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Chicago Hotel Guide - Oak Street hotels in Chicago, United States of America.

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Check prices for these dates

Tonight
22 Sept - 23 Sept
Tomorrow
23 Sept - 24 Sept
This weekend
25 Sept - 27 Sept
Next weekend
2 Oct - 4 Oct

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Our top choices for Oak Street hotels

A cityscape with a river, a bridge, and a dining area with tables and chairs.
A modern hotel room with large floor-to-ceiling windows offering a city view.
A pool area with a view of a cityscape, a lounge with wicker furniture, and a person relaxing in the pool.
A high-rise hotel with a prominent 'TRUMP' sign, reflecting in the water, surrounded by other tall buildings.

1. Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago
River North, 1.3 km from Oak Street
United States
Jorge
€540
includes taxes & fees
4 Oct - 5 Oct
Trump International Hotel & Tower Chicago
A modern hotel lobby with a spiral staircase, seating areas, and large windows offering city views.
A modern interior with a spiral staircase, large windows, and a geometric patterned floor.
A modern living room with a large sectional sofa, a flat-screen TV mounted on the wall, a dining area with a table and chairs, and a view of the cityscape through large windows.
A lobby with wicker furniture, a fire feature, and a view of the outdoors.

2. Residence Inn Chicago Downtown Magnificent Mile

Residence Inn Chicago Downtown Magnificent Mile
Streeterville, 0.8 km from Oak Street
United States
Brian
€330
includes taxes & fees
27 Sept - 28 Sept
Residence Inn Chicago Downtown Magnificent Mile
A couple dining at a table with a view of a cityscape and a sunset.
A modern living room with a sofa, chairs, a coffee table, and a TV. A large window offers a view of a cityscape and a tower.
A woman sitting by a window with a city view, holding a cup and saucer.
A modern hotel room with a large bed, a seating area, a TV, and a view of the city and ocean.

3. Park Hyatt Chicago

Park Hyatt Chicago
Streeterville, 0.4 km from Oak Street
United States
Catherine
€700
includes taxes & fees
18 Oct - 19 Oct
Park Hyatt Chicago
An outdoor seating area with tables and chairs, a planter with greenery, and a large brick structure in the background.
A view from a room with a large window overlooking a cityscape at night, featuring a river and illuminated buildings.
A modern living room with a large window overlooking a body of water, a tripod, and a sofa.
A spacious outdoor dining area with large windows overlooking the sea, featuring multiple tables and stools.

4. Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton
Streeterville, 2.1 km from Oak Street
United States
Shanequa
€354
includes taxes & fees
27 Sept - 28 Sept
Sable at Navy Pier Chicago, Curio Collection by Hilton
A grand foyer with a wooden staircase, a chandelier, and a large window.
A courtyard with brick arches, outdoor seating, and potted plants.
A stone entrance with a black metal gate, a black mat, and two lion statues.
A room with a wooden table, a coffee machine, a clock, and a framed sign on the wall.

5. Villa D' Citta

Villa D' Citta
3.1 km from Oak Street
United States
Jeffrey
€257
includes taxes & fees
5 Oct - 6 Oct
Villa D' Citta
A rooftop pool with lounge chairs and a city skyline in the background.
A bartender preparing a cocktail with various ingredients and bottles of liquor on the bar counter.

6. Viceroy Chicago

Viceroy Chicago
0.3 km from Oak Street
United States
Margaret
€521
includes taxes & fees
22 Oct - 23 Oct
Viceroy Chicago
A person sitting by a window with a view of a cityscape, including a tall tower.
A modern bar area with a central bar and multiple stools, surrounded by a high ceiling with a decorative light fixture.
A couple walking through a spacious lobby with marble flooring, large white floral arrangements, and a modern staircase in the background.
A group of people on a boat with a city skyline in the background.

7. Four Seasons Hotel Chicago

Four Seasons Hotel Chicago
Streeterville, 0.2 km from Oak Street
United States
Teresa
€652
includes taxes & fees
4 Oct - 5 Oct
Four Seasons Hotel Chicago
A modern hotel with a colorful awning and a glass facade.
A modern lobby with a reception desk, seating area, and a large illuminated number '5' on the wall.
A bakery display with various baked goods and a coffee machine.
A hotel room with a wooden wardrobe, a minibar with coffee cups and a bottle, a safe, and a towel rack with a hanging bag.

8. Aloft by Marriott Chicago Downtown River North

Aloft by Marriott Chicago Downtown River North
River North, 1.1 km from Oak Street
United States
Michelle
€248
includes taxes & fees
27 Sept - 28 Sept
Aloft by Marriott Chicago Downtown River North
A restaurant with tables and chairs arranged in a corridor, large windows, and hanging lamps.
A rooftop pool area with city views, two lounge chairs, and a small table with a vase.
A dining area with wicker chairs and tables, overlooking a marina with boats and a Ferris wheel.
A modern hotel lobby with a large seating area, a view of the city, and a green accent wall.

