Oakland Vacations from $230

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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.
The Allegro Royal Sonesta Hotel Chicago Loop
Hotel Riu Plaza Chicago
The Emily Hotel
Hilton Chicago O'Hare Airport
Level Chicago Fulton Market

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
$168 nightly
The price is $197 total per night from Sep 22 to Sep 23
$197 total
Sep 22 - Sep 23
Total with taxes and fees
7.8/10 Good! (9,216 reviews)
"Could use more front desk staff. Quite a line formed behind me"

Reviewed on Sep 18, 2025

Congress Plaza Hotel
Warwick Allerton - Chicago

Warwick Allerton - Chicago

4 out of 5
701 North Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
$148 nightly
The price is $174 total per night from Sep 22 to Sep 23
$174 total
Sep 22 - Sep 23
Total with taxes and fees
8.2/10 Very Good! (2,922 reviews)
"Cafe was convenient"

Reviewed on Sep 19, 2025

Warwick Allerton - Chicago
citizenM Chicago Downtown

citizenM Chicago Downtown

4 out of 5
80 East Wacker Place, Chicago, IL
Fully refundableReserve now, pay when you stay
$156 nightly
The price is $184 total per night from Sep 22 to Sep 23
$184 total
Sep 22 - Sep 23
Total with taxes and fees
9.2/10 Wonderful! (3,813 reviews)
"Please try to restock luggage tag bands"

Reviewed on Sep 17, 2025

citizenM Chicago Downtown
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.