Oakland Holidays from £674
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Your Oakland Holiday
Book a customized holiday package to Oakland and experience the wonders of this neighbourhood from morning till night. From its nature and walking to its unique vibe and personality, there are plenty of fantastic reasons to visit Oakland. Not sure what to see and do during your trip to Oakland? Nearby attractions like University of Chicago, Soldier Field and John G. Shedd Aquarium are great places to start. No matter what your ideal Oakland holiday looks like, you can make it a reality with Expedia.
Price found within the past 48 hours. Click for updated prices.
Chicago Lake Shore Hotel
Kenwood
£674
per person
26 Nov - 1 Dec
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
7/10 Good! (1,004 reviews)
Great location. Very clean-looks refurbished. The staff is amazing-very helpful & they try to help you have a good experience!
Reviewed on 15 Sept 2026
Level Chicago Fulton Market
Downtown Chicago
£827
per person
10 Dec - 15 Dec
found 1 day ago
Return direct flight included
Glasgow (GLA) to Chicago (ORD)
9.2/10 Wonderful! (561 reviews)
I was excited to stay here and I truly never leave negative reviews, but others should avoid making the same mistake I did paying for this hotel. The staff was very nice and the property looks nice, but it's extremely overpriced. Don't be fooled into paying more for the amenities because none of them work!!
- There was no deadbolt on the hotel room door. If I'm paying $200+ a night, I shouldn't have to barricade the door every night. The balcony door was also unlocked when I arrived.
- No hangers or lotion in the room.
- Sauna and hot tub were "closed for cleaning" for three full days of my stay.
- I needed to consent to a background check in order to confirm my reservation. I called to confirm this because I found it incredibly invasive and unnecessary. Turns out it was real. Wild. Also, there is a $200 PER NIGHT deposit upon arrival. I travel often and I've never seen that before.
- Nonexistent water pressure in the shower. And someone's trash was left in the shower when I arrived.
- Washing machine reeked of mold and was therefore unusable.
- TV and oven didn't work
Overall, if this hotel was $60-80 a night, it'd be great. But, it's a total waste of money. Again, the staff was very nice and helpful (I didn't even include the things they resolved for me during my stay) but I'm not going to bother them about every single amenity that is supposedly included with the room. The things that would make this hotel worth the money are unfortunately all a facade.
Reviewed on 15 Sept 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
River Hotel
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
£140
20 Sept - 21 Sept
includes taxes & fees
8.8/10 Excellent! (5,459 reviews)
"Location was perfect. Staff were nice."
Reviewed on 16 Sept 2026
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
£134
20 Sept - 21 Sept
includes taxes & fees
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
£153
27 Sept - 28 Sept
includes taxes & fees
8/10 Very good! (10,257 reviews)
"The Congress Plaza Hotel is old, but affordable. If you're not after a high level of comfort and just need a clean and conveniently located place to sleep that is probably more affordable than anywhere else in downtown Chicago, then this hotel should do nicely for you."
Reviewed on 16 Sept 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 travel package cost?
Maybe less than you might think — from just £674, in fact! By bundling hotels, flights and car rentals into a customized travel package, your Oakland escape is only clicks away.
If I'm not able to travel, can I cancel my Oakland travel package?
Yes you can, and we're here to help. You may be able to cancel or amend your Oakland travel package for free within 24 hours of booking. But you may be charged a fee by your hotel, airline or car rental company for older bookings. If life gets in the way of your holiday, have a look at our Customer Service Portal for more information.
How do I get a cheap travel package to Oakland?
One of the easiest ways to save cash (and time) is to bundle your bookings with Expedia. Hotels, flights, activities and rental cars — we've got them all covered. Pick the combination that suits your style and see your savings pile up. Of course, a travel package is never a one-size-fits-all. That's why we offer over 550 airlines and 1,000,000 hotel options across the globe, which lets you customize your Oakland holiday.
Does Expedia offer Book Now, Pay Later Oakland holidays?
Expedia has partnered with online lender Klarna to make your next trip easier on your budget. Paying by instalment means you can spread the costs of your next dream escape, leaving you with more money to play with while you're away. Klarna has several payment plans to choose from, so you're sure to find something that works with your budget. Browse these flexible payment options:
- Pay monthly holidays: Klarna offers convenient monthly payment plans that fit all budgets, so you can jet away on that well-earned holiday sooner.
- Pay in instalments holidays: If you'd like to pay off your escape across multiple transactions, holidays paid in instalments might be right for your Book Now, Pay Later holiday through Klarna.
- Low deposit holidays: Clicking on the "book now" button is easier with this payment plan. Just put down a small deposit on your booking and then get on your way.
Where should I stay in Oakland?
Most people who travel to Oakland include Millennium Park and Wrigley Field on their bucket lists. Why not consider a hotel right near these great attractions?
What are the top hotels in Oakland?
Get your escape off to a fantastic start by booking a stay at Hyatt Regency Chicago. It's one of most popular properties in Oakland. Another welcoming option is The Godfrey Hotel Chicago.
How far in advance should I book my Oakland holiday?
Travellers can normally look up international flights on Expedia up to 12 months prior to departure. Booking last minute? With a stroke of luck, it's still possible to score a cheaper ticket just weeks before your flight.
What does an Expedia Oakland travel package include?
Expedia has all you need to book your Oakland trip, but what your package looks like is your choice. Choose from any combination of flights, hotels and rental cars. In search of some tours or experiences to keep you entertained? Once you've made your booking, you can add them too. No matter your style or budget, there's a package to suit your needs.
What should I know before booking an Oakland travel package?
When you book your flights, hotels and car rentals together, you'll walk away with amazing discounts. Whether you're planning an outdoor getaway in a chalet or prefer to stay in an upscale city hotel, Expedia can make it happen for less.
Can I choose my airline with an Oakland Expedia travel package?
Yes — and it's easy too. Expedia has access to more than 550 partner airlines worldwide. Our travel packages give you the flexibility to take your pick of available flights, hotels and activities that suit you.
Things to do
Chicago: Willis Tower Skydeck and The Ledge Ticket
£35
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
£18
per adult
90% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.