A cityscape with modern skyscrapers, a river, and a bridge.

Hotels in Oakland

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Where to stay in Oakland?

A large, historic building with a central courtyard surrounded by trees.

A restaurant interior with wooden tables and chairs, a carpeted floor, and framed pictures on the walls.

A marina with numerous boats docked, surrounded by a cityscape with high-rise buildings and a stadium.

A hotel room with two beds, a desk with a television, a chair, a desk lamp, and a painting on the wall.

1. Hilton Chicago

The Loop, 5.7 km from Oakland

JoAnne

$161

$220 total

includes taxes & fees

Oct 24 - Oct 25

A modern interior with a bar area, seating, and decorative wooden panels.

A reception area with a marble counter, decorative Buddha statues, and a wall with a quote.

A hotel room with a flat-screen TV, a wooden cabinet, a round table, a blue sofa, a desk with a computer, and a large window with curtains.

A hotel room with a large bed, a flat-screen TV, a desk with a lamp, and a chair.

2. Best Western Grant Park Hotel

The Loop, 5.4 km from Oakland

Jamison

$170

$202 total

includes taxes & fees

Oct 25 - Oct 26

A building with a sign reading "111" and "III West Adams Street" indicating a pub and restaurant.

A hotel room with a large window, a bed, and a suitcase.

A bar with a brick archway, wooden bar counter, and stools.

A modern living room with a fireplace, leather sofas, and a wooden floor.

3. Club Quarters Hotel, Central Loop, Chicago

Theatre District, 6.6 km from Oakland

Brandi

$139

$166 total

includes taxes & fees

Sep 27 - Sep 28

An indoor swimming pool with clear glass walls, a wooden ceiling, and a view of a red brick building.

A modern hotel lobby with a reception desk, seating area, and a large window providing a view of the outdoors.

A modern outdoor patio with tables and chairs, a glass railing, and a view of a high-rise building.

A modern hotel entrance with glass doors, a visible reception desk, and signage for Hilton Garden Inn and Homewood Suites.

4. Hilton Garden Inn Chicago Downtown South Loop

The Loop, 5.4 km from Oakland

Laurel

$187

$222 total

includes taxes & fees

Oct 25 - Oct 26

A modern hotel room with a sofa, armchairs, a coffee table, a flat-screen TV, and a patterned wall.

A bar area with a long counter, multiple liquor bottles, and a variety of glasses.

A hotel room with two beds, a nightstand, a telephone, and a wall with printed text.

A reception area with a desk, a seating area with a blue sofa, and a bookshelf filled with books.

5. Hilton Vacation Club Hotel Blake Chicago

The Loop, 6.1 km from Oakland

Akiko

$316

$376 total

includes taxes & fees

Oct 14 - Oct 15

A spacious lobby with a central sofa, multiple seating areas, and a decorative ceiling.

A spacious bar area with a central bar, multiple seating options including bar stools and tables, and a well-lit ceiling with recessed lighting.

A cityscape with various buildings, including a prominent skyscraper and a classical building with arched windows.

Outdoor seating with yellow umbrellas labeled "Twisted Tea," wicker chairs, and tables.

6. Congress Plaza Hotel

The Loop, 6 km from Oakland

Angela

$161

$191 total

includes taxes & fees

Oct 26 - Oct 27

A modern hotel lobby with large windows, leather sofas, and a view of the cityscape.

A hotel room with a bed, a desk with a chair, a sofa, and a view of a building through the window.

A compact kitchen with a microwave, coffee maker, and sink.

A restaurant with booths, tables, and a green wall in the background.

7. Travelodge by Wyndham Downtown Chicago

The Loop, 5.9 km from Oakland

Mara

$159

$187 total

includes taxes & fees

Oct 25 - Oct 26

A person pouring champagne into a glass near a window overlooking a cityscape with a Ferris wheel.

A rooftop terrace with a view of a beach and a Ferris wheel, featuring lounge chairs and a colorful mural.

A modern bar area with high stools, a bar counter, and shelves of liquor bottles.

A modern hotel room with a large window offering a view of the sea and a cityscape. There is a seating area with a sofa and a small table.

8. The Wade

Streeterville, 7.9 km from Oakland

Zion

$149

$177 total

includes taxes & fees

Sep 27 - Sep 28

A multi-story hotel with a prominent sign reading "Crowne Plaza."

A hotel room with a large bed, a desk with a computer, a TV, and a seating area with a chair and ottoman.

A modern restaurant with round tables and booths, a high ceiling with exposed beams, and a brick accent wall with the text "RVE DELTA".

A spacious lobby with high wooden pillars, a seating area with sofas and a bench, a fire feature, and a modern design.

9. Crowne Plaza Chicago West Loop by IHG

7.3 km from Oakland

Sherie

$169

$201 total

includes taxes & fees

Sep 27 - Sep 28

An outdoor seating area with wicker chairs, a glass-top table, and a sofa with cushions.

A grilled pineapple on top of a stack of meat, served on a pan.

A conference room with a long table, chairs, and a projector screen.

The exterior of the Hyatt Centric The Loop hotel with a prominent American flag, a classic facade, and a glass entrance.

