Hotels in Oakland

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Tonight
Sep 13 - Sep 14
Tomorrow
Sep 14 - Sep 15
Next weekend
Sep 18 - Sep 20
In two weeks
Sep 25 - Sep 27

Where to stay in Oakland?

A modern interior with a bar area, seating, and decorative wooden panels.
A hotel room with a large bed, a flat-screen TV, a desk with a lamp, and a chair.
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 modern hotel with a prominent "Grant Park Hotel" sign and "Best Western" branding.

1. Best Western Grant Park Hotel

Best Western Grant Park Hotel
The Loop, 5.4 km from Oakland
United States
Migdalia
$179
$213 total
includes taxes & fees
Sep 29 - Sep 30
Best Western Grant Park Hotel
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 modern hotel lobby with a curved white sofa, two side tables with lamps, a black coffee table, and a large chandelier.

2. Hilton Chicago

Hilton Chicago
The Loop, 5.7 km from Oakland
United States
Nikkole
$223
$295 total
includes taxes & fees
Sep 25 - Sep 26
Hilton Chicago
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 grand ballroom with ornate ceiling decorations, multiple chandeliers, and a central table with a white tablecloth.
Outdoor seating with yellow umbrellas labeled "Twisted Tea," wicker chairs, and tables.

3. Congress Plaza Hotel

Congress Plaza Hotel
The Loop, 6 km from Oakland
United States
Donna
$174
$207 total
includes taxes & fees
Sep 27 - Sep 28
Congress Plaza Hotel
An outdoor seating area with tables and chairs, a planter with greenery, and a large brick structure in the background.
A modern living room with a large window overlooking a body of water, a tripod, and a sofa.
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.

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

Sable at Navy Pier Chicago, Curio Collection by Hilton
Streeterville, 7.5 km from Oakland
United States
Monica
$285
$373 total
includes taxes & fees
Sep 27 - Sep 28
Sable at Navy Pier Chicago, Curio Collection by Hilton
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 lobby with a checkered floor, an ATM, a potted plant, a reception desk, computers, and a staircase.
A compact kitchen with a microwave, coffee maker, and sink.

5. Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago
The Loop, 5.9 km from Oakland
United States
Dagmar
$153
$180 total
includes taxes & fees
Sep 27 - Sep 28
Travelodge by Wyndham Downtown Chicago
A hotel room with a large window, a bed, a desk, a chair, and a lamp.
A tall, modern hotel with a brick facade and numerous windows.

6. Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
Streeterville, 8.6 km from Oakland
United States
Chantell
$129
$153 total
includes taxes & fees
Oct 14 - Oct 15
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
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 lobby with a grand fireplace, elegant columns, and a seating area with chairs and a table.

7. The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast
Gold Coast, 9.4 km from Oakland
United States
Raul
$179
$213 total
includes taxes & fees
Oct 13 - Oct 14
The Chicago Hotel Collection Ambassador Gold Coast
An indoor swimming pool with clear glass walls, a wooden ceiling, and a view of a red brick building.
A hot tub with a metal ladder, surrounded by white tiled walls and floor, with a large window providing a view of the cityscape.
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.

8. Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop
The Loop, 5.4 km from Oakland
United States
Laurel
$232
$276 total
includes taxes & fees
Sep 27 - Sep 28
Hilton Garden Inn Chicago Downtown South Loop
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 spacious lobby with a seating area, a reception desk, and a large screen.
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

Crowne Plaza Chicago West Loop by IHG
7.3 km from Oakland
United States
Sherie
$164
$195 total
includes taxes & fees
Sep 20 - Sep 21
Crowne Plaza Chicago West Loop by IHG
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.

10. Le Méridien Essex Chicago

Le Méridien Essex Chicago
The Loop, 5.6 km from Oakland
United States
Michael
$219
$278 total
includes taxes & fees
Sep 20 - Sep 21
Le Méridien Essex Chicago
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 modern living room with a fireplace, leather sofas, and a wooden floor.
A restaurant interior with brick walls, wooden tables and chairs, and a bar area.

11. Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago
Theatre District, 6.6 km from Oakland
United States
Carrie
$186
$221 total
includes taxes & fees
Sep 27 - Sep 28
Club Quarters Hotel, Central Loop, Chicago
A marble-floored lobby with double doors and elevators, each marked with a 'CQ' sign.
A hotel entrance with a sign for the Club Quarters Hotel, number 75, and a River Hotel sign.
A man in a suit sitting by a window with a vase of red flowers.
A hotel room with a grey sofa, a bed with a white mattress, a wooden dresser, and a large window with curtains.

12. River Hotel

River Hotel
The Loop, 7.4 km from Oakland
United States
Anthony
$152
$181 total
includes taxes & fees
Sep 27 - Sep 28
River Hotel
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.
Transparent igloo-like structures with seating inside, set on a wooden deck with snow on the ground, surrounded by tall buildings.

13. DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile
Streeterville, 7.8 km from Oakland
United States
Felisha
$183
$217 total
includes taxes & fees
Sep 27 - Sep 28
DoubleTree by Hilton Chicago - Magnificent Mile
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 grand hallway with ornate ceiling, chandeliers, and a reception desk at the end.
A modern living room with a round dining table, bar stools, a purple armchair, and a sofa with cushions.

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

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
Theatre District, 6.7 km from Oakland
United States
Tricia
$159
$189 total
includes taxes & fees
Sep 27 - Sep 28
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
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 cityscape with modern skyscrapers, a waterfront, and a winter setting.
A man and a woman walking down a marble staircase in a hotel lobby with a chandelier and a sign indicating an exit.

15. Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown
Theatre District, 6.7 km from Oakland
United States
Dudley
$194
$261 total
includes taxes & fees
Sep 21 - Sep 22
Silversmith Hotel Chicago Downtown
A modern building with a colorful facade and a red circular seating area.
A modern high-rise building with a glass facade, surrounded by other tall buildings.
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.

16. citizenM Chicago Downtown

citizenM Chicago Downtown
Theatre District, 7.3 km from Oakland
United States
IVANNA
$193
$229 total
includes taxes & fees
Sep 20 - Sep 21
citizenM Chicago Downtown
A cozy room with a sofa, a dining table, and a window with a view of buildings.
A cozy seating area with a round table and two chairs, a brick wall, and a window with a view of buildings.
A modern hotel lobby with a dark wood console, a large mirror, and a view of the city through large windows.
A hotel room with a large bed, a small dining table with chairs, a brick wall, and a window with blinds.

17. LIVN - West Loop Chicago

LIVN - West Loop Chicago
6.8 km from Oakland
United States
Cheri
$166
$195 total
includes taxes & fees
Sep 20 - Sep 21
LIVN - West Loop Chicago
An outdoor rooftop lounge with seating, a fire feature, and a view of the city skyline at night.
A rooftop venue with white chairs and a sofa, draped with white fabric and floral arrangements, overlooking a cityscape.
The Chicago Hotel Collection building with a glass facade, American flag, and signage for Barista Bar and Seighity events.
A modern lounge area with leather sofas, wooden coffee tables, and ambient lighting.

18. The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile
Streeterville, 8.2 km from Oakland
United States
Courtney
$144
$172 total
includes taxes & fees
Sep 20 - Sep 21
The Chicago Hotel Collection - Magnificent Mile
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 indoor swimming pool with blue seating and a view of the city through large windows.
A gym with treadmills, ellipticals, and weight machines.
A modern high-rise hotel with multiple floors, large windows, and a well-lit entrance area.

19. Aloft by Marriott Chicago Mag Mile

Aloft by Marriott Chicago Mag Mile
Streeterville, 7.9 km from Oakland
United States
Mark
$190
$226 total
includes taxes & fees
Sep 20 - Sep 21
Aloft by Marriott Chicago Mag Mile
A Holiday Inn & Suites building with multiple parking spaces and a modern architectural design.
A modern lobby with a central seating area, a reception desk, and elevators.
A spacious lobby with two elevators, a reception area, and a seating area with blue and white ottomans.
A breakfast buffet with a variety of fruits, pastries, and beverages on a wooden table, set against a modern room with a white sofa and a wooden accent wall.

20. Holiday Inn & Suites Chicago - Downtown by IHG

Holiday Inn & Suites Chicago - Downtown by IHG
West Loop, 6.4 km from Oakland
United States
Kenesha
$186
$233 total
includes taxes & fees
Sep 20 - Sep 21
Holiday Inn & Suites Chicago - Downtown by IHG
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Our prices for hotels in Chicago are cheapest in January
Price trends for hotels in Chicago
Pricing is based on two traveler single night rates
View properties in September
Typical weather for Chicago
September
High 23°C / low 17°C. Sunny most days.
View properties in September
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Monthly weather averages (˚C)

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, 63rd Street Beach, and 12th Street Beach.
See properties

Check out reviews of Oakland hotels guests love

River Hotel

River Hotel

10/10 Excellent
"Great staff easy to work with.and have good per and recomsations they were very pesonable"
David 1-night trip
Posted less than an hour ago
River Hotel
Hilton Chicago

Hilton Chicago

10/10 Excellent
"The staff was extremely helpful and courteous."
Nicole 2-night trip
Posted 1 hour ago
Hilton Chicago
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

10/10 Excellent
"Nice location, clean spacious room, comfortable bed all of the things you would expect were there My only issue was a lack of electrical outlets next to the bed. In today world there should be an available outlet or two next to the bed"
Greg 1-night trip
Posted 3 hours ago
The Chicago Hotel Collection Ambassador Gold Coast
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

10/10 Excellent
"Clean comfortable room. Great place to stay if you have an early flight. It’s a short walk to terminal and you don’t even have to go outside."
Cynthia 1-night trip
Posted 4 hours ago
Hilton Chicago O'Hare Airport
The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown

10/10 Excellent
"Clean rooms and welcoming staff! Family oriented, great with children! Close to events, activities and restaurants! Enjoyed our stay !"
Nancy 2-night trip
Posted 10 hours ago
The Royal Sonesta Chicago Downtown
Hampton Inn Chicago Downtown/Magnificent Mile

Hampton Inn Chicago Downtown/Magnificent Mile

10/10 Excellent
"Wonderful location! Nice continental breakfast! The fitness center was nice. The outdoor rooftop pool was not filled during our time there. The elevators were quick."
Adina 1-night trip
Posted 13 hours ago
Hampton Inn Chicago Downtown/Magnificent Mile
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

10/10 Excellent
"Great"
Hiba 3-night trip
Posted 16 hours ago
Fairmont Chicago at Millennium Park
Congress Plaza Hotel

Congress Plaza Hotel

10/10 Excellent
"Love the Victorian vibes this place gives, as well as the updated modern rooms while still giving us that beautiful space to sleep in. Would recommend!"
Donna 1-night trip
Posted 21 hours ago
Congress Plaza Hotel
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