Oakland Holidays
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Price found within the past 48 hours. Click for updated prices.
Cambridge Inn on Main
€2,708
per person
17 Dec - 21 Dec
found 17 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.6/10 Exceptional! (74 reviews)
Everything about this hotel was great! A very historic Boutique Hotel that takes you back in time! Each room has a theme of its own which is unique to the period. The owner was very friendly and made sure that I had everything that I needed to make my stay excellent! If you're ever in that area or even doing business in the Madison Wisconsin area you may consider taking an extra half hour to drive to this hotel and stay there. I don't think you'll be disappointed at all as a matter of fact I would be surprised if you didn't like it. I've been in hotels halfway around the world and I must say that next time I'm back in that area I will be staying here!
Reviewed on 4 Oct 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
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.
Magnificent Mile
Shopaholics need look no further this glittering street packed with boutique and luxury shops, famous department stores and cafes.
The Loop
Bordered roughly by the surrounding elevated train circuit, this Chicago neighborhood has restaurants, galleries, parks and a giant silver bean.
River North
Known for its fantastic nightlife, stunning river views and popular shops, there's plenty to explore in River North. Top attractions like Merchandise Mart and Bally's Casino Chicago are major draws. Catch the metro at Merchandise Mart Station or Chicago Station (Brown Line) to see more of the city.
Lincoln Park
Both a neighborhood and a park, this northern Chicago area has gorgeous scenery, residential streets lined with stately homes and extensive shopping and dining.
Top hotels in Oakland
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
€135
1 Nov - 2 Nov
includes taxes & fees
8/10 Very good! (10,192 reviews)
"Old hotel! Front desk wasn’t helpful l, ask for several things and they never showed up. No A.C., coffee pot broken, ran out of toilet paper and towels. No ice in machine, vending machine served hot beverages. Maintenance men were very nice, Christian at the bar was excellent! I’ll never stay there ..."
Reviewed on 6 Oct 2026
River Hotel
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
€170
25 Oct - 26 Oct
includes taxes & fees
8.8/10 Excellent! (5,493 reviews)
"Elevators slow and small and housekeeping is always in them. Housekeeping rude. No lobby store. Rooms small and outdated."
Reviewed on 5 Oct 2026
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
€151
1 Nov - 2 Nov
includes taxes & fees
8/10 Very good! (2,422 reviews)
"The property was in a prime location for access around the city, the staff was friendly and attentive, two things though the housekeeping service didn’t clean my room not once during my stay I stayed for four days, and the bathroom needs ventilation aka a fan. The overall experience was 3.5/5 if ..."
Reviewed on 5 Oct 2026
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 €2,708. 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.
Stay near popular Oakland attractions
41st Street Beach
Why not spend a lazy afternoon at 41st Street Beach during your trip to Chicago? Stroll along the beaches or visit the shops while you're in the area.
Things to do
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.