What is the cheapest airline to fly from New Haven to Chicago round-trip?

Currently priced at $97, Avelo Airlines will fly you from New Haven to Chicago and back. In addition to Avelo Airlines, many other airlines offer competitively priced options for your trip. You may be able to fly from New Haven to Chicago for 48% less than the average price by searching for this airline.

What is the cheapest day to fly from New Haven to Chicago?

Travelers seeking maximum savings on their New Haven to Chicago flight should consider departing on Friday mornings when fares are most often at their lowest. Thursday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

What are the cheapest flights from New Haven to Chicago?

Looking at all options, your cheapest flight can be booked for $65. While the most popular route (Tweed-New Haven - Chicago O'Hare Intl) can be booked for $97 on average our data indicates $103 when flying from New Haven to Chicago.

What is the cheapest day to fly round-trip from New Haven to Chicago?

Leaving on a Sunday is a viable option for saving on travel. Heavily demanded days of the week can typically drive up the prices you see. Booking your travel for a less competitive day can save up to 57% on the overall cost on flights from New Haven to Chicago.

How far in advance should I book a flight from New Haven to Chicago?

To save on the cost of your flight from New Haven to Chicago, book at least 36 days before your planned departure. Booking around this time can save you about 93% on the cost of this flight compared to booking a flight leaving this week. We have found prices from $234 if you need a flight within two weeks. For flights within the next 72 hours, you can find tickets from as low as $367.

What is the cheapest month to fly from New Haven to Chicago?

Our data shows that September tends to be the cheapest month to fly to Chicago from New Haven. Users have commonly found prices around $232 for the month, but tickets can be as low as $75. Due to multiple factors, prepare for potentially higher prices in June.

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

For a flight from New Haven to Chicago, you will be flying from Tweed-New Haven. Tweed-New Haven (HVN) is just 3.6 mi from the center of the city. Tweed-New Haven is the only New Haven airport and it handles 0 outbound flights to Chicago per day. 1 airline has flights to Chicago from Tweed-New Haven on a regular basis.

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

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

How can I find direct flights from New Haven to Chicago?

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

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

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

$44+ Flights from New Haven to Chicago

Q: How much does it cost to fly round-trip from New Haven to Chicago?

Airfare is below average for this route at the moment. New Haven to Chicago flights typically cost between $184 and $260 in August. The cheapest round-trip price found within the last 3 days was $93 on Avelo Airlines (Aug 24-Aug 31).

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Cheap flight deals from New Haven to Chicago

Round-trip from	$97 (CheapOair)
One-way from	$44 (Cheapflightsfares)
Popular in	December
Cheapest in	January
Average price	$216
Good round-trip deal	$104 or less
Good one-way deal	$76 or less

From Tweed-New Haven to Chicago (CHI)

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One-way flight from Tweed-New Haven to Chicago (CHI)

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High demand for flights, 8% potential price rise

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Cheapest flight prices on average. 6% potential price decrease ($12 potential savings vs. average RT price).

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Average for round-trip flights in July 2025

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Price to beat on a round-trip flight from Tweed-New Haven to Chicago (CHI).

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Price to beat on a one-way flight from Tweed-New Haven to Chicago (CHI).

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Find flight deals from New Haven to Chicago

Cheapest flights from New Haven to Chicago
Explore the most affordable flight options available from New Haven to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 30, 2025.

Sun 8/241:45 pmHVN - ORD

Nonstop2h 20mAvelo Airlines

Sun 8/313:55 pmORD - HVN

Nonstop2h 10mAvelo Airlines

Deal found 7/27

$93

Thu 8/289:05 amHVN - ORD

1 stop10h 23mMultiple Airlines

Sun 8/313:55 pmORD - HVN

Nonstop2h 10mMultiple Airlines

Deal found 7/28

$145

Best flights from New Haven to Chicago
Discover carefully curated flight deals from New Haven to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 30, 2025.

Sun 8/241:45 pmHVN - ORD

Nonstop2h 20mAvelo Airlines

Sun 8/313:55 pmORD - HVN

Nonstop2h 10mAvelo Airlines

Deal found 7/27

$93

Thu 8/289:05 amHVN - ORD

1 stop10h 23mMultiple Airlines

Sun 8/313:55 pmORD - HVN

Nonstop2h 10mMultiple Airlines

Deal found 7/28

$145

Last-minute flights from New Haven to Chicago
Discover last-minute flight deals from New Haven to Chicago. Data last updated July 30, 2025 and is based on user searches.

Thu 8/71:45 pmHVN - ORD

Nonstop2h 20mAvelo Airlines

Thu 8/143:55 pmORD - HVN

Nonstop2h 10mAvelo Airlines

Deal found 7/28

$273

Thu 8/71:45 pmHVN - ORD

Nonstop2h 20mMultiple Airlines

Mon 8/115:01 amORD - HVN

2 stops13h 19mMultiple Airlines

Deal found 7/30

$290

Sun 8/241:45 pmHVN - ORD

Nonstop2h 20mAvelo Airlines

Sun 8/313:55 pmORD - HVN

Nonstop2h 10mAvelo Airlines

Deal found 7/27

$93

Thu 8/289:05 amHVN - ORD

1 stop10h 23mMultiple Airlines

Sun 8/313:55 pmORD - HVN

Nonstop2h 10mMultiple Airlines

Deal found 7/28

$145

One-way flights from New Haven to Chicago
Search for one-way flight options from New Haven to Chicago. Find affordable one-way fares based on user searches. Data last updated July 30, 2025.

Sun 9/143:50 pmHVN - ORD

Nonstop2h 21mAvelo Airlines

Deal found 7/29

$44

Fly from

Fly to

Route

Depart

Return

Price

New HavenChicago

HVN - ORD

HVNORD

Tweed-New Haven

Sun 8/24

1:45 pm-3:05 pm

Nonstop2h 20m

Chicago O'Hare Intl

Sun 8/31

3:55 pm-7:05 pm

Nonstop2h 10m

$93

New HavenChicago

HVN - ORD

HVNORD

Tweed-New Haven

Thu 8/28

9:05 am-6:28 pm

1 stop10h 23m

Chicago O'Hare Intl

Sun 8/31

3:55 pm-7:05 pm

Nonstop2h 10m

$145

New HavenChicago

HVN - ORD

HVNORD

Tweed-New Haven

Sun 9/14

3:50 pm-5:11 pm

Nonstop2h 21m

$44

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/29

Best time to book a flight from New Haven to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago 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

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

Currently, August is the cheapest month in which you can book a flight from New Haven to Chicago (average of $245). Flying from New Haven to Chicago in March is currently the most expensive (average of $321). 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 CHI?

It’s typically best to fly out from New Haven to Chicago in the afternoon. Doing so could potentially save you 48% on the flight price compared to flying in the evening, which is usually more expensive.

How much does it cost to fly round-trip from New Haven to Chicago?

Reviews of airlines servicing Chicago

Peruse reviews from past customers who have flown with Avelo Airlines from New Haven to Chicago to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.

Avelo Airlines

7.5

Good

Reviews

1 / 6

2.0

Mediocre

Cindy,Sep 2023

MCO - DAY

I was emailed and told that if I check my luggage early I get a 10 dollar discount, also on the website, if it's under 50 lbs. it would be $40.00 I was charged $65.00 on first flight and $60.00 on second flight (second flight I checked in early, did not receive the discount, both flights my luggage was under 40 lbs.). Avelo destroyed my luggage, wheels were tore off, and plastic was ripped off.

Avelo Airlines

7.5

Good

Avelo Airlines

7.5

Good

Reviews

1 / 6

2.0

Mediocre

Cindy,Sep 2023

MCO - DAY

Related info for your journey

What airport do you fly from for flights from New Haven to Chicago?
For a flight from New Haven to Chicago, you will be flying from Tweed-New Haven. Tweed-New Haven (HVN) is just 3.6 mi from the center of the city. Tweed-New Haven is the only New Haven airport and it handles 0 outbound flights to Chicago per day. 1 airline has flights to Chicago from Tweed-New Haven on a regular basis.
What is the cheapest airline to fly from New Haven to Chicago round-trip?
Currently priced at $97, Avelo Airlines will fly you from New Haven to Chicago and back. In addition to Avelo Airlines, many other airlines offer competitively priced options for your trip. You may be able to fly from New Haven to Chicago for 48% less than the average price by searching for this airline.
What are the cheapest flights from New Haven to Chicago?
Looking at all options, your cheapest flight can be booked for $65. While the most popular route (Tweed-New Haven - Chicago O'Hare Intl) can be booked for $97 on average our data indicates $103 when flying from New Haven to Chicago.
Can I find deals for flights from New Haven to Chicago that include hotel bookings?
Yes. In addition to deals on New Haven to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.
How can I find direct flights from New Haven to Chicago?
After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from New Haven to Chicago.
Can I find deals for business class flights from New Haven to Chicago?
Yes. Cheapflights offers flight deals from New Haven to Chicago 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?
Currently, August is the cheapest month in which you can book a flight from New Haven to Chicago (average of $245). Flying from New Haven to Chicago in March is currently the most expensive (average of $321). 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.

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Top airline flying from New Haven to Chicago

Airline	Cheapest	Average	Flexibility	On-time
Avelo Airlines	Cheapest$77	Average$167	FlexibilityNo cancel fee	On-timeN/A

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$44+ Cheap flights from New Haven (HVN) to Chicago (CHI)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/14. Fares are subject to change and may not be available on all flights or dates of travel.

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Find flight deals from New Haven to Chicago

Cheapest flights from New Haven to ChicagoExplore the most affordable flight options available from New Haven to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 30, 2025.

Explore the most affordable flight options available from New Haven to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 30, 2025.

Cheapflights Fare Finder

Use the filters below to find and compare flights from New Haven to Chicago that are best for you.

Best time to book a flight from New Haven to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from New Haven with our price prediction graph.

Cheapflights Insights

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

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

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

Find hourly flight availability from New Haven to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 30, 2025.

How much does it cost to fly round-trip from New Haven to Chicago?

Reviews of airlines servicing Chicago

Peruse reviews from past customers who have flown with Avelo Airlines from New Haven to Chicago to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.

Related info for your journey

Find useful and relevant information for your journey from New Haven to Chicago. 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?

What is the cheapest airline to fly from New Haven to Chicago round-trip?

What are the cheapest flights from New Haven to Chicago?

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

How can I find direct flights from New Haven to Chicago?

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

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

Traveling to a place near Chicago?

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Alternative routes for New Haven to Chicago

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Top airline flying from New Haven to Chicago

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Cheapest flights from New Haven to Chicago
Explore the most affordable flight options available from New Haven to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 30, 2025.