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Hotels in Oakland

October 2026
17
November 2026

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Next weekend
Oct 23 - Oct 25
In two weeks
Oct 30 - Nov 1

Where to stay in Oakland?

A modern interior with a bar area, seating, and decorative wooden panels.
A modern hotel with a prominent "Grant Park Hotel" sign and "Best Western" branding.
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.

1. Best Western Grant Park Hotel

Best Western Grant Park Hotel
The Loop, 5.4 km from Oakland
United States
Jamison
$107
$127 total
includes taxes & fees
Nov 10 - Nov 11
Best Western Grant Park 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 view from a room with a large window overlooking a cityscape at night, featuring a river and illuminated buildings.
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

Sable at Navy Pier Chicago, Curio Collection by Hilton
Streeterville, 7.5 km from Oakland
United States
Kendra
$189
$259 total
includes taxes & fees
Nov 12 - Nov 13
Sable at Navy Pier Chicago, Curio Collection by Hilton
An indoor swimming pool with clear glass walls, a wooden ceiling, and a view of a red brick building.
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.
A modern hotel lobby with a reception desk, seating area, and a large window providing a view of the outdoors.

3. Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop
The Loop, 5.4 km from Oakland
United States
Kimberly
$127
$151 total
includes taxes & fees
Nov 9 - Nov 10
Hilton Garden Inn Chicago Downtown South Loop
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 conference room with a long table, chairs, and a large screen.
A marina with numerous boats docked, surrounded by a cityscape with high-rise buildings and a stadium.

4. Hilton Chicago

Hilton Chicago
The Loop, 5.7 km from Oakland
United States
Armen
$169
$230 total
includes taxes & fees
Nov 13 - Nov 14
Hilton Chicago
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 bar area with a long counter, multiple bar stools, and a mix of seating options including a high table and chairs.
A modern restaurant interior with a long counter, booths, and tables.

5. Homewood Suites by Hilton Chicago Downtown South Loop

Homewood Suites by Hilton Chicago Downtown South Loop
The Loop, 5.4 km from Oakland
United States
Kellie
$144
$171 total
includes taxes & fees
Nov 10 - Nov 11
Homewood Suites by Hilton Chicago Downtown South Loop
A hotel room with two beds, a nightstand, a telephone, and a wall with printed text.
A gym with treadmills, elliptical machines, and stationary bikes, large windows with a city view.
A bar area with a long counter, multiple liquor bottles, and a variety of glasses.
A restaurant with booths and tables, a television on the wall, and a view of the street outside.

6. Hilton Vacation Club Hotel Blake Chicago

Hilton Vacation Club Hotel Blake Chicago
The Loop, 6.1 km from Oakland
United States
Salvino Angelo
$172
$204 total
includes taxes & fees
Nov 3 - Nov 4
Hilton Vacation Club Hotel Blake Chicago
A spacious lobby with a central sofa, multiple seating areas, and a decorative ceiling.
Outdoor seating with yellow umbrellas labeled "Twisted Tea," wicker chairs, and tables.
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.

7. Congress Plaza Hotel

Congress Plaza Hotel
The Loop, 6 km from Oakland
United States
Nancy
$129
$153 total
includes taxes & fees
Nov 10 - Nov 11
Congress Plaza Hotel
A modern hotel lobby with large windows, leather sofas, and a view of the cityscape.
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.
A compact kitchen with a microwave, coffee maker, and sink.

8. Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago
The Loop, 5.9 km from Oakland
United States
Mara
$112
$133 total
includes taxes & fees
Nov 11 - Nov 12
Travelodge by Wyndham Downtown Chicago
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 modern bar area with a bar counter, multiple stools, and a chandelier.

9. Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown
Theatre District, 6.7 km from Oakland
United States
Joanna
$161
$222 total
includes taxes & fees
Nov 1 - Nov 2
Silversmith Hotel Chicago Downtown
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.
Transparent igloo-like structures with seating inside, set on a wooden deck with snow on the ground, surrounded by tall buildings.
A cozy room with a patterned carpet, a wooden table, and a green sofa with a white throw blanket.

10. DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile
Streeterville, 7.8 km from Oakland
United States
Claire
$128
$153 total
includes taxes & fees
Nov 1 - Nov 2
DoubleTree by Hilton Chicago - Magnificent Mile
A hotel reception desk with a framed cityscape poster, a sign for Hilton Honors, and a counter with a display of toiletries.
Lobby
A fitness room with treadmills, an elliptical, and a stationary bike, equipped with digital displays.
Room

11. Hampton Inn Majestic Chicago Theatre District

Hampton Inn Majestic Chicago Theatre District
Theatre District, 6.7 km from Oakland
United States
Naidy
$148
$175 total
includes taxes & fees
Nov 1 - Nov 2
Hampton Inn Majestic Chicago Theatre District
A rooftop lounge with a city view, featuring a sofa, tables, and a fire feature.
A modern interior with a long counter, glass partitions, and a brick wall backdrop.
A modern lounge area with seating, a bar, and large windows offering views.
A view from a window with a cityscape in the background, including modern buildings and a clear sky.

12. Hyatt House Chicago/West Loop-Fulton Market

Hyatt House Chicago/West Loop-Fulton Market
7.9 km from Oakland
United States
Meggan
$195
$232 total
includes taxes & fees
Nov 1 - Nov 2
Hyatt House Chicago/West Loop-Fulton Market
The Claridge House building with a sign, American and another flag, and outdoor seating with umbrellas.
A modern kitchen with a central island, bar stools, a chandelier, and a large flat-screen TV.
A bar area with a long counter, multiple stools, and a modern chandelier.
A modern hotel room with a large bed, a chair, a small table, and a window with a view.

13. Claridge House Chicago, Tapestry Collection by Hilton

Claridge House Chicago, Tapestry Collection by Hilton
9.3 km from Oakland
United States
Martin
$118
$170 total
includes taxes & fees
Nov 9 - Nov 10
Claridge House Chicago, Tapestry Collection by Hilton
An indoor swimming pool with a glass ceiling, wooden walls, and seating areas.
A grand ballroom with ornate chandeliers, round tables with floral centerpieces, and elegant chairs.
A formal dining room with a round table set for eight, surrounded by leather chairs, a chandelier, and potted plants.
A modern building with large glass windows and a covered walkway.

14. Palmer House a Hilton Hotel

Palmer House a Hilton Hotel
Theatre District, 6.7 km from Oakland
United States
Sergio
$190
$256 total
includes taxes & fees
Oct 31 - Nov 1
Palmer House a Hilton Hotel
A multi-story hotel with a prominent sign reading "Crowne Plaza."
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.
A modern restaurant with round tables and booths, a high ceiling with exposed beams, and a brick accent wall with the text "RVE DELTA".

15. Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG
7.3 km from Oakland
United States
Bethany
$161
$191 total
includes taxes & fees
Nov 1 - Nov 2
Crowne Plaza Chicago West Loop by IHG
A bar area with a checkered floor, leather seating, and a bar counter with a visible liquor selection.
A hotel room with a bed, desk, lamp, and a wall with a handprint design.
A modern lounge with a green sofa, armchairs, a coffee table, and a piano.
A lounge area with a checkered floor, blue sofas, a bench, and a patterned coffee table.

16. ACME Hotel Chicago, Outset Collection by Hilton

ACME Hotel Chicago, Outset Collection by Hilton
River North, 7.9 km from Oakland
United States
Alexandra
$118
$141 total
includes taxes & fees
Nov 1 - Nov 2
ACME Hotel Chicago, Outset Collection by Hilton
A high-rise hotel with a prominent curved glass facade, multiple floors, and a visible "EMBASSY" sign.
A conference room with a long table, chairs, a projector screen, and a carpeted floor.
A large banquet hall with round tables, blue tablecloths, and white chairs with blue sashes.
A hotel room with a bed, a TV, a window with curtains, and a view of tall buildings.

17. Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Embassy Suites by Hilton Chicago Downtown Magnificent Mile
Streeterville, 7.6 km from Oakland
Canada
Tania
$145
$202 total
includes taxes & fees
Nov 1 - Nov 2
Embassy Suites by Hilton Chicago Downtown Magnificent Mile
A person relaxing on a sofa with a window view of a building, a table with a glass of wine, and a vase with flowers.
A modern restaurant with high ceilings, wooden flooring, and a central chandelier. Tables are set with wine glasses and red cushions.
A room with a bed, a window with curtains, a small table with a vase of flowers, and a chair.
A bar area with a long counter, multiple shelves of bottles, and four bar stools.

