getaway. Puppers welcome!, holiday rental in Chicago
Quiet, family getaway. Puppers welcome!, holiday rental in Chicago
Quiet, family getaway. Puppers welcome!, holiday rental in Chicago

Quiet, family getaway. Puppers welcome!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Calm and Serene - Downtown Oak Park, Pets OK, holiday rental in Chicago
Calm and Serene - Downtown Oak Park, Pets OK, holiday rental in Chicago
Calm and Serene - Downtown Oak Park, Pets OK, holiday rental in Chicago

Calm and Serene - Downtown Oak Park, Pets OK

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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StayGia | Contemporary 1BR Corner Suite w/ Michigan Lake View by LU 1, holiday rental in Chicago
StayGia | Contemporary 1BR Corner Suite w/ Michigan Lake View by LU 1, holiday rental in Chicago
StayGia | Contemporary 1BR Corner Suite w/ Michigan Lake View by LU 1, holiday rental in Chicago

StayGia | Contemporary 1BR Corner Suite w/ Michigan Lake View by LU 1

Condo/Apartment in Edgewater, Far North Side
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Modern Victorian With Old World Charm, holiday rental in Chicago
Modern Victorian With Old World Charm, holiday rental in Chicago
Modern Victorian With Old World Charm, holiday rental in Chicago

Modern Victorian With Old World Charm

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Elegant, Urban Retreat, Child/Family Friendly!, holiday rental in Chicago
Elegant, Urban Retreat, Child/Family Friendly!, holiday rental in Chicago
Elegant, Urban Retreat, Child/Family Friendly!, holiday rental in Chicago

Elegant, Urban Retreat, Child/Family Friendly!

Condo/Apartment in Edgewater Beach, Edgewater, Far North Side
3 bedrooms
1 bathroom
Sleeps 8
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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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Condo, holiday rental in Chicago

Condo

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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** Home Away From Home **, holiday rental in Chicago
** Home Away From Home **, holiday rental in Chicago
** Home Away From Home **, holiday rental in Chicago

** Home Away From Home **

Holiday Rental House
7 bedrooms
3 bathrooms
Sleeps 16
Match: Sleeps
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Rockin' 2BR Apartment in the Heart of Oak Park, holiday rental in Chicago
Rockin' 2BR Apartment in the Heart of Oak Park, holiday rental in Chicago
Rockin' 2BR Apartment in the Heart of Oak Park, holiday rental in Chicago

Rockin' 2BR Apartment in the Heart of Oak Park

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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*Extended Stay* Modern finishes w/King bed!, holiday rental in Chicago
*Extended Stay* Modern finishes w/King bed!, holiday rental in Chicago
*Extended Stay* Modern finishes w/King bed!, holiday rental in Chicago

*Extended Stay* Modern finishes w/King bed!

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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A5 Luxurious Garden Unit Near Chicago, holiday rental in Chicago
A5 Luxurious Garden Unit Near Chicago, holiday rental in Chicago
A5 Luxurious Garden Unit Near Chicago, holiday rental in Chicago

A5 Luxurious Garden Unit Near Chicago

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Stylish & Urban - Oak Park/Forest Park, Pets OK, holiday rental in Chicago
Stylish & Urban - Oak Park/Forest Park, Pets OK, holiday rental in Chicago
Stylish & Urban - Oak Park/Forest Park, Pets OK, holiday rental in Chicago

Stylish & Urban - Oak Park/Forest Park, Pets OK

Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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The Mid Century II - Downtown Oak Park, Pets OK, holiday rental in Chicago
The Mid Century II - Downtown Oak Park, Pets OK, holiday rental in Chicago
The Mid Century II - Downtown Oak Park, Pets OK, holiday rental in Chicago

The Mid Century II - Downtown Oak Park, Pets OK

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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The Book Nook - Downtown Oak Park, Pets OK, holiday rental in Chicago
The Book Nook - Downtown Oak Park, Pets OK, holiday rental in Chicago
The Book Nook - Downtown Oak Park, Pets OK, holiday rental in Chicago

The Book Nook - Downtown Oak Park, Pets OK

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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The Mid Century - Downtown Oak Park, Pets OK, holiday rental in Chicago
The Mid Century - Downtown Oak Park, Pets OK, holiday rental in Chicago
The Mid Century - Downtown Oak Park, Pets OK, holiday rental in Chicago

The Mid Century - Downtown Oak Park, Pets OK

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Simple & Suite (1) - Extended Stay, Pets OK, holiday rental in Chicago
Simple & Suite (1) - Extended Stay, Pets OK, holiday rental in Chicago
Simple & Suite (1) - Extended Stay, Pets OK, holiday rental in Chicago

