Holiday rentals near Milton Lee Olive Park
We found 2,978 holiday rentals — enter your dates for availability
Take a look at holiday rentals close to Milton Lee Olive Park that can be your home away from home. Whether you’re travelling with friends, family or just with your pet, holiday homes have the best amenities for hanging out with the people that matter most, which might include air conditioning and a pool. Whatever you're looking for, you'll find a property to rent to meet everyone's needs, including a place that is accessible or non-smoking.
Holiday rentals with weekly discounts - Milton Lee Olive Park
Showing deals for:27 Mar - 3 Apr
Image gallery for Charming 2-bedroom apartment in hip Chicago
1010 out of 10, Exceptional, (5 reviews)
Exceptional
(5 reviews)
Charming 2-bedroom apartment in hip Chicago
Chicago
14% off
Price is NZ$2,607
NZ$2,607
for 7 nights, 1 apartment
NZ$372 per night
includes taxes & fees
Image gallery for BoHo House - A Chic, 1903 Chicago Workers Cottage
1010 out of 10, Exceptional, (18 reviews)
Exceptional
(18 reviews)
BoHo House - A Chic, 1903 Chicago Workers Cottage
Chicago
11% off
Price is NZ$5,294
NZ$5,294
for 7 nights, 1 home
NZ$756 per night
includes taxes & fees
Image gallery for 1 mile walk to 43rd St .beach. In Historic North Kenwood. 6.3 miles to Navy Pier
1010 out of 10, Exceptional, (70 reviews)
Exceptional
(70 reviews)
1 mile walk to 43rd St .beach. In Historic North Kenwood. 6.3 miles to Navy Pier
Chicago
7% off
Price is NZ$5,327
NZ$5,327
for 7 nights, 1 home
NZ$761 per night
includes taxes & fees
Image gallery for 1 #23 - 4 Bedroom Condo - McCormick Place, Wintrust Arena, Chinatown
9.89.8 out of 10, Exceptional, (10 reviews)
Exceptional
(10 reviews)
1 #23 - 4 Bedroom Condo - McCormick Place, Wintrust Arena, Chinatown
Chicago
11% off
Price is NZ$5,942
NZ$5,942
for 7 nights, 1 home
NZ$849 per night
includes taxes & fees
Image gallery for 4 #2N - 4 Bedroom / 4 Bath Condo - McCormick Place, Wintrust Arena, Chinatown
9.29.2 out of 10, Wonderful, (13 reviews)
Wonderful
(13 reviews)
4 #2N - 4 Bedroom / 4 Bath Condo - McCormick Place, Wintrust Arena, Chinatown
Chicago
11% off
Price is NZ$6,009
NZ$6,009
for 7 nights, 1 home
NZ$858 per night
includes taxes & fees
Image gallery for Luxurious, custom built single family home near Wrigley
1010 out of 10, Exceptional, (18 reviews)
Exceptional
(18 reviews)
Luxurious, custom built single family home near Wrigley
Chicago
7% off
Price is NZ$16,884
NZ$16,884
for 7 nights, 1 home
NZ$2,412 per night
includes taxes & fees
Image gallery for Ridgeland Retreat/ Street level Apt easy access
9.29.2 out of 10, Wonderful, (7 reviews)
Wonderful
(7 reviews)
Ridgeland Retreat/ Street level Apt easy access
Berwyn
8% off
Price is NZ$3,406
NZ$3,406
for 7 nights, 1 apartment
NZ$487 per night
includes taxes & fees
Image gallery for Gorgeous 7BD Home
8.88.8 out of 10, Excellent, (6 reviews)
Excellent
(6 reviews)
Gorgeous 7BD Home
Chicago
7% off
Price is NZ$10,513
NZ$10,513
for 7 nights, 1 home
NZ$1,502 per night
includes taxes & fees
Image gallery for Stylish Luxe King bed w/Free Parkng near DT Oak Pk
9.69.6 out of 10, Exceptional, (96 reviews)
Exceptional
(96 reviews)
Stylish Luxe King bed w/Free Parkng near DT Oak Pk
Oak Park
7% off
Price is NZ$2,421
NZ$2,421
for 7 nights, 1 apartment
NZ$346 per night
includes taxes & fees
Image gallery for First floor of Historic Oak Park Villa, Grge:2Cars
9.69.6 out of 10, Exceptional, (26 reviews)
Exceptional
(26 reviews)
First floor of Historic Oak Park Villa, Grge:2Cars
Oak Park
12% off
Price is NZ$5,375
NZ$5,375
for 7 nights, 1 apartment
NZ$768 per night
includes taxes & fees
Image gallery for Luxury Apartment in Bronzeville, Just Minutes from Downtown - RSV Now!
8.88.8 out of 10, Excellent, (15 reviews)
Excellent
(15 reviews)
Luxury Apartment in Bronzeville, Just Minutes from Downtown - RSV Now!
Chicago
7% off
Price is NZ$7,197
NZ$7,197
for 7 nights, 1 apartment
NZ$1,028 per night
includes taxes & fees
Image gallery for Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24
9.89.8 out of 10, Exceptional, (182 reviews)
Exceptional
(182 reviews)
Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24
Chicago
14% off
Price is NZ$6,996
NZ$6,996
for 7 nights, 1 home
NZ$999 per night
includes taxes & fees
Image gallery for Prime Location! Modern 3 Bed 3 Bath Rental in Chicago
1010 out of 10, Exceptional, (31 reviews)
Exceptional
(31 reviews)
Prime Location! Modern 3 Bed 3 Bath Rental in Chicago
Chicago
7% off
Price is NZ$5,986
NZ$5,986
for 7 nights, 1 apartment
NZ$855 per night
includes taxes & fees
Image gallery for Vintage City Chic: The Artist's Haven. 5 Blocks from Lake Michigan!
