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

  • Plan, book, fly with confidence

  • trending down icon

    Be in the know

    Get alerts if flight prices drop or rise*
  • bex rewards loyalty icon

    Book smarter

    Save on select hotels after you book a flight*
  • payments icon

    Find the right fit

    We search billions of combinations of flights to help you find your next adventure

Frequently asked questions

Is it cheaper to buy a plane ticket from ORD to WSZ last minute?
Being a spontaneous soul is an amazing way to see the world, but it isn't necessarily the wisest way to land a bargain plane ticket. It's better to book your O'Hare Airport to WSZ trip well in advance rather than leaving it until the last minute. Based on flight pricing and demand studies in 2022, we have found that the best time to book domestic flights is between 28 – 35 days ahead of the departure date, and international flights three to four months in advance. Leave all that spontaneity for when you reach your destination!
Can I change the date of my flight from O'Hare Intl. Airport (ORD) to WSZ?
We know life happens and plans change, so Expedia is here to help make amending your flight as easy as possible. First, find your ORD to WSZ itinerary through the Expedia Trips portal and read the fare conditions and rules about what sorts of changes are allowed. If you purchased your ticket in the last 24 hours, some airlines will let you cancel without charge and organize new flights. If you bought your ticket more than 24 hours ago, connect with us via our Customer Service portal to find out your options.

Travel information

Travel information

Origin airport
O'Hare Intl.
Destination airport
Westport
Distance
13611 km

Book with confidence

Book with confidence