The Best Hotels Closest to Oak Street in Chicago - 2026 Updated Prices

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Our top choices for Oak Street hotels

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 bar area with a long counter, multiple shelves of bottles, and four bar stools.

1. L7 Chicago by LOTTE

Theatre District, 1 mi from Oak Street

Emily

£174

includes taxes & fees

2 Nov - 3 Nov

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

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

2. The Peninsula Chicago

Streeterville, 0.3 mi from Oak Street

Levi

£560

includes taxes & fees

1 Nov - 2 Nov

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

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

3. The Langham, Chicago

River North, 0.8 mi from Oak Street

Saramae

£511

includes taxes & fees

25 Oct - 26 Oct

A modern hotel lobby with a spiral staircase, seating areas, and large windows offering city views.

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

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

A modern interior with a spiral staircase, large windows, and a geometric patterned floor.

4. Residence Inn Chicago Downtown Magnificent Mile

Streeterville, 0.5 mi from Oak Street

Brian

£197

includes taxes & fees

1 Nov - 2 Nov

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

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

5. Trump International Hotel & Tower Chicago

River North, 0.8 mi from Oak Street

Mark

£413

includes taxes & fees

1 Nov - 2 Nov

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

A modern hotel room with a large bed, a seating area, a TV, and a view of the city and ocean.

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

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.

6. Park Hyatt Chicago

Streeterville, 0.3 mi from Oak Street

Tom

£492

includes taxes & fees

1 Nov - 2 Nov

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

A waterfront cityscape with modern buildings, a Ferris wheel, and several cruise ships docked.

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.

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

Streeterville, 1.3 mi from Oak Street

Shanequa

£256

includes taxes & fees

29 Oct - 30 Oct

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

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.

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

8. citizenM Chicago Downtown

Theatre District, 1 mi from Oak Street

Kimberly

£152

includes taxes & fees

1 Nov - 2 Nov

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

A room with a diamond-patterned bookshelf filled with books, a wooden floor, and a lamp.

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.

9. Arlo Chicago

Theatre District, 1.1 mi from Oak Street

Ashley Nacole

£177

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

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

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

10. Moxy Chicago Downtown

River North, 0.7 mi from Oak Street

Justin

£145

includes taxes & fees

1 Nov - 2 Nov

A modern hotel with a colorful awning and a glass facade.

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

A modern lobby with a reception desk, seating area, and a large illuminated number '5' on the wall.

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.

11. Aloft by Marriott Chicago Downtown River North

River North, 0.7 mi from Oak Street

Eric

£166

includes taxes & fees

1 Nov - 2 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 room with a green sofa, two round tables, a city view, and a chandelier.

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

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

Streeterville, 0.6 mi from Oak Street

Jessica

£456

includes taxes & fees

31 Oct - 1 Nov

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.

13. Hyatt Regency Chicago

The Loop, 0.9 mi from Oak Street

Mark

£274

includes taxes & fees

30 Oct - 31 Oct

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 reception desk with a sleek design, large windows offering a view of the cityscape, and a contemporary ceiling with linear wood paneling.

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

14. Springhill Suites by Marriott Chicago Downtown/ River North

River North, 0.8 mi from Oak Street

Sugar

£166

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

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

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

15. Hotel Riu Plaza Chicago

Streeterville, 0.5 mi from Oak Street

Sean Robert

£166

includes taxes & fees

2 Nov - 3 Nov

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

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.

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 modern interior with a central fireplace, seating area, and wall-mounted lighting.

16. The Royal Sonesta Chicago Downtown

The Loop, 0.9 mi from Oak Street

ShaRona

£194

includes taxes & fees

1 Nov - 2 Nov

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

A banquet hall with round tables set for dining, featuring a high ceiling with exposed beams and a modern chandelier.

A modern lounge area with a sofa, two armchairs, a coffee table, and a patterned carpet.

