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

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Flight from Oshkosh to Chicago route information
Origin airport
Wittman Regional
Destination airport
O'Hare Intl.
Distance
229 km

Compare flights from Oshkosh to Chicago easily and book in confidence

For travelling on business or for pleasure, Expedia makes it easy to book your flights from Oshkosh to Chicago. Operating between them flights per day, airlines cover the route. And fly direct, getting you to O'Hare Intl. in just hours. If you have a preferred carrier, use our advanced search tool to find the right flight from Wittman Regional to O'Hare Intl..  

To make things even better, in the advanced search, you can also choose to fly economy, premium economy, business or first class, select your maximum number of stops, and pick your preferred departure and arrival time. You can also opt for refundable and direct flights. 

Grab a great deal on your flight from Wittman Regional (OSH) to O'Hare Intl. (ORD) 

The easiest way to view the best deals on flights from Oshkosh to Chicago today is to enter your travel dates and hit search. From here, you can sort your results by price to see the cheapest flights first. Right now, return flights from Wittman Regional to O'Hare Intl. start at just and range up to .  

To find an even better deal, try  

  • being flexible on your dates – midweek flights can be cheaper
  • looking for other airports near Oshkosh and Chicago
  • booking your flight during , the cheapest month on this route
  • varying your flight times – early morning and late at night are sometimes cheaper 

Why you should book your Oshkosh to Chicago flight with Expedia!

We cater for all flight types, cabin classes and airlines. So whether you’re booking flights from Wittman Regional to O'Hare Intl. for a budget break or a business trip with a bit of pleasure thrown in, we make it easy to secure the seat that’s right for you.  

Thanks to our supersized inventory that offers great choice all in one place, you know you’ll get a great deal with Expedia. Especially if you bundle your flight together with your hotel, you will unlock amazing savings. For added peace of mind, you can choose flexible bookings or filter to find refundable options, so you won’t pay a fee to change your flight.  

Frequently asked questions

How much is a flight from OSH to O'Hare Intl. Airport (ORD)?
Based on fares available within the last 7 days on Expedia for flights departing within the next year, round-trip journeys from OSH to ORD start from . Book today to score the best price for your exciting adventure. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from OSH to ORD?
Most flights can be cancelled online, but whether or not you incur a fee depends on your airline. If you do have to cancel your getaway, follow the instructions in the Customer Service Portal.
How do I find cheap flights from OSH to ORD that have flexible change policies?
Many airlines offer the option to reschedule your flight without a change fee. All you pay is the difference between the original flight and the new flight. When you’re searching for OSH to O’Hare Airport flights, you’ll see a “no change fees” filter for you to select.
How far is the flight from OSH to O'Hare Airport?
With a flight distance of 230 kilometres, it’s only a short hop from OSH to O’Hare Intl. Airport (ORD). It might be a quick one, but it’s still worth bringing a book to read.
Which airlines fly direct from OSH to O'Hare Intl. Airport (ORD)?
Flying directly between OSH and ORD isn’t possible at this time. However, you’ll still be able to book a flight to Chicago with at least one stop.
Are OSH to ORD flight tickets cheaper when they're purchased at the last minute?
Booking your trip from OSH to ORD last minute could be your ticket to an awesome deal. However, it could end up costing you a whole lot more! If you’d rather err on the side of caution, book well ahead of your departure date. In fact, Expedia has some of the best bargains up to 12 months in advance. If your preferred carrier hasn’t released tickets yet, check back frequently as deals are updated on Expedia all the time.
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*Available to Expedia members.