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

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

    notification illustration

    Be in the know

    Get alerts if flight prices drop or rise*
    deals illustration

    Book smarter

    Save up to 30% on select hotels after you book a flight*
    trophy illustration

    Earn twice

    Earn your airline miles on top of our OneKeyCash
    Learn about One Key

Alternative airports near Bridgeport

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Westchester County HPN. Average driving time to city center is 46 minutes. Flights from $486
HPN
Westchester County
Average driving time to city center46 min
Flights from $486
Select flight to MacArthur ISP. Cheapest option available. Average driving time to city center is 2 hours 13 minutes. Flights from $149
ISP
MacArthur
Cheapest
Average driving time to city center2 h 13 min
Flights from $149

Frequently asked questions

How much does a flight from Midway Intl. Airport (MDW) to Igor I. Sikorsky Memorial Airport (BDR) cost?
Lock in a cheap one-way flight or cheap return flight from Midway Intl. Airport (MDW) to Igor I. Sikorsky Memorial Airport (BDR) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight deals on this route.
What is the cheapest month to fly from Midway Intl. Airport (MDW) to Igor I. Sikorsky Memorial Airport (BDR)?
is the cheapest month to fly from MDW to BDR. Traveling outside of peak seasons is often the key to scoring lower fares.
What is the cheapest airline that flies from Midway Intl. Airport (MDW) to Igor I. Sikorsky Memorial Airport (BDR)?
Expedia's filter tool lets you easily compare different airlines, departure times and fares all in one place. Tailor the search to your trip, then sort by "Price (lowest to highest)" to see which carrier offers the cheapest MDW to BDR flight.
How many flights per day from Midway Intl. Airport (MDW) to Igor I. Sikorsky Memorial Airport (BDR)?
Nonstop flights from Midway Intl. Airport (MDW) to Igor I. Sikorsky Memorial Airport (BDR) aren't available daily, so you'll have to take a flight with a layover. Explore your options with Expedia's filters. Enter your travel details and choose either "1 Stop" or "2+ Stops."
What day of the week has the most flights from MDW to BDR?
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 Midway Intl. Airport (MDW) to Igor I. Sikorsky Memorial Airport (BDR)?
Book a flight from Midway Intl. Airport (MDW) to Igor I. Sikorsky Memorial Airport (BDR) that leaves before 3 PM to reduce the likelihood of delays and cancellations. Departures after this time 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 Igor I. Sikorsky Memorial Airport (BDR) last-minute?
Booking your plane ticket from MDW to BDR just before your journey is generally more expensive. But if there's some wiggle room with your travel times and dates, you could bag a cheap last-minute fare.
Can I cancel or change the date of my flight from Midway Intl. Airport (MDW) to Igor I. Sikorsky Memorial Airport (BDR)?
It's usually possible to reschedule or cancel your MDW to BDR flight. However, if it's been more than 24 hours since booking, additional fees may apply. Check your airline's policies in your itinerary to see what changes are allowed and whether any costs are involved. You'll also find further details on our Customer Service portal.

Travel information

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

Book with confidence

Chicago to Bridgeport Flights

The cheapest times to fly from Chicago to Bridgeport

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

 

The best time to book a flight from Chicago to Bridgeport

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

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 Bridgeport 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 Bridgeport 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 Bridgeport 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 Bridgeport Flights

Explore a world of travel with Expedia

*Available to One Key members.