Hotels in Oakland

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Where to stay in Oakland?

A hotel entrance with a marquee and string lights above the entrance.

A hotel entrance with a classic facade, an American flag, and a sign for Hotel Blake Chicago.

A hotel entrance with a marquee, American flag, and a person standing in front.

1. Hilton Vacation Club Hotel Blake Chicago

The Loop, 6.1 km from Oakland

Akiko

$181

$216 total

includes taxes & fees

Sep 7 - Sep 8

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 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.

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

Streeterville, 7.5 km from Oakland

Monica

$177

$245 total

includes taxes & fees

Sep 8 - Sep 9

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

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

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 grand ballroom with ornate ceiling decorations, multiple chandeliers, and a central table with a white tablecloth.

3. Congress Plaza Hotel

The Loop, 6 km from Oakland

VICENTE

$115

$136 total

includes taxes & fees

Sep 7 - Sep 8

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

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.

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

4. Best Western Grant Park Hotel

The Loop, 5.4 km from Oakland

Migdalia

$152

$181 total

includes taxes & fees

Sep 8 - Sep 9

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

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

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

A hot tub with a metal ladder, surrounded by white tiled walls and floor, with a large window providing a view of the cityscape.

5. Hilton Garden Inn Chicago Downtown South Loop

The Loop, 5.4 km from Oakland

Laurel

$165

$197 total

includes taxes & fees

Sep 7 - Sep 8

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 living room with a sofa, chairs, a coffee table, and a bookshelf.

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

6. Le Méridien Essex Chicago

The Loop, 5.6 km from Oakland

Michael

$159

$207 total

includes taxes & fees

Sep 7 - Sep 8

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

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

A restaurant interior with brick walls, wooden tables and chairs, and a bar area.

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

7. Club Quarters Hotel, Central Loop, Chicago

Theatre District, 6.6 km from Oakland

Kevin

$133

$158 total

includes taxes & fees

Sep 7 - Sep 8

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

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

A modern room with a checkered floor, two round tables, two armchairs, and a large window with a view of the outside.

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

8. Fairfield Inn & Suites Chicago Downtown / Magnificent Mile

Streeterville, 7.9 km from Oakland

Andrew

$129

$153 total

includes taxes & fees

Sep 7 - Sep 8

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

A modern hotel lobby with a curved white sofa, two side tables with lamps, a black coffee table, and a large chandelier.

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.

9. Hilton Chicago

The Loop, 5.7 km from Oakland

Nikkole

$199

$266 total

includes taxes & fees

Sep 7 - Sep 8

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

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

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

10. Homewood Suites by Hilton Chicago Downtown South Loop

The Loop, 5.4 km from Oakland

Marlene

$173

$206 total

includes taxes & fees

Sep 7 - Sep 8

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

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

11. LIVN - West Loop Chicago

6.8 km from Oakland

Cheri

$137

$161 total

includes taxes & fees

Sep 7 - Sep 8

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

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

A lobby with a checkered floor, an ATM, a potted plant, a reception desk, computers, and a staircase.

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

12. Travelodge by Wyndham Downtown Chicago

The Loop, 5.9 km from Oakland

Natalie

$134

$159 total

includes taxes & fees

Sep 8 - Sep 9

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

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.

13. LIVN - Millennium Park Downtown Chicago

Theatre District, 6.7 km from Oakland

Puneet

$147

$173 total

includes taxes & fees

Sep 7 - Sep 8

A hotel room with a large window offering a city view, a bed, a desk, and a chair.

A coffee shop interior with a display case of pastries, a coffee machine, and a menu board.

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

14. Courtyard by Marriott Chicago Magnificent Mile

Streeterville, 7.9 km from Oakland

Cindy

$144

$171 total

includes taxes & fees

Sep 7 - Sep 8

A modern kitchen with a marble island, fruit bowls, and a city view.

A modern lounge area with a central bar, seating arrangements, and a decorative chandelier.

A modern hotel room with a city view, a seating area with two sofas and a coffee table, and a dining area with a table and chairs.

A modern bar area with a central bar, seating, and a distinctive ceiling design.

15. Fairmont Chicago at Millennium Park

The Loop, 7.1 km from Oakland

Deborah

$199

$272 total

includes taxes & fees

Sep 8 - Sep 9

A spacious lobby with a central coffee table, sofas, and a large mirror.

A balcony with a table set for a meal, featuring a charcuterie board and two glasses of wine, overlooking a cityscape.

A spacious lobby with high ceilings, large arched windows, and a grand staircase.

A spacious lounge area with leather sofas, round tables, and comfortable chairs, featuring a wooden ceiling and elegant decor.

16. The Chicago Hotel Collection Ambassador Gold Coast

Gold Coast, 9.4 km from Oakland

Zhiwen

$143

$170 total

includes taxes & fees

Sep 7 - Sep 8

A modern lobby with leather sofas, a wooden coffee table, a TV mounted on the wall, and a bookshelf.

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

17. Central Loop Hotel

Theatre District, 6.6 km from Oakland

Pauline

$122

$145 total

includes taxes & fees

Sep 7 - Sep 8

A modern lobby with a grey sofa, checkered ottomans, and a coffee table. There are black chairs, a blue sofa, and a TV on a stand.

