Oakland Holidays

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

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    Packages with flights are ATOL protected

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.
  • 2 restaurants; breakfast, lunch and dinner served
    Jul 30 - Aug 3

    LondonHouse Chicago, Curio Collection by Hilton + Flight

    Downtown Chicago
    4 nights
    4.5 star property
    9.4/10 - Exceptional (3,730 reviews)
    "We stayed in this hotel in our daughter's wedding weekend. It was wonderful, the river and city view from our 18th story room was spectacular. I recommend it to.all ages."
    Reviewed June 7, 2026
    Return • Dublin (DUB) - Chicago (ORD)
    DUB - ORD • 1 stop ORD - DUB • 1 stop
    £1,713
    £1,296
    per traveller
    found 1 day ago
    LondonHouse Chicago, Curio Collection by Hilton
  • Terrace/patio
    Jul 30 - Aug 3

    Sable at Navy Pier Chicago, Curio Collection by Hilton + Flight

    Downtown Chicago
    4 nights
    4.0 star property
    9.4/10 - Exceptional (2,535 reviews)
    "This is an amazing place. Everything you can think of all under 1 roof. My hotel view was amazing. I am looking forward to coming annually."
    Reviewed June 8, 2026
    Return • Dublin (DUB) - Chicago (ORD)
    DUB - ORD • 1 stop ORD - DUB • 1 stop
    £1,877
    £1,398
    per traveller
    found 1 day ago
    Sable at Navy Pier Chicago, Curio Collection by Hilton
  • Full-sized fridge, microwave, oven, stovetop
    Aug 20 - Aug 25

    Level Chicago – Old Town + Flight

    Downtown Chicago
    5 nights
    4.0 star property
    9.0/10 - Wonderful (490 reviews)
    "Great location to the red line and buses. Our kids loved the game room, pool, and basketball court."
    Reviewed June 9, 2026
    Return • London (LHR) - Chicago (ORD)
    LHR - ORD • Direct ORD - LHR • Direct
    £1,964
    £1,495
    per traveller
    found 16 hours ago
    Level Chicago – Old Town
  • Dinner served
    Jul 30 - Aug 4

    Kimpton Gray Hotel by IHG + Flight

    Downtown Chicago
    5 nights
    4.5 star property
    9.4/10 - Exceptional (1,000 reviews)
    "Nice staff clean room would stay again."
    Reviewed June 6, 2026
    Return • Dublin (DUB) - Chicago (ORD)
    DUB - ORD • 1 stop ORD - DUB • 1 stop
    £2,062
    £1,606
    per traveller
    found 1 day ago
    Kimpton Gray Hotel by IHG
  • Breakfast and dinner served
    Jul 30 - Aug 3

    Omni Chicago Hotel + Flight

    Downtown Chicago
    4 nights
    4.5 star property
    9.2/10 - Wonderful (1,800 reviews)
    "Old hotel and rooms. All the outlets in our room were titled and so hard to plug things in them. The outlets near the nightstands on either sides can’t accommodate a charger because they’re stuck on the side of the nightstand between it and the side of the bed. Hairdryer so old and didn’t work. Check in was exactly at 4, they weren’t lenient when I showed up at 2:40."
    Reviewed June 10, 2026
    Return • Dublin (DUB) - Chicago (ORD)
    DUB - ORD • 1 stop ORD - DUB • 1 stop
    £1,701
    £1,330
    per traveller
    found 1 day ago
    Omni Chicago Hotel

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 £121 per night from 29 Jun to 30 Jun
£121
29 Jun - 30 Jun
includes taxes & fees
8/10 Very Good! (10,237 reviews)
"First, this is a historic hotel, and visitors should be aware that the rooms reflect the historic vibe. If you want modern, you need to stay down the street at the Hilton. The rooms were very cute and clean, and the tiling in the bathroom was beautiful. The hotel has a prime location with easy walking ..."

Reviewed on 10 Jun 2026

Congress Plaza Hotel
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
The price is £142 per night from 1 Jul to 2 Jul
£142
1 Jul - 2 Jul
includes taxes & fees
7.8/10 Good! (1,551 reviews)
"Enjoyed our stay"

Reviewed on 10 Jun 2026

The Chicago Hotel Collection - Magnificent Mile
Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
The price is £136 per night from 28 Jun to 29 Jun
£136
28 Jun - 29 Jun
includes taxes & fees
8.8/10 Excellent! (2,642 reviews)
"The door to the restroom kept getting jammed and wouldn’t close properly. Our room also had no WiFi… the staff couldn’t figure out why it wasn’t working."

Reviewed on 10 Jun 2026

Hyatt Regency O'Hare Chicago
See all 4,575 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 , 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

4.5/5(40 reviews)

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

Wrigley Field
Navy Pier

Navy Pier

4/5(127 reviews)

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

Navy Pier
Millennium Park

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

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

£18
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
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
Chicago C3® : Save on admission to your choice of 3 top attractactions

Chicago C3® by CityPASS®

£81
per adult
88% of travellers recommend
Chicago C3® by CityPASS®
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.