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

Popular airlines from Chicago O'Hare Intl. Airport (ORD) to Oshkosh, WI (OSH-Wittman Regional)

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Alternative airports near Oshkosh

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Appleton Intl. ATW. Cheapest option available. Average driving time to city center is 25 minutes. Flights from $244
ATW
Appleton Intl.
Cheapest
Average driving time to city center25 min
Flights from $244

Frequently asked questions

How much does a flight from O'Hare Intl. Airport (ORD) to Oshkosh, WI (OSH-Wittman Regional) cost?
Secure a cheap one-way flight or cheap return flight from O'Hare Intl. Airport (ORD) 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 O'Hare Intl. Airport (ORD) to Oshkosh, WI (OSH-Wittman Regional)?
The cheapest month to fly from ORD to OSH is , when there's less demand. Off-peak months are generally when better flight deals are available between these airports.
What is the cheapest airline that flies from O'Hare Intl. Airport (ORD) to Oshkosh, WI (OSH-Wittman Regional)?
Use the filters on Expedia to compare different airlines and find the most affordable carrier that'll take you from ORD to OSH. Then, sort your results by "Price (lowest to highest)" to pick up the best deal available.
How many flights per day from O'Hare Intl. Airport (ORD) to Oshkosh, WI (OSH-Wittman Regional)?
There are no daily nonstop flights available from O'Hare Intl. Airport (ORD) to Oshkosh, WI (OSH-Wittman Regional). But you can opt for flights with layovers. Filter your search results on Expedia to include one or more stops, and you'll be on your way in no time.
What day of the week has the most flights from ORD to OSH?
Friday is typically the busiest day for flights, while Tuesday tends to be the quietest.* Just remember that flight schedules can vary depending on a number of factors, such as the time of year and airline.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from O'Hare Intl. Airport (ORD) to Oshkosh, WI (OSH-Wittman Regional)?
To arrive at Oshkosh, WI (OSH-Wittman Regional) without delays, pick a flight that leaves from O'Hare Intl. Airport (ORD) before 3 PM. The likelihood of cancellations is 22% higher, on average, for departures after this hour.**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.
What airports do you fly into for Oshkosh from O'Hare Intl. Airport (ORD)?
You can land at Appleton Intl. Airport (ATW) or Austin Straubel Intl. Airport (GRB) when traveling to Oshkosh on a direct flight from O'Hare Intl. Airport (ORD).
Is it cheaper to buy a plane ticket from O'Hare Intl. Airport (ORD) to Oshkosh, WI (OSH-Wittman Regional) last-minute?
Last-minute bookings from ORD to OSH are usually more expensive. To lock in the cheapest rates, start searching for flights early. That being said, if your travel plans are flexible, it's possible to score a cheap ticket right before your journey.
Is it cheaper to book an ORD to OSH flight and hotel package?
Compared with arranging hotels and flights separately, booking an ORD to OSH flight and hotel package with Expedia could result in significant savings. What's more, having everything in one convenient place will take the stress out of travel planning. Simply secure your flights and choose from our extensive range of hotels, then customize your trip with other add-ons like car rentals and activities.
Can I cancel or change the date of my flight from O'Hare Intl. Airport (ORD) to Oshkosh, WI (OSH-Wittman Regional)?
If you reserved your ORD to OSH flight within the last 24 hours, you may be able to modify or cancel it at no cost. Depending on the airline and the type of ticket you have, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal if you want more information.

Travel information

Origin airport
O'Hare Intl.
Destination airport
Wittman Regional
Distance
143 mi

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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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*Available to One Key members.