$51 Cheap Flights to Oakland City, IN

Popular airlines to Oakland City

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How much is the cheapest flight to Oakland City?

Prices were available within the past 7 days and start at $51 for one-way flights and $127 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Breeze Airways
Breeze Airways
Breeze Airways
Delta
American Airlines

What you need to know for your flight to Oakland City

Flights to Oakland City at a glance

Traveling to Oakland City is a breeze; simply choose between full-service and budget airlines, compare flight durations, and select the option that best matches your budget and schedule as you plan to explore the city's iconic attractions and neighborhoods.

  • Major airports near Oakland City: Evansville Regional Airport (EVV), Owensboro-Daviess County Regional Airport (OWB)
  • Closest airport to Oakland City: Evansville Regional Airport, EVV (around 22 miles)
  • Flights per week: 550+ flights arriving across Oakland City airports
  • Number of airlines that fly to Oakland City: around 5+ carriers

Popular airports near Oakland City

Oakland City is a charming destination perfect for outdoor adventures, family getaways, and scenic retreats. Visitors are drawn to its appealing mix of nature, romance, and urban experiences. The city is conveniently accessible through two major airports.

  • Evansville Regional Airport (EVV): Situated in Vanderburgh County, Indiana, approximately 22 miles from Oakland City, this airport caters to both domestic and international travelers. It connects to over 65 domestic cities and 5 international destinations. Travelers can opt for first class and premium economy seating for enhanced comfort, depending on airlines and routes, with American Airlines, Delta, and Breeze being key carriers.
  • Owensboro-Daviess County Regional Airport (OWB): Found in Daviess County, Kentucky, around 42 miles away from Oakland City, this regional airport primarily offers domestic flights to about 2 cities nationwide. Contour Airlines is the prominent airline serving this airport.

Top routes to Oakland City

  • Orlando (MCO) to Oakland City (EVV), with one-way flights starting at around $50
  • Chicago (ORD) to Oakland City (EVV/OWB), with one-way flight options from around $60
  • Dallas (DFW) to Oakland City (EVV), with one-way flights starting at around $180
  • Denver (DEN) to Oakland City (EVV), with one-way flight options from around $190
  • Tampa (TPA) to Oakland City (EVV), with one-way airfare from around $130

Cheapest routes to Oakland City

  • Orlando (MCO) to Oakland City (EVV), with affordable one-way prices from around $50
  • Chicago (ORD) to Oakland City (EVV/OWB), with low one-way fares from around $60
  • Charlotte (CLT) to Oakland City (EVV/OWB), with cheap one-way fares from around $60
  • San Juan (SJU) to Oakland City (EVV), with budget one-way fares from around $130
  • Tampa (TPA) to Oakland City (EVV), with cheap one-way fares from around $130

*Flight times and fares vary by season and availability and are based on one-way routes

Top airlines with flights to Oakland City

  • American Airlines: Operating flights to Evansville Regional Airport (EVV), this airline represents about 57% of arrivals to Oakland City. One-way fares are generally around $290, with premium cabin service potentially including first class based on the route.
  • Delta: Providing service to Evansville Regional Airport (EVV), Delta accounts for nearly 35% of arrivals to Oakland City. The average one-way ticket is roughly $310, with premium service options possibly featuring premium economy and first class depending on the specific route.
  • Contour Airlines: Flying into Owensboro-Daviess County Regional Airport (OWB), Contour Airlines comprises about 5% of arrivals to Oakland City. Passengers can expect average one-way fares of approximately $80.
  • Breeze: Servicing Evansville Regional Airport (EVV), Breeze makes up around 3% of arrivals to Oakland City. The average cost for a one-way fare is about $80.
  • Aeromexico: Offering flights to Evansville Regional Airport (EVV), Aeromexico has an average one-way fare of approximately $460.

Best time to fly to Oakland City

The most popular months for travelers to fly to Oakland City are February, March, and April, when peak temperatures in Oakland City can reach up to 55.8°F in April. If you prefer quieter travel, consider September, the least busy and relatively cheaper time to visit with fewer crowds and temperatures around 70°F. For better deals, August usually offers the lowest average one-way fare around $261, roughly 10% cheaper than the yearly average. Looking for additional cheaper months to fly? May, July, and September offer average one-way fares of around $270, making them good options for flexible travelers.

calendar iconMonthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinesscrowd level iconDemandprice iconAverage one-way Fare
January32.5°F (0.3°C)Light RainMostly CloudyAverage$338
February36.0°F (2.2°C)Light RainMostly CloudyModerately High$310
March46.4°F (8.0°C)Light RainMostly SunnyModerately High$317
April55.8°F (13.2°C)Light RainMostly SunnyModerately High$310
May65.8°F (18.8°C)Light RainMostly SunnyAverage$268
June74.5°F (23.6°C)Light RainMostly SunnyAverage$279
July77.0°F (25.0°C)Light RainMostly SunnyAverage$269
August75.6°F (24.2°C)Light RainMostly SunnyAverage$261
September70.0°F (21.1°C)Light RainMostly SunnyModerately Low$272
October58.5°F (14.7°C)Light RainMostly SunnyAverage$290
November45.9°F (7.7°C)Light RainMostly SunnyModerately Low$290
December38.5°F (3.6°C)Light RainMostly CloudyModerately Low$298

*Average one-way fare is based on Expedia flight booking data from January 2025 to April 2026 for the specified route and travel class and may change depending on availability, dates, and demand.

