Cheap Flights from Chicago (ORD) to Chicago (MDW)

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Find available prices by choosing your travel dates.

Frequently asked questions

How much does a flight from O'Hare Intl. Airport (ORD) to Midway Intl. Airport (MDW) cost?
Discover the latest flight deals from ORD to MDW 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 ORD to MDW?
The cheapest flights from ORD to MDW are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
What is the cheapest airline that flies from ORD to MDW?
Use the filter tool on Expedia to compare airlines and find the cheapest carrier that’ll take you from ORD to MDW. Sort your results by “Price (lowest to highest)” to snap up a great deal.
How many flights per day from O'Hare Intl. Airport (ORD) to Midway Intl. Airport (MDW)?
Direct flights from O’Hare Intl. Airport (ORD) to Midway Intl. Airport (MDW) aren’t available daily, so you’ll need to take a flight with a layover. Explore your options with Expedia’s filter tool. Enter your travel details and click on either “1 Stop” or “2+ Stops.”
What day of the week has the most flights from ORD to MDW?
Typically you’ll find the most flight options available on a Friday. Tuesdays tend to be the quietest.* But this can change depending on the season, airline and other factors.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What airline has the least delays from ORD to MDW?
With 100% of flights generally arriving as scheduled, United Airlines has the best on-time performance for nonstop flights from O’Hare Intl. Airport (ORD) to Midway Intl. Airport (MDW). To monitor your flight status and get notified about any changes, simply head to the Expedia App.
What is the best time to fly from O'Hare Intl. Airport (ORD) to Midway Intl. Airport (MDW)?
To avoid possible delays on the O’Hare Intl. Airport (ORD) to Midway Intl. Airport (MDW) route, fly before 3 PM. Later departures 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 O'Hare Intl. Airport (ORD) to Midway Intl. Airport (MDW) last-minute?
Booking your flight from ORD to MDW right before your journey is typically more expensive. But if there’s some wiggle room with your itinerary, you could score a cheap last-minute fare.
Is it cheaper to book an ORD to MDW flight and hotel package?
You’ll typically save money by booking an ORD to MDW flight and hotel package compared to booking separately. In fact, you could save hundreds of dollars by bundling with Expedia. And it’s simple to manage it all in one convenient place. After choosing your ideal accommodations and flights, consider adding extras such as activities, car rentals and tours.
Can I cancel or change the date of my flight from O'Hare Intl. Airport (ORD) to Midway Intl. Airport (MDW)?
If you booked your ORD to MDW flight within the last 24 hours, you may be able to cancel or modify it at no cost. Depending on the airline and the fare type you purchased, additional charges may apply for changes after that time. Airline policies and contact information can be found in your itinerary or confirmation email. Or, visit our Customer Service portal for further details.
*Available to One Key members.