Oakland Holidays from £1,007

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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.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was £1,321, price is now £1,007 per person
£1,007
per person
9 Jul - 15 Jul
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
8.2/10 Very Good! (2,636 reviews)
The staff were extremely impressed and helpful. Help me with restaurant choices, where to go for tours. Only thing I regretted was not packing the proper clothes for the chance of weather. It was my personal birthday present to me and I did enjoyed myself.

Reviewed on 24 Apr 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was £1,810, price is now £1,241 per person
£1,241
per person
9 Jul - 15 Jul
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (455 reviews)
Great staff, full kitchen and living room, good location, friendly people, safe. I would stay here again.

Reviewed on 23 Apr 2026

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was £1,793, price is now £1,244 per person
£1,244
per person
16 Jun - 21 Jun
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9/10 Wonderful! (3,280 reviews)
Really good spot and location. Staff was super helpful and nice.

Reviewed on 22 Apr 2026

Hilton Chicago

Hilton Chicago

4 out of 5
Downtown Chicago
Price was £1,495, price is now £1,125 per person
£1,125
per person
9 Jul - 15 Jul
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
8.6/10 Excellent! (2,742 reviews)
Staff were nice. Hotel was at maximum capacity per security and it just felt overwhelming and claustrophobic at times.

Reviewed on 22 Apr 2026

Holiday Inn Express Chicago - Magnificent Mile by IHG

Holiday Inn Express Chicago - Magnificent Mile by IHG

2.5 out of 5
Downtown Chicago
Price was £1,431, price is now £1,113 per person
£1,113
per person
9 Jul - 15 Jul
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
8.4/10 Very Good! (1,018 reviews)
Clean comfortable room , staff helpful, breakfast standard and location good

Reviewed on 24 Apr 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

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 £100 per night from 26 Apr to 27 Apr
£100
26 Apr - 27 Apr
includes taxes & fees
8/10 Very Good! (10,133 reviews)
wifi wouldn’t connect, when we called the front desk to ask (I had work I needed to do, and specifically checked before booking that the room included wifi) was met with attitude to “just connect” even though the wifi network wasn’t visible or available. also, you have no control over the temperature ...

Reviewed on 24 Apr 2026

Congress Plaza Hotel
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
The price is £104 per night from 25 May to 26 May
£104
25 May - 26 May
includes taxes & fees
8.8/10 Excellent! (5,123 reviews)
Wonderful and helpful sstaff. Excellent location

Reviewed on 24 Apr 2026

River Hotel
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
111 W Huron St Chicago IL
Fully refundableReserve now, pay when you stay
The price is £98 per night from 29 Apr to 30 Apr
£98
29 Apr - 30 Apr
includes taxes & fees
8.2/10 Very Good! (2,636 reviews)
The staff were extremely impressed and helpful. Help me with restaurant choices, where to go for tours. Only thing I regretted was not packing the proper clothes for the chance of weather. It was my personal birthday present to me and I did enjoyed myself.

Reviewed on 24 Apr 2026

Hotel Felix River North/Magnificent Mile
See all 4,655 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
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Family Friendly Holidays

Frequently asked questions

How much does an Oakland travel package cost?
Maybe less than you might think — from just £1,007, 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

Wrigley Field

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

Wrigley Field
Navy Pier

Navy Pier

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

Navy Pier
Scene of Chicago street bridge with traffic among modern buildings of Downtown Chicago at Michigan avenue in Chicago, Illinois, United States, Business and Modern Transportation concept

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

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

£20
per adult
88% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

£32
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
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.