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

Popular airlines from Chicago Midway Airport (MDW) to New Haven, CT (HVN-Tweed - New Haven Regional)

  • Plan, book, fly with confidence

  • trending down icon

    Be in the know

    Get alerts if flight prices drop or rise*
  • bex rewards loyalty icon

    Book smarter

    Save up to 30% on select hotels after you book a flight*
  • one key icon

    Earn twice

    Earn your airline miles on top of our OneKeyCash
    Learn about One Key
Flights from Chicago (MDW) to New Haven (HVN)
Origin airport
Midway Intl.
Destination airport
Tweed - New Haven Regional
Distance
767 mi

Chicago to New Haven Flights

The cheapest times to fly from Chicago to New Haven

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

 

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

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

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 Chicago to New Haven 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 Chicago to New Haven 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 Chicago to New Haven 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

How much does a flight from Midway Intl. Airport (MDW) to Tweed - New Haven Regional Airport (HVN) cost?
Discover the latest flight deals from MDW to HVN by entering your preferred travel dates and searching on Expedia. Easily compare prices by departure date if you have flexibility with your schedule and use handy filters to explore prices for your preferred journey. As a member of One Key™, our free loyalty program, you can use Price Tracking to watch fares and receive notifications if prices go up or down.
What is the cheapest month to fly from MDW to HVN?
The cheapest flights from MDW to HVN are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
What is the cheapest airline that flies from MDW to HVN?
Use the filter tool on Expedia to compare airlines and find the cheapest carrier that'll take you from MDW to HVN. Sort your results by "Price (lowest to highest)" to snap up a great deal.
How many flights per day from Midway Intl. Airport (MDW) to Tweed - New Haven Regional Airport (HVN)?
There are no daily direct flights departing from Midway Intl. Airport (MDW) to Tweed - New Haven Regional Airport (HVN). But you can opt for flights with layovers. Filter your search results on Expedia to include one or two stops, and you'll be cruising above the clouds before you know it.
What day of the week has the most flights from MDW to HVN?
You'll usually find Tuesday the quietest day for flights, while Fridays are often the busiest.* However this can change from season to season and during public holidays or peak travel times.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What airline has the least delays from MDW to HVN?
With 83% of journeys typically arriving on schedule, Avelo Airlines has the best on-time performance for nonstop flights from Midway Intl. Airport (MDW) to Tweed - New Haven Regional Airport (HVN). To keep track of your flight status and receive notifications if anything changes, head to the Expedia App.
What is the best time to fly from Midway Intl. Airport (MDW) to Tweed - New Haven Regional Airport (HVN)?
Choose a flight from Midway Intl. Airport (MDW) to Tweed - New Haven Regional Airport (HVN) that takes off before 3 PM to reduce the likelihood of delays and cancellations. Departures after this time are on average 22% more likely to be canceled.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports do you fly into for New Haven from Midway Intl. Airport (MDW)?
If you're traveling on a direct flight from Midway Intl. Airport (MDW) to New Haven, Bradley Intl. Airport (BDL) is the only airport you can touch down at.
Is it cheaper to buy a plane ticket from Midway Intl. Airport (MDW) to Tweed - New Haven Regional Airport (HVN) last-minute?
Last-minute fares from MDW to HVN are typically more expensive. For the best prices, start looking for flights as early as possible. That said, if you can play around with your travel dates, you may score a cheap fare right before you leave.
Is it cheaper to book a MDW to HVN flight and hotel package?
Compared with arranging flights and hotels separately, booking a MDW to HVN flight and hotel package with Expedia could lead to significant savings. Better yet, managing everything in one place will take the stress out of planning your trip. Simply pick your flights and choose from our wide range of stays, then customize your trip with other add-ons like activities, tours and car rentals.
Can I cancel or change the date of my flight from Midway Intl. Airport (MDW) to Tweed - New Haven Regional Airport (HVN)?
If you reserved your MDW to HVN flight within the last 24 hours, you may be able to modify or cancel it at no cost. Depending on the airline and the type of ticket you have, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal for further details.

Explore a world of travel with Expedia

*Available to One Key members.