Oakland Holidays

  • Plan, book, travel with confidence

  • Better together

    Save up to €900 when you book a flight and hotel together*

  • Find the right fit

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

  • Rest easy

    Plan, book, and manage your trip all in one place
Price found within the past 48 hours. Click for updated prices.
  • Bar (on property)
    Jul 16 - Jul 20

    The Whitehall Hotel, BW Premier Collection + Flight

    Downtown Chicago
    4 nights
    3.5 star property
    8.4/10 - Very good (3,933 reviews)
    "Beautiful old hotel in great area of Chicago. Steps to great restaurants, and shopping! I had a lower floor room and my only comment was related to noise from the plumbing or A/C system that did keep me up part of the night. The staff was great!"
    Reviewed June 8, 2026
    Return • Dublin (DUB) - Chicago (ORD)
    DUB - ORD • Direct ORD - DUB • Direct
    €1,289
    €1,009
    per traveller
    found 1 day ago
    The Whitehall Hotel, BW Premier Collection
  • Lobby
    Jul 9 - Jul 13

    Hotel Felix River North/Magnificent Mile + Flight

    Downtown Chicago
    4 nights
    4.0 star property
    8.2/10 - Very good (2,778 reviews)
    "Hotel Felix was in a fantastic location. The staff were very friendly. Our room on the 9th floor with 2 double beds was small, with only a mini fridge. The curtains were old and difficult to open and close. The WiFi would drop or was very slow. The television also provided issues, turning off or to the starting screen, multiple times. The hotel offered only coffee/tea and fresh fruit until 9am. The staff made our stay more enjoyable."
    Reviewed June 8, 2026
    Return • Dublin (DUB) - Chicago (ORD)
    DUB - ORD • Direct ORD - DUB • Direct
    €1,414
    €1,039
    per traveller
    found 1 day ago
    Hotel Felix River North/Magnificent Mile
  • Lobby sitting area
    Jul 16 - Jul 20

    Hotel Saint Clair- Magnificent Mile + Flight

    Downtown Chicago
    4 nights
    4.0 star property
    8.4/10 - Very good (1,967 reviews)
    "The staff was able to help us get a room earlier than the check-in time."
    Reviewed June 9, 2026
    Return • Dublin (DUB) - Chicago (ORD)
    DUB - ORD • Direct ORD - DUB • Direct
    €1,427
    €1,050
    per traveller
    found 1 day ago
    Hotel Saint Clair- Magnificent Mile
  • Smart TV
    Jul 16 - Jul 20

    Level Chicago Fulton Market + Flight

    Downtown Chicago
    4 nights
    4.0 star property
    9.2/10 - Wonderful (493 reviews)
    "Fully equipmet"
    Reviewed June 2, 2026
    Return • Dublin (DUB) - Chicago (ORD)
    DUB - ORD • Direct ORD - DUB • Direct
    €1,600
    €1,196
    per traveller
    found 1 day ago
    Level Chicago Fulton Market
  • Breakfast and dinner served
    Jul 16 - Jul 20

    Omni Chicago Hotel + Flight

    Downtown Chicago
    4 nights
    4.5 star property
    9.2/10 - Wonderful (1,797 reviews)
    "beautiful room city view excellent location quiet and comfortable"
    Reviewed June 9, 2026
    Return • Dublin (DUB) - Chicago (ORD)
    DUB - ORD • Direct ORD - DUB • Direct
    €1,437
    €1,108
    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 €140 per night from 29 Jun to 30 Jun
€140
29 Jun - 30 Jun
includes taxes & fees
8/10 Very Good! (10,224 reviews)
"This is a very nice hotel in an absolutely ideal part of downtown Chicago. Many areas an easy, lovely walk away and those further out a quick cab ride or train ride. The room was clean and comfortable."

Reviewed on 9 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 €125 per night from 28 Jun to 29 Jun
€125
28 Jun - 29 Jun
includes taxes & fees
7.8/10 Good! (1,545 reviews)
"Our room was spacious and very clean"

Reviewed on 8 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 €157 per night from 28 Jun to 29 Jun
€157
28 Jun - 29 Jun
includes taxes & fees
8.8/10 Excellent! (2,638 reviews)
"Upsetting that I was given a room that I had to haul all of my luggage up 16 steep stairs. No other room options. I had reserved a room months in advance. The front desk lady said a few stairs, which I found odd being that there is an elevator. Beware…the top floor is by stairs only! Front desk lady ..."

Reviewed on 9 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.

Frequently asked questions

How much does an Oakland holiday package cost?
Customize your Oakland package from an affordable . 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.

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
Chicago Skyline, Chicago, Illinois shows amazing architecture in panoramic format

Naval Base Great Lakes

After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area.

Naval Base Great Lakes
Navy Pier

Navy Pier

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

Navy Pier

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

€23
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skyline Queen showcasing the Chicago Skyline!

Chicago Sightseeing River and Lake Cruise

€37
per adult
100% of travellers recommend
Chicago Sightseeing River and Lake Cruise
Art Institute of Chicago

Art Institute of Chicago

€34
per adult
92% of travellers recommend
Art Institute of Chicago
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.