The Best Hotels Closest to Oak Street in Chicago for 2026

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Our top choices for Oak Street hotels

A spacious kitchen with white cabinetry, a central island with bar stools, pendant lighting, and a large window with a view.

A living room with a fireplace, a sofa, a coffee table, and a TV mounted on the wall.

A modern kitchen with white cabinetry, stainless steel appliances, and a wooden dining table.

A modern kitchen with white cabinetry, stainless steel appliances, and a wooden dining table with benches.

1. The Sono Chicago

Old Town Chicago, 1.5 km from Oak Street

Bronwyn

₩206,451

₩242,360 total

includes taxes & fees

Sep 2 - Sep 3

A high-rise hotel with multiple floors, large windows, and a prominent Tiffany & Co. store on the ground level.

A spacious hotel lobby with multiple seating areas, a grand staircase, and large windows offering views of the city.

A rooftop bar with seating and a view of the city skyline at night.

A modern indoor pool area with large windows, potted palm plants, and lounge chairs.

2. The Peninsula Chicago

Streeterville, 0.5 km from Oak Street

Angela

₩860,213

₩1,022,708 total

includes taxes & fees

Aug 30 - Aug 31

A modern hotel lobby with a reception desk, seating area, and large windows offering city views.

A modern hotel room with a large window offering a city view, three armchairs arranged around a central coffee table, and a decorative hanging plant.

A spacious lobby with a modern sofa, armchairs, and a coffee table. A large window offers a view of the cityscape.

A swimming pool with a ceiling of lights, large windows, and potted plants.

3. The Langham, Chicago

River North, 1.4 km from Oak Street

Michael

₩853,331

₩1,014,528 total

includes taxes & fees

Aug 30 - Aug 31

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 lobby with wicker furniture, a fire feature, and a view of the outdoors.

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.

4. Residence Inn Chicago Downtown Magnificent Mile

Streeterville, 0.8 km from Oak Street

Claudia

₩302,795

₩359,993 total

includes taxes & fees

Sep 7 - Sep 8

A cityscape with a river, a bridge, and a dining area with tables and chairs.

A pool area with a view of a cityscape, a lounge with wicker furniture, and a person relaxing in the pool.

A modern hotel room with large floor-to-ceiling windows offering a city view.

A high-rise hotel with a prominent 'TRUMP' sign, reflecting in the water, surrounded by other tall buildings.

5. Trump International Hotel & Tower Chicago

River North, 1.3 km from Oak Street

Jorge

₩696,772

₩828,391 total

includes taxes & fees

Sep 7 - Sep 8

A rooftop terrace with a city skyline view, featuring a mix of modern and classic architecture, and several potted plants.

A modern staircase with glass railings and pendant lighting.

A modern hotel room with a green sofa, two round tables, a city view, and a chandelier.

A modern urban street with high-rise buildings, including a prominent 'The Gwent' and 'Nordstrom' sign.

6. The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago

Streeterville, 1 km from Oak Street

Jennifer

₩595,473

₩748,890 total

includes taxes & fees

Sep 6 - Sep 7

A couple dining at a table with a view of a cityscape and a sunset.

A rooftop terrace with a dining table, chairs, and a view of the cityscape, including the Water Tower Place building.

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.

7. Park Hyatt Chicago

Streeterville, 0.4 km from Oak Street

Jennifer

₩761,804

₩905,709 total

includes taxes & fees

Sep 7 - Sep 8

A modern building with a colorful facade and a red circular seating area.

A modern high-rise building with a glass facade, surrounded by other tall buildings.

A modern hotel room with a large window offering a city view, a contemporary light fixture, and a clean, minimalist design.

A modern bar area with a checkered floor, wooden ceiling, and various bar equipment.

8. citizenM Chicago Downtown

Theatre District, 1.5 km from Oak Street

lakadria

₩233,978

₩278,177 total

includes taxes & fees

Sep 8 - Sep 9

A spacious bar area with high ceilings and large windows, offering views of a cityscape.

A multi-level hotel lobby with a glass elevator, a seating area, and a dining space.

A bar with a circular liquor display, seating with stools, and a city view through large windows.

A hotel room with a bed, a sofa with cushions, a large window with a view of a cityscape and water.

9. Hyatt Regency Chicago

The Loop, 1.5 km from Oak Street

Abdulsamad

₩280,774

₩382,906 total

includes taxes & fees

Sep 7 - Sep 8

A person relaxing on a sofa with a laptop, a glass of red wine, and a small table with a vase of flowers and a telephone.

A room with a bed against a window overlooking a cityscape. There is a small table with a book, a vase with flowers, and a cup.

A modern restaurant with high ceilings, wooden flooring, and a central chandelier. Tables are set with wine glasses and red cushions.

A modern hotel lobby with leather sofas, a coffee table, and a floor lamp.

