Oakland Vacations

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Where to stay in Oakland

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

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.

Find hotels in Downtown Chicago

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
The price is NT$5,642 per night from Sep 14 to Sep 15
NT$5,642
NT$6,623 total
Sep 14 - Sep 15
includes taxes & fees
7.8/10 Good! (8,963 reviews)
"Its location is the main reason why I chose to stay. The room has been updated; it is roomy and clean. Staffs are very friendly and helpful."

Reviewed on 2025/8/17

Congress Plaza Hotel
The Wade

The Wade

4.5 out of 5
644 N Lake Shore Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is NT$4,529 per night from Sep 1 to Sep 2
NT$4,529
NT$5,317 total
Sep 1 - Sep 2
includes taxes & fees
8.2/10 Very Good! (1,194 reviews)
"Staff was kind and friendly."

Reviewed on 2025/8/17

The Wade
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St, Chicago, IL
The price is NT$4,819 per night from Sep 3 to Sep 4
NT$4,819
NT$5,657 total
Sep 3 - Sep 4
includes taxes & fees
8.4/10 Very Good! (4,717 reviews)
"Kids really enjoyed the pool. Breakfast was good as well"

Reviewed on 2025/8/17

Embassy Suites by Hilton Chicago Downtown River North
See all 4,562 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 . 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 featuring cbd, a sporting event and a city

Wrigley Field

4.5/5(2,128 reviews)

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

Wrigley Field
Magnificent Mile - River North showing night scenes, a city and signage

Michigan Avenue

4.5/5(332 reviews)

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.

Michigan Avenue
Navy Pier featuring a sunset and rides

Navy Pier

4.5/5(4,870 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.