Flights from Chicago to Connecticut

Flight deals from Chicago to Connecticut

Looking for cheap tickets from Chicago to Connecticut, or a last-minute trip? Find the lowest prices on one-way and return tickets right here.

Hartford.R 1,157 per passenger.Departing Wed, 12 Nov.One-way flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Wed, 12 Nov, arriving in Hartford Bradley International.Price includes taxes and charges.From R 1,157, select.

New Haven.R 1,632 per passenger.Departing Mon, 29 Sep.One-way flight with Spirit Airlines.Outbound indirect flight with Spirit Airlines, departs from Chicago O'Hare International on Mon, 29 Sep, arriving in New Haven.Price includes taxes and charges.From R 1,632, select.

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Flying from Chicago to Connecticut

Arm yourself with these facts on the fly.

Cheapest flight found	R 1,157
Cheapest month to fly	November
Average flight time	2 hrs, 8 mins
Cheapest airport to fly from	Chicago O'Hare International
Most popular airline	American Airlines

How to find cheap flights from Chicago to Connecticut

We've compared the best online travel agents and flight providers on the internet to find the cheapest plane tickets from Chicago to Connecticut. Other savvy travellers recently found return flights from R 2,446 and one-way tickets from R 1,157 one-way. Ready to join them? Here are a few tips to help you do it the smart way.

Fly from Chicago O'Hare International into New Haven

At the moment, the lowest priced flight tickets to Connecticut are from Chicago O'Hare International Airport to New Haven Airport.

Fly in November

We crunched the flight calendar and found the cheapest time to fly from Chicago to Connecticut is currently November.

Flex your dates for the best rates

If you’re flexible on your departure dates, you can use Skyscanner's whole month tool to find the cheapest day of the year to fly from Chicago to anywhere you choose in Connecticut.

Watch as fares rise and fall

With Price Alerts, we'll let you know when flight prices from Chicago to Connecticut go up or down so you can book when the time is just right.

Relax – these are fee-free flight tickets

With us, there are no added fees – the Connecticut to Connecticut flight price you see when you search with us is what you pay to the provider.

Frequently asked questions

What's the average Chicago to Connecticut flight price?

We looked at all of the upcoming return flights from Chicago to Connecticut we could find over the next 12 months. It looks like R 2,446 is the best price. This is good, compared to the average Connecticut ticket price of R 2,468.

What is the cheapest month to fly from Chicago to Connecticut?

The cheapest month to fly from Chicago to New Haven Airport is currently November. The cheapest month to fly from Chicago to Hartford Bradley International Airport is usually September

Which upcoming date is cheapest to fly from Chicago to Connecticut on?

After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Chicago to Connecticut on Thursday, 6 November 2025.

Are there any direct flights from Chicago to Connecticut?

Chicago O'Hare International Airport offers direct flights to Connecticut.

If I'm flying from Chicago, where in Connecticut is cheapest to fly into?

If you're flying from Chicago, the cheapest city in Connecticut to fly into is New Haven. The cheapest airport serving New Haven at the moment is New Haven.