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

This weekend
May 29 - May 31
Next weekend
Jun 5 - Jun 7

Where to stay in Oakland?

Terrace/patio

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, (2,511 reviews)
"Great place to stay. Very clean and the staff was very helpful"
United States
Lateisha
The price is CNY1,448
CNY1,956 total
includes taxes & fees
May 26 - May 27
Sable at Navy Pier Chicago, Curio Collection by Hilton
Room service - dining

The Wade

The Wade
4.5 star property
Streeterville, 7.9 km from Oakland
8.4 out of 10, Very Good, (1,841 reviews)
"the beach view was beautiful!"
United States
Schwarzenegger
The price is CNY1,033
CNY1,228 total
includes taxes & fees
May 26 - May 27
The Wade
2 bars/lounges

Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk
4.0 star property
Streeterville, 7.4 km from Oakland
8.6 out of 10, Excellent, (1,632 reviews)
"Great location, clean room, family-friendly."
United States
Eddy
The price is CNY1,693
CNY2,255 total
includes taxes & fees
May 26 - May 27
Sheraton Grand Chicago Riverwalk
Indoor wedding

Swissotel - Chicago

Swissotel - Chicago
4.5 star property
7.2 km from Oakland
9.0 out of 10, Wonderful, (3,341 reviews)
"This is becoming my go-to hotel in Chicago. Very reliable, very good location. Great restaurants/bars. Just the perfect business traveler place to stay."
United States
Tanya
The price is CNY1,347
CNY1,841 total
includes taxes & fees
May 27 - May 28
Swissotel - Chicago
Outdoor pool, cabanas (surcharge), pool umbrellas

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, (2,486 reviews)
"Great location, great staff. Very comforting rooms."
United States
Satya
The price is CNY1,149
CNY1,366 total
includes taxes & fees
May 26 - May 27
DoubleTree by Hilton Chicago - Magnificent Mile
Exterior

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
8.2 out of 10, Very Good, (2,852 reviews)
"I love staying here! Nice location and nice rooms. "
United States
Sandra
The price is CNY1,040
CNY1,436 total
includes taxes & fees
May 26 - May 27
Embassy Suites by Hilton Chicago Downtown Magnificent Mile
Executive lounge

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park
4.5 star property
The Loop, 7.1 km from Oakland
8.8 out of 10, Excellent, (2,166 reviews)
"Great location and helpful staff"
United States
Julie
The price is CNY1,365
CNY1,865 total
includes taxes & fees
May 26 - May 27
Fairmont Chicago at Millennium Park
Lobby

Aloft by Marriott Chicago Mag Mile

Aloft by Marriott Chicago Mag Mile
3.0 star property
Streeterville, 7.9 km from Oakland
8.6 out of 10, Excellent, (3,246 reviews)
"Great staff. Great location"
United States
Brandon
The price is CNY931
CNY1,107 total
includes taxes & fees
May 26 - May 27
Aloft by Marriott Chicago Mag Mile
Bar (on property)

Ivy Boutique Hotel

Ivy Boutique Hotel
4.5 star property
Streeterville, 7.9 km from Oakland
8.8 out of 10, Excellent, (1,272 reviews)
"I stayed in a suite. Gorgeous large room with great amenities. Staff kind and courteous."
United States
Margaret
The price is CNY1,034
CNY1,214 total
includes taxes & fees
May 26 - May 27
Ivy Boutique Hotel
Lobby

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
3.0 star property
Streeterville, 8.6 km from Oakland
8.6 out of 10, Excellent, (2,472 reviews)
"Clean room and nice breakfast!"
United States
James
The price is CNY1,104
CNY1,312 total
includes taxes & fees
May 26 - May 27
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
Room, 2 Double Beds, Hearing Accessible | Pillowtop beds, desk, blackout drapes, iron/ironing board

Fairfield Inn & Suites Chicago Downtown / Magnificent Mile

Fairfield Inn & Suites Chicago Downtown / Magnificent Mile
3.0 star property
Streeterville, 7.9 km from Oakland
9.0 out of 10, Wonderful, (1,002 reviews)
"Clean room, breakfast was good "
United States
Jody
The price is CNY1,013
CNY1,204 total
includes taxes & fees
May 26 - May 27
Fairfield Inn & Suites Chicago Downtown / Magnificent Mile
Exterior

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites
3.5 star property
Streeterville, 8.6 km from Oakland
9.0 out of 10, Wonderful, (4,337 reviews)
"Clean room, helpful staff, would stay again"
United States
Lance
The price is CNY1,208
CNY1,436 total
includes taxes & fees
May 27 - May 28
Hilton Chicago/Magnificent Mile Suites
Shopping mall

Millennium Hotel Knickerbocker Chicago

Millennium Hotel Knickerbocker Chicago
4.0 star property
Streeterville, 8.6 km from Oakland
8.6 out of 10, Excellent, (1,977 reviews)
"Everyone is kind here the rooms are clean and comfortable. Location is perfect. "
Canada
Denise
The price is CNY979
CNY1,325 total
includes taxes & fees
May 26 - May 27
Millennium Hotel Knickerbocker Chicago
2 bars/lounges

Hyatt Regency Chicago

Hyatt Regency Chicago
4.0 star property
The Loop, 7.3 km from Oakland
9.4 out of 10, Exceptional, (3,494 reviews)
"This hotel is great! Great location, great staff. "
United States
Vanessa
The price is CNY1,611
CNY2,158 total
includes taxes & fees
May 26 - May 27
Hyatt Regency Chicago
Exterior

