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Booking Avelo Airlines from New Haven, CT to Chicago (Midway), IL
Everyday low fares
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Tweed-New Haven Airport (HVN)
Tweed-New Haven Airport (HVN) offers remarkable convenience for travelers, especially those from the Greater New Haven area, due to its close proximity to downtown. With shorter security lines, fewer crowds, and essential amenities, it provides a streamlined and stress-free experience for both business and leisure travelers. Learn more
Reliable service
Ranked #2 in On-time Performance in 2023.
We pride ourselves in being amongst the industry leaders in on-time performance. Learn more
Free family seating
Families can travel with ease knowing children 14 and under will be seated with an accompanying adult at no extra cost. Learn more
Convenient Flights from New Haven, CT to Chicago (Midway), IL
New Haven, CT
Tweed-New Haven Airport (HVN)
What do New Haven, Auckland, London, and Istanbul have in common? They are all on the prestigious New York Times 2023 “52 Places to Go” list. With a nod to the human need to explore the world around us...
Learn more about New Haven, CT
Chicago (Midway), IL
Chicago Midway International Airport (MDW)
The city of Chicago is known for its rich architecture and unmistakable skyline. Located by the shore of Lake Michigan, Chi-town hosts over 58 million visitors each year and was voted as one of America’s best...
Learn more about Chicago (Midway), IL
Book Cheap Flights from New Haven, CT to Chicago (Midway), IL
Flights from New Haven, CT (HVN) to Chicago (Midway), IL (MDW)
Sunday
Dec 22
One-way fares from$499*
24 HR RISK-FREE CANCELLATION
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Flights from New Haven, CT (HVN) to Chicago (Midway), IL (MDW)
Tuesday
Dec 24
One-way fares from$106*
24 HR RISK-FREE CANCELLATION
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Flights from New Haven, CT (HVN) to Chicago (Midway), IL (MDW)
Thursday
Dec 26
One-way fares from$170*
24 HR RISK-FREE CANCELLATION
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Flights from New Haven, CT (HVN) to Chicago (Midway), IL (MDW)
Sunday
Dec 29
One-way fares from$187*
24 HR RISK-FREE CANCELLATION
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Flights from New Haven, CT (HVN) to Chicago (Midway), IL (MDW)
Tuesday
Dec 31
One-way fares from$59*
24 HR RISK-FREE CANCELLATION
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Flights from New Haven, CT (HVN) to Chicago (Midway), IL (MDW)
Thursday
Jan 2
One-way fares from$154*
24 HR RISK-FREE CANCELLATION
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Flights from New Haven, CT (HVN) to Chicago (Midway), IL (MDW)
Sunday
Jan 5
One-way fares from$140*
24 HR RISK-FREE CANCELLATION
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Flights from New Haven, CT (HVN) to Chicago (Midway), IL (MDW)
Tuesday
Jan 7
One-way fares from$59*
24 HR RISK-FREE CANCELLATION
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FAQs for Flights from New Haven, CT to Chicago (Midway), IL
How long is the flight from New Haven to Chicago?
Flying from Tweed-New Haven Airport (HVN) to Chicago Midway International Airport (MDW) with Avelo Airlines takes approximately 2 hours and 30 minutes, providing a direct and efficient journey to your destination.
How many weekly flights does Avelo operate from New Haven to Chicago?
Avelo Airlines operates multiple flights each week between New Haven and Chicago. The number of flights can vary depending on seasonal demand, so it’s best to check our Low Fare Calendar for the most current schedule.
Which day typically offers the lowest fares from New Haven to Chicago?
Airfare prices can fluctuate based on demand and booking timing, but mid-week flights, particularly on Tuesdays and Wednesdays, generally offer the lowest fares. For the latest fare information and best deals, consult our Low Fare Calendar on the homepage.
Are there nonstop flights from New Haven to Chicago on weekends?
Yes, Avelo offers nonstop flights from New Haven to Chicago on weekends. To view the latest schedule and fares, search for your preferred travel dates on our homepage.
Can I rent a car at Chicago Midway International Airport?
Yes, car rental services are available at Chicago Midway International Airport (MDW). Major rental car companies such as Alamo, Avis, Budget, Enterprise, Hertz, and National operate at this location. It is recommended to book your rental car in advance to ensure availability.
How can I check the status of my flight from New Haven to Chicago?
You can check the status of any Avelo flight on our Flight Status page. If you have additional questions or concerns about your flight, our customer service team is here to assist you.