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Cheap flights from New Haven to Chicago from $74

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 9/21. 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

Avelo Airlines Logo
3:05 pm - 4:37 pmHVN-ORD
2h 32mnonstop
Avelo Airlines Logo
5:20 pm - 8:26 pmORD-HVN
2h 06mnonstop
$112Avelo Airlines
Find Deal
Thu, Jan 29 - Sun, Feb 1
Avelo Airlines Logo
1:45 pm - 3:06 pmHVN-ORD
2h 21mnonstop
Avelo Airlines Logo
3:51 pm - 6:59 pmORD-HVN
2h 08mnonstop
$153Avelo Airlines
Find Deal
Thu, Oct 2 - Thu, Oct 9
Avelo Airlines Logo
1:50 pm - 3:20 pmHVN-ORD
2h 30mnonstop
Avelo Airlines Logo
4:35 pm - 7:40 pmORD-HVN
2h 05mnonstop
$156Avelo Airlines
Find Deal
Sun, Dec 14 - Sun, Dec 21
Avelo Airlines Logo
1:45 pm - 3:06 pmHVN-ORD
2h 21mnonstop
Avelo Airlines Logo
6:05 pm - 9:09 pmORD-HVN
2h 04mnonstop
$166Avelo Airlines
Find Deal
Thu, Oct 30 - Thu, Nov 6
Avelo Airlines Logo
3:50 pm - 5:11 pmHVN-ORD
2h 21mnonstop
Avelo Airlines Logo
6:02 pm - 9:10 pmORD-HVN
2h 08mnonstop
$171Avelo Airlines
Find Deal
Sun, Sep 21 - Thu, Sep 25
Logo
3:02 pm - 3:08 pmHVN-ORD
25h 06m2 stops
Logo
5:25 am - 6:46 pmORD-HVN
12h 21m1 stop
$242
Find Deal
Fri, Oct 31 - Sun, Nov 2
Logo
2:42 pm - 4:23 pmHVN-ORD
26h 41m1 stop
Logo
1:50 pm - 5:46 pmORD-HVN
26h 56m1 stop
$243
Find Deal
Tue, Oct 28 - Thu, Nov 6
Logo
7:26 pm - 7:34 amHVN-ORD
13h 08m1 stop
Logo
6:23 pm - 1:57 pmORD-HVN
18h 34m1 stop
$250
Find Deal
Thu, Oct 16 - Mon, Oct 20
Logo
2:42 pm - 9:58 pmHVN-ORD
8h 16m1 stop
Logo
5:17 pm - 7:08 pmORD-HVN
24h 51m1 stop
$256
Find Deal
Tue, Sep 23 - Wed, Sep 24
Logo
2:46 pm - 11:39 pmHVN-ORD
33h 53m2 stops
Logo
6:23 pm - 1:57 pmORD-HVN
18h 34m1 stop
$259
Find Deal
Wed, Oct 15 - Mon, Oct 20

Avelo Airlines flights from New Haven to Chicago

Our best Avelo Airlines deals on New Haven to Chicago flight tickets
Avelo Airlines
Jan 29
HVN3:05 pmTweed-New Haven
2h 32m
ORD4:37 pmChicago O'Hare Intl
Feb 1
ORD5:20 pmChicago O'Hare Intl
2h 06m
HVN8:26 pmTweed-New Haven
$112
Find similar
Avelo Airlines
Oct 2
HVN1:45 pmTweed-New Haven
2h 21m
ORD3:06 pmChicago O'Hare Intl
Oct 9
ORD3:51 pmChicago O'Hare Intl
2h 08m
HVN6:59 pmTweed-New Haven
$153
Find similar
Avelo Airlines
Dec 14
HVN1:50 pmTweed-New Haven
2h 30m
ORD3:20 pmChicago O'Hare Intl
Dec 21
ORD4:35 pmChicago O'Hare Intl
2h 05m
HVN7:40 pmTweed-New Haven
$156
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 September 11, 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

Thu 1/29

3:05 pm-4:37 pm

Nonstop2h 32m

Chicago O'Hare Intl

Sun 2/1

5:20 pm-8:26 pm

Nonstop2h 06m

$112

New HavenChicago

HVN - ORD

HVNORD

Tweed-New Haven

Thu 10/2

1:45 pm-3:06 pm

Nonstop2h 21m

Chicago O'Hare Intl

Thu 10/9

3:51 pm-6:59 pm

Nonstop2h 08m

$153

New HavenChicago

HVN - ORD

HVNORD

Tweed-New Haven

Sun 12/14

1:50 pm-3:20 pm

Nonstop2h 30m

Chicago O'Hare Intl

Sun 12/21

4:35 pm-7:40 pm

Nonstop2h 05m

$156

New HavenChicago

HVN - ORD

HVNORD

Tweed-New Haven

Thu 10/30

1:45 pm-3:06 pm

Nonstop2h 21m

Chicago O'Hare Intl

Thu 11/6

6:05 pm-9:09 pm

Nonstop2h 04m

$166

New HavenChicago

HVN - ORD

HVNORD

Tweed-New Haven

Sun 9/21

3:50 pm-5:11 pm

Nonstop2h 21m

Chicago O'Hare Intl

Thu 9/25

6:02 pm-9:10 pm

Nonstop2h 08m

$171

New HavenChicago

HVN - ORD

HVNORD

Tweed-New Haven

Fri 10/31

3:02 pm-3:08 pm

2 stops25h 06m

Chicago O'Hare Intl

Sun 11/2

5:25 am-6:46 pm

1 stop12h 21m

$242

New HavenChicago

HVN - ORD

HVNORD

Tweed-New Haven

Tue 10/28

2:42 pm-4:23 pm

1 stop26h 41m

Chicago O'Hare Intl

Thu 11/6

1:50 pm-5:46 pm

1 stop26h 56m

$243

New HavenChicago

HVN - ORD

HVNORD

Tweed-New Haven

Thu 10/16

7:26 pm-7:34 am

1 stop13h 08m

Chicago O'Hare Intl

Mon 10/20

6:23 pm-1:57 pm

1 stop18h 34m

$250

New HavenChicago

HVN - ORD

HVNORD

Tweed-New Haven

Tue 9/23

2:42 pm-9:58 pm

1 stop8h 16m

Chicago O'Hare Intl

Wed 9/24

5:17 pm-7:08 pm

1 stop24h 51m

$256

New HavenChicago

HVN - ORD

HVNORD

Tweed-New Haven

Wed 10/15

2:46 pm-11:39 pm

2 stops33h 53m

Chicago O'Hare Intl

Mon 10/20

6:23 pm-1:57 pm

1 stop18h 34m

$259

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 $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 $259. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $365.

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 $199.
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)
Search flight deals

  • 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?

  • 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
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.

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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