Cheap Flights from Chicago (ORD) to New Haven (HVN)

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Find available prices by choosing your travel dates.
Flights from Chicago (ORD) to New Haven (HVN)
Origin airport
O'Hare Intl.
Destination airport
Tweed - New Haven Regional
Distance
775 mi

Chicago to New Haven Flights

The cheapest times to fly from Chicago to New Haven

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

The best time to book a flight from Chicago to New Haven

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

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 New Haven 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 New Haven 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 New Haven 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

Is it cheaper to buy a plane ticket from ORD to HVN last minute?
Booking your flight from O’Hare Airport to Tweed - New Haven Regional Airport (HVN) last minute could help you save if you stumble on a real bargain. However, tickets generally don’t get cheaper closer to the departure date. If you hold out, flights could also be booked solid or the best seats taken. If you don’t want to risk it, book well in advance of the date you want to leave. In fact, some of the best deals are available on Expedia up to a year in advance. If your preferred airline hasn’t released its airfares yet, check back regularly as offers are constantly updated on Expedia.
What airports do you fly into for New Haven from Chicago?
With Tweed - New Haven Regional Airport (HVN), MacArthur Airport (ISP) and Hartford, CT (HFD-Hartford - Brainard) to pick from, making your way from Chicago to New Haven is simple. The city’s busiest terminal, Tweed - New Haven Regional Airport (HVN), is about 3 mi southeast of the downtown area. As well as the price of tickets, consider factors like bus or train options from the airport and the distance to your hotel before making your choice. Get your New Haven adventure off to an exciting start by discovering Yale University and Southern Connecticut State University.
Can I change the date of my flight from O'Hare Airport to Tweed - New Haven Regional Airport?
We know plans can change, so Expedia is here to help make amending your trip as easy as possible. First, find your O’Hare Intl. Airport (ORD) to Tweed - New Haven Regional Airport itinerary through the Expedia Trips portal and read the fare rules and restrictions to see if you can make changes. If you booked in the last 24 hours, some carriers will let you cancel without charge and book new flights. If you booked your fare more than 24 hours ago, contact us via our Customer Service portal to find out your options.

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