Oakland Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 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.
  • View from property
    Jul 1 - Jul 4

    The Talbott, Autograph Collection + Flight

    Downtown Chicago
    3 nights
    4.5 star property
    9.4/10 - Exceptional (117 reviews)
    "We thoroughly enjoyed our stay. The location was excellent, conveniently close to everything we needed. The room was spacious and spotless. The breakfast was fantastic, offering a wide variety of options to choose from. "
    Reviewed May 17, 2026
    Roundtrip • Toronto (YTZ) - Chicago (ORD)
    YTZ - ORD • Nonstop ORD - YKF • Nonstop
    CA $1,162
    CA $787
    per traveller
    found 1 day ago
    The Talbott, Autograph Collection
  • Smart TV
    Aug 2 - Aug 8

    Level Chicago Fulton Market + Flight

    Downtown Chicago
    6 nights
    4.0 star property
    9.2/10 - Wonderful (488 reviews)
    "Room was not cleaned/ towels weren't replaced for the duration of our 3 night stay which I found rather peculiar. They also only provided 1 key for our room. I had believed it was common practice to provide 2. Other than that, the room was clean when we arrived, the bedding was comfortable, and the gym was lovely."
    Reviewed May 22, 2026
    Roundtrip • Toronto (YTZ) - Chicago (MDW)
    YTZ - MDW • Nonstop MDW - YTZ • Nonstop
    CA $2,919
    CA $1,699
    per traveller
    found 1 day ago
    Level Chicago Fulton Market
  • Full-size fridge, microwave, oven, stovetop
    Aug 2 - Aug 8

    Level Chicago – Old Town + Flight

    Downtown Chicago
    6 nights
    4.0 star property
    9.0/10 - Wonderful (481 reviews)
    "Nice and big"
    Reviewed May 24, 2026
    Roundtrip • Toronto (YTZ) - Chicago (MDW)
    YTZ - MDW • Nonstop MDW - YTZ • Nonstop
    CA $2,741
    CA $1,702
    per traveller
    found 1 day ago
    Level Chicago – Old Town
  • Lobby
    Aug 6 - Aug 9

    JW Marriott Chicago + Flight

    Downtown Chicago
    3 nights
    4.5 star property
    9.2/10 - Wonderful (1,003 reviews)
    Roundtrip • Toronto (YTZ) - Chicago (ORD)
    YTZ - ORD • Nonstop ORD - YYZ • Nonstop
    CA $1,405
    CA $950
    per traveller
    found 1 day ago
    JW Marriott Chicago
  • Terrace/patio
    Aug 6 - Aug 9

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

    Downtown Chicago
    3 nights
    4.0 star property
    9.4/10 - Exceptional (2,515 reviews)
    "Great views of the lake, staff very helpful the rooms were clean and comfortable. Would stay there again!"
    Reviewed May 26, 2026
    Roundtrip • Toronto (YTZ) - Chicago (ORD)
    YTZ - ORD • Nonstop ORD - YYZ • Nonstop
    CA $1,495
    CA $1,049
    per traveller
    found 1 day ago
    Sable at Navy Pier Chicago, Curio Collection by Hilton

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

Oakland Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
The price is CA $187 per night from May 27 to May 28
CA $187
CA $222 total
May 27 - May 28
includes taxes & fees
8/10 Very Good! (10,141 reviews)
"Everything was perfect. Great customer service."

Reviewed on May 25, 2026

Congress Plaza Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
The price is CA $330 per night from Jun 16 to Jun 17
CA $330
CA $432 total
Jun 16 - Jun 17
includes taxes & fees
9.4/10 Exceptional! (4,252 reviews)
"This hotel is amazing, Great location, super clean and stuff was kind, informative and very respectful! The breakfast was well organized considering the amount people served! Not a missing items at any moment! The rooftop bar was very pleasant place to sit and chill. Strongly recommended!!!"

Reviewed on May 26, 2026

Hotel Riu Plaza Chicago
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 CA $263 per night from Jun 3 to Jun 4
CA $263
CA $312 total
Jun 3 - Jun 4
includes taxes & fees
7.8/10 Good! (1,477 reviews)
"El staff es un poco malhumorado Cuando tienes preguntas, la mayoria. Los tickets de comida o drinks gratis en realidad son descuentos, tienes q pagar. Excepto por el desayuno, solo use una vez cada uno, no me agrado, sali afuera. Regrese todos los demas tickets al hacer checkout. Gracias"

Reviewed on May 26, 2026

The Chicago Hotel Collection - Magnificent Mile
See all 4,604 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 Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does an Oakland vacation 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 vacation 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 vacation 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 fulfill those vacation 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 vacation?
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 vacation.
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 organizing a fancy romantic getaway or a budget solo adventure, check out our vacation packages today.
Can I choose my airline with an Oakland Expedia vacation 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 vacation.
If I'm not able to travel, can I cancel my Oakland vacation package?
It's hard to predict what the future holds, so it's good to know that you can change or cancel your Oakland vacation 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.

Discover the most popular places to visit in Oakland

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

CA $37
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

CA $60
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
Flyover in Chicago

Flyover in Chicago

CA $31
per child
98% of travellers recommend
Flyover in 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.