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

Popular airlines from Oxford, CT (OXC-Waterbury - Oxford) to Chicago O'Hare Intl. Airport (ORD)

Flights from Oxford (OXC) to Chicago (ORD)
Origin airport
Waterbury - Oxford
Destination airport
O'Hare Intl.
Distance
761 mi

Oxford to Chicago Flights

The cheapest times to fly from Oxford to Chicago

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

 

The best time to book a flight from Oxford to Chicago

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

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 Oxford to Chicago 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 Oxford to Chicago 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 Oxford to Chicago 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 Waterbury - Oxford Airport (OXC) to O'Hare Intl. Airport (ORD) cost?
Get a cheap one-way flight or cheap return flight from Waterbury - Oxford Airport (OXC) to O'Hare Intl. Airport (ORD) 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 Waterbury - Oxford Airport (OXC) to O'Hare Intl. Airport (ORD)?
Planning your trip for is a good way to save, as it's the cheapest month for flights between OXC and ORD. You'll usually find the lowest prices during off-peak months.
Which airlines fly direct from Waterbury - Oxford Airport (OXC) to O'Hare Intl. Airport (ORD)?
Although Oxford, CT (OXC-Waterbury - Oxford) doesn't offer any direct flights to O'Hare Intl. Airport (ORD), other airports have nonstop routes. Taking off from LaGuardia Airport (LGA) will get you to Chicago without any layovers.
What is the cheapest airline that flies from Waterbury - Oxford Airport (OXC) to O'Hare Intl. Airport (ORD)?
Use the filter tool on Expedia to compare different airlines and find the most affordable carrier that'll take you from OXC to ORD. Then, sort your results by "Price (lowest to highest)" to snap up a great deal.
How many flights per day from Waterbury - Oxford Airport (OXC) to O'Hare Intl. Airport (ORD)?
There are no daily nonstop flights departing from Waterbury - Oxford Airport (OXC) to O'Hare Intl. Airport (ORD). But you can book flights with layovers. Filter your search results on Expedia to include one or two stops, and you'll be cruising above the clouds in no time at all.
What day of the week has the most flights from OXC to ORD?
Usually you'll find the widest variety of flight choices on a Friday. Tuesdays tend to be the quietest.* But this can vary depending on the time of year, carrier and other factors.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Waterbury - Oxford Airport (OXC) to O'Hare Intl. Airport (ORD)?
Opt for a flight from Waterbury - Oxford Airport (OXC) to O'Hare Intl. Airport (ORD) that leaves before 3 PM to reduce the risk of cancellations and delays. Departures after this time 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 Waterbury - Oxford Airport (OXC) to O'Hare Intl. Airport (ORD) last-minute?
Last-minute fares from OXC to ORD are usually more expensive. To lock in the best prices, start looking for flights ahead of time. That said, if you're flexible with your travel plans, you may find a cheap fare right before you leave.
Is it cheaper to book an OXC to ORD flight and hotel package?
You can save money by securing an OXC to ORD flight and hotel package compared to booking separately. In fact, you could save hundreds of dollars by bundling with Expedia. And it's easy to manage it all in one convenient place. After selecting your preferred accommodations and flights, you can add extras like tours, car rentals and activities.
Can I cancel or change the date of my flight from Waterbury - Oxford Airport (OXC) to O'Hare Intl. Airport (ORD)?
In most cases, you're able to cancel or reschedule your OXC to ORD flight. However, there may be additional charges, especially if your booking was made more than 24 hours ago. Check your itinerary for the airline's fees and guidelines on flight changes, or if you need more details, visit our Customer Service portal.

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*Available to One Key members.