Oakland Vacations from $317
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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.
Waldorf Astoria Chicago
Downtown Chicago
Save 100% on your flight
Price was $2,179, price is now $1,374 per person
$1,374
per person
Mar 14 - Mar 20
just found
Roundtrip non-stop flight included
Burbank (BUR) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
When we arrived at check in time, we were informed that our room was not ready but that we could upgrade at a discounted additional cost to a suite. At first, we didn't want to do that and decided to wait. The host provided complimentary round of drinks and meal for the wait. We decided to upgrade and I'm so glad that we did. The room was incredible and the service, from concierge, staff and valets, here is top notch. We ordered the Waldorf salad and Waldorf chocolate chip cookies because you have to if you stay here. Loved this place and will definitely return.
Reviewed on Jan 5, 2026
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was $689, price is now $445 per person
$445
per person
Mar 26 - Mar 29
found 9 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
Staff was friendly did amazing job with checking us in
Reviewed on Dec 25, 2025
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $766, price is now $499 per person
$499
per person
Mar 22 - Mar 28
found 9 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (2,365 reviews)
When showering the floor gets wet because of how small the shower is and nothing prevents water from getting on the floor
Reviewed on Jan 6, 2026
The Emily Hotel
Downtown Chicago
Price was $582, price is now $389 per person
$389
per person
Mar 20 - Mar 22
found 11 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,264 reviews)
Had a great dinner at Fora before a very short walk to the new years eve event we were headed to and then came back for a great night's sleep in a very comfortable room! All the staff we interacted with were great!
Reviewed on Jan 1, 2026
Where to stay in Oakland
Find the best Oakland areas and neighborhoods for the activities you enjoy most. Learn more about Oakland
Downtown Chicago
5 out of top 10 points of interest in this area
The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.
Oakland Hotel Deals
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
$89 nightly
The price is $105 total per night from Jan 13 to Jan 14
$105 total
Jan 13 - Jan 14
Total with taxes and fees
8.8/10 Excellent! (3,660 reviews)
We had a wonderful stay at the Hilton. The staff was exceptionally helpful in providing any information we neede. A shout out to Latis and Christian, who were extremely friendly, always created us with a smile and we’re eager to help. We will definitely stay here again.
Reviewed on Jan 6, 2026
Hilton Chicago
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
$164 nightly
The price is $192 total per night from Jan 13 to Jan 14
$192 total
Jan 13 - Jan 14
Total with taxes and fees
8.4/10 Very Good! (2,494 reviews)
I paid for a king room and had that for the first half of my stay, but something went wrong with the water heater for the floor(?). It wasn't explained well to us, but we were moved into another room on a higher level which I assumed would have been similar but it was much smaller and had a queen ...
Reviewed on Jan 5, 2026
Palmer House a Hilton Hotel
17 E Monroe St Chicago IL
Fully refundableReserve now, pay when you stay
$168 nightly
The price is $192 total per night from Jan 13 to Jan 14
$192 total
Jan 13 - Jan 14
Total with taxes and fees
8.4/10 Very Good! (2,226 reviews)
Room was very clean and staff was great
Reviewed on Jan 6, 2026
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
Michigan Avenue
You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.
Wrigley Field
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
Navy Pier
A Ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
Things to do
Skydeck - Willis Tower Admission
$44
per adult
100% of travellers recommend
Chicago Bulls Basketball Game at United Center
$83
per adult
80% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
$25
per adult
88% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.