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Cheap flights from New Haven (HVN) to Midway (MDW)

HVN — MDW
Aug 5 — Aug 121
Tue 8/5
Tue 8/12
1 adult, Economy
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Cheap flight deals from New Haven to Midway

Discover tips and strategies to find the most affordable flight options for your journey from New Haven (HVN) to Midway (MDW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated July 31, 2025.

Popular in

June

Cheapest in

September

Average price

$267
Highest demand for flights based on searches. 12% potential increase in price ($32 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($5 potential savings vs. average RT price).
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Average for round-trip flights in July 2025
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Best time to book a flight from New Haven to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from New Haven with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from New Haven to Chicago Midway Airport

What is the cheapest month to book a flight from New Haven to Chicago Midway Airport?

Currently, April is the cheapest month in which you can book a flight from New Haven to Chicago Midway Airport (average of $160). Flying from New Haven to Chicago Midway Airport in November is currently the most expensive (average of $249). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from HVN to MDW?

Find hourly flight availability from New Haven to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 31, 2025.

When flying from New Haven to Chicago Midway Airport, the time of day you fly usually plays a role in the price. Save by searching for a flight at noon, which can drop the price by up to 15% versus a flight in the morning.

Related info for your journey

Find useful and relevant information for your journey from New Haven to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from New Haven to Chicago Midway?

    Most people fly from Tweed-New Haven (HVN) if they book a flight from New Haven to Chicago Midway. On average, Tweed-New Haven has 0 outbound flights to Chicago Midway per day from 1 airline. Tweed-New Haven is conveniently located just 3.6 mi from New Haven’s city center.

  • Can I find deals for flights from New Haven to Midway that include hotel bookings?

    Yes. In addition to deals on New Haven to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from New Haven to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from New Haven to Midway.

  • Can I find deals for business class flights from New Haven to Midway?

    Yes. Cheapflights offers flight deals from New Haven to Midway by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from New Haven to Chicago Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from New Haven to Chicago Midway Airport (average of $160). Flying from New Haven to Chicago Midway Airport in November is currently the most expensive (average of $249). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Valparaiso
Chesterton

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Top airline flying from New Haven to Midway

Discover the top airline that operate flights from New Haven to Midway. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
Avelo AirlinesCheapest$77Average$167FlexibilityNo cancel feeOn-timeN/A

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