Jackson Park Highlands Vacation Rentals & Ski-in/Ski-out Homes

Compare Vacation Rentals & Ski-in/Ski-out Homes in Jackson Park Highlands, Chicago, Illinois, USA

New Stay, Relax & Explore Chicago
House
Stay, Relax & Explore Chicago
From US $316 per night
8.0 (1 Review)
2 Bedrooms 10 Guests
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The Brown House - A luxurious UChicago Campus stay
Apartment
The Brown House - A luxurious UChicago Campus stay
From US $407 per night
10.0 (3 Reviews)
3 Bedrooms 6 Guests
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Sophy Hyde Park
Hotel
Sophy Hyde Park
From US $305 per night
|
9.6 (986 Reviews)
1 Bedroom 2 Guests
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Beautiful 4 bedroom 2 bathroom apartment near everything
Apartment
Beautiful 4 bedroom 2 bathroom apartment near everything
From US $250 per night
|
10.0 (2 Reviews)
4 Bedrooms 12 Guests
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Hyatt Place Chicago-South/University Medical Center
Hotel
Hyatt Place Chicago-South/University Medical Center
From US $199 per night
|
8.8 (1012 Reviews)
1 Bedroom 2 Guests
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New Homey Vibes Furnished 1BR Apt
Apartment
Homey Vibes Furnished 1BR Apt
From US $206 per night
New
1 Bedroom 2 Guests
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1 Mi to University of Chicago Urban Escape!
Apartment
1 Mi to University of Chicago Urban Escape!
From US $251 per night
|
10.0 (1 Review)
2 Bedrooms 4 Guests
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Capital O Empire Motel Chicago I-94
Hotel
Capital O Empire Motel Chicago I-94
From US $75 per night
3.8 (17 Reviews)
1 Bedroom 2 Guests
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Well-Equipped Studio Apartment - Dorchester 511
Apartment
Well-Equipped Studio Apartment - Dorchester 511
From US $407 per night
10.0 (1 Review)
1 Bedroom 2 Guests
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New 2 Mi to South Shore Beach: Unit w/Balcony & Yard!
Apartment
2 Mi to South Shore Beach: Unit w/Balcony & Yard!
From US $122 per night
New
3 Bedrooms 6 Guests
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Lively & Fully Furnished 1BR Apartment - Kenwood 408
Apartment
Lively & Fully Furnished 1BR Apartment - Kenwood 408
From US $213 per night
10.0 (1 Review)
1 Bedroom 2 Guests
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New Scott House in Woodlawn - Basement
Apartment
Scott House in Woodlawn - Basement
From US $47 per night
New
1 Bedroom 2 Guests
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Afrique Francaise de Woodlawn 1
House
Afrique Francaise de Woodlawn 1
From US $76 per night
9.3 (13 Reviews)
1 Bedroom 2 Guests
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Modern Apt Near U of Chicago!
Condo
Modern Apt Near U of Chicago!
From US $248 per night
10.0 (7 Reviews)
2 Bedrooms 6 Guests
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BOUTIQUE GARDEN HOUSE CHICAGO 3-STORY sleeps 12
House
BOUTIQUE GARDEN HOUSE CHICAGO 3-STORY sleeps 12
From US $449 per night
|
9.3 (3 Reviews)
5 Bedrooms 12 Guests
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1 Mi to University of Chicago: Urban Escape!
Apartment
1 Mi to University of Chicago: Urban Escape!
From US $239 per night
10.0 (7 Reviews)
2 Bedrooms 4 Guests
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Cozy & Radiant 2BR Apartment - BStone 605
Apartment
Cozy & Radiant 2BR Apartment - BStone 605
From US $494 per night
9.3 (3 Reviews)
2 Bedrooms 4 Guests
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Come experience The Lake Shore!
Apartment
Come experience The Lake Shore!
From US $295 per night
10.0 (3 Reviews)
2 Bedrooms 5 Guests
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Shared, spacious condo near UChicago and Obama Center
House
Shared, spacious condo near UChicago and Obama Center
From US $107 per night
9.2 (6 Reviews)
3 Bedrooms 6 Guests
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High-end 2Bdrm Garden Apt. Where Comfort Meets Style
Apartment
High-end 2Bdrm Garden Apt. Where Comfort Meets Style
From US $267 per night
10.0 (3 Reviews)
2 Bedrooms 5 Guests
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7 Mi to Downtown Luxe Chicago Condo
Apartment
7 Mi to Downtown Luxe Chicago Condo
From US $514 per night
|
9.2 (5 Reviews)
3 Bedrooms 7 Guests
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Bedroom with private full bathroom, linen and towels are provided.
Apartment
Bedroom with private full bathroom, linen and towels are provided.
From US $188 per night
10.0 (2 Reviews)
1 Bedroom 2 Guests
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Chateau de Woodlawn - Room I - La Tour Eiffel
House
Chateau de Woodlawn - Room I - La Tour Eiffel
From US $45 per night
9.0 (10 Reviews)
1 Bedroom 2 Guests
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Modern 2-bedroom 2 -bath condo in wonderful Woodlawn Chicago.
Condo
Modern 2-bedroom 2 -bath condo in wonderful Woodlawn Chicago.
From US $364 per night
10.0 (1 Review)
2 Bedrooms 4 Guests
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FRONTDESK Dashing 1 BR Apt near The Smart Museum
Apartment
FRONTDESK Dashing 1 BR Apt near The Smart Museum
From US $73 per night
|
9.0 (4 Reviews)
1 Bedroom 2 Guests
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Bright & Cozy 1BR Near UChicago
Apartment
Bright & Cozy 1BR Near UChicago
From US $255 per night
10.0 (1 Review)
1 Bedroom 2 Guests
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1BR Tranquil Hyde Park Apartment - Harper 202 & 402 rep
Apartment
1BR Tranquil Hyde Park Apartment - Harper 202 & 402 rep
From US $1,600 per night
9.0 (2 Reviews)
1 Bedroom 2 Guests
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Bright 1BR Unit in a Prime Spot
Apartment
Bright 1BR Unit in a Prime Spot
From US $252 per night
10.0 (1 Review)
1 Bedroom 2 Guests
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1BR Modern Apartment in Chicago - Del Prado 811
Apartment
1BR Modern Apartment in Chicago - Del Prado 811
From US $419 per night
9.0 (2 Reviews)
1 Bedroom 2 Guests
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Modern 1BR in Historic HydePark
Apartment
Modern 1BR in Historic HydePark
From US $241 per night
10.0 (1 Review)
1 Bedroom 4 Guests
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Modern & Spacious 3BR Apt with In-Unit Laundry - Bstone 2
Apartment
Modern & Spacious 3BR Apt with In-Unit Laundry - Bstone 2
From US $659 per night
|
9.0 (1 Review)
3 Bedrooms 6 Guests
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Parisian Retreat 6min to Main Quandrangle U of C
