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

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

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

New Haven to Chicago Flights

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

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

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

Is it cheaper to buy a plane ticket from Tweed - New Haven Regional Airport to O'Hare Airport last minute?
Being the spontaneous type is a fantastic way to see the world, but it isn’t always the smartest method to track down a cheap plane ticket. Think about booking your Tweed - New Haven Regional Airport (HVN) to O’Hare Intl. Airport (ORD) trip in advance instead of leaving it to the last minute. Based on flight pricing and demand studies in 2022, we have found that the best time to book domestic flights is between 28 – 35 days ahead of the departure date, and international flights three to four months in advance. Save up that spontaneity for when you arrive at your destination!
What airports do you fly into for Chicago from New Haven?
O’Hare Intl. Airport (ORD), Midway Intl. Airport (MDW) and Lewis University Airport (LOT) are your options when jetting off from New Haven to Chicago. About 16 mi northwest of downtown Chicago, O’Hare Intl. Airport (ORD) is the city’s main gateway. Think about things such as flight departure and arrival times and the distance to your hotel before choosing your airport. Wrigley Field and Millennium Park are two terrific attractions to put on your must-see list when you arrive at your destination.
Can I change the date of my flight from HVN to ORD?
Easily make changes to your HVN to O’Hare Intl. Airport (ORD) journey through the Expedia Trips portal. But before doing so, read through the conditions in your itinerary to learn what you’re able to do and what fees apply for changes. Some airlines charge a change fee per person, on top of any difference in ticket prices. However, if you booked in the last 24 hours, you may be able to cancel for free and book new flights. You can also stop by our Customer Service portal for more info and to connect with our Virtual Agent.

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*Available to One Key members.