Hotels in Oakland

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Tonight
Oct 30 - Oct 31
Tomorrow
Oct 31 - Nov 1
This weekend
Oct 30 - Nov 1
Next weekend
Nov 6 - Nov 8

Where to stay in Oakland?

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

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

Sable at Navy Pier Chicago, Curio Collection by Hilton
4.0 star property
Streeterville, 7.5 km from Oakland
9.4 out of 10, Exceptional, (2,751 reviews)
"Very nice stay. Water views were beautiful."
United States
Shonnel
The price is $131
$190 total
includes taxes & fees
Nov 22 - Nov 23
Sable at Navy Pier Chicago, Curio Collection by Hilton
A multi-story building with a prominent entrance featuring a large archway and a sign.

2. Hilton Chicago

Hilton Chicago
4.0 star property
The Loop, 5.7 km from Oakland
8.6 out of 10, Excellent, (3,496 reviews)
"I absolutely love this property!"
United States
Carrie
The price is $108
$158 total
includes taxes & fees
Nov 27 - Nov 28
Hilton Chicago
An indoor swimming pool with clear glass walls, a wooden ceiling, and a view of a red brick building.

3. Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop
3.0 star property
The Loop, 5.4 km from Oakland
8.8 out of 10, Excellent, (2,198 reviews)
"We had a great experience staying here. The hotel and rooms were nice and the people working there were courteous and helpful. We would stay there again!"
United States
Linda
The price is $97
$115 total
includes taxes & fees
Nov 23 - Nov 24
Hilton Garden Inn Chicago Downtown South Loop
A modern interior with a bar area, seating, and decorative wooden panels.

4. Best Western Grant Park Hotel

Best Western Grant Park Hotel
2.5 star property
The Loop, 5.4 km from Oakland
8.2 out of 10, Very good, (2,743 reviews)
"The room and hotel are clean and conveniently located. The staff was friendly and helpful"
United States
Julie
The price is $98
$117 total
includes taxes & fees
Nov 23 - Nov 24
Best Western Grant Park Hotel
A modern kitchen with a large window, a dining area, and a view of the sea.

5. Homewood Suites by Hilton Chicago Downtown South Loop

Homewood Suites by Hilton Chicago Downtown South Loop
3.0 star property
The Loop, 5.4 km from Oakland
8.8 out of 10, Excellent, (2,525 reviews)
"Very clean very friendly staff would stay again"
United States
Josue
The price is $105
$125 total
includes taxes & fees
Nov 23 - Nov 24
Homewood Suites by Hilton Chicago Downtown South Loop
A modern hotel lobby with a long blue sofa, numbered cushions, and hanging planters.

6. Hilton Vacation Club Hotel Blake Chicago

Hilton Vacation Club Hotel Blake Chicago
4.0 star property
The Loop, 6.1 km from Oakland
9.6 out of 10, Exceptional, (1,215 reviews)
"Very clean hotel with a great location to the Downtown area. Very close walk to the park and 5 minute walk to train stations. Friendly staff and a clean room with a spacious bathroom."
United States
Alisha
The price is $160
$191 total
includes taxes & fees
Nov 22 - Nov 23
Hilton Vacation Club Hotel Blake Chicago
A dining table set for six with a cityscape view through large windows.

7. Swissotel - Chicago

Swissotel - Chicago
4.5 star property
7.2 km from Oakland
9.0 out of 10, Wonderful, (3,569 reviews)
"Room was clean staff was pleasant and helpful"
United States
amy
The price is $117
$174 total
includes taxes & fees
Nov 26 - Nov 27
Swissotel - Chicago
A hotel entrance with a glass door, a sign above the door, and two potted plants on either side.

8. Hampton Inn Majestic Chicago Theatre District

Hampton Inn Majestic Chicago Theatre District
3.0 star property
Theatre District, 6.7 km from Oakland
9.2 out of 10, Wonderful, (1,000 reviews)
"Excellent hotel! Very clean staff very nice and respectful. Breakfast was very tasty."
United States
Naidy
The price is $114
$136 total
includes taxes & fees
Nov 23 - Nov 24
Hampton Inn Majestic Chicago Theatre District
A swimming pool with lounge chairs and umbrellas, surrounded by tall buildings.

9. DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile
4.0 star property
Streeterville, 7.8 km from Oakland
8.8 out of 10, Excellent, (2,580 reviews)
"Wonderful staff, clean rooms, and a great location!"
United States
Claire
The price is $101
$120 total
includes taxes & fees
Nov 23 - Nov 24
DoubleTree by Hilton Chicago - Magnificent Mile
The Claridge House building with a sign, American and another flag, and outdoor seating with umbrellas.

