Cheap Flights from Brandon (YBR) to Chicago (MDW)

Popular airlines from Brandon, MB (YBR) to Chicago Midway Airport (MDW)

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Flights from Brandon (YBR) to Chicago (MDW)
Origin airport
Brandon
Destination airport
Midway Intl.
Distance
810 mi

Brandon to Chicago Flights

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

 

The best time to book a flight from Brandon to Chicago

Sunday is one of the best days to book for cheap flights from Brandon 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 Brandon 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 Brandon 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 Brandon 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 Brandon 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 Brandon Airport (YBR) to Midway Intl. Airport (MDW) cost?
Get a cheap one-way flight or cheap return flight from Brandon Airport (YBR) to Midway Intl. Airport (MDW) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight offers on this route.
What is the cheapest month to fly from Brandon Airport (YBR) to Midway Intl. Airport (MDW)?
The cheapest month to fly from YBR to MDW is , when demand is low. Off-peak months are usually when you'll find cheap fares for travel between these airports.
What is the cheapest airline that flies from Brandon Airport (YBR) to Midway Intl. Airport (MDW)?
Expedia's filter tool lets you easily compare different airlines, travel time and fares all in one place. Select your preferences, then sort by "Price (lowest to highest)" to see which carrier offers the cheapest YBR to MDW flight.
How many flights per day from Brandon Airport (YBR) to Midway Intl. Airport (MDW)?
You'll need to catch a flight with a layover when traveling from Brandon Airport (YBR) to Midway Intl. Airport (MDW). Direct flights don't operate daily on this route. However, simply filter your search to include one or more stops to discover the best option for your trip.
What day of the week has the most flights from YBR to MDW?
Friday is usually the busiest day for flights, while Tuesday is often the quietest.* Keep in mind that flight schedules can vary depending on various factors, including the time of year and airline.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Brandon Airport (YBR) to Midway Intl. Airport (MDW)?
Choose a flight from Brandon Airport (YBR) to Midway Intl. Airport (MDW) that leaves before 3 PM to reduce the risk of cancellations. Departures after this hour have a 22% higher chance of being canceled, on average.**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 Brandon Airport (YBR) to Midway Intl. Airport (MDW) last-minute?
Booking your flight from YBR to MDW right before your getaway is usually more expensive. However, if there's some wiggle room with your departure dates and times, you could score a cheap last-minute fare.
Is it cheaper to book a YBR to MDW flight and hotel package?
Compared with arranging hotels and flights separately, booking a YBR 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 planning your trip. Just pick your flights and choose from our wide range of hotels, then personalize your trip with extras like tours, car rentals and activities.
Can I cancel or change the date of my flight from Brandon Airport (YBR) to Midway Intl. Airport (MDW)?
If you booked your YBR to MDW flight in the last 24 hours, you may be able to modify or cancel it without any fees. Depending on the airline and the type of ticket you purchased, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, go to our Customer Service portal for more information.

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