How to save money on a flight to Oakland City

Getting some of the best deals on flights to Oakland City is all about timing and flexibility. Here are some key tips to help you save:

  1. Compare flight options—use Expedia's search tool to compare airlines, routes, direct vs. non-direct flights, and flight times. You can also sort by price to find the most affordable options.
  2. Set up price alerts—as an Expedia member you can use Price Tracking to receive notifications when flight prices change.
  3. Bundle and save—book a flight and unlock a hotel deal on Expedia.*
  4. Think about luggage-nowadays, it's important to check the airline's baggage policies to find the best value. That may be paying for an additional carry-on bag or booking a ticket with checked luggage included. Either way, double-check your baggage allowance before confirming your booking to avoid excess baggage fees at the airport.
  5. Earn miles—you can earn airline miles when you book your Oakland City flight with Expedia. Just select your frequent flyer program and enter your program number when confirming your booking.

*For members. Select hotels.

Arriving in Oakland City

Oakland City welcomes travelers through its range of transport options based on price, convenience, and proximity. Here's how to reach Oakland City efficiently:

  • Public transportation: From Evansville Regional Airport, the Evansville Bus Station, a bus station, is located about 8.5 miles away by car, offering convenient access for travelers needing ground transportation.
  • Hotel transfer: Transfers offer a convenient way to reach your hotel in Oakland City, with private rides that can be arranged in advance.
  • Car rental: Renting a car in Oakland City is a good option if you plan to explore and sightsee beyond the city. Browse cheap car rentals in Oakland City on Expedia.
  • Taxi/ride-hailing: Taxis and ride-hailing services may be available from designated pickup areas outside the terminal, check locally on arrival.

Where to stay around Oakland City

  • Mount Olympus: Located 10 miles away from Oakland City, Mount Olympus is a charming village that attracts sports enthusiasts. Visitors will find a variety of sports experiences, with notable attractions including a modern sports facility stadium. Culture seekers can explore historic sites like Oakland City University and Rogers Clark National Historical Park, while Wabash Valley College offers a glimpse into contemporary education. Whether you’re looking to enjoy a game or soak in some local history, Mount Olympus has something for everyone.
  • Elberfeld: Elberfeld is located 14 miles away from Oakland City and is an ideal spot for family outings and outdoor adventures. This welcoming village features golf courses and recreational areas, making it perfect for a day of fun in the sun. Key highlights include McCutchanville Park, an urban park that's great for family activities, and the Wabash Erie Canal Park, where you can appreciate the scenic waterways. The University of Evansville adds a modern educational twist to this charming destination.
  • Somerville: Situated only 5 miles away from Oakland City, Somerville is a quaint city perfect for couples seeking romance and outdoor beauty. The area is known for its picturesque scenery and also offers educational opportunities. Notable attractions include the historic Oakland City University and the modern University of Evansville. For family-friendly fun, Swonder Ice Arena provides entertainment options suitable for all ages, ensuring that Somerville is a delightful stop for visitors.

Tips for short-haul flights to Oakland City

For quick getaways, efficiency is key. Here is how to make your short-haul journey smoother:

  • Pack light and skip checked bags—when flying with budget airlines, traveling with just a carry-on is often more economical. Save space by using mini toiletries, wearing your bulkiest clothing, and efficiently planning your outfits. This approach also helps you avoid the wait at baggage claim upon arrival.
  • Bring your own entertainment—many short-haul flights may lack in-flight entertainment options. Download your favorite TV shows, movies, music, or podcasts ahead of time, and consider bringing a book to keep yourself entertained. Remember to fully charge your devices before you board.
  • Arrive at the airport in plenty of time—even for short or domestic flights, it’s wise to arrive at least 1.5 to 2 hours before your departure, taking into account potential traffic and security lines.
  • Bring your own snacks and water—pack snacks and carry a refillable water bottle to stay hydrated and save money while at the airport.

