Cheap Flights from Chicago (ORD) to Westport (WSZ)

Popular airlines from Chicago O'Hare Intl. Airport (ORD) to Westport (WSZ)

Flights from Chicago (ORD) to Westport (WSZ)
Origin airport
O'Hare Intl.
Destination airport
Westport
Distance
8506 mi

Chicago to Westport Flights

The cheapest times to fly from Chicago to Westport

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

 

The best time to book a flight from Chicago to Westport

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

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 Westport 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 Westport 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 Westport 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 O'Hare Intl. Airport (ORD) to Westport (WSZ) cost?
Get a cheap one-way flight or cheap return flight from O'Hare Intl. Airport (ORD) to Westport (WSZ) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight offers on this route.
What is the cheapest month to fly from O'Hare Intl. Airport (ORD) to Westport (WSZ)?
is the least expensive month to fly from ORD to WSZ. Planning your trip for the off-season is often the key to better flight prices.
What is the cheapest airline that flies from O'Hare Intl. Airport (ORD) to Westport (WSZ)?
Expedia's filter tool lets you easily compare different airlines, flight durations and fares all in one place. Choose your preferences, then sort by "Price (lowest to highest)" to find the carrier with the cheapest ORD to WSZ flight.
How many flights per day from O'Hare Intl. Airport (ORD) to Westport (WSZ)?
Direct flights from O'Hare Intl. Airport (ORD) to Westport (WSZ) aren't available daily, so you'll need to take a flight with a layover. Explore your options with our filter tool. Enter your dates and choose either "1 Stop" or "2+ Stops."
What day of the week has the most flights from ORD to WSZ?
You'll generally find Tuesday the quietest day for flights, while Fridays are often the busiest.* However this can vary from season to season and during public holidays or peak travel times.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from O'Hare Intl. Airport (ORD) to Westport (WSZ)?
Opt for a flight from O'Hare Intl. Airport (ORD) to Westport (WSZ) that leaves before 3 PM to reduce the likelihood of delays. Later departures 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 O'Hare Intl. Airport (ORD) to Westport (WSZ) last-minute?
Booking your flight from ORD to WSZ shortly before your journey is generally more expensive. However, if you're flexible with your travel times and dates, you could land a cheap last-minute fare.
Can I cancel or change the date of my flight from O'Hare Intl. Airport (ORD) to Westport (WSZ)?
It's generally possible to reschedule or cancel your ORD to WSZ flight. However, if the booking was made more than 24 hours ago, additional charges may apply. Refer to your airline's policies in your itinerary to see what changes are allowed and if any costs are involved. You'll also find more details on our Customer Service portal.

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*Available to One Key members.