What is the cheapest airline that flies from Tweed-New Haven to Chicago?

Avelo Airlines is the most popular carrier operating from Tweed-New Haven to Chicago

How many flights depart from New Haven to Chicago on average per week?

The number of flights available between New Haven and Chicago is 2 per week as of September 2025. The most frequent departure day is Thu, with 50% of weekly flights leaving on this day.

What airlines fly to Chicago?

American Airlines, United Airlines and Delta are the top three most popular airlines that fly to Chicago from New Haven according to our data. American Airlines is the first choice among our users, with 49% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 7 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

When did momondo last update prices for flights from Tweed-New Haven Airport to Chicago?

Prices for flights from Tweed-New Haven Airport to Chicago are refreshed on a daily basis.

How old do you have to be to fly from Tweed-New Haven Airport to Chicago?

The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Tweed-New Haven Airport to Chicago.

What documentation or ID do you need to fly to Chicago?

The travel and health documents you'll need for your trip to Chicago may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

$45 Cheap Flights from New Haven to Chicago in 2025/26

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Find the cheapest flights from New Haven to Chicago

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

5:10 pm - 6:40 pmHVN-ORD

2h 30mnonstop

4:35 pm - 7:40 pmORD-HVN

2h 05mnonstop

$88Avelo Airlines

Find Deal

Wed, Dec 24 - Thu, Dec 25

1:50 pm - 3:20 pmHVN-ORD

2h 30mnonstop

4:05 pm - 7:10 pmORD-HVN

2h 05mnonstop

$141Avelo Airlines

Find Deal

Thu, Dec 4 - Sun, Dec 7

1:45 pm - 3:06 pmHVN-ORD

2h 21mnonstop

6:05 pm - 9:09 pmORD-HVN

2h 04mnonstop

$143Avelo Airlines

Find Deal

Sun, Nov 2 - Thu, Nov 6

2:20 pm - 3:50 pmHVN-ORD

2h 30mnonstop

4:35 pm - 7:40 pmORD-HVN

2h 05mnonstop

$166Avelo Airlines

Find Deal

Sun, Dec 28 - Thu, Jan 1

6:26 pm - 11:28 pmHVN-ORD

6h 02m1 stop

1:50 pm - 5:46 pmORD-HVN

26h 56m1 stop

$186Multiple Airlines

Find Deal

Mon, Nov 10 - Sun, Nov 16

6:26 pm - 11:28 pmHVN-ORD

6h 02m1 stop

1:50 pm - 5:46 pmORD-HVN

26h 56m1 stop

$198Multiple Airlines

Find Deal

Mon, Nov 10 - Thu, Nov 13

6:26 pm - 11:28 pmHVN-ORD

6h 02m1 stop

1:50 pm - 5:46 pmORD-HVN

26h 56m1 stop

$200Multiple Airlines

Find Deal

Fri, Nov 14 - Sun, Nov 16

11:06 am - 11:28 pmHVN-ORD

13h 22m1 stop

6:40 am - 5:46 pmORD-HVN

34h 06m2 stops

$209Multiple Airlines

Find Deal

Thu, Oct 30 - Thu, Nov 6

11:06 am - 11:28 pmHVN-ORD

13h 22m1 stop

7:51 pm - 1:57 pmORD-HVN

17h 06m1 stop

$211Multiple Airlines

Find Deal

Thu, Oct 30 - Mon, Nov 3

6:26 pm - 11:28 pmHVN-ORD

6h 02m1 stop

2:42 pm - 5:46 pmORD-HVN

26h 04m2 stops

$212Multiple Airlines

Find Deal

Mon, Nov 10 - Thu, Nov 13

Avelo Airlines flights from New Haven to Chicago

Our best Avelo Airlines deals on New Haven to Chicago flight tickets

Avelo Airlines

Dec 24

HVN5:10 pmTweed-New Haven

2h 30m

ORD6:40 pmChicago O'Hare Intl

Dec 25

ORD4:35 pmChicago O'Hare Intl

2h 05m

HVN7:40 pmTweed-New Haven

$88

Find similar

Avelo Airlines

Dec 4

HVN1:50 pmTweed-New Haven

2h 30m

ORD3:20 pmChicago O'Hare Intl

Dec 7

ORD4:05 pmChicago O'Hare Intl

2h 05m

HVN7:10 pmTweed-New Haven

$141

Find similar

Avelo Airlines

Nov 2

HVN1:45 pmTweed-New Haven

2h 21m

ORD3:06 pmChicago O'Hare Intl

Nov 6

ORD6:05 pmChicago O'Hare Intl

2h 04m

HVN9:09 pmTweed-New Haven

$143

Find similar

Fly from

Fly to

Route

Depart

Return

Price

New HavenChicago

HVN - ORD

HVNORD

Tweed-New Haven

Wed 12/24

5:10 pm-6:40 pm

Nonstop2h 30m

Chicago O'Hare Intl

Thu 12/25

4:35 pm-7:40 pm

Nonstop2h 05m

$88

New HavenChicago

HVN - ORD

HVNORD

Tweed-New Haven

Thu 12/4

1:50 pm-3:20 pm

Nonstop2h 30m

Chicago O'Hare Intl

Sun 12/7

4:05 pm-7:10 pm

Nonstop2h 05m

$141

New HavenChicago

HVN - ORD

HVNORD

Tweed-New Haven

Sun 11/2

1:45 pm-3:06 pm

Nonstop2h 21m

Chicago O'Hare Intl

Thu 11/6

6:05 pm-9:09 pm

Nonstop2h 04m

$143

New HavenChicago

HVN - ORD

HVNORD

Tweed-New Haven

Sun 12/28

2:20 pm-3:50 pm

Nonstop2h 30m

Chicago O'Hare Intl

Thu 1/1

4:35 pm-7:40 pm

Nonstop2h 05m

$166

New HavenChicago

HVN - ORD

HVNORD

Tweed-New Haven

Mon 11/10

6:26 pm-11:28 pm

1 stop6h 02m

Chicago O'Hare Intl

Sun 11/16

1:50 pm-5:46 pm

1 stop26h 56m

$186

New HavenChicago

HVN - ORD

HVNORD

Tweed-New Haven

Mon 11/10

6:26 pm-11:28 pm

1 stop6h 02m

Chicago O'Hare Intl

Thu 11/13

1:50 pm-5:46 pm

1 stop26h 56m

$198

New HavenChicago

