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Cheap flights from New Haven to Chicago from $49

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from New Haven to Chicago departing on 12/25. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Cheap round-trip flights

Enter your travel dates to find the best prices.
Avelo Airlines Logo
1:50 pm - 3:20 pmHVN-ORD
2h 30mnonstop
Avelo Airlines Logo
4:05 pm - 7:10 pmORD-HVN
2h 05mnonstop
$96Avelo Airlines
Find Deal
Thu, Dec 4 - Sun, Dec 7
Avelo Airlines Logo
1:50 pm - 3:20 pmHVN-ORD
2h 30mnonstop
Avelo Airlines Logo
4:35 pm - 7:40 pmORD-HVN
2h 05mnonstop
$101Avelo Airlines
Find Deal
Sun, Dec 14 - Thu, Dec 18
Avelo Airlines Logo
3:50 pm - 5:20 pmHVN-ORD
2h 30mnonstop
Avelo Airlines Logo
6:05 pm - 9:09 pmORD-HVN
2h 04mnonstop
$121Avelo Airlines
Find Deal
Sun, Nov 9 - Thu, Nov 13
Avelo Airlines Logo
2:40 pm - 3:57 pmHVN-ORD
2h 17mnonstop
Avelo Airlines Logo
5:10 pm - 8:29 pmORD-HVN
2h 19mnonstop
$128Avelo Airlines
Find Deal
Fri, Feb 27 - Mon, Mar 2
Avelo Airlines Logo
5:10 pm - 6:40 pmHVN-ORD
2h 30mnonstop
Avelo Airlines Logo
4:35 pm - 7:40 pmORD-HVN
2h 05mnonstop
$138Avelo Airlines
Find Deal
Wed, Dec 17 - Sun, Dec 21
Avelo Airlines Logo
1:35 pm - 3:05 pmHVN-ORD
2h 30mnonstop
Avelo Airlines Logo
4:25 pm - 7:30 pmORD-HVN
2h 05mnonstop
$143Avelo Airlines
Find Deal
Thu, Nov 20 - Sun, Nov 23
Multiple Airlines Logo
8:50 am - 9:19 pmHVN-ORD
13h 29m1 stop
Multiple Airlines Logo
4:05 pm - 7:10 pmORD-HVN
2h 05mnonstop
$154Multiple Airlines
Find Deal
Fri, Dec 5 - Sun, Dec 7
Avelo Airlines Logo
2:20 pm - 3:50 pmHVN-ORD
2h 30mnonstop
Avelo Airlines Logo
4:35 pm - 7:40 pmORD-HVN
2h 05mnonstop
$171Avelo Airlines
Find Deal
Sun, Dec 21 - Sun, Dec 28
Multiple Airlines Logo
8:30 am - 9:19 pmHVN-ORD
13h 49m1 stop
Multiple Airlines Logo
4:05 pm - 7:10 pmORD-HVN
2h 05mnonstop
$181Multiple Airlines
Find Deal
Thu, Dec 4 - Sun, Dec 7
Multiple Airlines Logo
8:50 am - 12:19 amHVN-ORD
16h 29m2 stops
Multiple Airlines Logo
4:05 pm - 7:10 pmORD-HVN
2h 05mnonstop
$182Multiple Airlines
Find Deal
Fri, Dec 5 - Sun, Dec 7

Avelo Airlines flights from New Haven to Chicago O'Hare Intl Airport

Our best Avelo Airlines deals on New Haven to Chicago O'Hare Intl Airport flight tickets
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
$96
Find similar
Avelo Airlines
Dec 14
HVN1:50 pmTweed-New Haven
2h 30m
ORD3:20 pmChicago O'Hare Intl
Dec 18
ORD4:35 pmChicago O'Hare Intl
2h 05m
HVN7:40 pmTweed-New Haven
$101
Find similar
Avelo Airlines
Nov 9
HVN3:50 pmTweed-New Haven
2h 30m
ORD5:20 pmChicago O'Hare Intl
Nov 13
ORD6:05 pmChicago O'Hare Intl
2h 04m
HVN9:09 pmTweed-New Haven
$121
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from New Haven to Chicago O'Hare Intl Airport that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated October 16, 2025.
Use the filters below to find and compare flights from New Haven to Chicago O'Hare Intl Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

