Oakland Holidays from AU$808

Book a Hotel + Flight or Car together to unlock savings

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 Drake

The Drake

4 out of 5
Downtown Chicago
Price was AU$1,183, price is now AU$808 per person
AU$808
per person
16 Nov - 19 Nov
found 20 hours ago
Return flight included
Greensboro (GSO) to Chicago (ORD)
8.8/10 Excellent! (1,291 reviews)
Great location and wonderful staff. Stayed with my family of four and we were able to easily get to all the wonderful sites we wanted to visit. The historic charm and lastige spaces enhanced our stay and our breakfast was superb.

Reviewed on 14 Oct 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was AU$1,974, price is now AU$1,358 per person
AU$1,358
per person
16 Nov - 19 Nov
found 20 hours ago
Return flight included
Raleigh (RDU) to Chicago (ORD)
9.6/10 Exceptional! (1,002 reviews)
The front desk staff was super friendly and helpful. After waking up at 4am to catch an early flight, we were thrilled when they had a room ready for us for early check-in. Hyatt does a great job with room lay-outs. It was obvious that our room was recently renovated with a modern conveniences like motorized shades, a comfy window seat, hidden bar and Nespresso maker, and clean decor. Our friends were staying around the corner at the Ritz and liked our room better.

Reviewed on 14 Oct 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$2,045, price is now AU$1,417 per person
AU$1,417
per person
16 Nov - 19 Nov
found 20 hours ago
Return flight included
Greensboro (GSO) to Chicago (ORD)
9.4/10 Exceptional! (1,716 reviews)
Excellent luxury atmosphere with second to none customer service. The bathroom was very nice. Although the toilet has a slight odor that was unexpected for the high quality room and hotel.

Reviewed on 15 Oct 2025

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was AU$1,193, price is now AU$850 per person
AU$850
per person
16 Nov - 19 Nov
found 20 hours ago
Return flight included
Greensboro (GSO) to Chicago (ORD)
9/10 Wonderful! (2,765 reviews)
Hotel was clean and staff was friendly.

Reviewed on 15 Oct 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was AU$1,417, price is now AU$1,025 per person
AU$1,025
per person
16 Nov - 19 Nov
found 20 hours ago
Return flight included
Greensboro (GSO) to Chicago (ORD)
9.4/10 Exceptional! (1,085 reviews)
I loved the hotel, however I would request an inside room next time. It was extremely noisy outside.

Reviewed on 11 Oct 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

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 AU$231 per night from 2 Nov to 3 Nov
AU$231
2 Nov - 3 Nov
includes taxes & fees
8/10 Very Good! (9,398 reviews)
"Was conveniently located"

Reviewed on 13 Oct 2025

Congress Plaza Hotel
Freehand Chicago

Freehand Chicago

4 out of 5
19 East Ohio Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$147 per night from 10 Nov to 11 Nov
AU$147
10 Nov - 11 Nov
includes taxes & fees
7.8/10 Good! (2,475 reviews)
"Room needs to be cleaned a little thoroughly and then repainted but generally, I like the place"

Reviewed on 15 Oct 2025

Freehand Chicago
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$203 per night from 16 Nov to 17 Nov
AU$203
16 Nov - 17 Nov
includes taxes & fees
8.8/10 Excellent! (3,088 reviews)
"Clean rooms, great service."

Reviewed on 13 Oct 2025

Hilton Chicago/Magnificent Mile Suites
See all 4,470 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$808. 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
Millennium Park showing modern architecture, a city and street scenes

Millennium Park

One of Chicago’s main focal points, where locals and visitors flock to see the striking art, architecture and landscape on show.

Millennium Park
Grant Park

Grant Park

Chicago’s front yard is a pretty landscaped park, which is home to public art displays, museums, themed gardens and international music festivals.

Grant Park

Activities

River tour boat in Chicago

Architecture River Tour

AU$74
per adult
96% of travellers recommend
Architecture River Tour
Skydeck Chicago Admission Ticket

Skydeck - Willis Tower Admission

AU$67
per adult
100% of travellers recommend
Skydeck - Willis Tower Admission
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

AU$37
per adult
84% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
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.