Cheap Flights from Chicago Midway to New Haven

Compare Chicago Midway to New Haven flight deals

Find the cheapest month or even day of the year to fly to New Haven

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Flight deals from Chicago Midway to New Haven

Looking for a cheap last-minute deal or the best return flight from Chicago Midway Airport to New Haven Airport? If you want to travel next month, return fares start from R 3,833. Find the lowest prices on one-way and return tickets right here.

Find the cheapest month to fly from Chicago Midway to New Haven

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Chicago Midway to New Haven flights are currently cheapest in May.

Chicago to New Haven: Flight information

The things to know before you go.
Cheapest flight foundR 2,105
Cheapest month to flyMay

Finding cheap flights from Chicago Midway to New Haven: Frequently asked questions

The best price we found for a return flight from Chicago Midway to New Haven is R 3,724. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
Currently, there are no airlines that fly direct from Chicago Midway to New Haven. But we found flights with one or more stops from R 3,724.
As of April 2026, there are no flights flying from Chicago Midway to New Haven.
The cheapest month to fly from Chicago Midway to New Haven is usually April.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Chicago Midway Airport to New Haven Airport on Thursday, 30 April 2026.
No airlines currently offer direct flights between Chicago Midway Airport and New Haven Airport. Most routes have one or more stops.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to New Haven but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.
We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to New Haven is around 40 days in advance, so don’t leave your flight to the last minute.
Currently, Frontier Airlines offers the cheapest flight tickets to New Haven.

Travelling from Chicago Midway International Airport (MDW) to New Haven Airport (HVN): what you need to know

  • New Haven's timezone is UTC-4, which makes New Haven one hour ahead of Chicago.

  • Get to the airport on time so you don't miss your MDW to HVN flight. Be there at least two hours ahead for international flights and an hour early for domestic departures to avoid any last-minute rush.

  • Flying during a peak month such as July? Major public holidays and other popular seasons can mean longer lines and delays at security. Play it safe and arrive up to four hours ahead of an international flight and two hours before domestic departures.

  • Avelo Airlines offers direct flights from Chicago Midway International Airport to New Haven Airport. Book with this popular carrier, then get ready to discover the sights in New Haven — and maybe even more of United States if you have time.

  • The airline with the highest passenger demand on this route is Avelo Airlines.

  • Among carriers operating MDW to HVN flights, Avelo Airlines leads the way for on-time arrivals.

How to find the cheapest flights from Chicago Midway International Airport (MDW) to New Haven Airport (HVN)

  • The lowest price we've seen for a one-way Chicago Midway International Airport to New Haven Airport flight is R 2,105. A round-trip plane ticket is currently R 3,724. Depending on the availability and when you book, these fares may change.

  • To pick up cheap tickets from MDW to HVN, book as early as you can. Airlines usually offer their best fares when flights are first made available.

  • If you're willing to be flexible with your trip dates, use the 'Whole month' search tool. It'll give you the lowest price across each month when looking for a flight from Chicago Midway International Airport to New Haven Airport.

  • Getting your hands on cheap flights from MDW to HVN is a breeze with Price Alerts. Simply set up one of these automatic alerts and we'll notify you when there's a better deal.

  • Choose your ideal arrival and departure times, airlines and number of stops with the filters. Alternatively, sort your results by 'Cheapest' to see the best deals on flights from Chicago Midway International Airport to New Haven Airport.

Handy information about Chicago Midway International Airport (MDW)

  • MDW's address is 5700 South Cicero.

  • 77.88% of flights that leave from Chicago Midway International Airport arrive at their destination on time.

  • Chicago Midway International Airport is about 19 kilometres from central Chicago. If you're driving, catching a cab or ride-sharing from the centre, it'll take 20 minutes or so to arrive, depending on the traffic.

  • Expect a trip time of roughly 45 minutes when using public transport.

  • Get your holiday off to a leisurely start by staying near MDW. Whether you're boarding an early flight from Chicago Midway International Airport to New Haven Airport or want to avoid feeling rushed, these stays have you covered:

Arriving at New Haven Airport (HVN)

Getting from New Haven Airport (HVN) to central New Haven

  • You'll find HVN at 155 Burr Street.

  • From New Haven Airport, New Haven is approximately 10 kilometres away. It takes around 15 minutes to drive to the centre.

  • Getting to the centre on public transport takes around 35 minutes.

When to fly to New Haven Airport (HVN)

  • It's time to work out your trip dates for your flight from Chicago Midway International Airport to New Haven Airport. August is the most popular month to visit New Haven. If you want a more low-key vibe, go in May.

  • The warmest month in New Haven is July, with the temperature ranging between 17ºC (63ºF) and 29ºC (84ºF). Lock in your flights from Chicago Midway International Airport to New Haven Airport in this month if this is the type of weather you enjoy.

  • January sees average temperatures of between -6ºC (21ºF) and 7ºC (45ºF). Search for cheap tickets from MDW to HVN sometime around then if you like travelling in cooler conditions.

Explore more of United States

  • New Haven is always a good idea, but there are so many other corners of United States just waiting to be discovered. About 113 kilometres south-west of New Haven, a trip to New York will keep you busy. Start with leading sights like Statue of Liberty, Central Park and Empire State Building.

  • Around 241 kilometres south-west of New Haven, Philadelphia is another essential stop in United States. No visit is complete without checking out Liberty Bell, Independence Hall and Philadelphia Museum of Art.

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.