Holiday rentals near Jackson Park
We found 2,133 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:18 Jul - 25 Jul
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 NZ$83,148
NZ$83,148
NZ$11,878 per night
includes taxes & fees
Image gallery for 3BR Luxury Modern Apartment
9.69.6 out of 10 rating
Exceptional
(7 reviews)
3BR Luxury Modern Apartment
Chicago, Illinois
7% off
Price is NZ$11,396
NZ$11,396
NZ$1,628 per night
includes taxes & fees
Image gallery for City Center, River North Condo HUGE 3BR, Patio, Parking(2x)
1010 out of 10 rating
Exceptional
(27 reviews)
City Center, River North Condo HUGE 3BR, Patio, Parking(2x)
Chicago, IL
12% off
Price is NZ$15,130
NZ$15,130
NZ$2,161 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 NZ$10,678
NZ$10,678
NZ$1,525 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 NZ$5,136
NZ$5,136
NZ$734 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
(38 reviews)
Stunning Corner 2BR in the Loop | City & Lake Views
Chicago, Illinois
7% off
Price is NZ$7,660
NZ$7,660
NZ$1,094 per night
includes taxes & fees
Image gallery for Spacious,Chic & Steps from MichiganAve|The Hermes
1010 out of 10 rating
Exceptional
(7 reviews)
Spacious,Chic & Steps from MichiganAve|The Hermes
Chicago, Illinois
7% off
Price is NZ$14,485
NZ$14,485
NZ$2,069 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
(31 reviews)
Modern Corner 2BR in Streeterville | Roof Deck | Lake Views
Chicago, Illinois
7% off
Price is NZ$7,687
NZ$7,687
NZ$1,098 per night
includes taxes & fees
Image gallery for Gorgeous 3BR River North Condo - Free Parking
1010 out of 10 rating
Exceptional
(12 reviews)
Gorgeous 3BR River North Condo - Free Parking
Chicago, IL
8% off
Price is NZ$16,303
NZ$16,303
NZ$2,329 per night
includes taxes & fees
Image gallery for Downtown Chicago Studio in Prime Location
9.69.6 out of 10 rating
Exceptional
(9 reviews)
Downtown Chicago Studio in Prime Location
Chicago, Illinois
5% off
Price is NZ$4,550
NZ$4,550
NZ$650 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 NZ$10,678
NZ$10,678
NZ$1,525 per night
includes taxes & fees
Image gallery for Kasa | Inviting 1 BD + Game Room Access | Chicago
9.89.8 out of 10 rating
Exceptional
(9 reviews)
Kasa | Inviting 1 BD + Game Room Access | Chicago
Chicago, Illinois
8% off
Price is NZ$5,621
NZ$5,621
NZ$803 per night
includes taxes & fees
Image gallery for Kasa | Family Friendly 3 BD + Pet Friendly | Chicago
9.49.4 out of 10 rating
Exceptional
(10 reviews)
Kasa | Family Friendly 3 BD + Pet Friendly | Chicago
Chicago, Illinois
8% off
Price is NZ$10,678
NZ$10,678
NZ$1,525 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 NZ$4,680
NZ$4,680
NZ$669 per night
includes taxes & fees
Image gallery for Splendid Corner 3BR in the Loop | City Views
9.29.2 out of 10 rating
Wonderful
(9 reviews)
Splendid Corner 3BR in the Loop | City Views
Chicago, Illinois
7% off
Price is NZ$9,702
NZ$9,702
NZ$1,386 per night
includes taxes & fees
Image gallery for #1511 - Kasa Magnificent Mile Chicago
9.69.6 out of 10 rating
Exceptional
(15 reviews)
#1511 - Kasa Magnificent Mile Chicago
Chicago, Illinois
8% off
Price is NZ$4,267
NZ$4,267
NZ$610 per night
includes taxes & fees
Image gallery for Kasa | Classic 2 BD + Near Grant Park | Chicago
1010 out of 10 rating
Exceptional
(6 reviews)
Kasa | Classic 2 BD + Near Grant Park | Chicago
Chicago, Illinois
8% off
Price is NZ$8,834
NZ$8,834
NZ$1,262 per night
includes taxes & fees
Image gallery for Kasa | Family Friendly 3 BD + Fast Wifi | Chicago
9.89.8 out of 10 rating
Exceptional
(11 reviews)
Kasa | Family Friendly 3 BD + Fast Wifi | Chicago
Chicago, Illinois
8% off
Price is NZ$10,678
NZ$10,678
NZ$1,525 per night
includes taxes & fees
Image gallery for Stunning Corner 2BR in Streeterville | Roof Deck | Lake Views
9.49.4 out of 10 rating
Exceptional
(39 reviews)
Stunning Corner 2BR in Streeterville | Roof Deck | Lake Views
Chicago, Illinois
7% off
Price is NZ$7,791
NZ$7,791
NZ$1,113 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 NZ$4,267
NZ$4,267
NZ$610 per night
includes taxes & fees
Image gallery for Spectacular Penthouse Corner 2BR in Streeterville | Roof Deck | Lake Views
9.49.4 out of 10 rating
Exceptional
(25 reviews)
Spectacular Penthouse Corner 2BR in Streeterville | Roof Deck | Lake Views
Chicago, Illinois
7% off
Price is NZ$8,375
NZ$8,375
NZ$1,196 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 NZ$5,136
NZ$5,136
NZ$734 per night
includes taxes & fees
Image gallery for Spectacular Corner 3BR in the Loop | City Views
8.88.8 out of 10 rating
Excellent
(20 reviews)
Spectacular Corner 3BR in the Loop | City Views
Chicago, Illinois
7% off
Price is NZ$9,787
NZ$9,787
NZ$1,398 per night
includes taxes & fees
Image gallery for LakeHouse
1010 out of 10 rating
Exceptional
(16 reviews)
LakeHouse
Chicago, IL
22% off
Price is NZ$3,691
NZ$3,691
NZ$527 per night
includes taxes & fees
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Find the best place to stay - Jackson Park
Spacious 4-bedroom apartment in fabulous Chicago with WiFi, AC
Sleeps 8 · 4 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
University of Chicago Condo-Upgraded and Spacious w/Parking
Sleeps 3 · 1 bedroom · 2 bathrooms
1010 out of 10
Exceptionalexceptional
3 reviews(3 reviews)
Chic 2-bedroom apartment near Hyde Park/ University of Chicago Campus
Sleeps 3 · 2 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
The Vibe Headquarters
Sleeps 6 · 3 bedrooms · 1 bathroom
8.88.8 out of 10
Excellentexcellent
3 reviews(3 reviews)
Spacious 3-bedroom apartment in cool Chicago with WiFi, AC
Sleeps 6 · 3 bedrooms · 1 bathroom
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