1010 out of 10, Exceptional, (11 reviews)
Exceptional
(11 reviews)
Vintage City Chic: The Artist's Haven. 5 Blocks from Lake Michigan!
Chicago
6% off
Price is NZ$2,882
NZ$2,882
for 7 nights, 1 apartment
NZ$412 per night
includes taxes & fees
Image gallery for 4 #1N - 4 Bedroom / 4 Bath Condo - McCormick Place, Wintrust Arena, Chinatown
9.09.0 out of 10, Wonderful, (12 reviews)
Wonderful
(12 reviews)
4 #1N - 4 Bedroom / 4 Bath Condo - McCormick Place, Wintrust Arena, Chinatown
Chicago
9% off
Price is NZ$6,171
NZ$6,171
for 7 nights, 1 apartment
NZ$882 per night
includes taxes & fees
Image gallery for Minutes from Downtown Gorgeous ,spacious 2BD/ 1BA w/ Parking
9.49.4 out of 10, Exceptional, (14 reviews)
Exceptional
(14 reviews)
Minutes from Downtown Gorgeous ,spacious 2BD/ 1BA w/ Parking
Chicago
14% off
Price is NZ$3,053
NZ$3,053
for 7 nights, 1 apartment
NZ$436 per night
includes taxes & fees
Image gallery for Modern Apt Near U of Chicago!
1010 out of 10, Exceptional, (10 reviews)
Exceptional
(10 reviews)
Modern Apt Near U of Chicago!
Chicago
7% off
Price is NZ$3,179
NZ$3,179
for 7 nights, 1 apartment
NZ$454 per night
includes taxes & fees
Image gallery for Stunning New 6 Bedroom Home w/ Parking in Chicago (Superhosts)
9.29.2 out of 10, Wonderful, (23 reviews)
Wonderful
(23 reviews)
Stunning New 6 Bedroom Home w/ Parking in Chicago (Superhosts)
Chicago
7% off
Price is NZ$8,627
NZ$8,627
for 7 nights, 1 home
NZ$1,232 per night
includes taxes & fees
Image gallery for Spacious / New Home - 8BD/4BTH - Sleeps 16 + Garage!
8.68.6 out of 10, Excellent, (10 reviews)
Excellent
(10 reviews)
Spacious / New Home - 8BD/4BTH - Sleeps 16 + Garage!
Chicago
7% off
Price is NZ$11,630
NZ$11,630
for 7 nights, 1 home
NZ$1,661 per night
includes taxes & fees
Image gallery for Spacious 4-bedroom apartment with WiFi, AC in brilliant Chicago
1010 out of 10, Exceptional, (6 reviews)
Exceptional
(6 reviews)
Spacious 4-bedroom apartment with WiFi, AC in brilliant Chicago
Chicago
7% off
Price is NZ$5,448
NZ$5,448
for 7 nights, 1 apartment
NZ$778 per night
includes taxes & fees
Image gallery for Stunning Duplex Retreat 3BR 2BR, Minutes from Downtown Chicago!
1010 out of 10, Exceptional, (5 reviews)
Exceptional
(5 reviews)
Stunning Duplex Retreat 3BR 2BR, Minutes from Downtown Chicago!
Chicago
11% off
Price is NZ$7,242
NZ$7,242
for 7 nights, 1 apartment
NZ$1,035 per night
includes taxes & fees
Image gallery for Rogers Park Cozy 1 bd, 1 bath unit. Gated parking.
8.88.8 out of 10, Excellent, (20 reviews)
Excellent
(20 reviews)
Rogers Park Cozy 1 bd, 1 bath unit. Gated parking.
Chicago
7% off
Price is NZ$2,604
NZ$2,604
for 7 nights, 1 apartment
NZ$372 per night
includes taxes & fees
Image gallery for Stylish, Inviting 2-BR near Logan Square and Wrigley Field
1010 out of 10, Exceptional, (67 reviews)
Exceptional
(67 reviews)
Stylish, Inviting 2-BR near Logan Square and Wrigley Field
Chicago
7% off
Price is NZ$2,247
NZ$2,247
for 7 nights, 1 apartment
NZ$321 per night
includes taxes & fees
Image gallery for Chic Suite/Mins to L Train /Laundry/Free Parking
9.69.6 out of 10, Exceptional, (57 reviews)
Exceptional
(57 reviews)
Chic Suite/Mins to L Train /Laundry/Free Parking
Oak Park
9% off
Price is NZ$1,663
NZ$1,663
for 7 nights, 1 apartment
NZ$238 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Milton Lee Olive Park
Sentral Michigan Avenue
Sleeps 4 · 2 bedrooms
9.29.2 out of 10
Wonderfulwonderful
1,019 reviews(1,019 reviews)
Level Chicago – Old Town
Sleeps 8
9.09.0 out of 10
Wonderfulwonderful
403 reviews(403 reviews)
Kasa Magnificent Mile Chicago
Sleeps 3 · 1 bedroom
9.29.2 out of 10
Wonderfulwonderful
653 reviews(653 reviews)
Wrigleyville Suites
Sleeps 22 · 9 bedrooms
9.69.6 out of 10
Exceptionalexceptional
26 reviews(26 reviews)
Kasa South Loop Chicago
Sleeps 2 · 1 bedroom
9.49.4 out of 10
Exceptionalexceptional
392 reviews(392 reviews)
NEW LUXURY PENTHOUSE CONDO
Sleeps 9 · 2 bedrooms · 2+ bathrooms
1010 out of 10
Exceptionalexceptional
201 reviews(201 reviews)
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
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