Hyatt Centric Chicago Magnificent Mile

Hyatt Centric Chicago Magnificent Mile
4.0 star property
Streeterville, 8 km from Oakland
9.0 out of 10, Wonderful, (1,095 reviews)
"Location, modern, convenient, amenities"
United States
Amy
The price is CNY1,353
CNY1,810 total
includes taxes & fees
May 26 - May 27
Hyatt Centric Chicago Magnificent Mile
Premium bedding, in-room safe, desk, blackout drapes

Courtyard by Marriott Chicago Magnificent Mile

Courtyard by Marriott Chicago Magnificent Mile
3.0 star property
Streeterville, 7.9 km from Oakland
9.0 out of 10, Wonderful, (1,905 reviews)
"Friendly staff, clean room, central location close to all the tourist attractions. "
United States
Emilia
The price is CNY1,190
CNY1,432 total
includes taxes & fees
May 26 - May 27
Courtyard by Marriott Chicago Magnificent Mile
Exterior

The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile
4.0 star property
Streeterville, 8.2 km from Oakland
7.8 out of 10, Good, (1,467 reviews)
"great location and spacious room. good value"
United States
Maureen
The price is CNY773
CNY920 total
includes taxes & fees
May 26 - May 27
The Chicago Hotel Collection - Magnificent Mile
Front of property

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago
4.0 star property
Streeterville, 7.9 km from Oakland
9.4 out of 10, Exceptional, (4,238 reviews)
"Wonderful stay, staff, breakfast, location were all awesome!"
United States
Jessica
The price is CNY1,187
CNY1,605 total
includes taxes & fees
May 27 - May 28
Hotel Riu Plaza Chicago
Lobby

Congress Plaza Hotel

Congress Plaza Hotel
3.5 star property
The Loop, 6 km from Oakland
8.0 out of 10, Very Good, (10,138 reviews)
"Great location and value with plenty to offer from check in to check out "
United States
Brandon
The price is CNY1,485
CNY1,765 total
includes taxes & fees
Jun 18 - Jun 19
Congress Plaza Hotel
Restaurant

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, (2,698 reviews)
"Our room was clean , staff was very friendly and extremely helpful. Will be staying again!"
United States
Kara
The price is CNY877
CNY1,043 total
includes taxes & fees
May 27 - May 28
Best Western Grant Park Hotel
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.
View all properties

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 May
Currently viewing crowd sizes and weather for May.
Typical weather for Chicago
May
High 17°C / low 11°C. Sunny most days.
View properties in May
17°
weather_sun
May, no crowd data, average high temperature 17 degrees Celsius, average low temperature 11 degrees Celsius. Sunny most days.
11°
23°
weather_sun
June, no crowd data, average high temperature 23 degrees Celsius, average low temperature 17 degrees Celsius. Sunny most days.
17°
26°
weather_sun
July, no crowd data, average high temperature 26 degrees Celsius, average low temperature 20 degrees Celsius. Sunny most days.
20°
26°
weather_sun
August, no crowd data, average high temperature 26 degrees Celsius, average low temperature 20 degrees Celsius. Sunny most days.
20°
23°
weather_sun
September, no crowd data, average high temperature 23 degrees Celsius, average low temperature 17 degrees Celsius. Sunny most days.
17°
16°
weather_sun
October, no crowd data, average high temperature 16 degrees Celsius, average low temperature 10 degrees Celsius. Sunny most days.
10°
8°
weather_partly_sunny
November, no crowd data, average high temperature 8 degrees Celsius, average low temperature 3 degrees Celsius. Partly sunny.
3°
3°
weather_cloudy
December, no crowd data, average high temperature 3 degrees Celsius, average low temperature -2 degrees Celsius. Cloudy most days.
-2°
-1°
ac_unit
January, no crowd data, average high temperature -1 degrees Celsius, average low temperature -6 degrees Celsius. Snow likely.
-6°
0°
ac_unit
February, no crowd data, average high temperature 0 degrees Celsius, average low temperature -6 degrees Celsius. Snow likely.
-6°
6°
weather_cloudy
March, no crowd data, average high temperature 6 degrees Celsius, average low temperature 0 degrees Celsius. Cloudy most days.
0°
11°
weather_partly_sunny
April, no crowd data, average high temperature 11 degrees Celsius, average low temperature 5 degrees Celsius. Partly sunny.
5°
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 57th Street Beach, 63rd Street Beach, and 12th Street Beach.
See properties

Check out reviews of Oakland hotels guests love

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

10/10 Excellent
"Everything was excellent"
Claudia 3-night trip
Posted less than an hour ago
Hilton Chicago/Magnificent Mile Suites

Frequently asked questions

Is Oakland expensive to stay in?
You can find great hotels from CNY920 in Oakland to suit a range of budgets. To find the best low-cost hotel on Hotels.com that meets your needs, apply your search filters and then sort hotels by "Price: low to high".
How can I find discounted rates and deals for Oakland hotels?
Discover great deals on hotels in Oakland with Hotels.com. Sign up for free to unlock member only prices and start earning rewards. It's also a good idea to look at hotel prices mid-week or during the low season as you're likely to find off-peak deals. If you're up for a spontaneous trip, don't forget to check out our last-minute deals on Oakland hotels.
Can I receive a refund if I cancel my Oakland hotel booking?
The majority of hotels offer free cancellation, so you can receive a refund if you need to cancel your booking. Some Oakland hotels require you to cancel more than 24 hours before check-in, so look at your booking beforehand. For extra peace of mind before you book, filter hotels by "Property cancellation options" and select "Fully refundable property".
Is it worth staying in Oakland?
There are 6 hotels in the area to find your perfect somewhere. Basing yourself in Oakland makes it easy to explore Chicago, including the neighborhoods of Downtown Chicago and Near West Side.
Find out more about Oakland

Keep exploring