Title: Oakland City Vacation Packages 2026 from $474 | Expedia.com

[Oakland City Travel Guide](https://expedia.com/Oakland-City.dx6283924)[Hotels in Oakland City](https://expedia.com/Oakland-City-Hotels.d6283924.Travel-Guide-Hotels)[Vacation Rentals in Oakland City](https://expedia.com/Oakland-City-Vacation-Rentals.d6283924.Travel-Guide-VacationRentals)[Flights to Oakland City](https://expedia.com/Cheap-Flights-To-Oakland-City.d6283924.Travel-Guide-Flights)[Car Rentals in Oakland City](https://expedia.com/Car-Rentals-In-Oakland-City.d6283924.Car-Rental-Guide)

![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_packages.jpeg?impolicy=fcrop&w=1200&h=300&q=medium)

# Oakland City Vacations from $474

## 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](https://www.expedia.com/Oakland-City-University-Oakland-City.d6281559.Vacation-Attraction). 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.

![PT6 INN](https://images.trvl-media.com/lodging/78000000/77860000/77859200/77859197/8f8361f9_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### PT6 INN

$474

per person

Apr 3 - Apr 5

found 1 day ago

Roundtrip flight included

Chicago (ORD) to Evansville (EVV)

4.4/10 (96 reviews)

Staff was nice and friendly

Reviewed on Nov 12, 2025

![New Harmony Inn Resort and Conference Center](https://images.trvl-media.com/lodging/2000000/1410000/1403900/1403845/efde89bd_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### New Harmony Inn Resort and Conference Center

$546

per person

Apr 3 - Apr 5

found 1 day ago

Roundtrip flight included

Chicago (ORD) to Evansville (EVV)

9/10 Wonderful! (491 reviews)

Very nice facility. Clean, comfortable, great restaurant on site, and very walkable to downtown.

Reviewed on Feb 16, 2026

![Envi Boutique Hotel Henderson-Evansville South](https://images.trvl-media.com/lodging/1000000/50000/49800/49726/a17cf382_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Envi Boutique Hotel Henderson-Evansville South

$517

per person

Apr 3 - Apr 5

found 1 day ago

Roundtrip flight included

Chicago (ORD) to Evansville (EVV)

8/10 Very Good! (280 reviews)

Room was good but the check in is by internet with a person from another country and it was difficult to understand them.

Reviewed on Feb 22, 2026

![Extended Stay America Suites Evansville East](https://images.trvl-media.com/lodging/1000000/50000/42500/42476/24c17903_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Extended Stay America Suites Evansville East

$523

per person

Apr 3 - Apr 5

found 1 day ago

Roundtrip flight included

Chicago (ORD) to Evansville (EVV)

7.6/10 Good! (268 reviews)

Kitchenette in room was awesome

Reviewed on Dec 20, 2025

![Clarion Pointe Evansville North](https://images.trvl-media.com/lodging/1000000/20000/13200/13172/daf3a615_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Clarion Pointe Evansville North

$509

per person

Apr 3 - Apr 5

found 1 day ago

Roundtrip flight included

Chicago (ORD) to Evansville (EVV)

6/10 (154 reviews)

The TV was a challenge to figure out how to get channels. The phone didn't work. The desk chair should be thrown away. The tub was not clean. The back door was broken. The bed was comfortable and clean. Minimal continental breakfast.

Reviewed on Nov 21, 2025

Don't see what you're looking for?

See all available trips from Columbus to Oakland City

[View all trips](https://expedia.com/go/package/search/FlightHotel/2026-03-26/2026-04-02/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=EVV&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh)

## 

The Annual Vacation Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.

[Book now](https://expedia.com/deals?rfrr=PKG_SPRING_PROMO_6283924)

### Discover the most popular places to visit in Oakland City

#### Oakland City University

4/5(25 reviews)

Explore the campus of Oakland City University, during your trip to Oakland City. 

[](https://expedia.com/Oakland-City-University-Oakland-City.d6281559.Vacation-Attraction)

## Oakland City Hotel Deals

![Oakland Courtyard](https://images.trvl-media.com/lodging/118000000/117630000/117625600/117625584/86a3f489_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Oakland Courtyard

1000 W Morton St, Oakland City Oakland City IN

$89 nightly

$100 total

Feb 27 - Feb 28

Total with taxes and fees

8.4/10 Very Good! (10 reviews)

Room very clean and spacious. Bed was comfortable.

Reviewed on Feb 7, 2026

[](https://expedia.com/Hotel-Search?startDate=2%2F27%2F2026&endDate=2%2F28%2F2026&selected=117625584&PinnedHotelID=117625584&HadPinnedHotel=true&regionId=6283924)

![Drury Inn & Suites Evansville East](https://images.trvl-media.com/lodging/1000000/120000/116600/116545/2ba5f829_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Drury Inn & Suites Evansville East

100 Cross Pointe Blvd Evansville IN

Fully refundableReserve now, pay when you stay

$115 nightly

$132 total

Mar 2 - Mar 3

Total with taxes and fees

9.4/10 Exceptional! (1,000 reviews)

Staff and stay were amazing!

Reviewed on Feb 22, 2026

[](https://expedia.com/Hotel-Search?startDate=3%2F2%2F2026&endDate=3%2F3%2F2026&selected=116545&PinnedHotelID=116545&HadPinnedHotel=true&regionId=6283924)

![La Quinta Inn & Suites by Wyndham Evansville](https://images.trvl-media.com/lodging/1000000/50000/42500/42483/29ca343a_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

La Quinta Inn & Suites by Wyndham Evansville

8015 East Division Street Evansville IN

Fully refundableReserve now, pay when you stay

$76 nightly

$87 total

Mar 8 - Mar 9

Total with taxes and fees

8.6/10 Excellent! (1,012 reviews)

Check in was very easy. I got to the room and there was a hot pocket wrapper stuffed by the box spring/headboard. Lots of hair everywhere, chair was ripped up and had stains all over it, shower curtain was dirty, ac smelt like a wet dog. Our room keys stopped working everyday so we had to go ge then ...

Reviewed on Feb 24, 2026

[](https://expedia.com/Hotel-Search?startDate=3%2F8%2F2026&endDate=3%2F9%2F2026&selected=42483&PinnedHotelID=42483&HadPinnedHotel=true&regionId=6283924)

[See all 183 properties in Oakland City](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=2%2F27%2F2026&endDate=2%2F28%2F2026&regionId=6283924)

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?

### What are the cheapest months to go to Oakland City?

### How many days is enough for Oakland City?

### How to find the best Oakland City package deals?

### Is it cheaper to book an Oakland City vacation as a package?

### When to book a vacation package to Oakland City?

### Does Expedia offer Book Now, Pay Later Oakland City vacation packages?

\* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.