9. The St. Regis Chicago

The St. Regis Chicago
1.6 km from Oak Street
United States
Xiomara
€761
includes taxes & fees
23 Oct - 24 Oct
The St. Regis Chicago
A hotel with a modern glass facade, signage for SpringHill Suites, and a well-lit entrance.
A bar area with a long counter, bar stools, and a bar stocked with bottles.
A modern hotel room with a large window, a desk, a chair, a sofa, and a small side table.
A modern reception desk with a sleek design, large windows offering a view of the cityscape, and a contemporary ceiling with linear wood paneling.

10. Springhill Suites by Marriott Chicago Downtown/ River North

Springhill Suites by Marriott Chicago Downtown/ River North
River North, 1.3 km from Oak Street
Canada
Sugar
€228
includes taxes & fees
27 Sept - 28 Sept
Springhill Suites by Marriott Chicago Downtown/ River North
A modern kitchen with stainless steel appliances, a built-in microwave, and a coffee maker.
A conference room with a long table, chairs, a projector screen, and a flat-screen TV displaying "LOEWS HOTELS".
A restaurant interior with multiple tables, chairs, and hanging pendant lights.
An outdoor patio area with multiple tables and chairs, umbrellas, and potted plants.

11. Loews Chicago Hotel

Loews Chicago Hotel
Streeterville, 1.3 km from Oak Street
United States
Ryan
€299
includes taxes & fees
4 Oct - 5 Oct
Loews Chicago Hotel
A modern indoor swimming pool with a clear blue water surface, a wooden ceiling, and a wall with a floral pattern.
A rooftop terrace with a view of a city skyline at dusk.
A modern hotel room with a large window offering a city view, a wooden desk with a laptop, and a small seating area.
A modern hotel room with a large window, a wooden desk, a bathroom with a mirror, and a view of the cityscape.

12. Nobu Hotel Chicago

Nobu Hotel Chicago
2.6 km from Oak Street
United States
Abhay
€531
includes taxes & fees
4 Oct - 5 Oct
Nobu Hotel Chicago
An outdoor seating area with a fire pit, wooden benches, and tables, surrounded by large windows and string lights.
A spacious indoor area with seating arrangements, large windows, and indoor plants.
A modern lounge area with a sofa, chairs, and a large potted plant.
A modern lobby with a sofa, coffee table, and potted plants.

13. The Emily Hotel

The Emily Hotel
2.6 km from Oak Street
United States
Althea
€290
includes taxes & fees
4 Oct - 5 Oct
The Emily Hotel
A modern kitchen with a large island, bar stools, and a city view.
A modern dining area with a wooden table and chairs, a central sink, and large windows.
A spacious living area with a large sofa, a dining table, and a TV mounted on the wall.
A modern living room with a grey sectional sofa, a round coffee table, and a glass desk with a chair. Large windows offer a city view.

14. Level Chicago – Old Town

Level Chicago – Old Town
Near North Side, 0.8 km from Oak Street
United States
Brian
€332
includes taxes & fees
27 Sept - 28 Sept
Level Chicago – Old Town
A modern hotel with a glass facade, multiple floors, and a prominent sign.
A modern dining area with a central island, chairs, pendant lights, and a decorative wall with a motivational quote.
A hotel pool area with a clear view of the cityscape through large windows, a pool with a metal ladder, and several lounge chairs.
A modern conference room with a large oval table, multiple chairs, and a city view through large windows.

15. Hampton Inn Chicago West Loop Fulton Market Area

Hampton Inn Chicago West Loop Fulton Market Area
2.3 km from Oak Street
United States
Rebecca
€213
includes taxes & fees
27 Sept - 28 Sept
Hampton Inn Chicago West Loop Fulton Market Area
A modern living room with a large TV, a sofa, a coffee table, and a chair. There is a large window with a city view.
A balcony with a city view, a table, and two chairs.
A modern bedroom with a large bed, a television, and a balcony with a city view.
A bedroom with a large window overlooking a cityscape.

16. Level Chicago - River North

Level Chicago - River North
1.4 km from Oak Street
United States
Frederico
€330
includes taxes & fees
27 Sept - 28 Sept
Level Chicago - River North
A modern lobby with a geometric light installation, a staircase, and a reception desk.
A modern lobby with a reception desk, seating area, staircase, and decorative lighting.
A modern restaurant with a long counter, bar stools, and high ceilings with exposed beams.
A modern hotel room with a kitchen area, a dining table with chairs, a sofa, and a large window with curtains.