17. Loews Chicago Hotel

Streeterville, 0.8 mi from Oak Street

Ryan

£264

includes taxes & fees

4 Oct - 5 Oct

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

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

A multi-story building with a grid of windows, surrounded by other high-rise buildings.

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

18. Staypineapple, An Iconic Hotel, The Loop

Theatre District, 1.2 mi from Oak Street

Myra

£172

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.

19. Viceroy Chicago

0.2 mi from Oak Street

Margaret

£289

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 dining area with a long table, chairs, and a fireplace. There are framed pictures on the walls and a large flat-screen TV mounted on the wall.

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

20. The Talbott, Autograph Collection

0.1 mi from Oak Street

Karina

£241

includes taxes & fees

1 Nov - 2 Nov

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Compare popular hotels close to Oak Street

Property	Property class	Guest rating
The Peninsula Chicago	9.8 Exceptional 1,000 reviews	View
L7 Chicago by LOTTE	9.6 Exceptional 4,931 reviews	View
The Langham, Chicago	9.8 Exceptional 1,000 reviews	View
Residence Inn Chicago Downtown Magnificent Mile	9.6 Exceptional 647 reviews	View
Trump International Hotel & Tower Chicago	9.6 Exceptional 2,038 reviews	View

Top Oak Street Hotel Reviews

Hotel Saint Clair- Magnificent Mile

8/10 Good

"Older hotel. Everything seemed tight (room, hallways, elevator. Sometimes it takes a while for valet since the drivers had to manage two hotels, averaging around 10-15min. The staff were very friendly though. Would I stay here again? Probably not."

The Chicago Hotel Collection Ambassador Gold Coast

10/10 Excellent

"Great experience on my first trip to Chicago"

River Hotel

10/10 Excellent

"The room and the facility were just right, and the location was lovely. But the best thing about the stay was the helpfulness and interest from the staff. From upgrading our room (to include the great view!), to helping us find one of the five Starbucks Roasterys in the world, and storing our luggage after we checked out, the service was personal and effective. Jock was especially helpful, and really seemed to enjoy helping us with every part of our stay. I would definitely return to this hotel for my next Chicago visit."

Warwick Allerton - Chicago

8/10 Good

"Clean room with plenty of room and bed to stretch out. Great restaurants and top retail stores within walking distance. Polished staff. Limited breakfast options."

Sofitel Chicago Magnificent Mile

10/10 Excellent

"I loved"

Hotel Felix River North/Magnificent Mile

8/10 Good

"Hotel was good but was overpriced in my opinion."

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

10/10 Excellent

"Excellent location!"

Hampton Inn Chicago Downtown/Magnificent Mile

10/10 Excellent

"Nice place! Perfect 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 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.

Search Hotels Near Oak Street, Chicago

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Treat yourself

Be picky

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Our top choices for Oak Street hotels

1. L7 Chicago by LOTTE

2. The Peninsula Chicago

3. The Langham, Chicago

4. Residence Inn Chicago Downtown Magnificent Mile

5. Trump International Hotel & Tower Chicago

6. Park Hyatt Chicago

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

8. citizenM Chicago Downtown

9. Arlo Chicago

10. Moxy Chicago Downtown

11. Aloft by Marriott Chicago Downtown River North

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

13. Hyatt Regency Chicago

14. Springhill Suites by Marriott Chicago Downtown/ River North

15. Hotel Riu Plaza Chicago

16. The Royal Sonesta Chicago Downtown

17. Loews Chicago Hotel

18. Staypineapple, An Iconic Hotel, The Loop

19. Viceroy Chicago

20. The Talbott, Autograph Collection

Compare popular hotels close to Oak Street

Top Oak Street Hotel Reviews

Hotel Saint Clair- Magnificent Mile

The Chicago Hotel Collection Ambassador Gold Coast

River Hotel

Warwick Allerton - Chicago

Sofitel Chicago Magnificent Mile

Hotel Felix River North/Magnificent Mile

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

Hampton Inn Chicago Downtown/Magnificent Mile

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