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

Popular airlines from Chicago O'Hare Intl. Airport (ORD) to New Haven, CT (HVN-Tweed - New Haven Regional)

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Flights from Chicago (ORD) to New Haven (HVN)
Origin airport
O'Hare Intl.
Destination airport
Tweed - New Haven Regional
Distance
775 mi
Average flight time
2 hours 10 mins

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

How much does a flight from O'Hare Intl. Airport (ORD) to Tweed - New Haven Regional Airport (HVN) cost?
You can find cheap return fares from O'Hare Intl. Airport (ORD) to Tweed - New Haven Regional Airport (HVN) starting from $93. Snag a seat and get ready to go. This information is based on the cheapest price found on Expedia for this return journey departing within the next three months. This airfare is for a Avelo Airlines flight leaving ORD on August 14 2025 and touching down at HVN. The price was last updated on July 23 2025 and has not changed since.
What is the cheapest month to fly from ORD to HVN?
The cheapest flights from ORD to HVN are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
What is the cheapest airline that flies from ORD to HVN?
Currently, the cheapest carrier offering one-way flights from ORD to HVN is Avelo Airlines. You can take off on this route from $49. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from ORD on August 28 2025. Prices were last updated on July 23 2025 and have not changed since.
How many flights per day from O'Hare Intl. Airport (ORD) to Tweed - New Haven Regional Airport (HVN)?
There aren't any daily direct flights available from O'Hare Intl. Airport (ORD) to Tweed - New Haven Regional Airport (HVN). But you can book flights with layovers. Filter your search on Expedia to include one or more stops, and you'll be cruising above the clouds in no time.
What day of the week has the most flights from ORD to HVN?
You'll usually find Tuesday the quietest day for flights, while Fridays tend to be the busiest.* However this can vary 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 O'Hare Intl. Airport (ORD) to Tweed - New Haven Regional Airport (HVN)?
To land at Tweed - New Haven Regional Airport (HVN) on schedule, opt for a flight that takes off from O'Hare Intl. Airport (ORD) before 3 PM. The chance of cancellations is 22% higher, on average, for departures after this hour.**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 New Haven from O'Hare Intl. Airport (ORD)?
If you're taking a direct flight from O'Hare Intl. Airport (ORD) to New Haven, you can arrive at either Bradley Intl. Airport (BDL) or Westchester County Airport (HPN).
Is it cheaper to buy a plane ticket from O'Hare Intl. Airport (ORD) to Tweed - New Haven Regional Airport (HVN) last-minute?
Waiting until right before your break to book a flight from ORD to HVN generally means paying more. While you may come across some last-minute offers, there's no guarantee. Keep your travel schedule open for a better chance of landing a bargain.
Is it cheaper to book an ORD to HVN flight and hotel package?
Compared with arranging flights and hotels separately, booking an ORD to HVN flight and hotel package with Expedia could result in significant savings. Better yet, having everything in one easy place will take the stress out of travel planning. Simply secure your flights and choose from our extensive range of hotels, then tailor your trip with extras like activities, tours and car rentals.
Can I cancel or change the date of my flight from O'Hare Intl. Airport (ORD) to Tweed - New Haven Regional Airport (HVN)?
It's usually possible to cancel or reschedule your ORD to HVN flight. However, for bookings made more than 24 hours ago, additional charges may apply. Check your airline's policies in your itinerary to see what changes are allowed and if any costs are involved. You'll also find more details on our Customer Service portal.

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