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

$96

New HavenChicago

HVN - ORD

HVNORD

Tweed-New Haven

Sun 12/14

1:50 pm-3:20 pm

Nonstop2h 30m

Chicago O'Hare Intl

Thu 12/18

4:35 pm-7:40 pm

Nonstop2h 05m

$101

New HavenChicago

HVN - ORD

HVNORD

Tweed-New Haven

Sun 11/9

3:50 pm-5:20 pm

Nonstop2h 30m

Chicago O'Hare Intl

Thu 11/13

6:05 pm-9:09 pm

Nonstop2h 04m

$121

New HavenChicago

HVN - ORD

HVNORD

Tweed-New Haven

Fri 2/27

2:40 pm-3:57 pm

Nonstop2h 17m

Chicago O'Hare Intl

Mon 3/2

5:10 pm-8:29 pm

Nonstop2h 19m

$128

New HavenChicago

HVN - ORD

HVNORD

Tweed-New Haven

Wed 12/17

5:10 pm-6:40 pm

Nonstop2h 30m

Chicago O'Hare Intl

Sun 12/21

4:35 pm-7:40 pm

Nonstop2h 05m

$138

New HavenChicago

HVN - ORD

HVNORD

Tweed-New Haven

Thu 11/20

1:35 pm-3:05 pm

Nonstop2h 30m

Chicago O'Hare Intl

Sun 11/23

4:25 pm-7:30 pm

Nonstop2h 05m

$143

New HavenChicago

HVN - ORD

HVNORD

Tweed-New Haven

Fri 12/5

8:50 am-9:19 pm

1 stop13h 29m

Chicago O'Hare Intl

Sun 12/7

4:05 pm-7:10 pm

Nonstop2h 05m

$154

New HavenChicago

HVN - ORD

HVNORD

Tweed-New Haven

Sun 12/21

2:20 pm-3:50 pm

Nonstop2h 30m

Chicago O'Hare Intl

Sun 12/28

4:35 pm-7:40 pm

Nonstop2h 05m

$171

New HavenChicago

HVN - ORD

HVNORD

Tweed-New Haven

Thu 12/4

8:30 am-9:19 pm

1 stop13h 49m

Chicago O'Hare Intl

Sun 12/7

4:05 pm-7:10 pm

Nonstop2h 05m

$181

New HavenChicago

HVN - ORD

HVNORD

Tweed-New Haven

Fri 12/5

8:50 am-12:19 am

2 stops16h 29m

Chicago O'Hare Intl

Sun 12/7

4:05 pm-7:10 pm

Nonstop2h 05m

$182

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from New Haven to Chicago O'Hare Intl Airport

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

What is the cheapest day to depart on your flight to Chicago O'Hare Intl Airport?

The cheapest day to depart on your flight to Chicago O'Hare Intl Airport 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. On the other hand, Sunday is the most expensive day to depart from New Haven because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $387.

What is the cheapest time of day to depart on your flight to Chicago O'Hare Intl Airport?

Flying to Chicago O'Hare Intl Airport from New Haven in the evening is the least expensive time of day to depart. momondo users have found prices as low as $270 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $367. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Tweed-New Haven to Chicago O'Hare Intl flight route?

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

What cabin class options are available on Tweed-New Haven to Chicago O'Hare Intl flights?

There is only 1 cabin class available to choose from on Tweed-New Haven to Chicago O'Hare Intl 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 O'Hare Intl Airport

Are you open to changing your travel dates? Check out the ideal times to fly from New Haven to Chicago O'Hare Intl Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap New Haven to Chicago O'Hare Intl Airport (HVN to ORD) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from New Haven to Chicago O'Hare Intl Airport

Best Price Found

$88

Fastest flight time

2h 17m

Direct flights

Mon, Wed, Thu, Fri and Sat
The best one-way flight to Chicago O'Hare Intl Airport from New Haven in the past 72 hours is $88. The best round-trip flight deal from New Haven to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $113.
The fastest flight from New Haven to Chicago O'Hare Intl Airport takes 2h 17m
Direct flights go from New Haven to Chicago O'Hare Intl Airport on Monday, Wednesday, Thursday, Friday and Saturday. The only airline offering direct flights is Avelo Airlines.
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  • How far is Tweed-New Haven to Chicago O'Hare Intl by plane?

    There are 773.2 mi between Tweed-New Haven and Chicago O'Hare Intl. Typically, this will take 2h 17m by plane in normal conditions.

  • When did momondo last update prices for flights from Tweed-New Haven Airport to Chicago O'Hare Intl Airport?

    Prices for flights from Tweed-New Haven Airport to Chicago O'Hare Intl Airport are updated daily.

  • How old do you have to be to fly from Tweed-New Haven Airport to Chicago O'Hare Intl Airport?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Tweed-New Haven Airport to Chicago O'Hare Intl Airport.

  • What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?

    The necessary travel and health documents for your Chicago O'Hare Intl Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from New Haven to Chicago O'Hare Intl Airport?

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lake Geneva
South Haven
Schaumburg
Rockford
Merrillville
Gurnee
Naperville
Rosemont
Kenosha
New Buffalo
Joliet
Oak Brook
Racine
Orland Park
Hammond
Tinley Park
Janesville
Elgin
Aurora
Benton Harbor

Why use momondo?

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

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from New Haven to Chicago. Millions of users trust and use momondo every year so you are in good hands.

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?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from New Haven to Chicago.

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 simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from New Haven and alert you when they change.

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