Hotels in Oakland

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Check prices for these dates

Tonight
Dec 20 - Dec 21
Tomorrow
Dec 21 - Dec 22
Next weekend
Dec 26 - Dec 28
In two weeks
Jan 2 - Jan 4

Where to stay in Oakland?

Cocktail bar
Freehand Chicago

Freehand Chicago

Freehand Chicago
4.0 star property
River North, 7.9 km from Oakland
8.0 out of 10, Very Good, (2652)
The price is CNY412
CNY608 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Freehand Chicago
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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When is the best time to visit Chicago?

Our prices for hotels in Chicago are cheapest in March
Price trends for hotels in Chicago
Pricing is based on two traveler single night rates
View properties in December
Currently viewing crowd sizes and weather for December.
Typical weather for Chicago
December
High crowds
High 3°C / low -2°C. Cloudy most days.
View properties in December
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December, High crowds, average high temperature 3 degrees Celsius, average low temperature -2 degrees Celsius. Cloudy most days.
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January, Low crowds, average high temperature -1 degrees Celsius, average low temperature -6 degrees Celsius. Snow likely.
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February, Low crowds, average high temperature 0 degrees Celsius, average low temperature -6 degrees Celsius. Snow likely.
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March, Low crowds, average high temperature 6 degrees Celsius, average low temperature 0 degrees Celsius. Cloudy most days.
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April, Low crowds, average high temperature 11 degrees Celsius, average low temperature 5 degrees Celsius. Partly sunny.
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May, Moderate crowds, average high temperature 17 degrees Celsius, average low temperature 11 degrees Celsius. Sunny most days.
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June, High crowds, average high temperature 23 degrees Celsius, average low temperature 17 degrees Celsius. Sunny most days.
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July, High crowds, average high temperature 26 degrees Celsius, average low temperature 20 degrees Celsius. Sunny most days.
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August, High crowds, average high temperature 26 degrees Celsius, average low temperature 20 degrees Celsius. Sunny most days.
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September, Moderate crowds, average high temperature 23 degrees Celsius, average low temperature 17 degrees Celsius. Sunny most days.
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October, Moderate crowds, average high temperature 16 degrees Celsius, average low temperature 10 degrees Celsius. Sunny most days.
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November, Moderate crowds, average high temperature 8 degrees Celsius, average low temperature 3 degrees Celsius. Partly sunny.
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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 57th Street Beach, 12th Street Beach, and Rainbow Beach.
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Check out reviews of Oakland hotels guests love

Homewood Suites by Hilton Chicago Downtown South Loop

Homewood Suites by Hilton Chicago Downtown South Loop

10/10 Excellent
"This was our first visit to Chicago. The room was clean and large for the 2 of us. Very inviting. Location was close to 2 major bus routes that took us every where we wanted to go."
BENSON 4-night trip
Posted 12 hours ago
Homewood Suites by Hilton Chicago Downtown South Loop

Frequently asked questions

Is Oakland expensive to stay in?
You can find great hotels from CNY667 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 7 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 South Side.
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