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Cheap flights from New Haven to Chicago from $44

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 12/24. 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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0 bags

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Cheap round-trip flights

Enter your travel dates to find the best prices.
Avelo Airlines Logo
11:05 am - 12:35 pmHVN-ORD
2h 30mnonstop
Avelo Airlines Logo
1:20 pm - 4:25 pmORD-HVN
2h 05mnonstop
$88Avelo Airlines
Find Deal
Tue, Nov 25 - Fri, Nov 28
Avelo Airlines Logo
3:05 pm - 4:37 pmHVN-ORD
2h 32mnonstop
Avelo Airlines Logo
5:20 pm - 8:26 pmORD-HVN
2h 06mnonstop
$103Avelo Airlines
Find Deal
Thu, Feb 5 - Sun, Feb 8
Avelo Airlines Logo
3:25 pm - 5:10 pmHVN-ORD
2h 45mnonstop
Avelo Airlines Logo
5:55 pm - 9:29 pmORD-HVN
2h 34mnonstop
$133Avelo Airlines
Find Deal
Fri, Feb 13 - Mon, Feb 16
Avelo Airlines Logo
1:50 pm - 3:20 pmHVN-ORD
2h 30mnonstop
Avelo Airlines Logo
4:05 pm - 7:10 pmORD-HVN
2h 05mnonstop
$162Avelo Airlines
Find Deal
Thu, Dec 11 - Sun, Dec 14
Multiple Airlines Logo
11:05 am - 12:35 pmHVN-ORD
2h 30mnonstop
Multiple Airlines Logo
3:43 pm - 2:42 pmORD-HVN
21h 59m2 stops
$164Multiple Airlines
Find Deal
Fri, Nov 28 - Tue, Dec 2
Multiple Airlines Logo
3:05 pm - 4:37 pmHVN-ORD
2h 32mnonstop
Multiple Airlines Logo
10:07 am - 10:59 pmORD-HVN
11h 52m1 stop
$165Multiple Airlines
Find Deal
Thu, Feb 5 - Sun, Feb 8
Multiple Airlines Logo
3:05 pm - 4:37 pmHVN-ORD
2h 32mnonstop
Multiple Airlines Logo
8:45 am - 10:19 pmORD-HVN
12h 34m1 stop
$167Multiple Airlines
Find Deal
Thu, Feb 5 - Mon, Feb 9
Multiple Airlines Logo
8:44 pm - 5:52 pmHVN-ORD
22h 08m1 stop
Multiple Airlines Logo
12:44 pm - 2:01 pmORD-HVN
24h 17m1 stop
$181Multiple Airlines
Find Deal
Thu, Feb 5 - Mon, Feb 9
Multiple Airlines Logo
1:25 pm - 11:13 pmHVN-ORD
10h 48m1 stop
Multiple Airlines Logo
4:05 pm - 7:10 pmORD-HVN
2h 05mnonstop
$182Multiple Airlines
Find Deal
Mon, Nov 24 - Thu, Dec 4
Multiple Airlines Logo
6:26 pm - 11:35 amHVN-ORD
18h 09m2 stops
Multiple Airlines Logo
5:35 am - 11:27 amORD-HVN
4h 52m1 stop
$189Multiple Airlines
Find Deal
Mon, Jan 5 - Fri, Jan 9

Avelo Airlines flights from New Haven to Chicago

Our best Avelo Airlines deals on New Haven to Chicago flight tickets
Avelo Airlines
Nov 25
HVN11:05 amTweed-New Haven
2h 30m
ORD12:35 pmChicago O'Hare Intl
Nov 28
ORD1:20 pmChicago O'Hare Intl
2h 05m
HVN4:25 pmTweed-New Haven
$88
Find similar
Avelo Airlines
Feb 5
HVN3:05 pmTweed-New Haven
2h 32m
ORD4:37 pmChicago O'Hare Intl
Feb 8
ORD5:20 pmChicago O'Hare Intl
2h 06m
HVN8:26 pmTweed-New Haven
$103
Find similar
Avelo Airlines
Feb 13
HVN3:25 pmTweed-New Haven
2h 45m
ORD5:10 pmChicago O'Hare Intl
Feb 16
ORD5:55 pmChicago O'Hare Intl
2h 34m
HVN9:29 pmTweed-New Haven
$133
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from New Haven to Chicago 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 November 13, 2025.
Use the filters below to find and compare flights from New Haven to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