Apartment
Parisian Retreat 6min to Main Quandrangle U of C
From US $486 per night
9.0 (1 Review)
3 Bedrooms 6 Guests
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Modern Studio Near UChicago
Apartment
Modern Studio Near UChicago
From US $197 per night
10.0 (1 Review)
1 Bedroom 2 Guests
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1BR Stylish & Modern Chicago Apartment - Kenwood 508 rep
Apartment
1BR Stylish & Modern Chicago Apartment - Kenwood 508 rep
From US $414 per night
9.0 (1 Review)
1 Bedroom 2 Guests
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Cozy Charm Studio Apt in Chicago
Apartment
Cozy Charm Studio Apt in Chicago
From US $192 per night
10.0 (1 Review)
1 Bedroom 2 Guests
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1BR Chic and Cozy Apartment in Chicago - Hyde Park 408
Apartment
1BR Chic and Cozy Apartment in Chicago - Hyde Park 408
From US $387 per night
9.0 (1 Review)
1 Bedroom 2 Guests
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Cozy & Near Downtown, Hyde Park & the Metra
House
Cozy & Near Downtown, Hyde Park & the Metra
From US $173 per night
10.0 (1 Review)
2 Bedrooms 4 Guests
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Sleek & Functional 2-Bedroom Apt
Apartment
Sleek & Functional 2-Bedroom Apt
From US $215 per night
9.4 (3 Reviews)
2 Bedrooms 4 Guests
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Modern Condo-Obama & University of Chicago Area
Condo
Modern Condo-Obama & University of Chicago Area
From US $202 per night
8.8 (13 Reviews)
2 Bedrooms 5 Guests
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Spacious two bedroom condo with a cozy feel!
Condo
Spacious two bedroom condo with a cozy feel!
From US $230 per night
8.8 (6 Reviews)
2 Bedrooms 4 Guests
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Charming 1BR/1BA Apt in Chicago
Apartment
Charming 1BR/1BA Apt in Chicago
From US $230 per night
New
1 Bedroom 2 Guests
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A secluded bedroom with a private full bathroom
House
A secluded bedroom with a private full bathroom
From US $157 per night
8.9 (15 Reviews)
1 Bedroom 2 Guests
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Best Motel By OYO Chicago I-90
Hotel
Best Motel By OYO Chicago I-90
From US $85 per night
3.4 (42 Reviews)
1 Bedroom 2 Guests
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Cozy Studio in Chicago
Apartment
Cozy Studio in Chicago
From US $214 per night
New
1 Bedroom 2 Guests
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Sleek 1-Bedroom Apt in Chicago - East Park Tower 0610 rep
Apartment
Sleek 1-Bedroom Apt in Chicago - East Park Tower 0610 rep
From US $358 per night
8.8 (4 Reviews)
1 Bedroom 4 Guests
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Villa Christina
House
Villa Christina
From US $450 per night
|
New
1 Bedroom 2 Guests
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Beautiful Big 3 bedroom Quiet Apt near downtown
Apartment
Beautiful Big 3 bedroom Quiet Apt near downtown
From US $260 per night
|
8.7 (20 Reviews)
5 Bedrooms 8 Guests
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Best Western Plus Hyde Park Chicago Hotel
Hotel
Best Western Plus Hyde Park Chicago Hotel
From US $140 per night
|
8.0 (1000 Reviews)
1 Bedroom 2 Guests
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Bright & Modern 1BR in Hyde Park
Apartment
Bright & Modern 1BR in Hyde Park
From US $188 per night
New
1 Bedroom 2 Guests
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Eco Stay by UChicago, Lakefront & Hyde Park!
Apartment
Eco Stay by UChicago, Lakefront & Hyde Park!
From US $183 per night
|
8.7 (3 Reviews)
2 Bedrooms 5 Guests
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< 2 Mi to UChicago: Pet-Friendly Getaway w/Yard
Apartment
< 2 Mi to UChicago: Pet-Friendly Getaway w/Yard
From US $187 per night
New
2 Bedrooms 4 Guests
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New Luxurious 5BD-2BA Home-FREE WINE-2CAR Parking
Apartment
New Luxurious 5BD-2BA Home-FREE WINE-2CAR Parking
From US $464 per night
8.7 (3 Reviews)
5 Bedrooms 10 Guests
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Hyde Park Modern Private Room - Near Univ of Chicago
House
Hyde Park Modern Private Room - Near Univ of Chicago
From US $52 per night
8.6 (38 Reviews)
1 Bedroom 2 Guests
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Blueground | Hyde Park, AC, w/d, nr museum
Apartment
Blueground | Hyde Park, AC, w/d, nr museum
From US $167 per night
New
1 Bedroom 2 Guests
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City Charm 1-Bedroom Oasis - Woodlawn 1E
Apartment
City Charm 1-Bedroom Oasis - Woodlawn 1E
From US $247 per night
|
8.5 (2 Reviews)
1 Bedroom 2 Guests
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Trendy Studio Apartment in Chicago - Kenwood 103 & 303 rep
Apartment
Trendy Studio Apartment in Chicago - Kenwood 103 & 303 rep
From US $386 per night
|
8.5 (2 Reviews)
1 Bedroom 2 Guests
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Beautiful 2-Bedroom Apt Near University of Chicago
Apartment
Beautiful 2-Bedroom Apt Near University of Chicago
From US $145 per night
New
2 Bedrooms 6 Guests
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Chateau de Woodlawn - Room II - Le Parisienne
House
Chateau de Woodlawn - Room II - Le Parisienne
From US $66 per night
8.4 (16 Reviews)
1 Bedroom 2 Guests
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Entire Apartment in Chicago
Apartment
Entire Apartment in Chicago
From US $131 per night
New
1 Bedroom 4 Guests
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Charming 3BD 2BTH Apartment
Apartment
Charming 3BD 2BTH Apartment
From US $90 per night
|
8.4 (8 Reviews)
3 Bedrooms 6 Guests
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Single Family Brick Home
Apartment
Single Family Brick Home
From US $125 per night
New
2 Bedrooms 2 Guests
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Modern and Minimalist Studio Apartment - Bstone 105 and 108 rep
Apartment
Modern and Minimalist Studio Apartment - Bstone 105 and 108 rep
From US $380 per night
|
8.3 (3 Reviews)
1 Bedroom 2 Guests
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Blueground | Hyde Park, AC, w/d, nr museum
Apartment
Blueground | Hyde Park, AC, w/d, nr museum
From US $123 per night
New
1 Bedroom 2 Guests
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Chateau de Woodlawn - Peaceful 3 bedroom apartment.
Apartment
Chateau de Woodlawn - Peaceful 3 bedroom apartment.
From US $126 per night
|
8.2 (11 Reviews)
3 Bedrooms 6 Guests
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About Jackson Park Highlands Vacation Rentals