10. L7 Chicago by LOTTE

Theatre District, 1.6 km from Oak Street

Girivasan

₩308,438

₩366,701 total

includes taxes & fees

Aug 30 - Aug 31

A modern lounge area with seating, a coffee table, and a view of the city at night.

A modern lounge area with seating, tables, and a view of the cityscape.

A modern hotel entrance with a neon sign, a covered walkway, and a cityscape view.

An outdoor seating area with a wooden table and metal stools, overlooking a cityscape with modern buildings and a street.

11. Moxy Chicago Downtown

River North, 1.1 km from Oak Street

Julia

₩227,096

₩269,993 total

includes taxes & fees

Sep 7 - Sep 8

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 hotel room with two beds, a desk, a chair, and a view of the cityscape.

A bakery display with various baked goods and a coffee machine.

12. Aloft by Marriott Chicago Downtown River North

River North, 1.1 km from Oak Street

Michelle

₩233,978

₩278,177 total

includes taxes & fees

Sep 7 - Sep 8

A modern kitchen with stainless steel appliances, a built-in microwave, and a coffee maker.

A conference room with tables, chairs, a projector, and a screen displaying "LOEWS HOTELS".

13. Loews Chicago Hotel

Streeterville, 1.3 km from Oak Street

Elisa

₩295,913

₩400,928 total

includes taxes & fees

Sep 7 - Sep 8

A hotel with a modern glass facade, signage for SpringHill Suites, and a well-lit entrance.

A hotel room with two beds, a desk, a chair, a lamp, and a view of a building through the window.

A modern hotel room with a large window, a desk, a chair, a sofa, and a small side table.

A bar area with a long counter, bar stools, and a bar stocked with bottles.

14. Springhill Suites by Marriott Chicago Downtown/ River North

River North, 1.3 km from Oak Street

Claudia

₩254,623

₩302,722 total

includes taxes & fees

Sep 7 - Sep 8

The Riu Plaza Chicago Hotel facade with a grand entrance, large windows, and a modern architectural design.

A spacious lobby with a marble floor, a reception desk, and a glass partition.

A couple dining at a table with a city view, surrounded by chairs and a variety of dishes.

A modern hotel lobby with a central seating area, a reception desk, and a decorative wall with a unique design.

15. Hotel Riu Plaza Chicago

Streeterville, 0.8 km from Oak Street

Peter

₩233,861

₩317,264 total

includes taxes & fees

Aug 30 - Aug 31

An outdoor seating area with tables and chairs, a planter with greenery, and a large brick structure in the background.

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.

A view from a room with a large window overlooking a cityscape at night, featuring a river and illuminated buildings.

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

Streeterville, 2.1 km from Oak Street

Ashraf

₩232,808

₩324,241 total

includes taxes & fees

Sep 7 - Sep 8

A high-rise hotel with a modern glass facade, multiple floors, and a prominent corner entrance.

A couple sitting at a table with a glass of wine and hors d'oeuvres, in a room with a view of lights outside.

A modern lobby with a fireplace, seating area, and large windows.

A modern reception area with a wooden ceiling and a reception desk.

17. Residence Inn by Marriott Chicago Downtown / River North

River North, 1.3 km from Oak Street

Josephine L

₩254,623

₩302,722 total

includes taxes & fees

Sep 7 - Sep 8

A restaurant interior with brick walls, hanging spherical light fixtures, and a visible kitchen area.

A bar area with multiple shelves of bottles, a bar counter, and three bar stools.

A high-rise building with a modern architectural design, featuring a prominent glass facade and a series of vertical lines.

A modern living room with a brick wall mural, a green sofa, leather chairs, and a wooden coffee table.

18. Arlo Chicago

Theatre District, 1.7 km from Oak Street

SUZAN

₩225,940

₩311,838 total

includes taxes & fees

Sep 7 - Sep 8

A dining area with a table set for four, large windows offering a cityscape view at dusk.

A high-rise hotel room with large windows offering a city view, round tables set for dining, and elegant decor with flowers and candles.

A rooftop terrace with outdoor seating and a fire pit, overlooking a cityscape with tall buildings.

A breakfast table with croissants, a bowl of berries, a glass of orange juice, and a smoothie, set against a cityscape view through a window.

19. The Royal Sonesta Chicago Downtown

The Loop, 1.5 km from Oak Street

Angel Limuel

₩280,773

₩377,855 total

includes taxes & fees

Sep 7 - Sep 8

A modern dining area with round tables and chairs, large windows, and a view of a cityscape.

A person in a white robe sitting by a window with a view of modern high-rise buildings.

A hotel room with a large bed, a chair, a window with a city view, and a bathroom area with a toilet and a sink.

Two people at a table with a tiered dessert display and glasses of champagne.

