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

Popular airlines from Chicago Midway Airport (MDW) to Oxford, CT (OXC-Waterbury - Oxford)

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Frequently asked questions

How much does a flight from Midway Intl. Airport (MDW) to Waterbury - Oxford Airport (OXC) cost?
Lock in a cheap one-way flight or cheap return flight from Midway Intl. Airport (MDW) to Waterbury - Oxford Airport (OXC) 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 Midway Intl. Airport (MDW) to Waterbury - Oxford Airport (OXC)?
The cheapest month to fly from MDW to OXC is , when demand is low. Off-peak months are usually when you'll find cheap fares for travel between these airports.
What is the cheapest airline that flies from Midway Intl. Airport (MDW) to Waterbury - Oxford Airport (OXC)?
Use the filters on Expedia to compare different airlines and find the cheapest carrier that'll take you from MDW to OXC. Then, sort your results by "Price (lowest to highest)" to score a good deal.
How many flights per day from Midway Intl. Airport (MDW) to Waterbury - Oxford Airport (OXC)?
You'll have to take a flight with a layover when traveling from Midway Intl. Airport (MDW) to Waterbury - Oxford Airport (OXC). Direct flights don't operate daily on this route. However, just filter your search to include one or more stops to discover the best option for your trip.
What day of the week has the most flights from MDW to OXC?
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 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 Midway Intl. Airport (MDW) to Waterbury - Oxford Airport (OXC)?
To avoid potential delays on the Midway Intl. Airport (MDW) to Waterbury - Oxford Airport (OXC) route, aim to travel before 3 PM. Later departures have a 22% higher chance of being 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.
What airports do you fly into for Oxford from Midway Intl. Airport (MDW)?
Take a direct flight from Midway Intl. Airport (MDW) to Oxford and arrive at LaGuardia Airport (LGA). An alternative gateway to the city is Bradley Intl. Airport (BDL).
Is it cheaper to buy a plane ticket from Midway Intl. Airport (MDW) to Waterbury - Oxford Airport (OXC) last-minute?
Booking your ticket from MDW to OXC shortly before your trip is typically more expensive. But if you're flexible with your schedule, you could score a cheap last-minute fare.
Is it cheaper to book a MDW to OXC flight and hotel package?
Booking a MDW 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. Choose from our extensive range of accommodations and then add flights, car rentals and activities to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Midway Intl. Airport (MDW) to Waterbury - Oxford Airport (OXC)?
Typically, it's possible to cancel or reschedule your MDW to OXC 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 possible and if any costs are involved. You'll also find more information on our Customer Service portal.

Travel information

Origin airport
Midway Intl.
Destination airport
Waterbury - Oxford
Distance
753 mi

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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 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 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.