Oakland Vacations from $397

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Your Oakland Vacation

With a tailor-made vacation package to Oakland, you'll spend less time planning and more time simply enjoying this appealing neighborhood. From its nature to its walking, there's plenty to discover here. Kick start your trip to Oakland by heading to nearby attractions such as University of Chicago, Chicago Museum of Science and Industry and Guaranteed Rate Field. No matter your travel goals or budget, booking your ideal Oakland vacation is easy with Expedia.

The Latest Oakland Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Palmer House a Hilton Hotel
The Wade
Virgin Hotels Chicago
theWit Chicago, a Hilton Hotel
Arlo Chicago

Where to stay in Oakland

Find the best Oakland areas and neighborhoods for the activities you enjoy most. Learn more about Oakland

Oakland Hotel Deals

Congress Plaza Hotel
Congress Plaza Hotel
3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
$179 nightly
The price is $210 total per night from Jul 27 to Jul 28
$210 total
Jul 27 - Jul 28
Total includes taxes and fees
7.8/10 Good! (8,941 reviews)
"Historical place to stay if in Chicago"

Reviewed on Jul 10, 2025

Congress Plaza Hotel
InterContinental Chicago Magnificent Mile by IHG
InterContinental Chicago Magnificent Mile by IHG
4.5 out of 5
505 N Michigan Ave, Chicago, IL
Fully refundable
$255 nightly
The price is $294 total per night from Jul 24 to Jul 25
$294 total
Jul 24 - Jul 25
Total includes taxes and fees
9/10 Wonderful! (2,023 reviews)
"Great location. Comfortable room. Staff was very helpful."

Reviewed on Jul 12, 2025

InterContinental Chicago Magnificent Mile by IHG
Hilton Chicago/Magnificent Mile Suites
Hilton Chicago/Magnificent Mile Suites
3.5 out of 5
198 E Delaware Pl, Chicago, IL
$162 nightly
The price is $191 total per night from Aug 10 to Aug 11
$191 total
Aug 10 - Aug 11
Total includes taxes and fees
8.8/10 Excellent! (2,425 reviews)
"Great location and rooms are spacious and clean."

Reviewed on Jul 11, 2025

Hilton Chicago/Magnificent Mile Suites
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.

Discover the most popular places to visit in Oakland

Things to do

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.