Cheap Flights from Chicago (MDW) to Oshkosh (OSH)

Popular airlines from Chicago Midway Airport (MDW) to Oshkosh, WI (OSH-Wittman Regional)

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Frequently asked questions

How much does a flight from Midway Intl. Airport (MDW) to Oshkosh, WI (OSH-Wittman Regional) cost?
Grab a cheap one-way flight or cheap return flight from Midway Intl. Airport (MDW) to Oshkosh, WI (OSH-Wittman Regional) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight offers on this route.
What is the cheapest month to fly from Midway Intl. Airport (MDW) to Oshkosh, WI (OSH-Wittman Regional)?
is the cheapest month to fly from MDW to OSH. Timing your trip outside of the busy season is often the key to finding better deals on flights.
What is the cheapest airline that flies from Midway Intl. Airport (MDW) to Oshkosh, WI (OSH-Wittman Regional)?
Use the filters on Expedia to compare different airlines and find the cheapest carrier that'll take you from MDW to OSH. Then, sort your results by "Price (lowest to highest)" to score a great deal.
How many flights per day from Midway Intl. Airport (MDW) to Oshkosh, WI (OSH-Wittman Regional)?
Nonstop flights from Midway Intl. Airport (MDW) to Oshkosh, WI (OSH-Wittman Regional) aren't available daily, so you'll need to take a flight with a layover. Explore your options with our filter tool. Enter your travel dates and click on either "1 Stop" or "2+ Stops."
What day of the week has the most flights from MDW to OSH?
Typically you'll find the largest variety of flight choices on a Friday. Tuesdays are often the quietest.* However, this can change based on the airline, season and other factors.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Midway Intl. Airport (MDW) to Oshkosh, WI (OSH-Wittman Regional)?
To avoid possible delays on the Midway Intl. Airport (MDW) to Oshkosh, WI (OSH-Wittman Regional) route, travel before 3 PM. Departures after this hour have a 22% higher chance of cancellation.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
Is it cheaper to buy a plane ticket from Midway Intl. Airport (MDW) to Oshkosh, WI (OSH-Wittman Regional) last-minute?
Booking your ticket from MDW to OSH just before your journey is generally more expensive. However, if you're flexible with your travel times and dates, you could land a cheap last-minute fare.
Is it cheaper to book a MDW to OSH flight and hotel package?
You'll typically save money by securing a MDW to OSH flight and hotel package compared to booking separately. In fact, travelers could save hundreds of dollars by bundling with Expedia. And it's simple to manage everything in one place. After selecting your preferred accommodations and flights, you can add extras such as activities, car rentals and tours.
Can I cancel or change the date of my flight from Midway Intl. Airport (MDW) to Oshkosh, WI (OSH-Wittman Regional)?
It's generally possible to cancel or reschedule your MDW to OSH flight. However, for bookings made more than 24 hours ago, additional charges may apply. Check your airline's policies in your itinerary to see what changes are possible and whether any costs are involved. You'll also find more details on our Customer Service portal.

Travel information

Travel information

Origin airport
Midway Intl.
Destination airport
Wittman Regional
Distance
157 mi

Book with confidence

Book with confidence

Chicago to Oshkosh Flights

The cheapest times to fly from Chicago to Oshkosh

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Chicago to Oshkosh are during the month of . You can find some of the cheapest flights from Chicago to Oshkosh with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Chicago to Oshkosh

Sunday is one of the best days to book for cheap flights from Chicago to Oshkosh: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Chicago to Oshkosh

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Chicago to Oshkosh in 2025. You can also book with separate airlines for your outbound and return journeys, from one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Chicago to Oshkosh flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Chicago to Oshkosh airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Chicago to Oshkosh Flights

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Explore a world of travel with Expedia

*Available to One Key members.