HVN - ORD

HVNORD

Tweed-New Haven

Fri 11/14

6:26 pm-11:28 pm

1 stop6h 02m

Chicago O'Hare Intl

Sun 11/16

1:50 pm-5:46 pm

1 stop26h 56m

$200

New HavenChicago

HVN - ORD

HVNORD

Tweed-New Haven

Thu 10/30

11:06 am-11:28 pm

1 stop13h 22m

Chicago O'Hare Intl

Thu 11/6

6:40 am-5:46 pm

2 stops34h 06m

$209

New HavenChicago

HVN - ORD

HVNORD

Tweed-New Haven

Thu 10/30

11:06 am-11:28 pm

1 stop13h 22m

Chicago O'Hare Intl

Mon 11/3

7:51 pm-1:57 pm

1 stop17h 06m

$211

New HavenChicago

HVN - ORD

HVNORD

Tweed-New Haven

Mon 11/10

6:26 pm-11:28 pm

1 stop6h 02m

Chicago O'Hare Intl

Thu 11/13

2:42 pm-5:46 pm

2 stops26h 04m

$212

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from New Haven to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Airlines

Other information

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Wednesday when prices can be found for as low as $295. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from New Haven to Chicago for around $389.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from New Haven to Chicago during this time can be as low as $261. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $368.

What is the cheapest Tweed-New Haven to Chicago flight route?

Fly from Tweed-New Haven to Chicago O'Hare Intl for the best Tweed-New Haven - Chicago flight prices

What cabin class options are available on Tweed-New Haven to Chicago flights?

There is only 1 cabin class available to choose from on Tweed-New Haven to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

When to book flights from New Haven to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from New Haven to Chicago according to our flight data. Find out which month and days have the cheapest flights.

Estimated round-trip price

Cheap New Haven to Chicago (HVN to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from New Haven to Chicago

Best Price Found	$77
Fastest flight time	2h 21m
Direct flights	Mon, Thu and Fri
Airports in Chicago	1 airport

The best one-way flight to Chicago from New Haven in the past 72 hours is $77. The best round-trip flight deal from New Haven to Chicago found on momondo in the last 72 hours is $178.

The fastest flight from New Haven to Chicago takes 2h 21m

Direct flights go from New Haven to Chicago on Monday, Thursday and Friday. The only airline offering direct flights is Avelo Airlines.

There is 1 airport near Chicago: Chicago O'Hare Intl (ORD)

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How far is Tweed-New Haven to Chicago by plane?
The straight-line distance from Tweed-New Haven to Chicago is 759.2 mi. By plane, this route typically takes 2h 21m.
When did momondo last update prices for flights from Tweed-New Haven Airport to Chicago?
Prices for flights from Tweed-New Haven Airport to Chicago are refreshed on a daily basis.
How old do you have to be to fly from Tweed-New Haven Airport to Chicago?
The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Tweed-New Haven Airport to Chicago.
What documentation or ID do you need to fly to Chicago?
The travel and health documents you'll need for your trip to Chicago may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from New Haven to Chicago?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from New Haven to Chicago is Boeing 737-800 Passenger/BBJ2 (winglets) (17.33% of total bookings). The next most popular plane models are Boeing 737-800 (16.00%), Boeing 737 MAX 8 (9.33%), and Boeing 737-700 (8.00%).
What is the most popular airline from New Haven to Chicago?
Based on momondo bookings for flights between New Haven and Chicago, the leading airline is Avelo Airlines, making up 100% of the total bookings.

Merrillville

New Buffalo

Hammond

Benton Harbor

Saint Joseph

Lansing

Portage

Schererville

Valparaiso

Crown Point

Munster

Chesterton

Monticello

Porter

Griffith

Saint John

Why use momondo?

Why should I use momondo to find a flight deal from New Haven to Chicago?

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from New Haven.

Can I find flights from New Haven to Chicago with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Chicago from New Haven with this policy.

How can momondo help me find flights from New Haven to Chicago?

Once you have performed a search for New Haven to Chicago flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

I’m not ready to book a flight from New Haven to Chicago right now. Can momondo alert me if prices change?

If you are not ready to book a flight from New Haven to Chicago now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Chicago and let you know when they change.