Oakland City Vacations from $637
Book a Hotel + Flight or Car together to unlock savings
Your Oakland City Vacation
Our vacation packages to Oakland City let you customize your own adventure. Tailor your getaway to suit your needs and interests and make every moment count in this fabulous city. Need some inspiration on what to see or do first during your trip to Oakland City? Check off well-known attractions such as Oakland City University. Your perfect Oakland City vacation is only clicks away. Search flights, hotels and more on Expedia for an adventure that's tailored to suit your style.
The Latest Oakland City vacation packages
Price found within the past 48 hours. Click for updated prices.
Residence Inn by Marriott Evansville East
$768
per person
Oct 17 - Oct 24
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Evansville (EVV)
8.6/10 Excellent! (553 reviews)
Very convenient. Staff were hospitable and the room very clean. Would definitely be my first choice if I find myself in Evansville again.
Reviewed on Aug 16, 2026
Holiday Inn Express Evansville West by IHG
$845
per person
Oct 17 - Oct 24
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Evansville (EVV)
8.6/10 Excellent! (596 reviews)
We got in our room and it stunk like wet clothes had laid in there for a week. They switched us rooms and the second room stunk like that to. Also they no longer have a hot tub in the pool area like it said they did. Also breakfast sucked.
Reviewed on Aug 16, 2026
Holiday Inn Express Princeton by IHG
$912
per person
Oct 17 - Oct 24
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Evansville (EVV)
8/10 Very Good! (362 reviews)
Probably the worst Holiday Inn Express … I checked into a room that hadn’t been cleaned and it was ex difficult understanding what the lady checking me in was saying. The pool was nice though.
Reviewed on Aug 9, 2026
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See all available trips from Columbus to Oakland City
View all tripsStay near popular Oakland City attractions
Oakland City University
7.2/10 (47 reviews)
Explore the campus of Oakland City University, during your trip to Oakland City.
Oakland City Hotel Deals
Oakland Courtyard
1000 W Morton St, Oakland City Oakland City IN
$172 nightly
$193 total
Aug 29 - Aug 30
Total with taxes and fees
Santas Lodge and Resort
91 W CHRISTMAS BLVD Santa Claus IN
Fully refundableReserve now, pay when you stay
$113 nightly
$127 total
Aug 17 - Aug 18
Total with taxes and fees
8/10 Very Good! (415 reviews)
"A little run down one rooms ac did not had to move rooms"
Reviewed on Aug 16, 2026
Jasper Inn
951 Wernsing Road Jasper IN
Fully refundableReserve now, pay when you stay
$85 nightly
$95 total
Sep 11 - Sep 12
Total with taxes and fees
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 City Vacation Packages
Oakland City Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Evansville Regional Airport (EVV) |
Population | 2,400 |
Max Temp Winter | 40ºF |
Max Temp Summer | 85ºF |
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Frequently asked questions
How much does an Oakland City vacation package cost?
You'll find cheap prices from $637 on Expedia for your Oakland City escape. However, factors like the hotel choice, length of stay and season will determine how much your vacation to Oakland City costs.
What are the cheapest months to go to Oakland City?
If you're hoping to score a cheap Oakland City vacation package, consider planning a trip in July, November and December. You're likely to find lower rates on flights and accommodations during these months — perfect for budget-conscious travelers.
How many days is enough for Oakland City?
The ideal duration for your Oakland City vacation depends on what you'd like to do and see. Usually, a few days to a week will give you enough time to check out all the major attractions and discover some hidden gems along the way.
How to find the best Oakland City package deals?
Use Expedia's filter tool to help you find some fabulous Oakland City package deals. When you begin your search, simply set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your trip for midweek, or search for Oakland City package deals in the low season. Play around with your travel dates and you may score even better discounts. As a rule of thumb, it's usually best to book your vacation package as soon as possible.
Is it cheaper to book an Oakland City vacation as a package?
An Expedia vacation package could land you great savings when compared to booking stays and flights individually. Better still, you can personalize your Oakland City trip to match your exact needs. Pick your preferred flight time, select the hotel type and add a rental car. Explore our bundles to see how much you can save.
When to book a vacation package to Oakland City?
Score fantastic discounts by reserving your flights ahead of time with Expedia. If spontaneity is more your thing, grab one of our last-minute deals for a spur-of-the-moment Oakland City escape.
Does Expedia offer Book Now, Pay Later Oakland City vacation packages?
Set off on your perfect escape to Oakland City with help from our Book Now, Pay Later vacations. There's no need to save like crazy or wait until the next payday — we've teamed up with online lender Affirm to give you financial flexibility. Our vacation packages with payment plans allow you to spread the cost over 3, 6 or 12 months. With no hidden charges or late payment fees, it's easy to budget for your trip and snap up travel deals while they last.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.