New HavenChicago

HVN - ORD

HVNORD

Tweed-New Haven

Tue 11/25

11:05 am-12:35 pm

Nonstop2h 30m

Chicago O'Hare Intl

Fri 11/28

1:20 pm-4:25 pm

Nonstop2h 05m

$88

New HavenChicago

HVN - ORD

HVNORD

Tweed-New Haven

Thu 2/5

3:05 pm-4:37 pm

Nonstop2h 32m

Chicago O'Hare Intl

Sun 2/8

5:20 pm-8:26 pm

Nonstop2h 06m

$103

New HavenChicago

HVN - ORD

HVNORD

Tweed-New Haven

Fri 2/13

3:25 pm-5:10 pm

Nonstop2h 45m

Chicago O'Hare Intl

Mon 2/16

5:55 pm-9:29 pm

Nonstop2h 34m

$133

New HavenChicago

HVN - ORD

HVNORD

Tweed-New Haven

Thu 12/11

1:50 pm-3:20 pm

Nonstop2h 30m

Chicago O'Hare Intl

Sun 12/14

4:05 pm-7:10 pm

Nonstop2h 05m

$162

New HavenChicago

HVN - ORD

HVNORD

Tweed-New Haven

Fri 11/28

11:05 am-12:35 pm

Nonstop2h 30m

Chicago O'Hare Intl

Tue 12/2

3:43 pm-2:42 pm

2 stops21h 59m

$164

New HavenChicago

HVN - ORD

HVNORD

Tweed-New Haven

Thu 2/5

3:05 pm-4:37 pm

Nonstop2h 32m

Chicago O'Hare Intl

Sun 2/8

10:07 am-10:59 pm

1 stop11h 52m

$165

New HavenChicago

HVN - ORD

HVNORD

Tweed-New Haven

Thu 2/5

3:05 pm-4:37 pm

Nonstop2h 32m

Chicago O'Hare Intl

Mon 2/9

8:45 am-10:19 pm

1 stop12h 34m

$167

New HavenChicago

HVN - ORD

HVNORD

Tweed-New Haven

Thu 2/5

8:44 pm-5:52 pm

1 stop22h 08m

Chicago O'Hare Intl

Mon 2/9

12:44 pm-2:01 pm

1 stop24h 17m

$181

New HavenChicago

HVN - ORD

HVNORD

Tweed-New Haven

Mon 11/24

1:25 pm-11:13 pm

1 stop10h 48m

Chicago O'Hare Intl

Thu 12/4

4:05 pm-7:10 pm

Nonstop2h 05m

$182

New HavenChicago

HVN - ORD

HVNORD

Tweed-New Haven

Mon 1/5

6:26 pm-11:35 am

2 stops18h 09m

Chicago O'Hare Intl

Fri 1/9

5:35 am-11:27 am

1 stop4h 52m

$189

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

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?

The cheapest day to depart on your flight to Chicago is on a Wednesday when prices can be found for as low as $292. 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 $384.

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 $271. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $367.

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

Fastest flight time

2h 30m

Direct flights

Wed, Thu, Fri and Sat

Airports in Chicago

1 airport
The fastest flight from New Haven to Chicago takes 2h 30m
Direct flights go from New Haven to Chicago on Wednesday, Thursday, Friday and Saturday. 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 30m.

  • 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?

  • What is the most popular airline from New Haven to Chicago?

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Portage
Lansing
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.

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport