5 Star Hotels near Oak Street

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Tonight
6 Oct - 7 Oct
Tomorrow
7 Oct - 8 Oct
This weekend
9 Oct - 11 Oct
Next weekend
16 Oct - 18 Oct

5 Star Hotels near Oak Street

Properties are selected based on real traveller reviews and popularity among guests who’ve booked a night near Oak Street on Hotels.com. These 5 Star Hotels close to Oak Street consistently deliver on quality, location and traveller experience. Last updated on 6 October 2026.
A cityscape with a river, a bridge, and a dining area with tables and chairs.

1. Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago
5.0 star property
River North, 0.8 mi from Oak Street
9.6 out of 10, Exceptional, (2,046 reviews)
The price is £414
includes taxes & fees
1 Nov - 2 Nov
Trump International Hotel & Tower Chicago
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.
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Compare popular hotels close to Oak Street

Property
Property class
Guest rating
Breakfast included
Pool
Spa
Pet-friendly
WiFi included
A high-rise hotel with multiple floors, large windows, and a prominent Tiffany & Co. store on the ground level.
The Peninsula Chicago
5.0 star property
9.8
Exceptional
1,002 reviews
View
A cityscape with a river, a bridge, and a dining area with tables and chairs.
Trump International Hotel & Tower Chicago
5.0 star property
9.6
Exceptional
2,046 reviews
View
A modern indoor swimming pool with a clear blue water surface, a wooden ceiling, and a wall with a floral pattern.
Nobu Hotel Chicago
5.0 star property
9.4
Exceptional
945 reviews
View
A person sitting by a window with a view of a cityscape, including a tall tower.
Four Seasons Hotel Chicago
5.0 star property
9.4
Exceptional
1,005 reviews
View
A modern lounge area with seating, a coffee table, and a view of the city at night.
Moxy Chicago Downtown
3.0 star property
9.4
Exceptional
1,008 reviews
View

Discover Oak Street's area and other top areas in Chicago

A cityscape with tall skyscrapers and a historic tower.

Downtown Chicago

Chicago's urban Downtown Chicago neighbourhood is loved for its skyscrapers and museums, and visitors often enjoy its varied attractions, including Navy Pier and Michigan Avenue.

A river with yellow boats, a bridge, and tall buildings.

The Loop

Chicago's urban The Loop neighbourhood is loved for its museums and art galleries, and visitors often enjoy its varied attractions, including Michigan Avenue and Lake Michigan.

A large, historic building with a central tower and multiple windows, located near a body of water.

Near North Side

Chicago's urban Near North Side neighbourhood is loved for its skyscrapers and museums, and visitors often enjoy its varied attractions, including Navy Pier and Michigan Avenue.

A river with a city skyline in the background, surrounded by green trees and grass.

Lincoln Park

Chicago's urban Lincoln Park neighbourhood is loved for its restaurants and bars, and visitors often enjoy its varied attractions, including Lake Michigan and Lincoln Hall.

A street lamp with a theater district sign, surrounded by tall buildings.

Theatre District

The Theatre District neighbourhood offers attractions, such as Michigan Avenue and State Street.

Other landmarks near Oak Street

A large indoor Christmas tree in a shopping mall.
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.
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