⭐ Top 10 Hotels Near Oak Street 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 spacious room with hardwood flooring, a stone fireplace, a door with glass panels, and a vase on the floor.

1. The Sono Chicago

1.5 km from Oak Street

Christie

S$287

includes taxes & fees

29 Oct - 30 Oct

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

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

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

A modern bar area with a checkered floor, bar stools, and a bartender.

2. The Peninsula Chicago

Streeterville, 0.5 km from Oak Street

Levi

S$954

includes taxes & fees

15 Nov - 16 Nov

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

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.

A modern dining area with round tables, comfortable chairs, and a dessert display.

3. The Langham, Chicago

River North, 1.4 km from Oak Street

Saramae

S$794

includes taxes & fees

15 Nov - 16 Nov

A person relaxing on a sofa with a window view of a building, a table with a glass of wine, and a vase with flowers.

A room with a bed, a window with curtains, a small table with a vase of flowers, and a chair.

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.

4. L7 Chicago by LOTTE

Theatre District, 1.6 km from Oak Street

Jeffrey Thomas

S$292

includes taxes & fees

1 Nov - 2 Nov

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.

5. Residence Inn Chicago Downtown Magnificent Mile

Streeterville, 0.8 km from Oak Street

Kaitlyn

S$335

includes taxes & fees

1 Nov - 2 Nov

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

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

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

A modern hotel room with large windows, white furniture, and a view of tall buildings.

6. Trump International Hotel & Tower Chicago

River North, 1.3 km from Oak Street

Cecille

S$702

includes taxes & fees

1 Nov - 2 Nov

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

Tom

S$811

includes taxes & fees

15 Nov - 16 Nov

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 lobby with a reception desk, seating area, staircase, and large windows.

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

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

Streeterville, 1 km from Oak Street

Jessica

S$645

includes taxes & fees

30 Oct - 31 Oct

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 interior with wooden shelves, colorful chairs, and hanging plants.

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

9. citizenM Chicago Downtown

Theatre District, 1.5 km from Oak Street

Katarina

S$259

includes taxes & fees

1 Nov - 2 Nov

A hotel room with a large bed, a wooden cabinet, a chair, and a view of the city skyline.

A modern dining area with a round table and chairs, large windows with a city view, and a decorative light fixture.

A rooftop pool with lounge chairs and a city skyline in the background.

10. Viceroy Chicago

0.3 km from Oak Street

Emily

S$511

includes taxes & fees

1 Nov - 2 Nov

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

A bar area with a marble countertop, bar stools, and a variety of bottles.

11. Hotel Riu Plaza Chicago

Streeterville, 0.8 km from Oak Street

Kevin

S$305

includes taxes & fees

11 Nov - 12 Nov

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.

12. Sofitel Chicago Magnificent Mile

0.2 km from Oak Street

Mohab

S$493

includes taxes & fees

1 Nov - 2 Nov

A corridor with ornate black metal railings and a patterned carpet.

A dining area with tables and chairs, a hanging light fixture, and a view of the street through a window.

A bed with a pillow featuring a pineapple design and the text "Sleep with me." A window reveals a cityscape at night.

A modern hotel room with a sofa, a small table, a bench, a TV, and a cabinet.

13. Staypineapple, An Iconic Hotel, The Loop

Theatre District, 2 km from Oak Street

RaeQuan

S$292

includes taxes & fees

1 Nov - 2 Nov

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 bar area with multiple shelves of bottles, a seating area with bar stools, and a counter with a cash register.

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

14. Moxy Chicago Downtown

River North, 1.1 km from Oak Street

Justin

S$246

includes taxes & fees

1 Nov - 2 Nov

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

A hotel room with a bed, a desk, a chair, a lamp, and a view of the cityscape.

A restaurant interior with multiple tables, chairs, and hanging pendant lights.

A reception desk with a textured surface, two laptops, and a potted orchid.

15. Loews Chicago Hotel

Streeterville, 1.3 km from Oak Street

Daniel

S$409

includes taxes & fees

15 Nov - 16 Nov

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 modern hotel entrance with a prominent "STREGIS" sign, large glass windows, and a well-lit facade.

A modern hotel lobby with a large seating area, a view of the city, and a green accent wall.

16. The St. Regis Chicago

1.6 km from Oak Street

Xiomara

S$846

includes taxes & fees

12 Nov - 13 Nov

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

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.

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

17. Springhill Suites by Marriott Chicago Downtown/ River North

River North, 1.3 km from Oak Street

Keith

S$259

includes taxes & fees

1 Nov - 2 Nov

A street view with outdoor seating, a building with a sign, and tall skyscrapers in the background.