20. Sofitel Chicago Magnificent Mile

0.2 km from Oak Street

Anton

₩356,472

₩464,727 total

includes taxes & fees

Sep 7 - Sep 8

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Compare popular hotels close to Oak Street

Property	Property class	Guest rating
The Sono Chicago	10.0 Exceptional 545 reviews	View
The Peninsula Chicago	9.8 Exceptional 1,000 reviews	View
The Langham, Chicago	9.8 Exceptional 1,001 reviews	View
Residence Inn Chicago Downtown Magnificent Mile	9.6 Exceptional 617 reviews	View
Trump International Hotel & Tower Chicago	9.6 Exceptional 1,988 reviews	View

Top Oak Street Hotel Reviews

The Chicago Hotel Collection Ambassador Gold Coast

10/10 Excellent

"We always stay here when we visit Chicago. Fantastic!"

Kasa Magnificent Mile Chicago

8/10 Good

"Check in can be slightly confusing however you get the hang of it quickly. It was close to many amenities, a train away or a longer walk. The loft was cleaning than most however there was still dust and some crumbs left behind. Over all we were pleased with our stay even though very pricey for 3 nights"

The Whitehall Hotel, BW Premier Collection

8/10 Good

"I appreciate the convince of the location, staff was helpful too, kind and friendly, I would’ve liked my room clean but overall good stay and walkable to most areas. Plus the nice touch of coffee downstairs"

Sofitel Chicago Magnificent Mile

10/10 Excellent

"Awesome clean rooms Staff was excellent"

InterContinental Chicago Magnificent Mile by IHG

10/10 Excellent

"Gorgeous huge room with giant windows. Amazing fast staff, especially the valet/bellhops. Beautiful property, amazing location. Awesome pool."

River Hotel

10/10 Excellent

"Awesome place in a great location"

Other attractions near Oak Street

A large indoor Christmas tree in a shopping mall.

900 North Michigan Shops

8.6/10 (55 reviews)

You can browse for the perfect souvenirs at 900 North Michigan Shops during your visit to Chicago. Stroll along the lakeside or experience the acclaimed theater scene in this vibrant area.

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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 with a visit to 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 acclaimed theater scene 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 lakeside or experience the fascinating museums 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 entertainment choices 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 art 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 fascinating museums.

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Bronzeville Black Chamber of Commerce

Find out about the history of Chicago with a stop at Bronzeville Black Chamber of Commerce. Discover the entertainment choices and notable monuments 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, check out the 697 hotels and other accommodations you'll find within a mile.

What's the best place to stay close to Oak Street?

Adjacent to Oak Street, Four Seasons Hotel Chicago is one of the top choices for your stay based on our traveler data, and this hotel offers a full-service spa and a restaurant. Other good choices close by include The Chicago Hotel Collection Ambassador Gold Coast and Kasa Magnificent Mile Chicago.

How many hotels should I expect to find close to Oak Street?

Expedia has 697 hotels and other accommodations 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! You'll find that most hotel reservations are refundable provided that you cancel prior to the accommodation's cancellation deadline, which often is within 24-48 hours of check in. If you booked a non-refundable reservation, you might be able to cancel it and be given a refund within a 24-hour period of booking. Enter your dates, click on "Search", then you can filter by "fully refundable" to review the top deals on offer near Oak Street.

Where can I learn more about changing or cancelling my trip in the area near Oak Street?

To access more information about picking new dates or cancelling your stay near Oak Street, click here.

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 Tribune Tower 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 theater.

How can I get to Oak Street?

With so many transportation options, seeing the area around Oak Street is a breeze. Take advantage of metro transit 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.

Find hotels near Oak Street, Chicago from ₩242,360

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Treat yourself

Be picky

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Our top choices for Oak Street hotels

1. The Sono Chicago

2. The Peninsula Chicago

3. The Langham, Chicago

4. Residence Inn Chicago Downtown Magnificent Mile

5. Trump International Hotel & Tower Chicago

6. The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago

7. Park Hyatt Chicago

8. citizenM Chicago Downtown

9. Hyatt Regency Chicago

10. L7 Chicago by LOTTE

11. Moxy Chicago Downtown

12. Aloft by Marriott Chicago Downtown River North

13. Loews Chicago Hotel

14. Springhill Suites by Marriott Chicago Downtown/ River North

15. Hotel Riu Plaza Chicago

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

17. Residence Inn by Marriott Chicago Downtown / River North

18. Arlo Chicago

19. The Royal Sonesta Chicago Downtown

20. Sofitel Chicago Magnificent Mile

Compare popular hotels close to Oak Street

Top Oak Street Hotel Reviews

The Chicago Hotel Collection Ambassador Gold Coast

Kasa Magnificent Mile Chicago

The Whitehall Hotel, BW Premier Collection

Sofitel Chicago Magnificent Mile

InterContinental Chicago Magnificent Mile by IHG

River Hotel

Other attractions near Oak Street

900 North Michigan Shops

875 North Michigan Avenue

Topgolf Swing Suite

Mariano Plaza

The Drake

Fourth Presbyterian Church

360 CHICAGO

Bronzeville Black Chamber of Commerce

Frequently asked questions