Oakland Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $1,096 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Top Holiday Package Deals in Oakland

Price found within the past 48 hours. Click for updated prices.
Chicago Marriott Suites Deerfield

Chicago Marriott Suites Deerfield

4 out of 5
Price was CA $827, price is now CA $608 per person
CA $608
per person
May 14 - May 18
found 4 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.6/10 Excellent! (1,000 reviews)
I booked this property after a day at O'Hare airport and multiple flight cancellations. I was greeted and checked in efficiently, had a drink and dinner and retired to a very comfortable and clean room. Breakfast the next day consusted of an excellent omelet. Overall a very comfortable and well appointed hotel. Thank you!

Reviewed on Mar 16, 2026

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 CA $2,222, price is now CA $1,421 per person
CA $1,421
per person
May 31 - Jun 3
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.4/10 Exceptional! (2,427 reviews)
Great place to stay

Reviewed on Apr 7, 2026

Sports Illustrated Resorts Chicago

Sports Illustrated Resorts Chicago

3.5 out of 5
Downtown Chicago
Price was CA $1,954, price is now CA $1,324 per person
CA $1,324
per person
May 31 - Jun 3
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.2/10 Wonderful! (1,409 reviews)
Very friendly staff, great location.

Reviewed on Apr 6, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was CA $1,999, price is now CA $1,393 per person
CA $1,393
per person
Jun 12 - Jun 16
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.2/10 Wonderful! (436 reviews)
Great location! Easy parking and the rooms were gorgeous! We will definitely stay here next time we visit Chicago

Reviewed on Apr 10, 2026

Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
Price was CA $2,415, price is now CA $1,715 per person
CA $1,715
per person
May 20 - May 27
found 12 hours ago
Roundtrip flight included
Toronto (YTZ) to Chicago (ORD)
9.2/10 Wonderful! (371 reviews)
I loved they had breakfast, lunch and dinner. They also had an option if you wanted to get drinks, and snacks before heading up. The air conditioning keep the room cool.

Reviewed on Mar 27, 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

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 CA $159 per night from Apr 26 to Apr 27
CA $159
CA $187 total
Apr 26 - Apr 27
includes taxes & fees
8/10 Very Good! (10,081 reviews)
Good in general

Reviewed on Apr 11, 2026

Congress Plaza Hotel
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $190 per night from Apr 26 to Apr 27
CA $190
CA $223 total
Apr 26 - Apr 27
includes taxes & fees
9/10 Wonderful! (4,100 reviews)
Recommend packing light if you self-park and walk to the hotel!

Reviewed on Apr 11, 2026

Hilton Chicago/Magnificent Mile Suites
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
Fully refundableReserve now, pay when you stay
The price is CA $215 per night from Apr 19 to Apr 20
CA $215
CA $253 total
Apr 19 - Apr 20
includes taxes & fees
8.6/10 Excellent! (5,833 reviews)
Perfect location for a family trip, the hotel amenities were amazing and the staff was very friendly. We did have an issue with having our room serviced during our stay, after a long day out we came back to it still not being serviced, after asking the front desk they said they would put in the request ...

Reviewed on Apr 9, 2026

Embassy Suites by Hilton Chicago Downtown River North
See all 4,672 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.
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 $608. 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

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

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

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

Navy Pier

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $37
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Wendella's Lake and River Architecture Tour

Wendella's Lake and River Architecture Tour

CA $61
per adult
94% of travellers recommend
Wendella's Lake and River Architecture Tour
Flyover in Chicago

Flyover in Chicago

CA $52
per adult
98% of travellers recommend
Flyover in Chicago
See all activities in Chicago
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.