Holiday rentals near Jackson Park
We found 2,267 holiday rentals — enter your dates for availability
Choose the perfect private holiday rental that's close to Jackson Park. Holiday rentals offer the amenities that you expect for you and your friends, family or even pets, such as parking and a TV. You'll be able to choose a property to rent to meet everyone's needs, including options that are accessible or non-smoking.
Holiday rentals with weekly discounts - Jackson Park
Showing deals for:19 Sept - 26 Sept
Image gallery for Chicago Gold Coast Luxury Home Best Location walking distance to anywhere!
1010 out of 10 rating
Exceptional
(20 reviews)
Chicago Gold Coast Luxury Home Best Location walking distance to anywhere!
Chicago, IL
8% off
Price is AU$51,006
AU$51,006
AU$7,287 per night
includes taxes & fees
Image gallery for River North 3BR/2BA: HUGE, Parking, Center Chicago
9.89.8 out of 10 rating
Exceptional
(14 reviews)
River North 3BR/2BA: HUGE, Parking, Center Chicago
Chicago, IL
7% off
Price is AU$10,102
AU$10,102
AU$1,443 per night
includes taxes & fees
Image gallery for Luxury Loft Collection 03 - Terrace - River North
9.29.2 out of 10 rating
Wonderful
(7 reviews)
Luxury Loft Collection 03 - Terrace - River North
Chicago, IL
8% off
Price is AU$11,733
AU$11,733
AU$1,676 per night
includes taxes & fees
Image gallery for Spectacular Corner 3BR Loft In Fulton Market | Featured In Architectural Digest
9.69.6 out of 10 rating
Exceptional
(38 reviews)
Spectacular Corner 3BR Loft In Fulton Market | Featured In Architectural Digest
Chicago, IL
7% off
Price is AU$11,020
AU$11,020
AU$1,574 per night
includes taxes & fees
Image gallery for #2011 - Kasa Magnificent Mile Chicago
9.89.8 out of 10 rating
Exceptional
(8 reviews)
#2011 - Kasa Magnificent Mile Chicago
Chicago, Illinois
8% off
Price is AU$2,765
AU$2,765
AU$395 per night
includes taxes & fees
Image gallery for #1613 - Kasa Magnificent Mile Chicago
9.89.8 out of 10 rating
Exceptional
(16 reviews)
#1613 - Kasa Magnificent Mile Chicago
Chicago, Illinois
8% off
Price is AU$3,371
AU$3,371
AU$482 per night
includes taxes & fees
Image gallery for 3BR Luxury Modern Apartment
9.69.6 out of 10 rating
Exceptional
(8 reviews)
3BR Luxury Modern Apartment
Chicago, Illinois
7% off
Price is AU$7,704
AU$7,704
AU$1,101 per night
includes taxes & fees
Image gallery for Kasa | Family Friendly 3 BD + Game Room Access | Chicago
9.69.6 out of 10 rating
Exceptional
(14 reviews)
Kasa | Family Friendly 3 BD + Game Room Access | Chicago
Chicago, Illinois
8% off
Price is AU$9,526
AU$9,526
AU$1,361 per night
includes taxes & fees
Image gallery for Luxury Loft Collection 902 - Terrace - River North
8.88.8 out of 10 rating
Excellent
(5 reviews)
Luxury Loft Collection 902 - Terrace - River North
Chicago, Illinois
8% off
Price is AU$10,674
AU$10,674
AU$1,525 per night
includes taxes & fees
Image gallery for Luxury Designer Penthouse South | Pool | Gold Coast
9.89.8 out of 10 rating
Exceptional
(8 reviews)
Luxury Designer Penthouse South | Pool | Gold Coast
Chicago, Illinois
8% off
Price is AU$9,469
AU$9,469
AU$1,353 per night
includes taxes & fees
Image gallery for Michigan Ave 2BR: Balcony, Exclusive Access
1010 out of 10 rating
Exceptional
(10 reviews)
Michigan Ave 2BR: Balcony, Exclusive Access
Chicago, Illinois
8% off
Price is AU$7,106
AU$7,106
AU$1,015 per night
includes taxes & fees
Image gallery for Corner 3BR in Streeterville | Views | Roof Deck
9.69.6 out of 10 rating
Exceptional
(29 reviews)
Corner 3BR in Streeterville | Views | Roof Deck
Chicago, Illinois
7% off
Price is AU$8,168
AU$8,168
AU$1,167 per night
includes taxes & fees
Image gallery for Modern Corner 2BR in Streeterville | Roof Deck | Lake Views
9.89.8 out of 10 rating
Exceptional
(33 reviews)
Modern Corner 2BR in Streeterville | Roof Deck | Lake Views
Chicago, Illinois
7% off
Price is AU$5,654
AU$5,654
AU$808 per night
