Cheap Flights from Chicago Midway Airport to Connecticut from $601 Return

Flight deals from Chicago Midway Airport to Connecticut

Looking for a cheap last-minute deal or the best return flight from Chicago Midway Airport to Connecticut? If you want to travel next month, return fares start from $602. Find the lowest prices on one-way and return tickets right here.

Hartford.$601 per passenger.Departing Tue, 4 Aug, returning Tue, 1 Sep.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 4 Aug, arriving in Hartford Bradley International.Inbound direct flight with Southwest Airlines departs from Hartford Bradley International on Tue, 1 Sep, arriving in Chicago Midway.Price includes taxes and charges.From $601, select.

New Haven.$658 per passenger.Departing Thu, 11 Jun, returning Mon, 15 Jun.Return flight with Frontier Airlines and Avelo Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago Midway on Thu, 11 Jun, arriving in New Haven.Inbound indirect flight with Avelo Airlines, departs from New Haven on Mon, 15 Jun, arriving in Chicago Midway.Price includes taxes and charges.From $658, select.

Show more deals

Flying from Chicago Midway Airport to Connecticut

Arm yourself with these facts on the fly.

Cheapest flight found	$601
Cheapest month to fly	August
Average flight time	2 hrs, 5 mins
Average flights per week	16
Most popular airline	Southwest Airlines

How to find cheap flights from Chicago Midway Airport to Connecticut

We've compared the best online travel agents and flight providers on the internet to find the cheapest plane tickets from Chicago Midway Airport to Connecticut. Other savvy travellers recently found return flights from $601 and one-way tickets from $299. Ready to join them? Here are a few tips to help you do it the smart way.

Fly in August

The cheapest time to fly from Chicago Midway Airport to Connecticut is currently August.

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 Midway Airport 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 Midway Airport to your chosen airport in 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 Airport to Connecticut flight price you see when you search with us is what you pay to the provider.

Frequently asked questions

Are there any direct flights from Chicago Midway Airport to Connecticut?

Yes - direct flights currently operate from Chicago Midway Airport to Hartford Bradley International Airport in Connecticut.

What is the average price of a flight from Chicago Midway Airport to Connecticut?

We looked at all of the upcoming return flights from Chicago Midway Airport to Connecticut we could find over the next 12 months. It looks like $601 is the best price. This is good, compared to the average Connecticut ticket price of $630.

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

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

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

After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Chicago Midway Airport to Connecticut on Tuesday, 4 August 2026.

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

If you're flying from Chicago Midway, the cheapest city in Connecticut to fly into is Hartford. The cheapest airport serving Hartford at the moment is Hartford Bradley International.