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

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

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Flights from Oshkosh (OSH) to Chicago (MDW)
Origin airport
Wittman Regional
Destination airport
Midway Intl.
Distance
157 mi

Oshkosh to Chicago Flights

The cheapest times to fly from Oshkosh to Chicago

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 Oshkosh to Chicago are during the month of . You can find some of the cheapest flights from Oshkosh to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Oshkosh to Chicago

Sunday is one of the best days to book for cheap flights from Oshkosh to Chicago: 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 Oshkosh to Chicago

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 Oshkosh to Chicago 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 Oshkosh to Chicago 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 Oshkosh to Chicago 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.

 

Frequently asked questions

How much does a flight from Oshkosh, WI (OSH-Wittman Regional) to Midway Intl. Airport (MDW) cost?
Discover the latest flight deals from OSH to MDW 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 OSH to MDW?
The cheapest flights from OSH to MDW 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 OSH to MDW?
Use the filter tool on Expedia to compare airlines and find the cheapest carrier that'll take you from OSH to MDW. Sort your results by "Price (lowest to highest)" to snap up a great deal.
How many flights per day from Oshkosh, WI (OSH-Wittman Regional) to Midway Intl. Airport (MDW)?
You'll have to hop on a flight with a layover when traveling from Oshkosh, WI (OSH-Wittman Regional) to Midway Intl. Airport (MDW). Direct flights don't operate daily on this route. However, just filter your search to include one or two stops to discover the best option for your trip.
What day of the week has the most flights from OSH to MDW?
You'll typically find Tuesday the quietest day for flights, while Fridays are often the busiest.* However this can vary from season to season and during public holidays or peak travel times.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Oshkosh, WI (OSH-Wittman Regional) to Midway Intl. Airport (MDW)?
To avoid possible delays on the Oshkosh, WI (OSH-Wittman Regional) to Midway Intl. Airport (MDW) route, fly before 3 PM. Departures after this hour have a 22% higher chance of being canceled.**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 Oshkosh, WI (OSH-Wittman Regional) to Midway Intl. Airport (MDW) last-minute?
Last-minute fares from OSH to MDW are usually more expensive. To secure the cheapest rates, start looking for flights as early as possible. That said, if you're flexible with your travel dates, you may land a cheap ticket just before your departure.
Is it cheaper to book an OSH to MDW flight and hotel package?
Compared with arranging flights and hotels separately, booking an OSH to MDW flight and hotel package with Expedia could lead to significant savings. What's more, managing everything in one place will take the hassle out of planning your trip. Just secure your flights and select from our wide range of stays, then tailor your trip with extras like tours, activities and car rentals.
Can I cancel or change the date of my flight from Oshkosh, WI (OSH-Wittman Regional) to Midway Intl. Airport (MDW)?
In most cases, you can cancel or modify your OSH to MDW flight. However, there may be additional charges, especially if your booking was made more than 24 hours ago. Check your itinerary for the airline's guidelines and fees on flight changes, or if you'd like further information, head to our Customer Service portal.

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*Available to One Key members.