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.Rs37,731 per passenger.Departing Wed, 11 Jun, returning Tue, 17 Jun.Return flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Wed, 11 Jun, arriving in Hartford Bradley International.Inbound direct flight with United departs from Hartford Bradley International on Tue, 17 Jun, arriving in Chicago O'Hare International.Price includes taxes and charges.From Rs37,731, select.

New Haven.Rs55,926 per passenger.Departing Thu, 19 Jun, returning Thu, 26 Jun.Return flight with Avelo Airlines.Outbound indirect flight with Avelo Airlines, departs from Chicago O'Hare International on Thu, 19 Jun, arriving in New Haven.Inbound indirect flight with Avelo Airlines, departs from New Haven on Thu, 26 Jun, arriving in Chicago O'Hare International.Price includes taxes and charges.From Rs55,926, select.

Flying from Chicago to Connecticut

Arm yourself with these facts on the fly.

Cheapest flight found	Rs18,864, Hartford
Cheapest month to fly	June
Average flight time	2 hrs, 8 mins
Cheapest airport to fly from	Chicago Midway
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 Rs37,731 and one-way tickets from Rs18,864 one-way. Ready to join them? Here are a few tips to help you do it the smart way.

Fly from Chicago Midway into Hartford

At the moment, the lowest priced flight tickets to Connecticut are from Chicago Midway Airport to Hartford Bradley International Airport.

Fly in June

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

Fly on a Tuesday

From our data, we can see that Tuesday seems to be the cheapest time to fly from Chicago to Connecticut.

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 Chicago 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 Rs37,731 is the best price. This is good, compared to the average Connecticut ticket price of Rs63,500.

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

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

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 Wednesday, 11 June 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 Hartford. The cheapest airport serving Hartford at the moment is Hartford Bradley International.

How long is the flight from Chicago to Connecticut?

The average flight time between Chicago and Connecticut is 2 hours and 8 minutes.