Oakland Vacation Packages

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Top Holiday Package Deals in Oakland

Price found within the past 48 hours. Click for updated prices.
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul. 21 - Jul. 27
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
8.6/10 Excellent! (1,480 reviews)
Hated that the gps kept taking me to the back of the hotel which made hard to find

Reviewed on May 3, 2024

Fairmont Chicago at Millennium Park Gold Experience

Fairmont Chicago at Millennium Park Gold Experience

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul. 21 - Jul. 27
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
9.2/10 Wonderful! (96 reviews)
Outstanding service and facility.

Reviewed on Jan. 10, 2024

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul. 21 - Jul. 27
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
9.4/10 Exceptional! (679 reviews)
There is such loud traffic nearby. I could not sleep for one minute.

Reviewed on May 13, 2024

Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul. 21 - Jul. 27
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
9.2/10 Wonderful! (1,005 reviews)
We have a plenty staying at this hotel has the best locations and restaurant is so good

Reviewed on May 13, 2024

Millennium Knickerbocker Chicago

Millennium Knickerbocker Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul. 28 - Aug. 4
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
7.8/10 Good! (1,745 reviews)
The staff is very friendly and helpful. This is my hotel of choice when I’m traveling to Chicago. Chiquita at the front desk is always helpful and very professional.

Reviewed on May 14, 2024

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

4 out of top 10 points of interest in this area

Known for its fascinating museums, stunning river views, and gorgeous architecture, there's plenty to explore in Downtown Chicago. Top attractions like Grant Park and Navy Pier are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.

Find hotel + flight trips in Downtown Chicago

Oakland Hotel Deals

Congress Plaza Hotel
Congress Plaza Hotel
3.5 out of 5
520 South Michigan Avenue, Chicago, IL
7.6/10 Good! (6,732 reviews)
"A great and easy hotel to stay in for a short trip to Chicago! This location had everything you needed even an oven and microwave to use!"

Reviewed on May 13, 2024

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Congress Plaza Hotel
Warwick Allerton - Chicago
Warwick Allerton - Chicago
4 out of 5
701 North Michigan Avenue, Chicago, IL
7.6/10 Good! (2,578 reviews)
"Very clean"

Reviewed on May 14, 2024

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Warwick Allerton - Chicago
The Westin Michigan Avenue Chicago
The Westin Michigan Avenue Chicago
4.5 out of 5
909 North Michigan Ave, Chicago, IL
Fully refundableReserve now, pay when you stay
8.6/10 Excellent! (1,000 reviews)
"We had a wonderful time in Chicago! This property was located in such a great area and easy walking to all the things we wanted to do...and eat. :)"

Reviewed on May 10, 2024

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The Westin Michigan Avenue Chicago
See all 4,085 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.

Explore other types of vacation packages

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does an Oakland vacation package cost?
Customize your Oakland package from an affordable CA $1,281. 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

Image for Wrigley Field

Wrigley Field

4.5/5(158 reviews)

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

Wrigley Field
Image for McCormick Place

McCormick Place

4.5/5(141 reviews)

Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.

McCormick Place
Image for Six Flags Great America

Six Flags Great America

4.5/5(5 reviews)

Spend a day at this sprawling theme park to enjoy an array of thrilling roller coaster rides, a water park and entertainment for kids of all ages.

Six Flags Great America

Things to do

Image for Odyssey Lake Michigan Premier Dinner Cruise

Odyssey Lake Michigan Premier Dinner Cruise

CA $311
Per adult
76% of travellers recommend
Odyssey Lake Michigan Premier Dinner Cruise
Image for Chicago Architecture Center River Cruise aboard Chicago's First Lady

Chicago Architecture Center River Cruise aboard Chicago's First Lady

CA $73
Per adult
92% of travellers recommend
Chicago Architecture Center River Cruise aboard Chicago's First Lady
See all activities in Chicago

Other vacations you might like

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