10. Claridge House Chicago, Tapestry Collection by Hilton

Claridge House Chicago, Tapestry Collection by Hilton
4.0 star property
9.3 km from Oakland
9.0 out of 10, Wonderful, (1,435 reviews)
"The staff are always so kind and helpful and the rooms are clean and lovely it’s like a home away from home"
United States
Martin
The price is $93
$139 total
includes taxes & fees
Nov 22 - Nov 23
Claridge House Chicago, Tapestry Collection by Hilton
A modern restaurant with high ceilings, exposed beams, and large windows. Tables are set with blue napkins and pink glassware.

11. The Hoxton, Chicago

The Hoxton, Chicago
4.0 star property
7.9 km from Oakland
9.2 out of 10, Wonderful, (1,001 reviews)
"Hotel staff was great very walkable location close to the train hotel rooms were very clean and I love the livelihood of the hotel"
United States
Chanel
The price is $179
$242 total
includes taxes & fees
Nov 24 - Nov 25
The Hoxton, Chicago
A grand lobby with a staircase, ornate chandeliers, and a clock on the wall.

12. Palmer House a Hilton Hotel

Palmer House a Hilton Hotel
4.0 star property
Theatre District, 6.7 km from Oakland
8.6 out of 10, Excellent, (2,720 reviews)
"Beautiful hotel with lots of personality and charm. Great staff, great location, lots of options for food easily available."
United States
Melinda
The price is $134
$189 total
includes taxes & fees
Nov 24 - Nov 25
Palmer House a Hilton Hotel
A spacious lobby with a central sofa, multiple seating areas, and a decorative ceiling.

13. Congress Plaza Hotel

Congress Plaza Hotel
3.5 star property
The Loop, 6 km from Oakland
8.0 out of 10, Very good, (10,061 reviews)
"A very convenient location, reasonably priced, and a clean and safe place to stay."
United States
Angela
The price is $116
$138 total
includes taxes & fees
Nov 10 - Nov 11
Congress Plaza Hotel
A multi-story hotel with a prominent sign reading "Crowne Plaza."

14. Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG
3.5 star property
7.3 km from Oakland
9.0 out of 10, Wonderful, (2,760 reviews)
"Great service, great location"
United States
Ulises
The price is $135
$161 total
includes taxes & fees
Nov 23 - Nov 24
Crowne Plaza Chicago West Loop by IHG
A modern hotel lobby with a reception desk, marble flooring, and elegant chandeliers.

15. Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown
4.0 star property
Theatre District, 6.7 km from Oakland
9.2 out of 10, Wonderful, (2,435 reviews)
"Great stay and convenient location in Chicago."
United States
Nicholas
The price is $127
$181 total
includes taxes & fees
Nov 22 - Nov 23
Silversmith Hotel Chicago Downtown
A modern hotel with a glass facade, multiple floors, and a visible entrance.

16. Hyatt Place Chicago/Downtown - The Loop

Hyatt Place Chicago/Downtown - The Loop
3.0 star property
The Loop, 7.1 km from Oakland
8.8 out of 10, Excellent, (1,686 reviews)
"Clean room, well maintained, friendly staff. Breakfast onsite was reasonably priced and convenient."
United States
Nadja
The price is $118
$140 total
includes taxes & fees
Nov 23 - Nov 24
Hyatt Place Chicago/Downtown - The Loop
A snack bar with various packaged snacks and beverages.

17. Cambria Hotel Chicago Loop - Theatre District

Cambria Hotel Chicago Loop - Theatre District
4.0 star property
Theatre District, 7.1 km from Oakland
8.8 out of 10, Excellent, (1,713 reviews)
"The location is wonderful. The hotel was clean and well appointed and it was easy to get to public transport."
United States
Jade
The price is $111
$132 total
includes taxes & fees
Nov 23 - Nov 24
Cambria Hotel Chicago Loop - Theatre District
Bar (on property)

18. ACME Hotel Chicago, Outset Collection by Hilton

ACME Hotel Chicago, Outset Collection by Hilton
3.5 star property
River North, 7.9 km from Oakland
9.0 out of 10, Wonderful, (1,973 reviews)
"Great location and helpful staff. Would stay again."
United States
Alexandra
The price is $101
$120 total
includes taxes & fees
Nov 23 - Nov 24
ACME Hotel Chicago, Outset Collection by Hilton
A rooftop terrace with outdoor seating, a view of the city skyline, and a river.

19. LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton
4.5 star property
The Loop, 7.4 km from Oakland
9.4 out of 10, Exceptional, (3,876 reviews)
"Beautiful hotel and location. Staff were very friendly and kind."
Canada
Sophie
The price is $144
$201 total
includes taxes & fees
Nov 23 - Nov 24
LondonHouse Chicago, Curio Collection by Hilton
A multi-story building with a prominent curved glass facade, surrounded by other high-rise buildings.

20. Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Embassy Suites by Hilton Chicago Downtown Magnificent Mile
4.0 star property
Streeterville, 7.6 km from Oakland
8.4 out of 10, Very good, (3,013 reviews)
"Great location and awesome staff! Breakfast and happy hour were pleasant surprises for our family. Enjoyed the amenities - simple but worked well for a short 4-day trip for our family with kids."
Canada
Tania
The price is $130
$184 total
includes taxes & fees
Nov 24 - Nov 25
Embassy Suites by Hilton Chicago Downtown Magnificent Mile
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Compare popular hotels in Oakland

Property
Property class
Guest rating
Breakfast included
Pool
Spa
Pet friendly
WiFi included
A modern hotel lobby with a long blue sofa, numbered cushions, and hanging planters.
Hilton Vacation Club Hotel Blake Chicago
4.0 star property
9.6
Exceptional
1,215 reviews
View
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.
L7 Chicago by LOTTE
4.5 star property
9.6
Exceptional
5,133 reviews
View
An outdoor seating area with tables and chairs, a planter with greenery, and a large brick structure in the background.
Sable at Navy Pier Chicago, Curio Collection by Hilton
4.0 star property
9.4
Exceptional
2,751 reviews
View
The Riu Plaza Chicago Hotel facade with a grand entrance, large windows, and a modern architectural design.
Hotel Riu Plaza Chicago
4.0 star property
9.4
Exceptional
5,616 reviews
View
A spacious bar area with high ceilings and large windows, offering views of a cityscape.
Hyatt Regency Chicago
4.0 star property
9.4
Exceptional
3,491 reviews
View

When is the best time to visit Chicago?

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 October
Currently viewing crowd sizes and weather for October.

October

High 16°C / low 10°C. Sunny most days.
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October, no crowd data, average high temperature 16 degrees Celsius, average low temperature 10 degrees Celsius. Sunny most days.
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November, no crowd data, average high temperature 8 degrees Celsius, average low temperature 3 degrees Celsius. Partly sunny.
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December, no crowd data, average high temperature 3 degrees Celsius, average low temperature -2 degrees Celsius. Cloudy most days.
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January, no crowd data, average high temperature -1 degrees Celsius, average low temperature -6 degrees Celsius. Snow likely.
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February, no crowd data, average high temperature 0 degrees Celsius, average low temperature -6 degrees Celsius. Snow likely.
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March, no crowd data, average high temperature 6 degrees Celsius, average low temperature 0 degrees Celsius. Cloudy most days.
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April, no crowd data, average high temperature 11 degrees Celsius, average low temperature 5 degrees Celsius. Partly sunny.
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May, no crowd data, average high temperature 17 degrees Celsius, average low temperature 11 degrees Celsius. Sunny most days.
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June, no crowd data, average high temperature 23 degrees Celsius, average low temperature 17 degrees Celsius. Sunny most days.
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July, no crowd data, average high temperature 26 degrees Celsius, average low temperature 20 degrees Celsius. Sunny most days.
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August, no crowd data, average high temperature 26 degrees Celsius, average low temperature 20 degrees Celsius. Sunny most days.
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September, no crowd data, average high temperature 23 degrees Celsius, average low temperature 17 degrees Celsius. 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

A modern hotel lobby with a long blue sofa, numbered cushions, and hanging planters.
Hilton Vacation Club Hotel Blake Chicago

Hilton Vacation Club Hotel Blake Chicago

Hilton Vacation Club Hotel Blake Chicago
Downtown Chicago

10/10 Exceptional

This was the fourth time I’ve stayed here, and I’ll keep coming back. The location is very handy for families of Columbia College, the rooms are clean, comfortable and well appointed. The staff is extremely friendly and helpful, and it’s priced well.
United States
Jennifer
Reviewed May 12, 2024
Hilton Vacation Club Hotel Blake Chicago