17. Hampton Inn & Suites Chicago Downtown

Hampton Inn & Suites Chicago Downtown
River North, 1.1 km from Oak Street
United States
Catherine
€242
includes taxes & fees
27 Sept - 28 Sept
Hampton Inn & Suites Chicago Downtown
A hotel room with a bed, a chair, a small table with flowers, and a large window with a city view.
A modern lobby with a seating area, a kitchen, and artwork on the walls.
A modern bar area with wooden tables and black bar stools, a central bar counter with bottles and glasses, and a large TV screen on the wall.
A high-rise hotel with a curved facade, multiple floors, and large windows.

18. Kinzie Hotel

Kinzie Hotel
River North, 1.3 km from Oak Street
United States
Erick
€282
includes taxes & fees
27 Sept - 28 Sept
Kinzie Hotel
A modern living room with a grey sofa, a round coffee table with a plant, and a TV mounted on the wall.
A modern high-rise building with multiple balconies, large windows, and a city skyline in the background.
A modern kitchen with a gas stove, white cabinets, and a view of the city through large windows.
A modern conference room with a long table, blue chairs, and a unique ceiling light fixture.

19. Level Chicago Fulton Market

Level Chicago Fulton Market
West Loop, 2.1 km from Oak Street
United States
Jessica
€349
includes taxes & fees
27 Sept - 28 Sept
Level Chicago Fulton Market
A dining area with tables set for four, large windows with a view of city buildings, and a curved ceiling structure.
A spacious lobby with a patterned carpet, wooden paneling, and modern lighting fixtures.
A multi-story building with a prominent storefront featuring a golden sign.

20. Omni Chicago Hotel

Omni Chicago Hotel
Streeterville, 0.7 km from Oak Street
United States
Shiaka
€326
includes taxes & fees
15 Oct - 16 Oct
Omni Chicago Hotel
View all properties

Compare popular hotels close to Oak Street

Property
Property class
Guest rating
Breakfast included
Pool
Spa
Pet-friendly
WiFi included
A cityscape with a river, a bridge, and a dining area with tables and chairs.
Trump International Hotel & Tower Chicago
9.6
Exceptional
2,027 reviews
View
A modern hotel lobby with a spiral staircase, seating areas, and large windows offering city views.
Residence Inn Chicago Downtown Magnificent Mile
9.6
Exceptional
638 reviews
View
A couple dining at a table with a view of a cityscape and a sunset.
Park Hyatt Chicago
9.6
Exceptional
1,002 reviews
View
An outdoor seating area with tables and chairs, a planter with greenery, and a large brick structure in the background.
Sable at Navy Pier Chicago, Curio Collection by Hilton
9.4
Exceptional
2,701 reviews
View
A grand foyer with a wooden staircase, a chandelier, and a large window.
Villa D' Citta
9.4
Exceptional
125 reviews
View

Top Oak Street Hotel Reviews

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

10/10 Excellent
"The hotel was truly remarkable! I can’t wait to go back in the future, the staff was truly amazing as well!"
Michael 2-night trip
Posted 1 hour ago
Hotel Riu Plaza Chicago
The Wade

The Wade

10/10 Excellent
"The room was very clean. Great staff. Very accommodating and quick. Great hotel in a great area. Good views of the Lake"
Richard 5-night trip
Posted 5 hours ago
The Wade
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

8/10 Good
"Stayed in a junior suite !! Very nice until the A/C broke (97* outside) had to drag all of our stuff back to the lobby just to get another room !! When, they should have come up and given us the key to the new room !! Next (2) days in the the room we had no hot water in the morning to take a shower so the next three days were cold showers in the morning (very annoying). I would love to stay there again but I’m not so sure."
Dawn 1-night trip
Posted 7 hours ago
The Chicago Hotel Collection - Magnificent Mile
Hyatt Regency Chicago

Hyatt Regency Chicago

10/10 Excellent
"Great location! Everything you need was at the hotel."
Angela 3-night trip
Posted 8 hours ago
Hyatt Regency Chicago
Hampton Inn Chicago Downtown/Magnificent Mile

Hampton Inn Chicago Downtown/Magnificent Mile

10/10 Excellent
"The hotel needs remodeling, but it was truly a wonderful stay. We had a comfortable bed, an air conditioned room, and the most helpful staff. It would have been nice to have more updated elevators, and for the breakfast to be with real plates, cups, and utensils. But otherwise, we really enjoyed the centralized location and comfortable suite."
Priscilla 3-night trip
Posted 9 hours ago
Hampton Inn Chicago Downtown/Magnificent Mile
The Godfrey Hotel Chicago