10. Hyatt Centric The Loop Chicago

Theatre District, 6.8 km from Oakland

Alesandra

$192

$253 total

includes taxes & fees

Sep 27 - Sep 28

A hotel room with a large bed, two armchairs, a desk, and a view of a cityscape through large windows.

A spacious lobby with a glass entrance, escalators, and a tiled floor.

A hotel room with a large window, a dining area with a table and chairs, a sofa, a TV, and a decorative light fixture.

A hotel room with a city view, a dining area, a sofa, and a TV.

11. The Buckingham Hotel

The Loop, 6.3 km from Oakland

"Our stay at the Buckingham was overall very nice. We enjoyed the views of the city so much, that alone was worth the price. The rooms were very spacious. Notes for improvement: The breakfast was okay (mainly pre packaged pastries) and a k cup coffee maker. Freshly brewed coffee would be nice. The beds were also a little too firm for our liking. Overall very nice though and a 8/10! We would return."

Christina

$175

$220 total

includes taxes & fees

Sep 27 - Sep 28

A modern kitchen with a large window, a dining area, and a view of the sea.

A modern living room with a sectional sofa, a fireplace, and a large window offering a city view.

A modern restaurant interior with a long counter, booths, and tables.

12. Homewood Suites by Hilton Chicago Downtown South Loop

The Loop, 5.4 km from Oakland

Marlene

$209

$249 total

includes taxes & fees

Oct 25 - Oct 26

A hotel room with a large bed, a TV, a desk, and a chair.

A person sitting on a couch with a laptop, reading a book, in a room with a large window and a framed picture on the wall.

13. Central Loop Hotel

Theatre District, 6.6 km from Oakland

Heather

$139

$166 total

includes taxes & fees

Sep 27 - Sep 28

A cozy room with a sofa, a dining table, and a window with a view of buildings.

A hotel room with a large bed, a small dining table with chairs, a brick wall, and a window with blinds.

A lobby with two brown leather chairs, a marble table, and a large potted plant.

A cozy seating area with a round table and two chairs, a brick wall, and a window with a view of buildings.

14. LIVN - West Loop Chicago

6.8 km from Oakland

Cheri

$184

$216 total

includes taxes & fees

Sep 27 - Sep 28

A modern living room with a sofa, armchairs, a coffee table, and a bookshelf.

A bar area with a large mural, bar stools, and a variety of bottles and glasses on the counter.

A modern hotel room with a large bed, a desk, a chair, a lamp, and a view of the city through large windows.

A restaurant with outdoor seating, covered by umbrellas, and decorated with hanging planters.

15. Le Méridien Essex Chicago

The Loop, 5.6 km from Oakland

Michael

$229

$290 total

includes taxes & fees

Sep 27 - Sep 28

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

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

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

A spacious outdoor dining area with large windows overlooking the sea, featuring multiple tables and stools.

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

Streeterville, 7.5 km from Oakland

Kendra

$318

$412 total

includes taxes & fees

Oct 23 - Oct 24

A spacious lobby with a checkered floor, a large sofa, and multiple chairs.

A hotel room with two beds, a desk with a computer, a chair, a TV, and a large mirror.

A modern kitchen with a built-in refrigerator, a coffee maker, and a flat-screen TV on the countertop.

A modern kitchen area with a long counter, various food items, and a coffee machine.

17. Fairfield Inn & Suites Chicago Downtown / Magnificent Mile

Streeterville, 7.9 km from Oakland

Dustin

$179

$213 total

includes taxes & fees

Sep 27 - Sep 28

A grand lobby with a central bar, high ceilings, and classical architecture.

A spacious lobby with a grand chandelier, a fireplace, and elegant seating arrangements.

A modern living room with a sofa set, ottoman, and armchairs.

A modern living room with a round dining table, bar stools, a purple armchair, and a sofa with cushions.

18. THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

Theatre District, 6.7 km from Oakland

Christina De

$199

$237 total

includes taxes & fees

Sep 27 - Sep 28

A street view with a row of parked cars, a building with a sign reading "SONDE," and another sign that says "Diamonds On Parade."

A modern kitchen with a dining area featuring two teal chairs, a round table, and a framed artwork on the wall.

A modern kitchen with white cabinets, a stainless steel refrigerator, and a coffee maker. There is a blue sofa and a round coffee table with a striped pattern. A dining area with a table and chairs is visible in the background.

A neatly arranged hotel room with a large bed, a nightstand, a lamp, and a window with a view of buildings.

19. LIVN - Millennium Park Downtown Chicago

Theatre District, 6.7 km from Oakland

Puneet

$251

$295 total

includes taxes & fees

Oct 1 - Oct 2

A modern hotel with a glass facade, multiple floors, and a visible entrance.

A gym with cardio machines, weight benches, and a large window offering a city view.

A hotel room with a large bed, a desk with a chair, a sofa, and a TV.

A reception area with a modern design, including a reception desk, a decorative wall, and a display case with snacks.