Explore over 539 vacation rentals in Jackson Park Highlands with SunSki Resorts. These accommodations, comprising vacation homes, cottages, cabins, and condos, boast excellent amenities at great value, ensuring comfort and luxury. Enhance your stay with SunSki Resorts in Jackson Park Highlands for more space and value.

In search of last-minute deals or the best bargains on vacation rentals? With SunSki Resorts, you can conveniently compare various options and deals in Jackson Park Highlands. Discover rentals with desirable amenities like swimming pools, hot tubs, and pet-friendly options. Find the ideal vacation rental in Jackson Park Highlands tailored to your preferences. On average, these rentals offer 663.63 ft² of space, and are priced at an average of US $393 per night.

SunSki Resorts simplifies and secures the process of finding and comparing vacation rentals in Jackson Park Highlands at prices typically 30-40% lower than hotels. Discover your perfect vacation rental and book now.

Frequently Asked Questions About Jackson Park Highlands?

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Discover the ideal vacation rental in Jackson Park Highlands with SunSki Resorts™. We provide an extensive selection of over 539 properties, encompassing vacation homes, private villas, cottages, and more. Explore our listings to find the perfect place to stay for your upcoming trip to Jackson Park Highlands.

Nearby Neighborhood (1)

Neighborhood Property Count
South Shore Vacation Rentals in Chicago, Illinois 29

There are 539 Jackson Park Highlands, IL Vacation Rentals

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