Oakland Vacations from NT$30,325

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The Latest Oakland Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Staypineapple, An Iconic Hotel, The Loop

Staypineapple, An Iconic Hotel, The Loop

4 out of 5
Downtown Chicago
Price was NT$38,664, price is now NT$30,325 per person
NT$30,325
per person
Jul 12 - Jul 16
found 24 hours ago
Roundtrip flight included
Ontario Intl. Airport (ONT) to Chicago (ORD)
9.4/10 Exceptional! (1,054 reviews)
The staff were fantastic, and the beds were insanely comfortable/blankets were soft and plush. The location is advantageous- lots of shopping, food, and things to do nearby. Getting an Uber from this location was a breeze and took less than five minutes. The Valet service for Staypineapple was also good. Would definitely recommend!

Reviewed on 2026/5/1

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was NT$52,839, price is now NT$37,068 per person
NT$37,068
per person
Jul 12 - Jul 16
found 24 hours ago
Roundtrip flight included
Ontario Intl. Airport (ONT) to Chicago (ORD)
9.4/10 Exceptional! (4,070 reviews)
Beautiful hotel, very impressed with the cleanliness, space in the room and the breakfast. So pleased we chose this hotel as the location was excellent 👌

Reviewed on 2026/5/7

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was NT$58,124, price is now NT$43,004 per person
NT$43,004
per person
Jul 12 - Jul 16
found 24 hours ago
Roundtrip flight included
Ontario Intl. Airport (ONT) to Chicago (ORD)
9.4/10 Exceptional! (2,478 reviews)
My stay was exceptional the staff were very polite and patient, they answered all my questions. I had a very nice view will definitely book again

Reviewed on 2026/5/6

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was NT$69,088, price is now NT$52,176 per person
NT$52,176
per person
Jul 12 - Jul 16
found 24 hours ago
Roundtrip flight included
Ontario Intl. Airport (ONT) to Chicago (ORD)
9.4/10 Exceptional! (1,863 reviews)
I love everything in the hotel everything

Reviewed on 2026/5/4

Le Méridien Essex Chicago

Le Méridien Essex Chicago

4 out of 5
Downtown Chicago
Price was NT$47,870, price is now NT$37,258 per person
NT$37,258
per person
Jul 12 - Jul 16
found 24 hours ago
Roundtrip flight included
Ontario Intl. Airport (ONT) to Chicago (ORD)
8.8/10 Excellent! (1,003 reviews)
Staff was attentive and friendly. Atmosphere was welcoming. Restaurant had a great selection food was good and prices reasonable. Rooms were comfy.

Reviewed on 2026/4/23

Where to stay in Oakland

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

Downtown Chicago

4 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.

Find hotels in Downtown Chicago

Oakland Hotel Deals

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
111 W Huron St Chicago IL
Fully refundableReserve now, pay when you stay
The price is NT$2,719 per night from May 20 to May 21
NT$2,719
NT$4,193 total
May 20 - May 21
includes taxes & fees
8.2/10 Very Good! (2,691 reviews)
The room was a little small, but fit my needs on a 3 day business trip. The bar downstairs served a limited breakfast... And had free fruit, and Coffee in the morning. The staff was extremely friendly, and very attentive to guests. In summary I would stay here again on business.

Reviewed on 2026/5/7

Hotel Felix River North/Magnificent Mile
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
The price is NT$4,511 per night from May 25 to May 26
NT$4,511
NT$5,363 total
May 25 - May 26
includes taxes & fees
8.8/10 Excellent! (5,182 reviews)
Everything was good. Nothing to complain

Reviewed on 2026/5/8

River Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is NT$4,678 per night from May 27 to May 28
NT$4,678
NT$6,457 total
May 27 - May 28
includes taxes & fees
9.4/10 Exceptional! (4,086 reviews)
The hotel was so clean and everyone was friendly! Great location!

Reviewed on 2026/5/7

Hotel Riu Plaza Chicago
See all 4,604 properties in Oakland
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.

Frequently asked questions

How much does an Oakland vacation package cost?
Customize your Oakland package from an affordable NT$30,325. Choose from any combination of hotels, flights and rental cars to build the escape of your dreams. Remember to add on a few activities!
How do I get a cheap travel package to Oakland?
Bundle, bundle, bundle. Flights, rental cars and hotels — combine whatever you need into an Oakland vacation package to save loads of cash. Score even better deals when you add extras such as tours or experiences to your booking. But that's not the only good part. You have the freedom to customize your vacation your way. We offer more than 550 partner airlines and 1,000,000 hotel options all over the world, so that everyone has a chance to travel and fulfill those vacation fantasies.
Where should I stay in Oakland?
Most visitors to Oakland include University of Chicago and Chicago Museum of Science and Industry on their bucket lists. Why not go for a hotel close to one of these great attractions?
How far in advance should I book my Oakland vacation?
It's tricky picking the ideal time for airfares, but we usually say the earlier, the better. Many international flights on Expedia become available to compare up to 12 months in advance. If you're unable to do so, don't despair. Cheap prices appear from time to time within a few weeks of departure dates.
What does an Expedia Oakland travel package include?
Flights, car rentals and hotels — we bring you the best deals. All you have to do is select your preferred combination. After you've made your booking, you can add on the fun stuff like activities and tours. Our travel packages make it simple to craft an exciting Oakland vacation.
What should I know before booking an Oakland travel package?
You'll land impressive savings when you bundle your hotels, flights and rental cars into a package. Not only that, booking everything together makes trip planning much easier. So why waste time or money? Whether you're organizing a fancy romantic getaway or a budget solo adventure, check out our vacation packages today.
Can I choose my airline with an Oakland Expedia vacation package?
Expedia offers access to more than 550 partner airlines globally, so you sure can! Just select the airline you want and create the perfect Oakland vacation.
If I'm not able to travel, can I cancel my Oakland vacation package?
It's hard to predict what the future holds, so it's good to know that you can change or cancel your Oakland vacation package. If your booking was made in the last 24 hours, you may be entitled to a refund. If your booking is older, your hotel, airline or car rental company may charge a fee. Visit our Customer Service Portal to learn more.

Discover the most popular places to visit in Oakland

Wrigley Field

Wrigley Field

4.5/5(2,149 reviews)

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Chicago Skyline, Chicago, Illinois shows amazing architecture in panoramic format

Naval Base Great Lakes

4.5/5(461 reviews)

After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area.

Naval Base Great Lakes
Navy Pier

Navy Pier

4.5/5(4,925 reviews)

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

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