725+ Vacation Rentals Near Midway Plaisance |
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Ocean Park Beach Resort - Vacation Rentals in Midway Plaisance

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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Gorgeous historic mansion on UChicago campus. Renovation with original detail. From US $725
         

10.0 (19 Reviews)
House
Gorgeous historic mansion on UChicago campus. Renovation with original detail.
  • Air Conditioner
  • TV
  • View

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Sophy Hyde Park From US $450
         

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

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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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Penthouse, Lux stay near Downtown, McComick & Lake From US $309
         

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

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Dubois Guest House Room 201 From US $292
         

7.4 (3 Reviews)
Bed & Breakfast
Dubois Guest House Room 201
  • Air Conditioner
  • Parking
  • TV

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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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High-end 2Bdrm Garden Apt. Where Comfort Meets Style From US $255
         

10.0 (5 Reviews)
Apartment
High-end 2Bdrm Garden Apt. Where Comfort Meets Style
  • Air Conditioner
  • Parking
  • TV

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Comfortable Condo in the Heart of Bronzeville by RedAwning From US $391
         

6.6 (4 Reviews)
Condo
Comfortable Condo in the Heart of Bronzeville by RedAwning
  • Air Conditioner
  • TV
  • Balcony/Terrace

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Bronzeville Jazz Room. Beautiful, cozy, centered, relaxing, rustic. From US $658
         

10.0 (4 Reviews)
House
Bronzeville Jazz Room. Beautiful, cozy, centered, relaxing, rustic.
  • Air Conditioner
  • Parking
  • TV

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Lovely three bedroom Loft, University Of Chicago, Obama Library From US $481
         

10.0 (4 Reviews)
House
Lovely three bedroom Loft, University Of Chicago, Obama Library
  • Air Conditioner
  • Parking
  • TV

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Luxe Loft vibe –4BR/3BA Apt– King Suite-11 minutes from downtown-Families-Groups From US $590
         

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

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Discover the Heart of Chicago from Our Modern 3 Bed/2.5 Bath Home From US $380
         

10.0 (3 Reviews)
House
Discover the Heart of Chicago from Our Modern 3 Bed/2.5 Bath Home
  • Air Conditioner
  • TV
  • Balcony/Terrace

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Cozy & Near Downtown, Hyde Park & the Metra From US $225
         

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

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ModernFarmHouseChicago-Spacious 3-bedroom condo Near Downtown Chicago From US $510
         

10.0 (2 Reviews)
Condo
ModernFarmHouseChicago-Spacious 3-bedroom condo Near Downtown Chicago
  • Air Conditioner
  • Parking
  • TV

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Spacious 3BDR Luxury Penthouse 10 min from Downtown Chicago From US $390
         

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

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Cozy 3BR Near Obama Presidential Center, Hyde Park & UChicago From US $341
         

10.0 (2 Reviews)
Apartment
Cozy 3BR Near Obama Presidential Center, Hyde Park & UChicago
  • Air Conditioner
  • TV
  • Security/Safety

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Superb townhome with Near Lake in vibrant Chicago From US $244
         

10.0 (2 Reviews)
House
Superb townhome with Near Lake in vibrant Chicago
  • Air Conditioner
  • Parking
  • TV

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Modern 2-bedroom 2 -bath condo in wonderful Woodlawn Chicago. From US $503
         

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 $329
         

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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Charming Newly Updated 3-bed Chicago Apartment. Extended Stay Discount From US $133
         

10.0 (1 Review)
Apartment
Charming Newly Updated 3-bed Chicago Apartment. Extended Stay Discount
  • Air Conditioner
  • TV
  • Balcony/Terrace

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Penthouse Condo in Chicago featuring Zero Gravity Massage Chair From US $390
         

9.8 (34 Reviews)
Condo
Penthouse Condo in Chicago featuring Zero Gravity Massage Chair
  • Air Conditioner
  • Parking
  • TV

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Lux Home in Chicago 7mins Downtown From US $679
         

9.8 (31 Reviews)
House
Lux Home in Chicago 7mins Downtown
  • Air Conditioner
  • Parking
  • TV

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Toca Bella ~ 7mins to Downtown From US $226
         

9.8 (25 Reviews)
Apartment
Toca Bella ~ 7mins to Downtown
  • Air Conditioner
  • Parking
  • Pet Friendly

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★ Pro Tip: Oceanparkbeachresort makes it easy to compare the best listings on Oceanparkbeachresort homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Oceanparkbeachresort 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 Midway Plaisance.

Weather in Midway Plaisance

View the weather forecast for Midway Plaisance before booking your Midway Plaisance 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 Midway Plaisance, IL

Oceanparkbeachresort offers a large selection of top attractions around Midway Plaisance. Research things to do on your vacation before you visit Midway Plaisance.


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

Midway Plaisance Vacation Rental Frequently Asked Questions

How many vacation rentals are available in Midway Plaisance?

Currently, the total number of properties listed in 2026 is over 725 in the Midway Plaisance area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Midway Plaisance.