A hotel entrance with a marquee sign, outdoor seating, and a well-lit facade.

A lobby with a checkered floor, seating area, and a glass entrance.

A bar with three wooden shelves filled with bottles and glasses.

18. The Talbott, Autograph Collection

0.2 km from Oak Street

Karina

S$387

includes taxes & fees

15 Nov - 16 Nov

A rooftop terrace with outdoor seating, a view of the city skyline, and a river.

A modern room with a view of a river and high-rise buildings.

A modern living room with a sofa, coffee table, and ottoman, a fireplace, and a large window with a city view.

A modern hotel room with a large bed, a desk, a sofa, and a view of the city.

19. LondonHouse Chicago, Curio Collection by Hilton

The Loop, 1.4 km from Oak Street

Keeven

S$382

includes taxes & fees

15 Nov - 16 Nov

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

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

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

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

20. Residence Inn by Marriott Chicago Downtown / River North

River North, 1.3 km from Oak Street

Kayla

S$266

includes taxes & fees

1 Nov - 2 Nov

View all properties

Compare popular hotels close to Oak Street

Property	Property class	Guest rating
The Sono Chicago	10.0 Exceptional 566 reviews	View
The Peninsula Chicago	9.8 Exceptional 1,001 reviews	View
The Langham, Chicago	9.8 Exceptional 1,005 reviews	View
L7 Chicago by LOTTE	9.6 Exceptional 5,038 reviews	View
Residence Inn Chicago Downtown Magnificent Mile	9.6 Exceptional 656 reviews	View

Top Oak Street Hotel Reviews

Hotel Riu Plaza Chicago

8/10 Good

"Good location, nice room and buffet breakfast!"

The Chicago Hotel Collection Ambassador Gold Coast

10/10 Excellent

"Had a great stay and the staff was fantastic"

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

8/10 Good

"Nice hotel and great walking distance to many attractions. Breakfast area was nice and room was large and clean."

Warwick Allerton - Chicago

10/10 Excellent

"Excellent"

Hilton Chicago/Magnificent Mile Suites

8/10 Good

"La ubicación es excelente. Las instalaciones están bien mantenidas y el equipo de limpieza muy atento, no es el caso con los del personal de recepción. El trato fue como segunda clase por una reservación a Travez de Expedía. Primero no encontraban la reservación y luego al terminar pregunté en expedía por el check out."

The Godfrey Hotel Chicago

10/10 Excellent

"Amazing locations and staff!"

The Chicago Hotel Collection River North

8/10 Good

"Nice property in a good location. I was concerned about the reviews I saw. However the key is if you don't want the extra charges everyone was concerned about. Don't book the All Inclusive Room Rate. Book a Room Rate Only. I was not charged the extra fees. The Train tracks can be loud at times, but didn't bother me when sleeping. If your a light sleeper. Something to consider. Wish their was a gym on site otherwise nice property."

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 trip to Chicago. Stroll along the lakeside or experience the acclaimed art galleries 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 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 685 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 685 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.

Hotels near Oak Street

Change your mind

Treat yourself

Be picky

Check prices for these dates

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Our top choices for Oak Street hotels

1. The Sono Chicago

2. The Peninsula Chicago

3. The Langham, Chicago

4. L7 Chicago by LOTTE

5. Residence Inn Chicago Downtown Magnificent Mile

6. Trump International Hotel & Tower Chicago

7. Park Hyatt Chicago

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

9. citizenM Chicago Downtown

10. Viceroy Chicago

11. Hotel Riu Plaza Chicago

12. Sofitel Chicago Magnificent Mile

13. Staypineapple, An Iconic Hotel, The Loop

14. Moxy Chicago Downtown

15. Loews Chicago Hotel

16. The St. Regis Chicago

17. Springhill Suites by Marriott Chicago Downtown/ River North

18. The Talbott, Autograph Collection

19. LondonHouse Chicago, Curio Collection by Hilton

20. Residence Inn by Marriott Chicago Downtown / River North

Compare popular hotels close to Oak Street

Top Oak Street Hotel Reviews

Hotel Riu Plaza Chicago

The Chicago Hotel Collection Ambassador Gold Coast

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

Warwick Allerton - Chicago

Hilton Chicago/Magnificent Mile Suites

The Godfrey Hotel Chicago

The Chicago Hotel Collection River North

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

Loyola University Museum of Art

Frequently asked questions