20. Hyatt Place Chicago/Downtown - The Loop

The Loop, 7.1 km from Oakland

Sue

$212

$252 total

includes taxes & fees

Oct 25 - Oct 26

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Our prices for hotels in Chicago are cheapest in January

Top landmarks in Oakland

41st Street Beach

When the beach is calling your name, you might want to head down to 41st Street Beach, located 4.3 mi (7 km) from central Chicago. Enjoy the sunset by the shore at Rainbow Beach, 57th Street Beach, and 63rd Street Beach.

See properties

Check out reviews of Oakland hotels guests love

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 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.

Staypineapple, An Iconic Hotel, The Loop

Downtown Chicago

10/10 Exceptional

Natalya

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 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.

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 hotel lobby with a reception desk, marble flooring, and elegant chandeliers.

A modern living room with a dark sofa set, a glass coffee table, and a decorative chandelier.

A modern bar area with a bar counter, multiple stools, and a chandelier.

A cityscape with modern skyscrapers, a waterfront, and a winter setting.

Silversmith Hotel Chicago Downtown

Downtown Chicago

10/10 Exceptional

Dorothy

Le Méridien Essex Chicago

Downtown Chicago

10/10 Exceptional

Extremely easy check in, attentive and friendly staff, the attached restaurant and staff where great, we where given a credit to use at the restaurant upon check in at the hotel. The rooms are a bit small, but will do if your single or a couple, we feel the like shower design could be better as it causes water to get on the floor, the downside is parking, but it’s the cost of being in a prime location, I would stay again

Arlo Chicago is in the perfect location for walkable access to so many Chicago sights, excellent food (please try the Broken English Taco Pub around the corner!), bars, shopping, etc. It was also very conveniently located to access the L when we needed to get to other parts of the city! The staff was BEYOND accommodating, friendly, and helpful. The room was clean and exceeded all comfort expectations! I also highly recommend the lobby bar for a great happy hour spot!!! Everyone at this hotel...

Lina

A dining table set for six with a cityscape view through large windows.

A modern hotel room with a large window offering a city skyline view, a round table with four chairs, and a ceiling with recessed lighting.

A modern hotel room with a large window offering a cityscape view, a green sofa, two armchairs, and a coffee table with flowers.

The exterior of the Swissotel building with its distinctive glass facade and the hotel's name displayed prominently.

Swissotel - Chicago

Downtown Chicago

10/10 Exceptional

Brian

A modern living room with a fireplace, leather armchairs, a sofa, and a coffee table.

A spacious lobby with a grand staircase, a large abstract painting, and a seating area with modern furniture.

A hotel with a classic facade, multiple flags, and a prominent entrance.

The Allegro Royal Sonesta Hotel Chicago Loop

Downtown Chicago

10/10 Exceptional

Philippe

Hotels in Oakland

Free cancellation options if plans change

Earn rewards on every night you stay

Save more with Member Prices

Check prices for these dates

Where to stay in Oakland?

1. Hilton Chicago

2. Best Western Grant Park Hotel

3. Club Quarters Hotel, Central Loop, Chicago

4. Hilton Garden Inn Chicago Downtown South Loop

5. Hilton Vacation Club Hotel Blake Chicago

6. Congress Plaza Hotel

7. Travelodge by Wyndham Downtown Chicago

8. The Wade

9. Crowne Plaza Chicago West Loop by IHG

10. Hyatt Centric The Loop Chicago

11. The Buckingham Hotel

12. Homewood Suites by Hilton Chicago Downtown South Loop

13. Central Loop Hotel

14. LIVN - West Loop Chicago

15. Le Méridien Essex Chicago

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

17. Fairfield Inn & Suites Chicago Downtown / Magnificent Mile

18. THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

19. LIVN - Millennium Park Downtown Chicago

20. Hyatt Place Chicago/Downtown - The Loop

Price trends for hotels in Chicago

September

Top landmarks in Oakland

41st Street Beach

Check out reviews of Oakland hotels guests love

Hilton Chicago

10/10 Exceptional

Hilton Vacation Club Hotel Blake Chicago

10/10 Exceptional

Sable at Navy Pier Chicago, Curio Collection by Hilton

10/10 Exceptional

Club Quarters Hotel, Central Loop, Chicago

10/10 Exceptional

Crowne Plaza Chicago West Loop by IHG

10/10 Exceptional

Hyatt Centric The Loop Chicago

10/10 Exceptional

Hilton Garden Inn Chicago Downtown South Loop

10/10 Exceptional

Staypineapple, An Iconic Hotel, The Loop

10/10 Exceptional

L7 Chicago by LOTTE

10/10 Exceptional

Best Western Grant Park Hotel

10/10 Exceptional

The Buckingham Hotel

10/10 Exceptional

Central Loop Hotel

10/10 Exceptional

Silversmith Hotel Chicago Downtown

10/10 Exceptional

Le Méridien Essex Chicago

10/10 Exceptional

citizenM Chicago Downtown

10/10 Exceptional

LondonHouse Chicago, Curio Collection by Hilton

10/10 Exceptional

Arlo Chicago

10/10 Exceptional

Swissotel - Chicago

10/10 Exceptional

The Allegro Royal Sonesta Hotel Chicago Loop

10/10 Exceptional