Home Vacation Condo Rentals By Owner In Chicago, IL

Showing 224 Of 224 Vacation Rentals
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Exceptional(11)

$187.95

/ Nightly
Condo

Bright 2 Bed/2 Bath Condo With Patio Less Than 10 Mins From Major Attractions

Chicago, Illinois, United States

BRIGHT HIGH FIRST FLOOR CORNER UNIT FEATURES TONS OF WINDOWS; HARDWOOD FLOORS THROUGHOUT. LARGE BALCONY RIGHT OFF OF THE LIVING AREA WITH HEATERS AND IN-UNIT WASHER/DRYER. EASY STREET PARKING AND LESS THAN 10 MINUTES TO UNIVERSITY OF CHICAGO, DOWNTOWN HYDE PARK AND LAKE MICHIGAN BEACHFRONT
Bed 2

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Bath 2

Bath

Sleep 4

Sleeps
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Exceptional(8)

$424.33

/ Nightly
Condo

Beautiful, modern 3 bed 2 bath condo near Hyde Park, Obama Center and Lakefront

Chicago, Illinois, United States

brbExperience Chicago/bbrExperience Chicago in this fabulous, all modern 3-bedroom 3-bath condo near Hyde Park, The Obama Center, an 18 hole golf course and the lakefront bike path. This newly rehabbed condo is just the place to enjoy the city.ul class=places-to-go style=margin:0px;liGet to the downtown in just 10min via Lake Shore Drive./liliBike the 26 miles of the lakefront (just 1 block north)./liliRelax at a local beach within walking distance./liliVisit the new Obama Center (coming soon)/liliTake in a round of golf at an 18 hole Golf Course./libr/ulbA great stay for the entire family/bbrThe kitchen is bright, modern and the perfect place to entertain. The unit has 2 large and 1 medium bedroom. The en-suite bath includes a beautiful walk-in shower and additional sunroom. This is the place for a great stay in the Windy City. (No parties or events allowed.)
Bed 3

Bed

Bath 2

Bath

Sleep 5

Sleeps
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$574.96

/ Nightly
Condo

Fabulous 3 Bedroom in the Heart of North Center

Chicago, Illinois, United States

Modern 3BR/1BA apartment in a prime Chicago neighborhood! Spacious apartment with large living room. Updated kitchen and bathroom with hardwood flooring throughout. 3 bedrooms with 1 king, and 2 queen sized beds. Free parking provided. The location is phenomenal! Close to Wrigley Field, Lincoln Square, and public transit for easy city access. Perfect for families or groups—comfort and convenience in one stylish space! Everything you need at your fingertips!
Bed 3

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Bath 1

Bath

Sleep 6

Sleeps
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$99.06

/ Nightly
Condo

Cozy Private Room in Chicago, Queen Bed, Up to 5 People, Free Parking, 32+ Stay

Chicago, Illinois, United States

Looking for a cozy room, convenient place to stay This charming room of 2 bedroom apartment in Roger’s Park is the perfect. This is private room unit features 1 queen bed, 1 sofa bed, heating, iron, WiFi, AC. One PhD student stays in another room. Imagine waking up in this tranquil space, ready to explore the city. Whether you're here for business or pleasure, our awesome condo is the perfect home base for your Chicago adventure. Location is everything; just a short walk to the subway (Red Line) and major bus stops, quick and easy access to downtown Chicago, close to Loyola University.
Bed 1

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Bath 1

Bath

Sleep 5

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Home Most popular vacation rentals in Chicago

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$2319.21

/ Nightly
Apartment

Luxury Loft Collection COMBO 02/03 | Terrace

Chicago, Illinois, United States

Bed 6

Bed

Bath 6

Bath

Sleep 22

Sleeps
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$2427.16

/ Nightly
Apart-hotel

New Construction Building in River North!

Chicago, Illinois, United States

Bed 11

Bed

Bath 10

Bath

Sleep 16

Sleeps
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$2731.80

/ Nightly
Apartment

Sleep 25 - Huge Downtown Vintage Lofts

Chicago, Illinois, United States

Bed 5

Bed

Bath 6

Bath

Sleep 16

Sleeps
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$2999.50

/ Nightly
Apartment

Unique Luxury Fulton Market Penthouse - Sleeps 32

Chicago, Illinois, United States

Bed 9

Bed

Bath 7

Bath

Sleep 32

Sleeps
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$3259.71

/ Nightly
Private vacation home

Private Historical Mansion,Luxury Home in Chicago’s Gold Coast, Event-Capable.

Chicago, Illinois, United States

Bed 5

Bed

Bath 5

Bath

Sleep 14

Sleeps
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$3780.16

/ Nightly
Condo

Downtown Mich Ave - 6 Penthouses, Sleep 25

Chicago, Illinois, United States

Bed 10

Bed

Bath 9

Bath

Sleep 16

Sleeps
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$320.07

/ Nightly
Apartment

LIVN West Loop Chicago King Studio

Chicago, Illinois, United States

Bed 1

Bed

Bath 1

Bath

Sleep 2

Sleeps
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$317.86

/ Nightly
Apartment

Roscoe Village- Only steps to cute shops & dining! Sleeps 4-6

Chicago, Illinois, United States

Bed 2

Bed

Bath 1

Bath

Sleep 6

Sleeps
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$318.18

/ Nightly
Apartment

Perfect for a Hip and Romantic Getaway - This Chic Studio Offers the Best of the City by AllSet Turnover

Chicago, Illinois, United States

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Bed

Bath 1

Bath

Sleep 2

Sleeps
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$318.68

/ Nightly
Apartment

Vintage City Chic: The Artist's Haven. 5 Blocks from Lake Michigan!

Chicago, Illinois, United States

Bed 2

Bed

Bath 1

Bath

Sleep 6

Sleeps

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