Oakland Holidays from AU$600

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Your Oakland Holiday

With a tailor-made holiday package to Oakland, you'll spend less time planning and more time simply enjoying this appealing neighbourhood. 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 holiday is easy with Expedia.

Top Holiday Package Deals in Oakland

Price found within the past 48 hours. Click for updated prices.
The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was AU$1,000, price is now AU$600 per person
AU$600
per person
9 Feb - 15 Feb
found 1 day ago
Return flight included
New York (NYC) to Chicago (ORD)
9.2/10 Wonderful! (2,241 reviews)
Everyone was great. A special shout out to Tareka and Nate who worked behind the bar!

Reviewed on 16 Dec 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was AU$2,949, price is now AU$1,659 per person
AU$1,659
per person
9 Feb - 15 Feb
found 1 day ago
Return flight included
New York (NYC) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Excellent stay. Loved everything about this hotel. Definitely coming back.

Reviewed on 18 Dec 2025

theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was AU$1,159, price is now AU$672 per person
AU$672
per person
9 Feb - 15 Feb
found 1 day ago
Return flight included
New York (NYC) to Chicago (ORD)
9/10 Wonderful! (1,001 reviews)
My family and I stayed at The Wit for Thanksgiving and were extremely pleased with the amenities and professionalism of the staff.

Reviewed on 8 Dec 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was AU$1,413, price is now AU$827 per person
AU$827
per person
9 Feb - 15 Feb
found 1 day ago
Return flight included
New York (NYC) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
Great location, clean room and friendly staff!

Reviewed on 14 Dec 2025

Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was AU$1,935, price is now AU$1,172 per person
AU$1,172
per person
9 Feb - 15 Feb
found 1 day ago
Return flight included
New York (NYC) to Chicago (ORD)
9.2/10 Wonderful! (317 reviews)
Room was nice. Service was good.

Reviewed on 17 Dec 2025

Our guide on where to stay in Oakland

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

Our pick of the best Oakland Hotel Deals

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 AU$158 per night from 5 Jan to 6 Jan
AU$158
5 Jan - 6 Jan 2026
includes taxes & fees
8.8/10 Excellent! (3,474 reviews)
Heating was perfect. Nice easy check in and out

Reviewed on 12 Dec 2025

Hilton Chicago/Magnificent Mile Suites
Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown

4 out of 5
10 S Wabash Ave Chicago IL
Fully refundableReserve now, pay when you stay
9.2/10 Wonderful! (2,130 reviews)
Clean room, attentive staff, great lounge!

Reviewed on 15 Dec 2025

Get rates
Silversmith Hotel Chicago Downtown
Club Quarters Hotel Wacker at Michigan, Chicago

Club Quarters Hotel Wacker at Michigan, Chicago

4 out of 5
75 E Wacker Dr Chicago IL
Fully refundableReserve now, pay when you stay
The price is AU$148 per night from 21 Dec to 22 Dec
AU$148
21 Dec - 22 Dec
includes taxes & fees
8.6/10 Excellent! (1,988 reviews)
Very clean and the staff was wonderful!

Reviewed on 13 Dec 2025

Club Quarters Hotel Wacker at Michigan, Chicago
See all 4,677 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 Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

Frequently asked questions

How much does an Oakland holiday package cost?
Customize your Oakland package from an affordable AU$600. 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 holiday 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 holiday 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 fulfil those holiday 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 holiday?
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 holiday.
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 organising a fancy romantic getaway or a budget solo adventure, check out our holiday packages today.
Can I choose my airline with an Oakland Expedia holiday 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 holiday.
If I'm not able to travel, can I cancel my Oakland holiday package?
It's hard to predict what the future holds, so it's good to know that you can change or cancel your Oakland holiday 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

Navy Pier

Navy Pier

A waterfront entertainment strip with fun diversions for both young and old, with shops, restaurants and even a Ferris wheel.

Navy Pier
United Center

United Center

Catch an event at United Center during your trip to Chicago. Amble around this vibrant area's lakeside or experience its acclaimed art galleries.

United Center
Chicago Riverwalk featuring a bay or harbour, a city and a river or creek

Chicago Riverwalk

Stroll along the waterfront of the Chicago River to pass some of the city’s most appealing attractions and appreciate how a once grim area has been successfully revamped.

Chicago Riverwalk

Activities

Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

AU$61
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
Art Institute of Chicago

Art Institute of Chicago

AU$60
per adult
92% of travellers recommend
Art Institute of Chicago
Lineup with Capone and Dillinger!

Chicago Crime and Mob Bus Tour

AU$67
per adult
92% of travellers recommend
Chicago Crime and Mob Bus Tour
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.