includes taxes & fees
Image gallery for Stunning Corner 2BR in the Loop | City & Lake Views
9.89.8 out of 10 rating
Exceptional
(39 reviews)
Stunning Corner 2BR in the Loop | City & Lake Views
Chicago, Illinois
7% off
Price is AU$6,405
AU$6,405
AU$915 per night
includes taxes & fees
Image gallery for Spectacular Corner 2BR Penthouse in the Loop | Roof Deck
9.49.4 out of 10 rating
Exceptional
(31 reviews)
Spectacular Corner 2BR Penthouse in the Loop | Roof Deck
Chicago, IL
7% off
Price is AU$7,102
AU$7,102
AU$1,015 per night
includes taxes & fees
Image gallery for Beautiful Corner 2 Bedroom in the Loop | Roof Deck
9.69.6 out of 10 rating
Exceptional
(51 reviews)
Beautiful Corner 2 Bedroom in the Loop | Roof Deck
Chicago, Illinois
7% off
Price is AU$6,805
AU$6,805
AU$972 per night
includes taxes & fees
Image gallery for 2BR Designer Loft: Modern Luxe in City Center
1010 out of 10 rating
Exceptional
(6 reviews)
2BR Designer Loft: Modern Luxe in City Center
Chicago, Illinois
7% off
Price is AU$5,851
AU$5,851
AU$836 per night
includes taxes & fees
Image gallery for Beautiful Unit CHI in Prime River North - 2
9.09.0 out of 10 rating
Wonderful
(12 reviews)
Beautiful Unit CHI in Prime River North - 2
Chicago, Illinois
15% off
Price is AU$6,171
AU$6,171
AU$882 per night
includes taxes & fees
Image gallery for Downtown Chicago Studio in Prime Location
9.69.6 out of 10 rating
Exceptional
(10 reviews)
Downtown Chicago Studio in Prime Location
Chicago, Illinois
5% off
Price is AU$2,922
AU$2,922
AU$417 per night
includes taxes & fees
Image gallery for Luxury Loft Collection 02 - Terrace - River North
1010 out of 10 rating
Exceptional
(18 reviews)
Luxury Loft Collection 02 - Terrace - River North
Chicago, IL
8% off
Price is AU$10,856
AU$10,856
AU$1,551 per night
includes taxes & fees
Image gallery for Unbeatable Top Floor: Views, Central, Modern
1010 out of 10 rating
Exceptional
(5 reviews)
Unbeatable Top Floor: Views, Central, Modern
Chicago, IL
8% off
Price is AU$6,217
AU$6,217
AU$888 per night
includes taxes & fees
Image gallery for Kasa | Family Friendly 3 BD + Laptop Friendly | Chicago
9.89.8 out of 10 rating
Exceptional
(20 reviews)
Kasa | Family Friendly 3 BD + Laptop Friendly | Chicago
Chicago, Illinois
8% off
Price is AU$9,526
AU$9,526
AU$1,361 per night
includes taxes & fees
Image gallery for #1515 - Kasa Magnificent Mile Chicago
1010 out of 10 rating
Exceptional
(23 reviews)
#1515 - Kasa Magnificent Mile Chicago
Chicago, Illinois
8% off
Price is AU$3,371
AU$3,371
AU$482 per night
includes taxes & fees
Image gallery for #2012 - Kasa Magnificent Mile Chicago
9.49.4 out of 10 rating
Exceptional
(10 reviews)
#2012 - Kasa Magnificent Mile Chicago
Chicago, Illinois
8% off
Price is AU$3,371
AU$3,371
AU$482 per night
includes taxes & fees
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Find properties near top attractions in Jackson Park
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Find the best place to stay - Jackson Park
Spacious 3-bedroom apartment in cool Chicago with WiFi, AC
Sleeps 6 · 3 bedrooms · 1 bathroom
Book the Great Migration Guest House. Family-sized condo near the Green Line.
Sleeps 8 · 3 bedrooms · 1+ bathroom
1010 out of 10
Exceptionalexceptional
Sonder by Marriott Bonvoy South Wabash Apartments South Loop
Sleeps 4 · 1 bedroom
8.88.8 out of 10
Excellentexcellent
534 reviews(534 reviews)
Trendy & Luxe 2BR/2BA - West Town near 'L' & Dtwn
Sleeps 6 · 2 bedrooms · 2 bathrooms
9.89.8 out of 10
Exceptionalexceptional
Near Lakefront! Minutes from the beach, museum, and 2 golf courses.
Sleeps 7 · 4 bedrooms · 3+ bathrooms
1010 out of 10
Exceptionalexceptional
2 reviews(2 reviews)
Cozy 3-bedroom condo near University of Chicago
Sleeps 6 · 3 bedrooms · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
Peace of mindOur Book with Confidence Guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value