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Holiday homes near Oak Street
Properties are selected based on real traveller reviews and popularity among guests who’ve booked a holiday rental stay near Oak Street on Hotels.com. These holiday rentals close to Oak Street consistently deliver on quality, location and traveller experience. Last updated on 16 October 2026.
9.4 out of 10, Exceptional, (960 reviews)
9.4/10
Exceptional
(960 reviews)
9.0 out of 10, Wonderful, (1,374 reviews)
9.0/10
Wonderful
(1,374 reviews)
The price is AU$243
AU$243
includes taxes & fees
9 Nov - 10 Nov
8.6 out of 10, Excellent, (68 reviews)
8.6/10
Excellent
(68 reviews)
The price is AU$377
AU$377
includes taxes & fees
1 Nov - 2 Nov
9.4 out of 10, Exceptional, (542 reviews)
9.4/10
Exceptional
(542 reviews)
9.4 out of 10, Exceptional, (216 reviews)
9.4/10
Exceptional
(216 reviews)
7.4 out of 10, Good, (22 reviews)
7.4/10
Good
(22 reviews)
9.2 out of 10, Wonderful, (541 reviews)
9.2/10
Wonderful
(541 reviews)
The price is AU$473
AU$473
includes taxes & fees
1 Nov - 2 Nov
7.6 out of 10, Good, (64 reviews)
7.6/10
Good
(64 reviews)
The price is AU$270
AU$270
includes taxes & fees
3 Nov - 4 Nov
9. River West, Third Floor Chicago by 747 Lofts
River West, Third Floor Chicago by 747 Lofts2.0 star property
West Town
9.0 out of 10, Wonderful, (25 reviews)
9.0/10
Wonderful
(25 reviews)
10. Ground Floor Studios in Chicago by 747 Lofts
Ground Floor Studios in Chicago by 747 Lofts2.0 star property
West Town
8.4 out of 10, Very good, (27 reviews)
8.4/10
Very good
(27 reviews)
11. Chicago Third Floor Studio by 747 Lofts
Chicago Third Floor Studio by 747 Lofts2.0 star property
West Town
9.8 out of 10, Exceptional, (7 reviews)
9.8/10
Exceptional
(7 reviews)
12. Chicago Second Floor Studio by 747 Lofts
Chicago Second Floor Studio by 747 Lofts2.0 star property
West Town
8.6 out of 10, Excellent, (17 reviews)
8.6/10
Excellent
(17 reviews)
13. River West, Second Floor Chicago by 747 Lofts
River West, Second Floor Chicago by 747 Lofts2.0 star property
West Town
8.8 out of 10, Excellent, (5 reviews)
8.8/10
Excellent
(5 reviews)
6.0 out of 10, Good, (2 reviews)
6.0/10
Good
(2 reviews)
8.0 out of 10, Very good, (109 reviews)
8.0/10
Very good
(109 reviews)
9.4 out of 10, Exceptional, (288 reviews)
9.4/10
Exceptional
(288 reviews)
The price is AU$379
AU$379
includes taxes & fees
12 Nov - 13 Nov
17. The Neighborhood Hotel-Little Italy
The Neighborhood Hotel-Little Italy4.0 star property
Near West Side
9.6 out of 10, Exceptional, (358 reviews)
9.6/10
Exceptional
(358 reviews)
9.4 out of 10, Exceptional, (8 reviews)
9.4/10
Exceptional
(8 reviews)
The price is AU$451
AU$451
includes taxes & fees
27 Oct - 28 Oct
9.6 out of 10, Exceptional, (13 reviews)
9.6/10
Exceptional
(13 reviews)
The price is AU$509
AU$509
includes taxes & fees
26 Oct - 27 Oct
8.8 out of 10, Excellent, (6 reviews)
8.8/10
Excellent
(6 reviews)
The price is AU$453
AU$453
includes taxes & fees
27 Oct - 28 Oct
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Other landmarks near Oak Street
Photo by Rita Irvine
Open Photo by Rita Irvine
900 North Michigan Shops
8.6/10 (55 reviews)
If you want to give your credit card some exercise, head out to 900 North Michigan Shops in Downtown Chicago. Why not take a stroll along the riverfront and watch the sunset while you're here? Splash some more cash at Michigan Avenue, Oak Street and Water Tower Place.
Loyola University Museum of Art
9.0/10 (2 reviews)
Loyola University Museum of Art is just one of the attractions in Downtown Chicago, Chicago so you might want to stop by during your trip. Why not take a stroll along the riverfront and watch the sunset while you're here? If you want to experience more of the culture Chicago has to offer, head to Millennium Park, Navy Pier, and Soldier Field.
About the destination
Where is Oak Street?
Oak Street is located in Downtown Chicago. It's in an artistic neighbourhood well known for its great entertainment and architecture. If you'd like to find things to see and do in the area, you may want to check out Navy Pier and Soldier Field.
Things to see and do near Oak Street
What to see near Oak Street
- Michigan Avenue
- Navy Pier
- Soldier Field
- McCormick Place
- Wrigley Field
Things to do near Oak Street
- State Street
- 900 North Michigan Shops
- Broadway Playhouse
- Water Tower Place
- Museum of Contemporary Art Chicago