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

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Flights from Oshkosh (OSH) to Chicago (ORD)
Origin airport
Wittman Regional
Destination airport
O'Hare Intl.
Distance
143 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 O'Hare Intl. Airport (ORD) cost?
Discover the latest flight deals from OSH to ORD 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 ORD?
The cheapest flights from OSH to ORD are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
Which airlines fly direct from Oshkosh, WI (OSH-Wittman Regional) to O'Hare Intl. Airport (ORD)?
While Oshkosh, WI (OSH-Wittman Regional) doesn’t offer any direct flights to O’Hare Intl. Airport (ORD), other airports have nonstop routes. Traveling from Appleton Intl. Airport (ATW) will get you to Chicago without any detours.
What is the cheapest airline that flies from OSH to ORD?
Use the filter tool on Expedia to compare airlines and find the cheapest carrier that’ll take you from OSH to ORD. 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 O'Hare Intl. Airport (ORD)?
Direct flights from Oshkosh, WI (OSH-Wittman Regional) to O’Hare Intl. Airport (ORD) aren’t available daily, so you’ll have to take a flight with a layover. Explore your options with Expedia’s filter tool. Enter your travel details and pick either “1 Stop” or “2+ Stops.”
What day of the week has the most flights from OSH to ORD?
You’ll usually find Tuesday the quietest day for flights, while Fridays tend to be the busiest.* However this can vary from season to season and during peak travel times or public holidays.*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 O'Hare Intl. Airport (ORD)?
To reach O’Hare Intl. Airport (ORD) on schedule, select a flight that leaves Oshkosh, WI (OSH-Wittman Regional) before 3 PM. The chance 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.
Is it cheaper to buy a plane ticket from Oshkosh, WI (OSH-Wittman Regional) to O'Hare Intl. Airport (ORD) last-minute?
Booking your flight from OSH to ORD shortly before your journey is generally more expensive. However, if there’s some wiggle room with your itinerary, you could bag a cheap last-minute fare.
Is it cheaper to book an OSH to ORD flight and hotel package?
Securing an OSH to ORD flight and hotel package tends to be cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your trip in one place. Choose from our impressive range of accommodations and then add car rentals, flights and activities to your booking. Bundle it all together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Oshkosh, WI (OSH-Wittman Regional) to O'Hare Intl. Airport (ORD)?
If you booked your OSH to ORD flight in the last 24 hours, you may be able to modify or cancel it without fees. 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, visit our Customer Service portal if you’d like more information.

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*Available to One Key members.