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

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

Old Town Chicago, 1.5 km from Oak Street

Bronwyn

￥33,730

￥39,596 total

includes taxes & fees

Sep 28 - Sep 29

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

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

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

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

2. The Peninsula Chicago

Streeterville, 0.5 km from Oak Street

Angela

￥111,157

￥132,154 total

includes taxes & fees

Sep 20 - Sep 21

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

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

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

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.

3. The Langham, Chicago

River North, 1.4 km from Oak Street

Michael

￥104,293

￥123,993 total

includes taxes & fees

Oct 4 - Oct 5

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

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

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

4. L7 Chicago by LOTTE

Theatre District, 1.6 km from Oak Street

christina

￥39,720

￥47,223 total

includes taxes & fees

Oct 1 - Oct 2

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

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

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

5. Residence Inn Chicago Downtown Magnificent Mile

Streeterville, 0.8 km from Oak Street

Zemene

￥41,550

￥49,399 total

includes taxes & fees

Sep 27 - Sep 28

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 windows, white furniture, and a view of tall buildings.

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

6. Trump International Hotel & Tower Chicago

River North, 1.3 km from Oak Street

Otilia

￥77,821

￥92,521 total

includes taxes & fees

Sep 20 - Sep 21

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

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

Catherine

￥102,801

￥122,219 total

includes taxes & fees

Oct 4 - Oct 5

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

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

A modern staircase with glass railings and pendant lighting.

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

￥65,774

￥82,758 total

includes taxes & fees

Sep 11 - Sep 12

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

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

9. Arlo Chicago

Theatre District, 1.7 km from Oak Street

Juana

￥36,927

￥48,729 total

includes taxes & fees

Sep 20 - Sep 21

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.

10. Hyatt Regency Chicago

The Loop, 1.5 km from Oak Street

Steve

￥45,655

￥59,764 total

includes taxes & fees

Sep 26 - Sep 27

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.

11. The Royal Sonesta Chicago Downtown

The Loop, 1.5 km from Oak Street

ShaRona

￥36,643

￥48,470 total

includes taxes & fees

Sep 27 - Sep 28

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

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

12. Hotel Riu Plaza Chicago

Streeterville, 0.8 km from Oak Street

Jarred

￥37,616

￥49,103 total

includes taxes & fees

Sep 20 - Sep 21

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

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

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.

13. Staypineapple, An Iconic Hotel, The Loop

Theatre District, 2 km from Oak Street

Jennifer

￥36,122

￥47,493 total

includes taxes & fees

Sep 27 - Sep 28

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 hotel room with a desk, a sofa, a coffee machine, a TV, and a unique wall art piece.

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

14. LondonHouse Chicago, Curio Collection by Hilton

The Loop, 1.4 km from Oak Street

Kamal

￥43,772

￥56,554 total

includes taxes & fees

Sep 20 - Sep 21

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 bakery display with various baked goods and a coffee machine.

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

15. Aloft by Marriott Chicago Downtown River North

River North, 1.1 km from Oak Street

Michelle

￥33,818

￥40,206 total

includes taxes & fees

Sep 20 - Sep 21

A modern hotel with a glass facade, outdoor seating, and a prominent 'ABT' sign.

A modern restaurant with a bar area, dining tables set with candles, and a kitchen in the background.

A modern lobby with geometric patterned flooring, glass tables with candles, and a visible bar area with shelves.

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

16. Hotel EMC2, Autograph Collection

Streeterville, 0.9 km from Oak Street

Abey

￥54,889

￥65,259 total

includes taxes & fees

Sep 27 - Sep 28

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

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

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

An outdoor patio area with multiple tables and chairs, umbrellas, and potted plants.

17. Loews Chicago Hotel

Streeterville, 1.3 km from Oak Street

Elisa

￥40,630

￥53,776 total

includes taxes & fees

Sep 20 - Sep 21

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.

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

18. Viceroy Chicago

0.3 km from Oak Street

CONRAD

￥68,718

￥86,777 total

includes taxes & fees

Oct 1 - Oct 2

A black luxury car parked in front of a hotel entrance with a glass canopy decorated with festive ornaments.