A modern hotel room with a bed, a sofa, a coffee table with flowers, a TV, and a large window with a city view.

A modern high-rise hotel with multiple floors, large windows, and a well-lit entrance area.

A modern indoor swimming pool with blue seating and a view of the city through large windows.

18. Aloft by Marriott Chicago Mag Mile

Streeterville, 7.9 km from Oakland

Mark

$154

$183 total

includes taxes & fees

Sep 7 - Sep 8

A swimming pool with lounge chairs and umbrellas, surrounded by tall buildings.

A hotel reception area with a modern design, featuring a wooden panel wall and a marble reception desk.

A cozy room with a patterned carpet, a wooden table, and a green sofa with a white throw blanket.

A modern lobby with a seating area, a bar, and a green wall.

19. DoubleTree by Hilton Chicago - Magnificent Mile

Streeterville, 7.8 km from Oakland

Felisha

$168

$200 total

includes taxes & fees

Sep 7 - Sep 8

A marble-floored lobby with double doors and elevators, each marked with a 'CQ' sign.

A man in a suit sitting by a window with a vase of red flowers.

A conference room with a long table, chairs, and a vase.

A hotel room with a grey sofa, a bed with a white mattress, a wooden dresser, and a large window with curtains.

20. River Hotel

The Loop, 7.4 km from Oakland

Deborah

$158

$188 total

includes taxes & fees

Sep 7 - Sep 8

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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, 49th Street Beach, and 63rd Street Beach.

See properties

Check out reviews of Oakland hotels guests love

Club Quarters Hotel, Central Loop, Chicago

10/10 Excellent

"Check in was super quick and easy!! The room has everything you need and would definitely stay here again!!"

The Chicago Hotel Collection - Magnificent Mile

10/10 Excellent

"Buen precio, el personal súper amable, el hotel es céntrico. Puedes hablar en inglés o español con la mayoría del personal del hotel."

Congress Plaza Hotel

10/10 Excellent

"Good place to stay location is amazing can’t get any better"

Hyatt Regency Chicago

10/10 Excellent

"A five-star hotel with a great staff. Everyone was very friendly. The view was great and all of the amenities were nice."

River Hotel

8/10 Good

"Clean rooms, great location, only thing writes the room didn’t have a microwave or refrigerator."

Hampton Inn Chicago Downtown/Magnificent Mile

8/10 Good

"Me and wife stay 3 nights is Hampton Inn from Aug 31 to Sept3 2026.It is 40 stories hotel. The hotel location is excellent, beautiful in Chicago, very close to Michgan Ave Magnificent Mile, the most beautiful area, high rise buildings and shopping stores. Close to Lake, close to chicago River side, close to Millennium park. Breakfast was ok, not high level, just so, so, Baggage in and out room service was not available when we reached we took our own bags to room. No swimming pool was available. Close to hospital block, .For food Asian food Indian restaurant available on walking distance. I recommend this hotel to tourists coming for Chicago buildings, and other attractions. Mahboob Mian Canada."

The Allegro Royal Sonesta Hotel Chicago Loop

10/10 Excellent

"very nice location"

InterContinental Chicago Magnificent Mile by IHG

10/10 Excellent

"Excellent location. Lots of energy and room was great. Highly recommend."

The Chicago Hotel Collection Ambassador Gold Coast

8/10 Good

"Good, 10/10 the rooftop is also beautiful"

Find out more about Oakland

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Book Hotels in Oakland on Hotels.com

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 Vacation Club Hotel Blake Chicago

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

3. Congress Plaza Hotel

4. Best Western Grant Park Hotel

5. Hilton Garden Inn Chicago Downtown South Loop

6. Le Méridien Essex Chicago

7. Club Quarters Hotel, Central Loop, Chicago

8. Fairfield Inn & Suites Chicago Downtown / Magnificent Mile

9. Hilton Chicago

10. Homewood Suites by Hilton Chicago Downtown South Loop

11. LIVN - West Loop Chicago

12. Travelodge by Wyndham Downtown Chicago

13. LIVN - Millennium Park Downtown Chicago

14. Courtyard by Marriott Chicago Magnificent Mile

15. Fairmont Chicago at Millennium Park

16. The Chicago Hotel Collection Ambassador Gold Coast

17. Central Loop Hotel

18. Aloft by Marriott Chicago Mag Mile

19. DoubleTree by Hilton Chicago - Magnificent Mile

20. River Hotel

Price trends for hotels in Chicago

Typical weather for Chicago

Top landmarks in Oakland

41st Street Beach

Check out reviews of Oakland hotels guests love

Club Quarters Hotel, Central Loop, Chicago

The Chicago Hotel Collection - Magnificent Mile

Congress Plaza Hotel

Hyatt Regency Chicago

River Hotel

Hampton Inn Chicago Downtown/Magnificent Mile

The Allegro Royal Sonesta Hotel Chicago Loop

InterContinental Chicago Magnificent Mile by IHG

The Chicago Hotel Collection Ambassador Gold Coast

Keep exploring