Cheap Flights from Chicago (PWK) to Oxford (OXC)

Popular airlines from Chicago, IL (PWK-Chicago Executive) to Oxford, CT (OXC-Waterbury - Oxford)

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Frequently asked questions

How much does a flight from Chicago Executive Airport (PWK) to Waterbury - Oxford Airport (OXC) cost?
Grab a cheap one-way flight or cheap return flight from Chicago Executive Airport (PWK) to Waterbury - Oxford Airport (OXC) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight deals on this route.
What is the cheapest month to fly from Chicago Executive Airport (PWK) to Waterbury - Oxford Airport (OXC)?
Planning your trip for can help you save, as it's the cheapest month for flights between PWK and OXC. You'll typically find the lowest fares during the off-season.
What is the cheapest airline that flies from Chicago Executive Airport (PWK) to Waterbury - Oxford Airport (OXC)?
Use the filters on Expedia to compare airlines and find the most affordable carrier that'll take you from PWK to OXC. Then, sort your results by "Price (lowest to highest)" to score a good deal.
How many flights per day from Chicago Executive Airport (PWK) to Waterbury - Oxford Airport (OXC)?
Nonstop flights from Chicago Executive Airport (PWK) to Waterbury - Oxford Airport (OXC) aren't available daily, so you'll need to take a flight with a layover. Explore your options with Expedia's filter tool. Enter your travel dates and click on either "1 Stop" or "2+ Stops."
What day of the week has the most flights from PWK to OXC?
You'll usually find Tuesday the quietest day for flights, while Fridays are often the busiest.* However this can change 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 Chicago Executive Airport (PWK) to Waterbury - Oxford Airport (OXC)?
Book a flight from Chicago Executive Airport (PWK) to Waterbury - Oxford Airport (OXC) that takes off before 3 PM to reduce the risk of delays and cancellations. Later departures 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 Chicago Executive Airport (PWK) to Waterbury - Oxford Airport (OXC) last-minute?
Waiting until just before your trip to book a ticket from PWK to OXC generally means paying more. While you may find some last-minute offers, they're not always guaranteed. Be flexible with your travel plans for the best chance of getting a bargain.
Is it cheaper to book a PWK to OXC flight and hotel package?
Securing a PWK to OXC flight and hotel package is typically cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels in one place. Pick from our impressive range of stays and then add activities, flights and car rentals 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 Chicago Executive Airport (PWK) to Waterbury - Oxford Airport (OXC)?
Typically, you're able to reschedule or cancel your PWK to OXC flight. However, additional fees may apply, especially if your booking was made more than 24 hours ago. Double-check your itinerary for the airline's fees and policies on flight changes, or if you need further information, visit our Customer Service portal.

Travel information

Origin airport
Chicago Executive
Destination airport
Waterbury - Oxford
Distance
760 mi

Book with confidence

Chicago to Oxford Flights

The cheapest times to fly from Chicago to Oxford

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

 

The best time to book a flight from Chicago to Oxford

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

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 Oxford 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 Chicago to Oxford 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 Oxford 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 Oxford Flights

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*Available to One Key members.