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

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Frequently asked questions

How much does a flight from Midway Intl. Airport (MDW) to Oshkosh, WI (OSH-Wittman Regional) cost?
Discover the latest flight deals from MDW to OSH by entering your preferred travel dates and searching on Expedia. Easily compare prices by departure date if you have flexibility with your schedule and use handy filters to explore prices for your preferred journey. As a member of One Key™, our free loyalty program, you can use Price Tracking to watch fares and receive notifications if prices go up or down.
What is the cheapest month to fly from MDW to OSH?
The cheapest flights from MDW to OSH are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
What is the cheapest airline that flies from MDW to OSH?
Use the filter tool on Expedia to compare airlines and find the cheapest carrier that’ll take you from MDW to OSH. Sort your results by “Price (lowest to highest)” to snap up 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.
*Available to One Key members.