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

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

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Flights from Chicago (MDW) to Chicago (ORD)
Origin airport
Midway Intl.
Destination airport
O'Hare Intl.
Distance
15 mi

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.

 

Frequently asked questions

How much does a flight from Midway Intl. Airport (MDW) to O'Hare Intl. Airport (ORD) cost?
Secure a cheap one-way flight or cheap return flight from Midway Intl. Airport (MDW) to O'Hare Intl. Airport (ORD) 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 Midway Intl. Airport (MDW) to O'Hare Intl. Airport (ORD)?
is the cheapest month to fly from MDW to ORD. Timing your trip outside of the busy season is often the key to better flight prices.
What is the cheapest airline that flies from Midway Intl. Airport (MDW) to O'Hare Intl. Airport (ORD)?
Use the filters on Expedia to compare airlines and find the cheapest carrier that'll take you from MDW to ORD. Then, sort your results by "Price (lowest to highest)" to pick up a great deal.
How many flights per day from Midway Intl. Airport (MDW) to O'Hare Intl. Airport (ORD)?
You'll need to hop on a flight with a layover when traveling from Midway Intl. Airport (MDW) to O'Hare Intl. Airport (ORD). There are no daily direct flights on this route. However, simply filter your search to include one or two stops to find an option that works for you.
What day of the week has the most flights from MDW to ORD?
Usually you'll find the greatest selection of flight options on a Friday. Tuesdays tend to be the quietest.* But this can vary depending on the time of year, carrier 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 MDW to ORD?
United Airlines has the strongest track record for on-time direct flights from Midway Intl. Airport (MDW) to O'Hare Intl. Airport (ORD), with an on-time rating of 100%. Use the Expedia App to look up your journey status before you take off and get real-time updates about any trip changes.
What is the best time to fly from Midway Intl. Airport (MDW) to O'Hare Intl. Airport (ORD)?
Opt for a flight from Midway Intl. Airport (MDW) to O'Hare Intl. Airport (ORD) that leaves before 3 PM to reduce the risk of cancellations and delays. Departures later than this are on average 22% more likely to be 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 Midway Intl. Airport (MDW) to O'Hare Intl. Airport (ORD) last-minute?
Last-minute bookings from MDW to ORD are usually more expensive. To lock in the best rates, start searching for flights ahead of time. That said, if you're flexible with your travel plans, it's possible to score a cheap ticket just before your departure.
Is it cheaper to book a MDW to ORD flight and hotel package?
You'll generally save money by booking a MDW to ORD flight and hotel package compared to booking separately. In fact, travelers could save hundreds of dollars by bundling with Expedia. And it's simple to manage everything in one place. Once you've chosen your ideal accommodations and flights, consider adding extras like activities, car rentals and tours.
Can I cancel or change the date of my flight from Midway Intl. Airport (MDW) to O'Hare Intl. Airport (ORD)?
In most cases, you can cancel or reschedule your MDW to ORD flight. However, additional charges may apply, especially if you booked more than 24 hours ago. Double-check your itinerary for the airline's rules and fees on flight changes, or if you want further information, head to our Customer Service portal.

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*Available to One Key members.