629+ Vacation Rentals Near Jackson Park |
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St Helena Vacation Rentals - Vacation Rentals in Jackson Park

Penthouse, Lux stay near Downtown, McComick & Lake From US $263
         

10.0 (18 Reviews)
Apartment
Penthouse, Lux stay near Downtown, McComick & Lake
  • Air Conditioner
  • Parking
  • TV

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Luxurious Stay at Modern Apartment with Self Check-in Mins Frm Downtown From US $299
         

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9.7 (18 Reviews)
Apartment
Luxurious Stay at Modern Apartment with Self Check-in Mins Frm Downtown
  • Air Conditioner
  • Parking
  • Pet Friendly

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Sophy Hyde Park From US $242
         

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9.6 (1002 Reviews)
Hotel
Sophy Hyde Park
  • Air Conditioner
  • TV
  • Wheelchair Accessible

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Gorgeous historic mansion on UChicago campus. Renovation with original detail. From US $691
         

10.0 (15 Reviews)
House
Gorgeous historic mansion on UChicago campus. Renovation with original detail.
  • Air Conditioner
  • TV
  • View

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A Stylish & Cozy Apartment near Downtown Chicago From US $150
         

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9.0 (1 Review)
Apartment
A Stylish & Cozy Apartment near Downtown Chicago
  • Air Conditioner
  • Parking
  • Child Friendly

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Hyatt Place Chicago-South/University Medical Center From US $158
         

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8.8 (1009 Reviews)
Hotel
Hyatt Place Chicago-South/University Medical Center
  • Air Conditioner
  • Parking
  • TV

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Beautiful, modern 3 bed 2 bath condo near Hyde Park, Obama Center and Lakefront From US $324
         

10.0 (8 Reviews)
Condo
Beautiful, modern 3 bed 2 bath condo near Hyde Park, Obama Center and Lakefront
  • Air Conditioner
  • TV
  • Security/Safety

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Lit & Trendy 1-Bedroom Apt in the Iconic Hyde Park From US $83
         

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5.0 (2 Reviews)
Apartment
Lit & Trendy 1-Bedroom Apt in the Iconic Hyde Park
  • Air Conditioner
  • Child Friendly
  • Internet

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Best Motel By OYO Chicago I-90 From US $92
         

3.6 (52 Reviews)
Hotel
Best Motel By OYO Chicago I-90
  • Air Conditioner
  • Parking
  • Bedding/Linens

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Spacious 3BR on UChicago Campus & Hospitals Free Street Parking From US $553
         

10.0 (7 Reviews)
Condo
Spacious 3BR on UChicago Campus & Hospitals Free Street Parking
  • Air Conditioner
  • Parking
  • TV

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South Shore Chicago Condo-1 Block to Lake-WiFi-AC-Elevator-420 Friendly From US $192
         

10.0 (4 Reviews)
Condo
South Shore Chicago Condo-1 Block to Lake-WiFi-AC-Elevator-420 Friendly
  • Air Conditioner
  • Parking
  • View

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Modern & Spacious Stay by Northwestern Hospital Bronzeville From US $340
         

10.0 (3 Reviews)
Apartment
Modern & Spacious Stay by Northwestern Hospital Bronzeville
  • Air Conditioner
  • Parking
  • Pet Friendly

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High-end 2Bdrm Garden Apt. Where Comfort Meets Style From US $262
         

10.0 (3 Reviews)
Apartment
High-end 2Bdrm Garden Apt. Where Comfort Meets Style
  • Air Conditioner
  • Parking
  • TV

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Cozy & Near Downtown, Hyde Park & the Metra From US $168
         

10.0 (3 Reviews)
House
Cozy & Near Downtown, Hyde Park & the Metra
  • Air Conditioner
  • Parking
  • Pet Friendly

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Cozy Charm Studio Apt in Chicago From US $153
         

10.0 (3 Reviews)
Apartment
Cozy Charm Studio Apt in Chicago
  • Pet Friendly
  • TV
  • Security/Safety

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Stylish 4BR South Loop Home From US $520
         

10.0 (2 Reviews)
Apartment
Stylish 4BR South Loop Home
  • TV
  • Wheelchair Accessible
  • Accessibility

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Luxe Loft vibe –4BR/3BA Apt– King Suite-11 minutes from downtown-Families-Groups From US $519
         

10.0 (2 Reviews)
Apartment
Luxe Loft vibe –4BR/3BA Apt– King Suite-11 minutes from downtown-Families-Groups
  • Air Conditioner
  • Parking
  • TV

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Spacious 3BDR Luxury Penthouse 10 min from Downtown Chicago From US $448
         

10.0 (2 Reviews)
Condo
Spacious 3BDR Luxury Penthouse 10 min from Downtown Chicago
  • Air Conditioner
  • Parking
  • TV

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Cozy 3-bedroom condo near University of Chicago From US $279
         

10.0 (2 Reviews)
Apartment
Cozy 3-bedroom condo near University of Chicago
  • Air Conditioner
  • TV
  • Security/Safety

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Studio Apt Comfy & Sunlit From US $161
         

10.0 (2 Reviews)
Apartment
Studio Apt Comfy & Sunlit
  • Pet Friendly
  • TV
  • Security/Safety

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Studio Unit | Chic + Prime Location From US $153
         

10.0 (2 Reviews)
Apartment
Studio Unit | Chic + Prime Location
  • Pet Friendly
  • TV
  • Security/Safety

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Hyde Park Luxury Stay 5BR Near Lake & UChicago From US $641
         

10.0 (1 Review)
Apartment
Hyde Park Luxury Stay 5BR Near Lake & UChicago
  • Air Conditioner
  • Pet Friendly
  • TV

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Modern 2-bedroom 2 -bath condo in wonderful Woodlawn Chicago. From US $364
         

10.0 (1 Review)
Condo
Modern 2-bedroom 2 -bath condo in wonderful Woodlawn Chicago.
  • Air Conditioner
  • Parking
  • TV

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Bright Vintage U of C Center Condo with WiFi, AC in enjoyable Chicago From US $290
         

10.0 (1 Review)
Condo
Bright Vintage U of C Center Condo with WiFi, AC in enjoyable Chicago
  • Air Conditioner
  • Parking
  • TV

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★ Pro Tip: Sthelenavacationrentals makes it easy to compare the best listings on Sthelenavacationrentals homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Sthelenavacationrentals homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Jackson Park.

Weather in Jackson Park

View the weather forecast for Jackson Park before booking your Jackson Park Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Top Attractions Around Jackson Park, IL

Sthelenavacationrentals offers a large selection of top attractions around Jackson Park. Research things to do on your vacation before you visit Jackson Park.


Navy Pier Wrigley Field McCormick Place Millennium Park Union Station Soldier Field Willis Tower Art Institute of Chicago United Center Grant Park John G. Shedd Aquarium Chicago Museum of Science and Industry Chicago Theatre Chicago Riverwalk Field Museum of Natural History University of Chicago John Hancock Center Lincoln Park Zoo Water Tower Place University of Illinois Chicago

Jackson Park Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Jackson Park?

There are a lot of options in Jackson Park. If you plan on staying in the Jackson Park area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Jackson Park:

How many vacation rentals are available in Jackson Park?

Currently, the total number of properties listed in 2026 is over 629 in the Jackson Park area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Jackson Park.