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

    notification illustration

    Be in the know

    Get alerts if flight prices drop or rise*
    deals illustration

    Book smarter

    Save on select hotels after you book a flight*
    trophy illustration

    Find the right fit

    We search billions of combinations of flights to help you find your next adventure

Frequently asked questions

Is it cheaper to buy a plane ticket from Midway Airport to OSH last minute?
Booking your trip from Midway Intl. Airport (MDW) to OSH last minute could save you a tidy sum if you stumble on a bargain. However, airfares generally don't get cheaper as the date of departure nears. If you wait, flights could also be booked up or the best seats gone (hello, middle seat!). If you'd prefer to play it safe, book well ahead of when you want to leave. Keep in mind that some of the best deals can be found up to a year in advance. If your favorite carrier hasn't released its airfares yet, check back regularly as offers are updated on Expedia all the time.
What airports do you fly into for Oshkosh from Chicago?
From Chicago, you can fly into Oshkosh through Oshkosh, WI (OSH-Wittman Regional), Appleton Intl. Airport (ATW) and Austin Straubel Intl. Airport (GRB). It's a good idea to check which hub is the most convenient for you before making your decision. If you choose Oshkosh, WI (OSH-Wittman Regional), it's approximately 3 kilometers south of the downtown area. Use the cash you save when booking your journey with Expedia to check out the city's popular attractions, such as EAA Aviation Museum and Lake Winnebago.
Can I change the date of my flight from Chicago Airport to OSH?
Make changes quickly to your Chicago Airport to OSH flight by logging in to the Expedia Trips portal. Before you make any amendments, browse the ticket rules in your itinerary to find out what the carrier will let you do and if any charges apply. Some carriers charge a change fee per person, plus any difference in fare prices. However, if you booked in the last 24 hours, you may be able to cancel for free and book new flights. You can also check out our Customer Service portal to find the answers to your questions and to chat with our Virtual Agent.

Travel information

Origin airport
Midway Intl.
Destination airport
Wittman Regional
Distance
252 km

Book with confidence

Chicago to Oshkosh Flights

Whether you’re looking for a grand adventure or just want to get away for a last-minute break, flights from Chicago to Oshkosh offer the perfect respite. Not only does exploring Oshkosh provide the chance to make some magical memories, dip into delectable dishes, and tour the local landmarks, but the cheap airfare means you won’t bust your budget. So no matter whether your ideal itinerary involves flying one way, non-stop, or round trip, you’re bound to find flights that match your schedule on Expedia, and at prices that won’t shock your wallet.

Bagging a cheap flight from Chicago to Oshkosh may mean more dollars to spend on for one-of-a-kind souvenirs when you arrive, but it doesn’t mean you have to skimp on your travel experience, as Expedia offers a sizzling selection of cheap airlines that’ll put you in your happy place on their planes, whether that’s getting lost in a hair-raising airport thriller, dreaming on the passing landscape over a glass of bubbly, or jotting down your vacation bucket list at 38,000 feet. There’s also bound to be plenty of opportunities to snap a few photos of the high life that will make your friends green with envy. After all, enjoying the journey is part of the fun.

With so many affordable flights and so many wonderful adventures awaiting you, there’s no reason to put off booking a fantastic flight from to today. So don’t leave it to the last minute to make your dream trip a reality: pack your bags with your go-to travel accessories, put together your list of must-see attractions and can’t-miss activities, and get ready to broaden your horizons – with Expedia, the wonders of Oshkosh are only a plane trip away. Book your travel arrangements with us today!

If you would like to book flights to Oshkosh more flexibly many prefer to purchase one-way tickets with options to take different airlines. A one way ticket to Oshkosh is now!

Chicago to Oshkosh Flights

Explore a world of travel with Expedia