Oakland Vacations from $381

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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.
Motel 6 Urbana, IL

Motel 6 Urbana, IL

2 out of 5
Price was $409, price is now $381 per person
$381
per person
Feb 20 - Feb 22
found 22 hours ago
Roundtrip non-stop flight included
White Plains (HPN) to Champaign (CMI)
7.8/10 Good! (709 reviews)
We got right in had a storm snow. They kept the floors nice and clean rooms were wonderful personnel was great thanks.

Reviewed on Dec 19, 2025

Capital O First Heritage Inn Rantoul IL I 57

Capital O First Heritage Inn Rantoul IL I 57

2 out of 5
Price was $498, price is now $448 per person
$448
per person
Feb 20 - Feb 22
found 22 hours ago
Roundtrip non-stop flight included
White Plains (HPN) to Champaign (CMI)
6.6/10 (375 reviews)
What you'd expect from a place like

Reviewed on Jun 17, 2025

Illini Inn & Suites Hotel - Rantoul/Gifford/Champaign/Urbana

Illini Inn & Suites Hotel - Rantoul/Gifford/Champaign/Urbana

2 out of 5
Price was $478, price is now $431 per person
$431
per person
Feb 20 - Feb 22
found 22 hours ago
Roundtrip non-stop flight included
White Plains (HPN) to Champaign (CMI)
8.8/10 Excellent! (338 reviews)
Our favorite place to stay for a weekend getaway. Breakfast is surprisingly delicious.

Reviewed on Jan 6, 2026

Courtesy Motel

Courtesy Motel

2.5 out of 5
Price was $428, price is now $393 per person
$393
per person
Feb 20 - Feb 22
found 22 hours ago
Roundtrip non-stop flight included
White Plains (HPN) to Champaign (CMI)
5.2/10 (17 reviews)
Champaign Garden Inn

Champaign Garden Inn

3 out of 5
Price was $501, price is now $464 per person
$464
per person
Feb 20 - Feb 22
found 22 hours ago
Roundtrip non-stop flight included
White Plains (HPN) to Champaign (CMI)
9.8/10 Exceptional! (531 reviews)
Contactless check in- check out was really easy. Room was ready upon arrival, clean and warmed to a comfy temperature. Easy off street parking. Great place for a weekend get away close to a lot of great downtime spots. Will definitely return.

Reviewed on Jan 11, 2026

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Oakland Hotel Deals

Unique Suites Hotel

Unique Suites Hotel

2.5 out of 5
920 W Lincoln Ave Charleston IL
Fully refundableReserve now, pay when you stay
$81 nightly
The price is $90 total per night from Feb 12 to Feb 13
$90 total
Feb 12 - Feb 13
Total with taxes and fees
8.2/10 Very Good! (724 reviews)
Room was very nice, a few light bulbs needed to be changed, but the room was clean and easy parking.

Reviewed on Dec 22, 2025

Unique Suites Hotel
Comfort Suites Mattoon East

Comfort Suites Mattoon East

2.5 out of 5
1408 Broadway Ave E Mattoon IL
Fully refundableReserve now, pay when you stay
$81 nightly
The price is $90 total per night from Jan 25 to Jan 26
$90 total
Jan 25 - Jan 26
Total with taxes and fees
8.6/10 Excellent! (891 reviews)
Staff at check in was friendly

Reviewed on Jan 10, 2026

Comfort Suites Mattoon East
Baymont by Wyndham Tuscola

Baymont by Wyndham Tuscola

2.5 out of 5
1006 Southline Road Tuscola IL
Fully refundableReserve now, pay when you stay
$76 nightly
The price is $85 total per night from Jan 20 to Jan 21
$85 total
Jan 20 - Jan 21
Total with taxes and fees
7.6/10 Good! (601 reviews)
Comfortable beds and convenient location off highway.

Reviewed on Jan 1, 2026

Baymont by Wyndham Tuscola
See all 68 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.

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 $381 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.