Oakland Holidays

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  • Better together

    Save up to Rp173.195 when you book a flight and hotel together*

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

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

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

4 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

Top hotels in Oakland

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 Rp2.900.794 per night from 27 Mar to 28 Mar
Rp2.900.794
Rp3.405.411 total
27 Mar - 28 Mar
includes taxes & fees
8/10 Very Good! (9,905 reviews)
Good

Reviewed on 2 Mar 2026

Congress Plaza Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
The price is Rp1.905.525 per night from 4 Mar to 5 Mar
Rp1.905.525
Rp2.712.237 total
4 Mar - 5 Mar
includes taxes & fees
9.4/10 Exceptional! (3,443 reviews)
The property was amazing the location was very convenient. I will recommend this hotel to anyone and everyone. I enjoy my day. Staff was amazing from check in to the bar. Thanks for a wonderful stay.

Reviewed on 3 Mar 2026

Hotel Riu Plaza Chicago
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 Rp1.862.227 per night from 5 Mar to 6 Mar
Rp1.862.227
Rp2.186.069 total
5 Mar - 6 Mar
includes taxes & fees
8.6/10 Excellent! (5,711 reviews)
Love the hotel just wish the pool water was warmer

Reviewed on 2 Mar 2026

Embassy Suites by Hilton Chicago Downtown River North
See all 4,707 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 holiday 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 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.

Popular places to visit

Wrigley Field featuring a city, a sporting event and city views

Wrigley Field

4.5/5(40 reviews)

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

Wrigley Field
Millennium Park which includes autumn colours, modern architecture and street scenes

Millennium Park

4.5/5(147 reviews)

A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.

Millennium Park
Grant Park showing a garden and night scenes

Grant Park

4.5/5(96 reviews)

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

Things to do

Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

Rp740.256
per adult
98% of travellers recommend
Skydeck - Willis Tower Admission
Art Institute of Chicago

Art Institute of Chicago

Rp672.960
per adult
92% of travellers recommend
Art Institute of Chicago
Flyover in Chicago

Flyover in Chicago

Rp639.648
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.