Oakland Vacations from $1,239

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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.
Capital O First Heritage Inn Rantoul IL I 57

Capital O First Heritage Inn Rantoul IL I 57

2 out of 5
Price was $1,274, price is now $1,239 per person
$1,239
per person
Jun 15 - Jun 18
found 10 hours ago
Roundtrip non-stop flight included
Missoula (MSO) to Champaign (CMI)
6.6/10 (384 reviews)
The parking was safe and easy. I worked nightshifts during the time I was there and I slept excellent, little to not noise, blackout curtains, nobody knock the door or interrupted my sleep. They ask me if I needed housekeeping just to let them know so they don’t interrupt my sleep. Friendly staff, attentive to anything you need like towels, bathroom rugs housekeeping (when you request it). It was overall a good experience. Consider if you are traveling for work!

Reviewed on Apr 11, 2026

Champaign Garden Inn

Champaign Garden Inn

3 out of 5
Price was $1,332, price is now $1,249 per person
$1,249
per person
Jun 15 - Jun 18
found 10 hours ago
Roundtrip non-stop flight included
Missoula (MSO) to Champaign (CMI)
9.8/10 Exceptional! (560 reviews)
Gorgeous and very memorable staying

Reviewed on Apr 25, 2026

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

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

2 out of 5
Price was $1,294, price is now $1,246 per person
$1,246
per person
Jun 15 - Jun 18
found 10 hours ago
Roundtrip non-stop flight included
Missoula (MSO) to Champaign (CMI)
8.8/10 Excellent! (417 reviews)
It was clean, quiet and breakfast was great! The room is spacious, clean and has the basic things you need. I will go baxk again.

Reviewed on May 2, 2026

Motel 6 Urbana, IL

Motel 6 Urbana, IL

2 out of 5
Price was $1,286, price is now $1,240 per person
$1,240
per person
Jun 15 - Jun 18
found 10 hours ago
Roundtrip non-stop flight included
Missoula (MSO) to Champaign (CMI)
8/10 Very Good! (742 reviews)
Very good value for the price of the stay.

Reviewed on May 3, 2026

TownePlace Suites by Marriott Champaign Urbana/Campustown

TownePlace Suites by Marriott Champaign Urbana/Campustown

3 out of 5
Campustown
Price was $1,524, price is now $1,481 per person
$1,481
per person
Jun 15 - Jun 18
found 10 hours ago
Roundtrip non-stop flight included
Missoula (MSO) to Champaign (CMI)
8.8/10 Excellent! (654 reviews)
Staff was incredibly nice and helpful.

Reviewed on Mar 18, 2026

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Oakland Hotel Deals

Comfort Suites Mattoon East

Comfort Suites Mattoon East

2.5 out of 5
1408 Broadway Ave E Mattoon IL
$93 nightly
The price is $104 total per night from Jun 4 to Jun 5
$104 total
Jun 4 - Jun 5
Total with taxes and fees
8.8/10 Excellent! (945 reviews)
Excellent help at check-in!

Reviewed on May 8, 2026

Comfort Suites Mattoon East
Hampton Inn Paris

Hampton Inn Paris

2.5 out of 5
2006 South Main Street Paris IL
Fully refundableReserve now, pay when you stay
$99 nightly
The price is $110 total per night from Jun 9 to Jun 10
$110 total
Jun 9 - Jun 10
Total with taxes and fees
9.6/10 Exceptional! (429 reviews)
The staff were so sweet and helpful. The hotel is clean, safe, and comfortable. I will be retuning here each time I visit for work. Thank you for a comfortable stay!

Reviewed on May 8, 2026

Hampton Inn Paris
Best Western Heartland Inn

Best Western Heartland Inn

2.5 out of 5
1416 Broadway Avenue East Mattoon IL
Fully refundableReserve now, pay when you stay
$84 nightly
The price is $94 total per night from May 12 to May 13
$94 total
May 12 - May 13
Total with taxes and fees
8.2/10 Very Good! (576 reviews)
Nice clean safe and located perfectly. Lots space to congregate in common areas for groups or families. I didn’t stay for breakfast but the common area was the breakfast area too. Looks like they put out a good one..

Reviewed on May 7, 2026

Best Western Heartland Inn
See all 83 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 $1,239 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.