A bar area with a polished marble floor, bar stools, a counter with bottles, and a decorative lamp.

A couple dining on a balcony with a cityscape view.

A bar area with a long counter, multiple stools, and a seating area with a booth.

19. Waldorf Astoria Chicago

0.2 km from Oak Street

Jolanta Ewa

￥88,197

￥104,857 total

includes taxes & fees

Sep 20 - Sep 21

A hotel lobby with a bar area, a chandelier, and a reception desk.

A high-rise building with a clock tower, large windows, and a busy street with vehicles.

A lobby with a sofa, a coffee table, and an ottoman. There are wooden columns and a chandelier.

A hotel lobby with leather seating, a flat-screen TV, and large windows with a view of the cityscape.

20. Residence Inn Chicago Downtown/Loop

Theatre District, 2.2 km from Oak Street

Karla

￥44,003

￥52,316 total

includes taxes & fees

Sep 26 - Sep 27

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Compare popular hotels close to Oak Street

Property	Star rating	Guest rating
The Sono Chicago	10.0 Exceptional 550 reviews	View
The Peninsula Chicago	9.8 Exceptional 1,009 reviews	View
The Langham, Chicago	9.8 Exceptional 1,010 reviews	View
L7 Chicago by LOTTE	9.6 Exceptional 4,773 reviews	View
Residence Inn Chicago Downtown Magnificent Mile	9.6 Exceptional 627 reviews	View

Top Oak Street Hotel Reviews

River Hotel

10/10 Excellent

"Perfect location."

Congress Plaza Hotel

8/10 Good

"The staff was great. However, the carpet smelled and hallways reeked of smoke. The elevator took forever to open and close."

The Wade

10/10 Excellent

"My room was so clean, staff was friendly, and the hotel was in such a perfect spot for the lake, shopping, and Navy Pier. I truly can’t wait to go back! Will say parking looked pricey, but the area is very walkable and I felt very safe being out so late and walking from Soldier Stadium to The Wade, from the Riverwalk to The Wade, Navy Pier to The Wade."

Hampton Inn Chicago Downtown/Magnificent Mile

10/10 Excellent

"It was a good stay."

Hilton Chicago/Magnificent Mile Suites

10/10 Excellent

"The staff was amazing"

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

10/10 Excellent

"Great place to stay at."

Eurostars Magnificent Mile

10/10 Excellent

"Attentive and accommodating staff, cleanliness throughout facility, great location with close proximity to shopping at both high and low end stores on and around Michigan Ave. Bally's casino one block away if thats you're thing!"

Hotel Saint Clair- Magnificent Mile

10/10 Excellent

"only complaint is the elevator is slow, plan accordingly"

Four Seasons Hotel Chicago

10/10 Excellent

"Everyone was accommodating, responsive and friendly."

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 art 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 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 theater 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 scene 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 theater 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 exploring the galleries in Loyola University Museum of Art during your trip to Chicago. Experience the acclaimed art scene 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, check out the 696 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 696 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 ￥39,596

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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. Arlo Chicago

10. Hyatt Regency Chicago

11. The Royal Sonesta Chicago Downtown

12. Hotel Riu Plaza Chicago

13. Staypineapple, An Iconic Hotel, The Loop

14. LondonHouse Chicago, Curio Collection by Hilton

15. Aloft by Marriott Chicago Downtown River North

16. Hotel EMC2, Autograph Collection

17. Loews Chicago Hotel

18. Viceroy Chicago

19. Waldorf Astoria Chicago

20. Residence Inn Chicago Downtown/Loop

Compare popular hotels close to Oak Street

Top Oak Street Hotel Reviews

River Hotel

Congress Plaza Hotel

The Wade

Hampton Inn Chicago Downtown/Magnificent Mile

Hilton Chicago/Magnificent Mile Suites

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

Eurostars Magnificent Mile

Hotel Saint Clair- Magnificent Mile

Four Seasons Hotel Chicago

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