The Godfrey Hotel Chicago

8/10 Good
"My husband and I just spent two evenings at The Godfrey Hotel. The location was super convenient. The rooftop bar was a perfect spot for an evening nightcap with an amazing view! Our room was clean and spacious, our only complaint was that the bed was extremely FIRM! Also, I’ll add that the city street noise was very loud in the evenings, I was glad that I brought along my white noise maker."
Jacqueline 2-night trip
Posted 11 hours ago
The Godfrey Hotel Chicago
River Hotel

River Hotel

10/10 Excellent
"Property is centrally located and staff is over the top accommodating! We’ve stayed two times already. This is our go to hotel in the loop"
Susan 3-night trip
Posted 11 hours ago
River Hotel
Sofitel Chicago Magnificent Mile

Sofitel Chicago Magnificent Mile

8/10 Good
"Due to a big mixup at check-in for our four-night stay, we were presented an initial bill that was a very substantial overcharge. With dread, I approached the staff in anticipation of an argument and their stubborn refusal to adjust the bill. But to my amazement and delight, the matter was quite professionally sorted and the error was promptly taken care of with a corrected bill. It would be great if all businesses treated customers with such respect and fairness. Kudos to the staff and thank you so much for handling the matter with integrity. Nice location and a good breakfast at a fair price, too!"
Roy 4-night trip
Posted 20 hours ago
Sofitel Chicago Magnificent Mile

Other attractions near Oak Street

A large indoor Christmas tree in a shopping mall.
Photo by Rita Irvine

900 North Michigan Shops

8.6/10 (55 reviews)
You can browse for the perfect souvenirs at 900 North Michigan Shops during your trip to Chicago. Stroll along the lakeside or experience the acclaimed art galleries in this vibrant area.
See properties
A tall skyscraper with a spire, a flagpole with an American flag, and a stone building with arched windows.

875 North Michigan Avenue

9.2/10 (2,926 reviews)
You can find out about the history of Chicago when you stop by 875 North Michigan Avenue. Amble around this vibrant area's lakeside or experience its fascinating museums.
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Topgolf Swing Suite

You can take time to visit Topgolf Swing Suite during your travels to Chicago. Stroll along the riverfront or experience the entertainment choices in this vibrant area.
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Mariano Plaza

After visiting Mariano Plaza, make a plan to see the other sights and activities in Chicago. Stroll along the riverfront or experience the acclaimed theatre scene in this vibrant area.
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The Drake

The Drake is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Stroll along the riverfront or experience the acclaimed art galleries in this vibrant area.
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Fourth Presbyterian Church

10.0/10 (2 reviews)
Fourth Presbyterian Church is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Amble around this vibrant area's lakeside or experience its acclaimed theatre scene.
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360 CHICAGO

You can learn about the history of Chicago with a visit to 360 CHICAGO. Amble around this vibrant area's riverfront or experience its entertainment choices.
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Loyola University Museum of Art

9.0/10 (2 reviews)
You can spend time studying the exhibits at Loyola University Museum of Art in Chicago. Experience the acclaimed art galleries and fascinating museums in this vibrant area.
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Frequently asked questions

What's the area like around Oak Street?
Oak Street is located in Chicago. This metropolitan area is known for its stunning architecture and top museums. If you're looking for a convenient place to stay, take a look at the 700 hotels and other accommodation options you'll find within a mile.
What's the best place to stay close to Oak Street?
Adjacent to Oak Street, Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical is one of the top choices for your stay based on our traveller data, and this hotel offers free breakfast and in-room kitchens. Other good choices close by include The Chicago Hotel Collection Ambassador Gold Coast and River Hotel.
How many hotels will I be able to find close to Oak Street?
Expedia has 700 hotels and other accommodation options within a mile from Oak Street.
If I need to cancel the hotel reservation for my stay near Oak Street, will I receive a refund?
Yes! Most hotel reservations are refundable if you cancel before the hotel's cancellation deadline, which is usually within 24-48 hours of check in. If you have a non-refundable reservation, you may still be able to cancel and receive a refund within 24 hours of booking. Add dates, click "Search", then use the filter option "fully refundable" to view the best deals available near Oak Street.
What can I see and do near Oak Street?
You might want to spend some time browsing the exhibits at Museum of Contemporary Art Chicago, Chicago History Museum or Art Institute of Chicago. Chicago Water Tower, Holy Name Cathedral and Former Medinah Temple are some of the local landmarks to explore. You can watch performances at Broadway Playhouse, Second City and House of Blues Chicago if you're interested in local theatre.
How can I get to Oak Street?
With so many transport options, seeing the area around Oak Street is simple. Take advantage of metro transport at State Station, Clark-Lake Station and Lake Station. If you want to journey outside of the area, jump aboard a train from Millennium Station, Chicago Van Buren Street Station or Chicago Union Station.