18. L7 Chicago by LOTTE

L7 Chicago by LOTTE
Theatre District, 7.2 km from Oakland
United States
Naomi Bullock
$187
$223 total
includes taxes & fees
Nov 1 - Nov 2
L7 Chicago by LOTTE
A spacious lobby with a wooden floor, a central round table with decorative items, a reception desk, and framed artwork on the walls.
A hotel room with two beds, a desk with a television, a chair, a ceiling fan, and a window with a view of a building.
A modern dining area with a central island, chairs, pendant lights, and a decorative wall with a motivational quote.
A modern office setup with two monitors, a keyboard, and leather chairs.

19. Homewood Suites by Hilton Chicago West Loop Fulton Mkt Area

Homewood Suites by Hilton Chicago West Loop Fulton Mkt Area
7.5 km from Oakland
United States
Carolyn
$193
$229 total
includes taxes & fees
Oct 30 - Oct 31
Homewood Suites by Hilton Chicago West Loop Fulton Mkt Area
The Intercontinental hotel facade with a large American flag and a floral display.
A bar area with a high bar counter, multiple stools, and a seating area with booths and tables.
A person lying on a bed with a bottle of champagne, surrounded by food and a magazine.
A person sitting by a window with a cityscape view.

20. InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG
Magnificent Mile, 7.7 km from Oakland
United States
Eduardo
$212
$287 total
includes taxes & fees
Oct 31 - Nov 1
InterContinental Chicago Magnificent Mile by IHG
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Pricing is based on two traveler single night rates
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October

High 16°C / low 10°C. Sunny most days.
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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, 57th Street Beach, and 63rd Street Beach.
See properties

Check out reviews of Oakland hotels guests love

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 view from a room with a large window overlooking a cityscape at night, featuring a river and illuminated buildings.
A spacious outdoor dining area with large windows overlooking the sea, featuring multiple tables and stools.

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago

10/10 Exceptional

United States
Griffin
Sable at Navy Pier Chicago, Curio Collection by Hilton
A hotel room with two beds, a nightstand, a telephone, and a wall with printed text.
A gym with treadmills, elliptical machines, and stationary bikes, large windows with a city view.
A bar area with a long counter, multiple liquor bottles, and a variety of glasses.
A restaurant with booths and tables, a television on the wall, and a view of the street outside.

Hilton Vacation Club Hotel Blake Chicago

Hilton Vacation Club Hotel Blake Chicago
Downtown Chicago

10/10 Exceptional

United States
Jennifer
Hilton Vacation Club Hotel Blake Chicago
An indoor swimming pool with clear glass walls, a wooden ceiling, and a view of a red brick building.
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.
A modern hotel lobby with a reception desk, seating area, and a large window providing a view of the outdoors.

Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop
Downtown Chicago

10/10 Exceptional

United States
Jason
Hilton Garden Inn Chicago Downtown South Loop
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 conference room with a long table, chairs, and a large screen.
A marina with numerous boats docked, surrounded by a cityscape with high-rise buildings and a stadium.

Hilton Chicago

Hilton Chicago
Downtown Chicago

10/10 Exceptional

United States
Melissa
Hilton Chicago
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 bar area with a long counter, multiple bar stools, and a mix of seating options including a high table and chairs.
A modern restaurant interior with a long counter, booths, and tables.

Homewood Suites by Hilton Chicago Downtown South Loop

Homewood Suites by Hilton Chicago Downtown South Loop
Downtown Chicago

10/10 Exceptional

United States
Abra
Homewood Suites by Hilton Chicago Downtown South Loop
A person relaxing on a sofa with a window view of a building, a table with a glass of wine, and a vase with flowers.
A modern restaurant with high ceilings, wooden flooring, and a central chandelier. Tables are set with wine glasses and red cushions.
A room with a bed, a window with curtains, a small table with a vase of flowers, and a chair.
A bar area with a long counter, multiple shelves of bottles, and four bar stools.

L7 Chicago by LOTTE

L7 Chicago by LOTTE
Downtown Chicago

10/10 Exceptional

United States
Erin
L7 Chicago by LOTTE
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 modern bar area with a bar counter, multiple stools, and a chandelier.

Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown
Downtown Chicago

10/10 Exceptional

United States
Dorothy
Silversmith Hotel Chicago Downtown
A modern interior with a bar area, seating, and decorative wooden panels.
A modern hotel with a prominent "Grant Park Hotel" sign and "Best Western" branding.
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.

Best Western Grant Park Hotel

Best Western Grant Park Hotel
Downtown Chicago

10/10 Exceptional

United States
brian
Best Western Grant Park Hotel
A restaurant interior with brick walls, hanging spherical light fixtures, and a visible kitchen area.
A high-rise building with a modern architectural design, featuring a prominent glass facade and a series of vertical lines.
A bar area with multiple shelves of bottles, a bar counter, and three bar stools.
A room with a diamond-patterned bookshelf filled with books, a wooden floor, and a lamp.