Simple & Suite (1) - Extended Stay, Pets OK

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Simple & Suite (2) - Extended Stay, Pets OK, holiday rental in Chicago
Simple & Suite (2) - Extended Stay, Pets OK, holiday rental in Chicago
Simple & Suite (2) - Extended Stay, Pets OK, holiday rental in Chicago

Simple & Suite (2) - Extended Stay, Pets OK

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Vacation Vibes - Downtown Oak Park, Pets OK, holiday rental in Chicago
Vacation Vibes - Downtown Oak Park, Pets OK, holiday rental in Chicago
Vacation Vibes - Downtown Oak Park, Pets OK, holiday rental in Chicago

Vacation Vibes - Downtown Oak Park, Pets OK

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Boho Retreat - Downtown Oak Park, Pets OK, holiday rental in Chicago
Boho Retreat - Downtown Oak Park, Pets OK, holiday rental in Chicago
Boho Retreat - Downtown Oak Park, Pets OK, holiday rental in Chicago

Boho Retreat - Downtown Oak Park, Pets OK

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
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The West is the Best! Pets OK, holiday rental in Chicago
The West is the Best! Pets OK, holiday rental in Chicago
The West is the Best! Pets OK, holiday rental in Chicago

The West is the Best! Pets OK

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Village Cottage-Oak Park/Forest Park, Pets OK, holiday rental in Chicago
Village Cottage-Oak Park/Forest Park, Pets OK, holiday rental in Chicago
Village Cottage-Oak Park/Forest Park, Pets OK, holiday rental in Chicago

Village Cottage-Oak Park/Forest Park, Pets OK

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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Happy Camper - Downtown Oak Park, Pets OK, holiday rental in Chicago
Happy Camper - Downtown Oak Park, Pets OK, holiday rental in Chicago
Happy Camper - Downtown Oak Park, Pets OK, holiday rental in Chicago

Happy Camper - Downtown Oak Park, Pets OK

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Southwest Oasis - Downtown Oak Park, Pets OK, holiday rental in Chicago
Southwest Oasis - Downtown Oak Park, Pets OK, holiday rental in Chicago
Southwest Oasis - Downtown Oak Park, Pets OK, holiday rental in Chicago

Southwest Oasis - Downtown Oak Park, Pets OK

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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StayGia | Stylish Modern 1BR  Suite by Loyola 3, holiday rental in Chicago
StayGia | Stylish Modern 1BR  Suite by Loyola 3, holiday rental in Chicago
StayGia | Stylish Modern 1BR  Suite by Loyola 3, holiday rental in Chicago

StayGia | Stylish Modern 1BR Suite by Loyola 3

Condo/Apartment in Edgewater, Far North Side
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Chicago Rover House in the woods 420 friendly, holiday rental in Chicago
Chicago Rover House in the woods 420 friendly, holiday rental in Chicago
Chicago Rover House in the woods 420 friendly, holiday rental in Chicago

Chicago Rover House in the woods 420 friendly

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 2
Match: Sleeps
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⭐|Stylish|Comfy|Lincoln Sq.| 2BR |✨|Near Wrigley|⭐, holiday rental in Chicago
⭐|Stylish|Comfy|Lincoln Sq.| 2BR |✨|Near Wrigley|⭐, holiday rental in Chicago
⭐|Stylish|Comfy|Lincoln Sq.| 2BR |✨|Near Wrigley|⭐, holiday rental in Chicago

⭐|Stylish|Comfy|Lincoln Sq.| 2BR |✨|Near Wrigley|⭐

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Taste of Provence-Extended Stay, W/D&DW, 2BR, Pets, holiday rental in Chicago
Taste of Provence-Extended Stay, W/D&DW, 2BR, Pets, holiday rental in Chicago
Taste of Provence-Extended Stay, W/D&DW, 2BR, Pets, holiday rental in Chicago

Taste of Provence-Extended Stay, W/D&DW, 2BR, Pets

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Hygee Hide-Away - Downtown Oak Park, Pets OK, holiday rental in Chicago
Hygee Hide-Away - Downtown Oak Park, Pets OK, holiday rental in Chicago
Hygee Hide-Away - Downtown Oak Park, Pets OK, holiday rental in Chicago

Hygee Hide-Away - Downtown Oak Park, Pets OK

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 1
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Frequently Asked Questions about Chicago





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.
More
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.