Cheap Flights from Bridgeport (BDR) to Chicago (MDW)

Popular airlines from Bridgeport, CT (BDR-Igor I. Sikorsky Memorial) to Chicago Midway Airport (MDW)

Frequently asked questions

How much does a flight from Igor I. Sikorsky Memorial Airport (BDR) to Midway Intl. Airport (MDW) cost?
Grab a cheap one-way flight or cheap return flight from Igor I. Sikorsky Memorial Airport (BDR) 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 Igor I. Sikorsky Memorial Airport (BDR) to Midway Intl. Airport (MDW)?
is the most affordable month to fly from BDR to MDW. Planning your trip for the off-season is often the key to better flight prices.
What is the cheapest airline that flies from Igor I. Sikorsky Memorial Airport (BDR) to Midway Intl. Airport (MDW)?
Expedia's filter tool lets you easily compare airlines, flight times and fares all in one place. Choose your preferences, then sort by "Price (lowest to highest)" to find out which carrier offers the cheapest BDR to MDW flight.
How many flights per day from Igor I. Sikorsky Memorial Airport (BDR) to Midway Intl. Airport (MDW)?
You'll have to catch a flight with a layover if you're traveling from Igor I. Sikorsky Memorial Airport (BDR) to Midway Intl. Airport (MDW). Direct flights don't operate daily on this route. However, just filter your search to include one or more stops to discover an option that works for you.
What day of the week has the most flights from BDR to MDW?
You'll usually find Tuesday the quietest day for flights, while Fridays are often the busiest.* However this can vary from season to season and during peak travel times or public holidays.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Igor I. Sikorsky Memorial Airport (BDR) to Midway Intl. Airport (MDW)?
To avoid potential delays on the Igor I. Sikorsky Memorial Airport (BDR) to Midway Intl. Airport (MDW) route, travel before 3 PM. Later departures are 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 Igor I. Sikorsky Memorial Airport (BDR) to Midway Intl. Airport (MDW) last-minute?
Booking your flight from BDR to MDW shortly before your trip is generally more expensive. However, if you're flexible with your departure times and dates, you could score a cheap last-minute fare.
Is it cheaper to book a BDR to MDW flight and hotel package?
Booking a BDR to MDW flight and hotel package is generally cheaper than booking separately. With Expedia, you can enjoy the convenience of organizing your travels in one place. Choose from our impressive range of accommodations and then add flights, car rentals and activities to your booking. Bundle it all together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Igor I. Sikorsky Memorial Airport (BDR) to Midway Intl. Airport (MDW)?
If you reserved your BDR to MDW flight within the last 24 hours, you may be able to cancel or modify it without any fees. Depending on the airline and the ticket 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 if you want more information.

Travel information

Origin airport
Igor I. Sikorsky Memorial
Destination airport
Midway Intl.
Distance
756 mi

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Bridgeport to Chicago Flights

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

 

The best time to book a flight from Bridgeport to Chicago

Sunday is one of the best days to book for cheap flights from Bridgeport 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 Bridgeport 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 Bridgeport to Chicago in 2026. 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 Bridgeport 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 Bridgeport 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.

 

Bridgeport to Chicago Flights

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*Available to One Key members.