Arlo Chicago

Arlo Chicago
Downtown Chicago

10/10 Exceptional

United States
Lina
Arlo Chicago
A hotel reception desk with a framed cityscape poster, a sign for Hilton Honors, and a counter with a display of toiletries.
Lobby
A fitness room with treadmills, an elliptical, and a stationary bike, equipped with digital displays.
Room

Hampton Inn Majestic Chicago Theatre District

Hampton Inn Majestic Chicago Theatre District
Downtown Chicago

10/10 Exceptional

United States
Anne
Hampton Inn Majestic Chicago Theatre District
A rooftop lounge with a city view, featuring a sofa, tables, and a fire feature.
A modern interior with a long counter, glass partitions, and a brick wall backdrop.
A modern lounge area with seating, a bar, and large windows offering views.
A view from a window with a cityscape in the background, including modern buildings and a clear sky.

Hyatt House Chicago/West Loop-Fulton Market

Hyatt House Chicago/West Loop-Fulton Market
Downtown Chicago

10/10 Exceptional

United States
Valia
Hyatt House Chicago/West Loop-Fulton Market
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.

Staypineapple, An Iconic Hotel, The Loop

Staypineapple, An Iconic Hotel, The Loop
Downtown Chicago

10/10 Exceptional

United States
Natalya
Staypineapple, An Iconic Hotel, The Loop
The Intercontinental hotel facade with a large American flag and a floral display.
A bar area with a high bar counter, multiple stools, and a seating area with booths and tables.
A person lying on a bed with a bottle of champagne, surrounded by food and a magazine.
A person sitting by a window with a cityscape view.

InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG
Downtown Chicago

10/10 Exceptional

United States
Rosemary
InterContinental Chicago Magnificent Mile by IHG
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.

Hyatt Regency Chicago

Hyatt Regency Chicago
Downtown Chicago

10/10 Exceptional

United States
Brooke
Hyatt Regency Chicago
A multi-story hotel with a prominent sign reading "Crowne Plaza."
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.
A modern restaurant with round tables and booths, a high ceiling with exposed beams, and a brick accent wall with the text "RVE DELTA".

Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG
Downtown Chicago

10/10 Exceptional

United States
Priya
Crowne Plaza Chicago West Loop by IHG
A modern restaurant with high ceilings, exposed beams, and large windows. Tables are set with blue napkins and pink glassware.
A spacious lobby with a fireplace, comfortable seating, and a modern chandelier.
A cozy reading area with a dark blue sofa, multiple bookshelves, and a small table with a drink and a glass.
A bar with multiple shelves of bottles, a long counter, and several stools.

The Hoxton, Chicago

The Hoxton, Chicago
Downtown Chicago

10/10 Exceptional

United States
Theoni
The Hoxton, Chicago
A spacious lobby with a long bar area, red curtains, and a patterned carpet.
A large, historic building with a classic architectural style, featuring multiple floors and large windows.
A modern living room with a yellow sectional sofa, a red armchair, a blue patterned rug, and a marble coffee table.
A modern room with a teal sofa, a Peloton exercise bike, and a city view through large windows.

Canopy by Hilton Chicago Central Loop

Canopy by Hilton Chicago Central Loop
Downtown Chicago

10/10 Exceptional

United States
Chelsea
Canopy by Hilton Chicago Central Loop
The Claridge House building with a sign, American and another flag, and outdoor seating with umbrellas.
A modern kitchen with a central island, bar stools, a chandelier, and a large flat-screen TV.
A bar area with a long counter, multiple stools, and a modern chandelier.
A modern hotel room with a large bed, a chair, a small table, and a window with a view.

Claridge House Chicago, Tapestry Collection by Hilton

Claridge House Chicago, Tapestry Collection by Hilton
Downtown Chicago

10/10 Exceptional

United States
jolynn
Claridge House Chicago, Tapestry Collection by Hilton
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.
Transparent igloo-like structures with seating inside, set on a wooden deck with snow on the ground, surrounded by tall buildings.
A cozy room with a patterned carpet, a wooden table, and a green sofa with a white throw blanket.

DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile
Downtown Chicago

10/10 Exceptional

United States
Rudy
DoubleTree by Hilton Chicago - Magnificent Mile