Oakland Vacations from $1,194
Book a Hotel + Flight or Car together to unlock savings
Your Oakland Vacation
Our vacation packages to Oakland give you endless opportunities to discover new sights, sounds and experiences. And with all of the travel arrangements taken care of, you'll be free to enjoy your city getaway without a worry in the world. During your trip to Oakland, give yourself plenty of time for sightseeing. A fantastic place to start exploring is Walnut Point State Park. Don't put off exploring this city any longer. Your dream Oakland vacation is a few clicks away with Expedia.
The Latest Oakland vacation packages
Price found within the past 48 hours. Click for updated prices.
Illini Inn & Suites Hotel - Rantoul/Gifford/Champaign/Urbana
$1,201
per person
Oct 12 - Oct 15
found 1 day ago
Roundtrip flight included
Charleston (CRW) to Champaign (CMI)
8.8/10 Excellent! (495 reviews)
The property is clearly dated, but it was EXTREMELY clean. Great breakfast! Full including eggs, bacon and french toast.
Reviewed on Aug 10, 2026
Stay near popular Oakland attractions
Walnut Point State Park
8.0/10 (1 review)
You can take time to visit Walnut Point State Park during your travels to Oakland.
Oakland Hotel Deals
Super 8 by Wyndham Mattoon
205 Mcfall Rd Mattoon IL
Fully refundableReserve now, pay when you stay
$67 nightly
$75 total
Aug 24 - Aug 25
Total with taxes and fees
Best Western Heartland Inn
1416 Broadway Avenue East Mattoon IL
Fully refundableReserve now, pay when you stay
$89 nightly
$100 total
Aug 16 - Aug 17
Total with taxes and fees
8.2/10 Very Good! (627 reviews)
"The staff was amazing ! Best Best Western we've ever stayed at."
Reviewed on Aug 12, 2026
Baymont by Wyndham Tuscola
1006 Southline Road Tuscola IL
Fully refundableReserve now, pay when you stay
$72 nightly
$81 total
Aug 23 - Aug 24
Total with taxes and fees
7.6/10 Good! (651 reviews)
"What needs to improve, the choices for breakfast. Be nice to have hot choices like most other places we have stayed. The dog fee is outrageous , I can see a one time fee but Not per night! We will try across the road next time… The pillows were great."
Reviewed on Aug 10, 2026
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.
Find the Best Oakland Vacation Packages
Oakland Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | University Of Illinois Urbana-Champaign Williard Airport (CMI) |
Population | 880 |
Max Temp Winter | 35ºF |
Max Temp Summer | 80ºF |
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Frequently asked questions
How much does an Oakland vacation package cost?
You can grab a vacation package to this top destination from $1,194 on Expedia. However, how much your vacation to Oakland costs will depend on the season, length of stay and hotel choice.
What are the cheapest months to go to Oakland?
If you're looking to book a cheap Oakland vacation package, consider traveling in November, December and January. You'll usually find better prices on hotels and flights during these quieter months — perfect for budget-conscious travelers.
How many days is enough for Oakland?
With a well-organized schedule, you can easily tick off the top Oakland sights in a few days. But if you prefer to discover hidden gems or go on day tours, think about booking your Oakland vacation for longer.
How to find the best Oakland package deals?
Landing a cheap Oakland package deal is a breeze with Expedia. Once you've entered your travel dates and destination under our "Packages" tab, set your budget, apply a few filters and browse what's available. You can tailor your search by "Property class," "Number of bedrooms," "Traveler experience" and more. Order the results by "Price: low to high" to discover the most pocket-friendly Oakland package deals. Want a simple trick to get the biggest savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are usually lower.
Is it cheaper to book an Oakland vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to arranging stays and flights individually. Better still, you can personalize your Oakland getaway to match your exact style. Choose your preferred flight time, select the hotel type and add a car rental. Check out our great deals to see how much you can save.
When to book a vacation package to Oakland?
Land amazing discounts by reserving your flights early with Expedia. If being spontaneous is more your thing, take advantage of our last-minute deals for a spur-of-the-moment Oakland getaway.
Does Expedia offer Book Now, Pay Later Oakland vacation packages?
If you're like us, you love going away but are not a fan of the big price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With the help of online lender Affirm, you can spread the overall cost of your Oakland vacation over 3, 6 or 12 months. There are also no hidden or late payment fees, so you can snap up cheap vacation packages with payment plans as soon as you see them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.