Photo by Eleonora Bertacchi
Holiday rentals near Oak Street
We found 2,801 holiday rentals — enter your dates for availability
Choose the right private holiday rental within close proximity to Oak Street. Holiday rentals offer the best amenities for your family, friends or furry companion, such as air conditioning and a pool. You're sure to find a property to rent to meet everyone's needs, including places that are non-smoking or accessible.
Holiday rentals with weekly discounts - Oak Street
Showing deals for:8 Aug - 15 Aug
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 NZ$12,517
NZ$12,517
NZ$1,788 per night
includes taxes & fees
Image gallery for Chic 2BR 2BA Condo with Balcony - River North Chicago
9.89.8 out of 10 rating
Exceptional
(24 reviews)
Chic 2BR 2BA Condo with Balcony - River North Chicago
Chicago, Illinois
8% off
Price is NZ$10,297
NZ$10,297
NZ$1,471 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
11% off
Price is NZ$12,516
NZ$12,516
NZ$1,788 per night
includes taxes & fees
Image gallery for #1514 - Kasa Magnificent Mile Chicago
9.89.8 out of 10 rating
Exceptional
(10 reviews)
#1514 - Kasa Magnificent Mile Chicago
Chicago, Illinois
8% off
Price is NZ$3,444
NZ$3,444
NZ$492 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$4,170
NZ$4,170
NZ$596 per night
includes taxes & fees
Image gallery for Spacious,Chic & Steps from MichiganAve|The Lion
9.89.8 out of 10 rating
Exceptional
(42 reviews)
Spacious,Chic & Steps from MichiganAve|The Lion
Chicago, Illinois
8% off
Price is NZ$11,290
NZ$11,290
NZ$1,613 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
8% off
Price is NZ$9,318
NZ$9,318
NZ$1,331 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$10,515
NZ$10,515
NZ$1,502 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 NZ$8,942
NZ$8,942
NZ$1,277 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
(32 reviews)
Modern Corner 2BR in Streeterville | Roof Deck | Lake Views
Chicago, Illinois
7% off
Price is NZ$6,288
NZ$6,288
NZ$898 per night
includes taxes & fees
Image gallery for Gorgeous 3BR River North Condo - Free Parking
1010 out of 10 rating
Exceptional
(14 reviews)
Gorgeous 3BR River North Condo - Free Parking
Chicago, IL
7% off
Price is NZ$13,818
NZ$13,818
NZ$1,974 per night
includes taxes & fees
Image gallery for Most Stylish Apartments You’ll Ever Stay In|TheNeo
9.69.6 out of 10 rating
Exceptional
(10 reviews)
Most Stylish Apartments You’ll Ever Stay In|TheNeo
Chicago, Illinois
8% off
Price is NZ$9,308
NZ$9,308
NZ$1,330 per night
includes taxes & fees
Image gallery for Splendid Corner 3BR in the Loop | City Views
9.29.2 out of 10 rating
Wonderful
(10 reviews)
Splendid Corner 3BR in the Loop | City Views
Chicago, Illinois
7% off
Price is NZ$8,324
NZ$8,324
NZ$1,189 per night
includes taxes & fees
Image gallery for 1676 Travelers Love This Place.See Why|TheChevelle
9.69.6 out of 10 rating
Exceptional
(38 reviews)
1676 Travelers Love This Place.See Why|TheChevelle
Chicago, Illinois
8% off
Price is NZ$10,382
NZ$10,382
NZ$1,483 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$4,170
NZ$4,170
NZ$596 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$10,515
NZ$10,515
NZ$1,502 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$5,339
NZ$5,339
NZ$763 per night
includes taxes & fees
Image gallery for Kasa | Relaxing 1 BD + Near Local Eateries | Chicago
1010 out of 10 rating
Exceptional
(12 reviews)
Kasa | Relaxing 1 BD + Near Local Eateries | Chicago
Chicago, Illinois
8% off
Price is NZ$3,976
NZ$3,976
NZ$568 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$3,444
NZ$3,444
NZ$492 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$3,456
NZ$3,456
NZ$494 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$10,515
NZ$10,515
NZ$1,502 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$4,618
NZ$4,618
NZ$660 per night
includes taxes & fees
Image gallery for Cloud9 |up to 14ppl Terrace @MagMile|The Artemis
9.49.4 out of 10 rating
Exceptional
(8 reviews)
Cloud9 |up to 14ppl Terrace @MagMile|The Artemis
Chicago, Illinois
7% off
Price is NZ$20,752
NZ$20,752
NZ$2,965 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$4,170
NZ$4,170
NZ$596 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Oak Street
Rare Gem! Indoor Pool, Rooftop Deck, Close to Magnificent Mile
Sleeps 2 · 1 bedroom · 1 bathroom
8.08.0 out of 10
Very goodvery good
68 reviews(68 reviews)
Level Chicago – Old Town
Sleeps 8
9.09.0 out of 10
Wonderfulwonderful
310 reviews(310 reviews)
Sonder Onterie
Sleeps 2 · 1 bedroom
8.28.2 out of 10
Very goodvery good
14 reviews(14 reviews)
Sonder Market Hall
Sleeps 2 · 1 bedroom
8.68.6 out of 10
Excellentexcellent
279 reviews(279 reviews)
Sonder The Opal
Sleeps 6 · 2 bedrooms
8.68.6 out of 10
Excellentexcellent
36 reviews(36 reviews)
Kasa Magnificent Mile Chicago
Sleeps 3 · 1 bedroom
9.29.2 out of 10
Wonderfulwonderful
398 reviews(398 reviews)
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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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