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

Popular airlines from Chicago O'Hare Intl. Airport (ORD) to Chicago Midway Airport (MDW)

Frequently asked questions

How much does a flight from O'Hare Intl. Airport (ORD) to Midway Intl. Airport (MDW) cost?
Snag a cheap one-way flight or cheap return flight from O'Hare Intl. Airport (ORD) to Midway Intl. Airport (MDW) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight deals on this route.
What is the cheapest month to fly from O'Hare Intl. Airport (ORD) to Midway Intl. Airport (MDW)?
is the least expensive month to fly from ORD to MDW. Timing your trip outside of the busy season is often the key to finding better deals on flights.
What is the cheapest airline that flies from O'Hare Intl. Airport (ORD) to Midway Intl. Airport (MDW)?
Use the filters on Expedia to compare airlines and find the cheapest carrier that'll take you from ORD to MDW. Then, sort your results by "Price (lowest to highest)" to pick up the best deal available.
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.

Travel information

Origin airport
O'Hare Intl.
Destination airport
Midway Intl.
Distance
15 mi

Book with confidence

Chicago to Chicago Flights

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

 

The best time to book a flight from Chicago to Chicago

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

 

Chicago to Chicago Flights

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*Available to One Key members.