Cheap Flights from Oakland (ODM) to Chicago (MDW)

Popular airlines from Oakland, MD (ODM-Garrett County) to Chicago Midway Airport (MDW)

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Frequently asked questions

How much does a flight from Oakland, MD (ODM-Garrett County) to Midway Intl. Airport (MDW) cost?
Secure a cheap one-way flight or cheap return flight from Oakland, MD (ODM-Garrett County) to Midway Intl. Airport (MDW) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight deals on this route.
What is the cheapest month to fly from Oakland, MD (ODM-Garrett County) to Midway Intl. Airport (MDW)?
is the cheapest month to fly from ODM to MDW. Traveling during an off-peak travel window is often the key to scoring lower fares.
What is the cheapest airline that flies from Oakland, MD (ODM-Garrett County) to Midway Intl. Airport (MDW)?
Use the filter tool on Expedia to compare different airlines and find the cheapest carrier that'll take you from ODM to MDW. Then, sort your results by "Price (lowest to highest)" to snag a good deal.
How many flights per day from Oakland, MD (ODM-Garrett County) to Midway Intl. Airport (MDW)?
There are no daily nonstop flights available from Oakland, MD (ODM-Garrett County) to Midway Intl. Airport (MDW). But you can book flights with layovers. Filter your search on Expedia to include one or more stops, and you'll be on your way in no time at all.
What day of the week has the most flights from ODM 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 Oakland, MD (ODM-Garrett County) to Midway Intl. Airport (MDW)?
To avoid possible delays on the Oakland, MD (ODM-Garrett County) to Midway Intl. Airport (MDW) route, aim to travel before 3 PM. Flights after this time 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 Oakland, MD (ODM-Garrett County) to Midway Intl. Airport (MDW) last-minute?
Last-minute fares from ODM to MDW are usually more expensive. To lock in the lowest prices, start looking for flights as soon as possible. That being said, if you're flexible with your travel dates, it's possible to land a cheap ticket just before your departure.
Is it cheaper to book an ODM to MDW flight and hotel package?
Compared with arranging hotels and flights separately, booking an ODM to MDW flight and hotel package with Expedia could lead to significant savings. What's more, having everything in one convenient place will take the hassle out of travel planning. Just secure your flights and choose from our extensive range of hotels, then personalize your trip with other add-ons like tours, activities and car rentals.
Can I cancel or change the date of my flight from Oakland, MD (ODM-Garrett County) to Midway Intl. Airport (MDW)?
Typically, it's possible to cancel or reschedule your ODM to MDW flight. However, if it's been more than 24 hours since booking, additional fees may apply. Refer to your airline's policies in your itinerary to see what changes are possible and whether any costs are involved. You'll also find more information on our Customer Service portal.

Travel information

Origin airport
Garrett County
Destination airport
Midway Intl.
Distance
465 mi

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Oakland to Chicago Flights

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

 

The best time to book a flight from Oakland to Chicago

Sunday is one of the best days to book for cheap flights from Oakland 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 Oakland 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 Oakland 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 Oakland 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 Oakland 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.

 

Oakland to Chicago Flights

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*Available to One Key members.