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

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

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

1. The Sono Chicago

Old Town Chicago, 1.5 km from Oak Street

Christie

P13,672

P16,049 total

includes taxes & fees

Sep 30 - Oct 1

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

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

P42,333

P50,329 total

includes taxes & fees

Oct 4 - Oct 5

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

3. Trump International Hotel & Tower Chicago

River North, 1.3 km from Oak Street

Jorge

P32,690

P38,865 total

includes taxes & fees

Oct 4 - Oct 5

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

4. Residence Inn Chicago Downtown Magnificent Mile

Streeterville, 0.8 km from Oak Street

Brian

P20,006

P23,785 total

includes taxes & fees

Sep 27 - Sep 28

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

A woman sitting by a window with a city view, holding a cup and saucer.

5. Park Hyatt Chicago

Streeterville, 0.4 km from Oak Street

Catherine

P42,333

P50,329 total

includes taxes & fees

Oct 18 - Oct 19

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 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.

6. Hotel Riu Plaza Chicago

Streeterville, 0.8 km from Oak Street

Sean Robert

P16,610

P21,535 total

includes taxes & fees

Oct 13 - Oct 14

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

A modern staircase with glass railings and pendant lighting.

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

Streeterville, 1 km from Oak Street

"“ The Gwen a Luxury Collection Hotel, Michigan Ave. Chicago” True, it is a hotel named The Gwen. True, it is a hotel. 2 day get away find the hotel address anywhere one the si Clean room with nice bathroom which appears newer than bedroom. Bring your own toiletries! Our bathroom had 1 hanging robe and one bar of face soap. Didn’t notice if there was a hair dryer. Food very good and big portions.Tasty cocktails served in glasses ½ sized from any we’ve seen. Restaurant service prompt service....

Laura

P36,312

P45,036 total

includes taxes & fees

Sep 25 - Sep 26

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, 1.5 km from Oak Street

Isayra

P12,938

P15,382 total

includes taxes & fees

Sep 27 - Sep 28

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

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

9. Viceroy Chicago

0.3 km from Oak Street

Margaret

P28,109

P35,495 total

includes taxes & fees

Oct 4 - Oct 5

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.

10. Moxy Chicago Downtown

River North, 1.1 km from Oak Street

Justin

P14,424

P17,149 total

includes taxes & fees

Sep 27 - Sep 28

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

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.

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.

11. Aloft by Marriott Chicago Downtown River North

River North, 1.1 km from Oak Street

Michelle

P14,424

P17,149 total

includes taxes & fees

Sep 27 - Sep 28

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

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

12. Arlo Chicago

Theatre District, 1.7 km from Oak Street

Miguel

P14,695

P19,440 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 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 desk, a sofa, a coffee machine, a TV, and a unique wall art piece.

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

13. LondonHouse Chicago, Curio Collection by Hilton

The Loop, 1.4 km from Oak Street

Sunny

P22,111

P28,153 total

includes taxes & fees

Oct 2 - Oct 3

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

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

A conference room with a long table, chairs, a projector screen, and a flat-screen TV displaying "LOEWS HOTELS".

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

14. Loews Chicago Hotel

Streeterville, 1.3 km from Oak Street

Ryan

P16,870

P22,296 total

includes taxes & fees

Oct 4 - Oct 5

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

A modern hotel with a blue facade, large windows, and a prominent entrance.

15. Hotel EMC2, Autograph Collection

Streeterville, 0.9 km from Oak Street

Abey

P21,888

P26,023 total

includes taxes & fees

Sep 27 - Sep 28

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

A couple dining on a balcony with a cityscape view.

An indoor swimming pool with a modern design, a reception area with a sign for Waldorf Astoria Chicago, and a seating area with two people.

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

16. Waldorf Astoria Chicago

0.2 km from Oak Street

Luis

P47,779

P56,804 total

includes taxes & fees

Oct 12 - Oct 13

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

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

17. The Royal Sonesta Chicago Downtown

The Loop, 1.5 km from Oak Street

ShaRona

P18,151

P23,590 total

includes taxes & fees

Sep 27 - Sep 28

A restaurant with tables and chairs arranged in a corridor, large windows, and hanging lamps.

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.

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

18. The St. Regis Chicago

1.6 km from Oak Street

Xiomara

P46,033

P54,728 total

includes taxes & fees

Oct 23 - Oct 24

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

19. Staypineapple, An Iconic Hotel, The Loop

Theatre District, 2 km from Oak Street

Andrea

P15,930

P20,799 total

includes taxes & fees

Sep 27 - Sep 28

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

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.

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

20. Springhill Suites by Marriott Chicago Downtown/ River North

River North, 1.3 km from Oak Street

Sugar

P13,829

P16,441 total

includes taxes & fees

Sep 27 - Sep 28

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Compare popular hotels close to Oak Street

Property	Property class	Guest rating
The Sono Chicago	10.0 Exceptional 555 reviews	View
The Peninsula Chicago	9.8 Exceptional 1,010 reviews	View
Trump International Hotel & Tower Chicago	9.6 Exceptional 2,025 reviews	View
Residence Inn Chicago Downtown Magnificent Mile	9.6 Exceptional 639 reviews	View
Park Hyatt Chicago	9.6 Exceptional 1,000 reviews	View

Top Oak Street Hotel Reviews

Hotel Saint Clair- Magnificent Mile

8/10 Good

"Nice stay"

The Whitehall Hotel, BW Premier Collection

10/10 Excellent

"Excellent stay"

The Chicago Hotel Collection Ambassador Gold Coast

10/10 Excellent

"Great Stay"

Hotel Riu Plaza Chicago

10/10 Excellent

"A wonderful hotel. The hotel is in a great location and very convenient. The breakfast is plentiful and delicious"

L7 Chicago by LOTTE

10/10 Excellent

"Everything was excellent"

Congress Plaza Hotel

10/10 Excellent

"I’ve stayed here for years. Every riot"

Hyatt Regency Chicago

10/10 Excellent

"Great place"

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 686 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, Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical is one of the top choices for your stay based on our traveler 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 should I expect to find close to Oak Street?

Expedia has 686 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.

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 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.

Hotels near Oak Street

Change your mind

Treat yourself

Be picky

Check prices for these dates

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Guest rating

Our top choices for Oak Street hotels

1. The Sono Chicago

2. The Peninsula Chicago

3. Trump International Hotel & Tower Chicago

4. Residence Inn Chicago Downtown Magnificent Mile

5. Park Hyatt Chicago

6. Hotel Riu Plaza Chicago

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

8. citizenM Chicago Downtown

9. Viceroy Chicago

10. Moxy Chicago Downtown

11. Aloft by Marriott Chicago Downtown River North

12. Arlo Chicago

13. LondonHouse Chicago, Curio Collection by Hilton

14. Loews Chicago Hotel

15. Hotel EMC2, Autograph Collection

16. Waldorf Astoria Chicago

17. The Royal Sonesta Chicago Downtown

18. The St. Regis Chicago

19. Staypineapple, An Iconic Hotel, The Loop

20. Springhill Suites by Marriott Chicago Downtown/ River North

Compare popular hotels close to Oak Street

Top Oak Street Hotel Reviews

Hotel Saint Clair- Magnificent Mile

The Whitehall Hotel, BW Premier Collection

The Chicago Hotel Collection Ambassador Gold Coast

Hotel Riu Plaza Chicago

L7 Chicago by LOTTE

Congress Plaza Hotel

Hyatt Regency 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