Tips for long-haul flights to Oakland City

Flying long-haul sometimes requires extra planning to ensure a comfortable journey:

  • Select your seat in advance—for longer flights, choosing your seat is essential for comfort. Full-service airlines often allow seat selection at no charge once online check-in opens, typically 24–48 hours before your flight. Some airlines may permit seat selection even earlier.
  • Arrive at the airport in plenty of time—make sure to arrive at least 3 hours before departure for international flights to accommodate check-in, security, and immigration processes.
  • Relax at the airport—if you have some extra time, take a moment to explore the shops, grab a coffee, or unwind at your gate or in a departure lounge if you have access. Most airports offer free Wi-Fi that you can use.
  • Adjust to the new time zone mid-flight—begin to sync your body clock by changing your watch and adjusting your sleep schedule to align with your destination's time zone. Aim to sleep or stay awake on the flight according to the local time of your arrival to help minimize jet lag.

Frequently asked questions

What month is the cheapest to fly to Oakland City?
Plan your trip for August if you're looking for a deal on your fare. It's the cheapest month to fly to Oakland City. If possible, avoid traveling during peak periods such as major public holidays or during big events.
Which US cities have the cheapest flights to Oakland City?
Land cheap flights to Oakland City from Charlotte, Atlanta and Dallas. These cities generally offer the best fares to this much-loved destination. But remember that holiday periods, demand and stopovers also influence rates, so stay flexible and book when you see a bargain.
Which US cities fly direct to Oakland City?
Charlotte and Atlanta are two cities in the US offering nonstop journeys to Oakland City. Explore your travel options on Expedia by selecting the "Direct flights only" filter. Decide on the most suitable departure for your trip, and then get ready to fly to Oakland City without any detours.
How to find a cheap flight to Oakland City?
If you're searching for cheap flights to Oakland City, consider traveling outside of peak season. Booking ahead of time may also save you money. Or, fly on a different day — flights on a Thursday are on average 16% cheaper than Sunday departures.* Opt to receive flight price alerts on the Expedia app and you'll be instantly notified when fares drop.*Best day of the week to book, depart and ideal booking window recommendations based on average round-trip ticket prices for January through August 2023, sourced from Airline Reporting Corporation's (ARC) global airline sales database. Percentages noted are averages.
How to get a cheap last-minute flight to Oakland City?
Although booking in advance is generally the best way to save money, don't worry if your Oakland City trip is last minute. You can still get cheap flights to Oakland City, especially if your plans have some flexibility. Try switching up your travel dates, exploring different ticket types or departing from an alternative airport.
How far in advance should I book a flight to Oakland City?
For some of the best deals on domestic journeys, book your flight to Oakland City 28 days ahead of your travel dates. For international flights, search for your ticket between two and four months in advance. This improves your chances of locking in the departure dates and times you want.**Best day of the week to book, depart and ideal booking window recommendations based on average round-trip ticket prices for January through August 2023, sourced from Airline Reporting Corporation's (ARC) global airline sales database. Percentages noted are averages.
Which day of the week is the cheapest day to buy a plane ticket to Oakland City?
You can save an average of 8% if you purchase tickets on a Sunday rather than Fridays, which tend to be the most expensive day to book.* When it comes to getting a cheap flight to Oakland City, it's all about having good timing.*Best day of the week to book, depart and ideal booking window recommendations based on average round-trip ticket prices for January through August 2023, sourced from Airline Reporting Corporation's (ARC) global airline sales database. Percentages noted are averages.
Which airlines fly to Oakland City?
There are 3 airlines connecting Oakland City with 4 airports across the globe. The principal entry point to Oakland City is Evansville Regional Airport (EVV). American Airlines and Delta Air Lines are two of the most popular airlines to Oakland City.
Where do you fly into Oakland City?
If you're flying to Oakland City, the main airport to arrive at is Evansville Regional Airport (EVV). Alternatively, you could fly to Oakland City via Lawrenceville, IL (LWV-Lawrenceville-Vincennes Intl.).
How far is the airport from central Oakland City?
If you're jetting into Evansville Regional Airport (EVV), you'll be about 20 mi southwest of the center of Oakland City.
Can I save money by booking an Oakland City trip package?
You could potentially save hundreds of dollars if you secure an Oakland City flight and hotel package deal on Expedia. And you'll save time and hassle by having all your travel plans in one place. Try bundling hotels and flights with extras like car rentals and activities for your own personalized Oakland City break.
Can I change or cancel my flight to Oakland City?
If you bought your flight to Oakland City in the last 24 hours, you can typically change or cancel it for free. After that, additional charges may apply depending on the airline's terms of service. For more information, head to our Customer Service Portal. Remember that some flights are non-refundable, so you may be offered a credit for future travel in place of a direct refund. When browsing Expedia, use the "Changes included" or "No cancel fee" boxes to find fares with flexible change policies.

*Flight schedules are subject to change.

*Available to One Key members.

 

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Travel information

Destination airport
Evansville Regional
Destination airport IATA code
EVV
Destination city name
Evansville
Roundtrip price
$126

Trending flights to Oakland City

Prices were available within the past 7 days and start at $51 for one-way flights and $127 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Breeze Airways

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