Oakland Holidays from £873

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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.
Bluegreen Vacations Hotel Blake, Ascend Resort Collection

Bluegreen Vacations Hotel Blake, Ascend Resort Collection

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
3 Oct - 7 Oct
found 7 hours ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.6/10 Exceptional! (1,005 reviews)
The room was great The staff was very friendly free coffee in the morning was nice

Reviewed on 14 Aug 2025

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
17 Sept - 22 Sept
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9/10 Wonderful! (654 reviews)
Loved everything. We stayed at Fultom before and the River North is really good as well. Only difference slighty better views with sky terrace at Fulton and from pool side and indoor spa. Riverside has game room which my kid and I enjoyed tons of chess. Great place hard to pick one both has pros and really no cons. Look forward to our next stay. Higher floor the better witb views from the room. Great staff as well!

Reviewed on 15 Aug 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
17 Sept - 22 Sept
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (1,679 reviews)
One of the best hotels. I will definitely stay here again.

Reviewed on 16 Aug 2025

Chicago Athletic Association, a Hyatt Hotel

Chicago Athletic Association, a Hyatt Hotel

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
17 Sept - 22 Sept
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9/10 Wonderful! (1,001 reviews)
Fantastic place to stay….close to the lake, shopping and dining.

Reviewed on 14 Aug 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
17 Sept - 22 Sept
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Nothing beats a stay at the Park Hyatt when in Chicago!

Reviewed on 10 Aug 2025

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

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 £116 per night from 1 Sept to 2 Sept
£116
1 Sept - 2 Sept
includes taxes & fees
7.8/10 Good! (8,984 reviews)
"Great location! Quiet and comfortable room. Love the history and architectural charm of this classic Chicago Hotel! Exercise room was the best equipped I've used!"

Reviewed on 14 Aug 2025

Congress Plaza Hotel
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is £169 per night from 4 Sept to 5 Sept
£169
4 Sept - 5 Sept
includes taxes & fees
8.4/10 Very Good! (1,852 reviews)
"Pleasant experience. Accommodations were good. Surrounding area was convenient to shopping, eateries and p parks."

Reviewed on 13 Aug 2025

Palmer House a Hilton Hotel
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3 out of 5
10 E Grand Ave, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is £132 per night from 25 Aug to 26 Aug
£132
25 Aug - 26 Aug
includes taxes & fees
8.4/10 Very Good! (3,675 reviews)
"Hotel was quiet. Room was comfortable. Location was great."

Reviewed on 13 Aug 2025

Hilton Garden Inn Chicago Downtown/Magnificent Mile
See all 4,546 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
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Frequently asked questions

How much does an Oakland travel package cost?
Maybe less than you might think — from just £873, 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.

Popular places to visit

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

Wrigley Field

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

Wrigley Field
Magnificent Mile - River North which includes street scenes, signage and night scenes

Michigan Avenue

You can find the perfect gifts to bring home when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Michigan Avenue
Navy Pier

Navy Pier

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier

Things to do

River tour boat in Chicago

Architecture River Tour

£31
per adult
96% of travellers recommend
Architecture River Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

£33
per adult
96% of travellers recommend
Chicago By Night River & Lake Cruise
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

£30
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture 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. Flight-inclusive packages are ATOL protected.