Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

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 5/10. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Find the cheapest flights from New Haven to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Avelo Airlines Logo
3:20 pm - 5:05 pm
HVN
-
ORD
2h 45mnonstop
Avelo Airlines Logo
6:00 pm - 9:34 pm
ORD
-
HVN
2h 34mnonstop
$87Avelo Airlines
Sun, Mar 15 - Thu, Mar 19
Avelo Airlines Logo
3:20 pm - 5:05 pm
HVN
-
ORD
2h 45mnonstop
Avelo Airlines Logo
6:00 pm - 9:34 pm
ORD
-
HVN
2h 34mnonstop
$89Avelo Airlines
Sun, Mar 22 - Sun, Mar 29
Avelo Airlines Logo
3:50 pm - 5:43 pm
HVN
-
ORD
2h 53mnonstop
Avelo Airlines Logo
6:35 pm - 10:07 pm
ORD
-
HVN
2h 32mnonstop
$110Avelo Airlines
Thu, Jul 23 - Sun, Jul 26
Avelo Airlines Logo
4:20 pm - 6:13 pm
HVN
-
ORD
2h 53mnonstop
Avelo Airlines Logo
7:07 pm - 10:39 pm
ORD
-
HVN
2h 32mnonstop
$121Avelo Airlines
Fri, May 1 - Fri, May 8
Avelo Airlines Logo
4:20 pm - 6:13 pm
HVN
-
ORD
2h 53mnonstop
Avelo Airlines Logo
6:35 pm - 10:07 pm
ORD
-
HVN
2h 32mnonstop
$123Avelo Airlines
Fri, Apr 24 - Sun, Apr 26
Avelo Airlines Logo
3:20 pm - 5:05 pm
HVN
-
ORD
2h 45mnonstop
Avelo Airlines Logo
6:00 pm - 9:34 pm
ORD
-
HVN
2h 34mnonstop
$132Avelo Airlines
Sun, Mar 29 - Sun, Apr 12
Avelo Airlines Logo
4:10 pm - 6:03 pm
HVN
-
ORD
2h 53mnonstop
Avelo Airlines Logo
6:35 pm - 10:07 pm
ORD
-
HVN
2h 32mnonstop
$149Avelo Airlines
Fri, Jul 3 - Sun, Jul 5
Avelo Airlines Logo
4:10 pm - 6:03 pm
HVN
-
ORD
2h 53mnonstop
Avelo Airlines Logo
6:35 pm - 10:07 pm
ORD
-
HVN
2h 32mnonstop
$151Avelo Airlines
Fri, Jul 10 - Sun, Jul 12
Multiple Airlines Logo
11:20 am - 12:40 am
HVN
-
ORD
14h 20m
2 stops
Multiple Airlines Logo
6:00 pm - 9:34 pm
ORD
-
HVN
2h 34mnonstop
$158Multiple Airlines
Thu, Feb 26 - Sun, Mar 1
Avelo Airlines Logo
3:50 pm - 5:43 pm
HVN
-
ORD
2h 53mnonstop
Avelo Airlines Logo
6:35 pm - 10:07 pm
ORD
-
HVN
2h 32mnonstop
$163Avelo Airlines
Thu, May 14 - Sun, May 17

Avelo Airlines flights from New Haven to Chicago

Our best Avelo Airlines deals on New Haven to Chicago flight tickets
Avelo Airlines
Mar 15
HVN3:20 pmTweed-New Haven
2h 45m
ORD5:05 pmChicago O'Hare Intl
Mar 19
ORD6:00 pmChicago O'Hare Intl
2h 34m
HVN9:34 pmTweed-New Haven
$87
Avelo Airlines
Mar 22
HVN3:20 pmTweed-New Haven
2h 45m
ORD5:05 pmChicago O'Hare Intl
Mar 29
ORD6:00 pmChicago O'Hare Intl
2h 34m
HVN9:34 pmTweed-New Haven
$89
Avelo Airlines
Jul 23
HVN3:50 pmTweed-New Haven
2h 53m
ORD5:43 pmChicago O'Hare Intl
Jul 26
ORD6:35 pmChicago O'Hare Intl
2h 32m
HVN10:07 pmTweed-New Haven
$110

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 February 6, 2026.
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

Sun 3/15

3:20 pm-5:05 pm

Nonstop2h 45m

Chicago O'Hare Intl

Thu 3/19

6:00 pm-9:34 pm

Nonstop2h 34m

$87

New HavenChicago

HVN - ORD

HVNORD

Tweed-New Haven

Sun 3/22

3:20 pm-5:05 pm

Nonstop2h 45m

Chicago O'Hare Intl

Sun 3/29

6:00 pm-9:34 pm

Nonstop2h 34m

$89

New HavenChicago

HVN - ORD

HVNORD

Tweed-New Haven

Thu 7/23

3:50 pm-5:43 pm

Nonstop2h 53m

Chicago O'Hare Intl

Sun 7/26

6:35 pm-10:07 pm

Nonstop2h 32m

$110

New HavenChicago

HVN - ORD

HVNORD

Tweed-New Haven

Fri 5/1

4:20 pm-6:13 pm

Nonstop2h 53m

Chicago O'Hare Intl

Fri 5/8

7:07 pm-10:39 pm

Nonstop2h 32m

$121

New HavenChicago

HVN - ORD

HVNORD

Tweed-New Haven

Fri 4/24

4:20 pm-6:13 pm

Nonstop2h 53m

Chicago O'Hare Intl

Sun 4/26

6:35 pm-10:07 pm

Nonstop2h 32m

$123

New HavenChicago

HVN - ORD

HVNORD

Tweed-New Haven

Sun 3/29

3:20 pm-5:05 pm

Nonstop2h 45m

Chicago O'Hare Intl

Sun 4/12

6:00 pm-9:34 pm

Nonstop2h 34m

$132

New HavenChicago

HVN - ORD

HVNORD

Tweed-New Haven

Fri 7/3

4:10 pm-6:03 pm

Nonstop2h 53m

Chicago O'Hare Intl

Sun 7/5

6:35 pm-10:07 pm

Nonstop2h 32m

$149

New HavenChicago

HVN - ORD

HVNORD

Tweed-New Haven

Fri 7/10

4:10 pm-6:03 pm

Nonstop2h 53m

Chicago O'Hare Intl

Sun 7/12

6:35 pm-10:07 pm

Nonstop2h 32m

$151

New HavenChicago

HVN - ORD

HVNORD

Tweed-New Haven

Thu 2/26

11:20 am-12:40 am

2 stops14h 20m

Chicago O'Hare Intl

Sun 3/1

6:00 pm-9:34 pm

Nonstop2h 34m

$158

New HavenChicago

HVN - ORD

HVNORD

Tweed-New Haven

Thu 5/14

3:50 pm-5:43 pm

Nonstop2h 53m

Chicago O'Hare Intl

Sun 5/17

6:35 pm-10:07 pm

Nonstop2h 32m

$163

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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 typical price of a round-trip flight between New Haven and Chicago?

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 $289. 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 $362.

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 $267. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $362.

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

$37

Fastest flight time

2h 45m

Direct flights

Mon, Fri and Sat

Airports in Chicago

3 airports
The best one-way flight to Chicago from New Haven in the past 72 hours is $37. The best round-trip flight deal from New Haven to Chicago found on momondo in the last 72 hours is $77.
The fastest flight from New Haven to Chicago takes 2h 45m
Direct flights go from New Haven to Chicago on Monday, Friday and Saturday. The only airline offering direct flights is Avelo Airlines.
There are 3 airports in Chicago. From New Haven there are direct flights to 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 45m.

  • 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 many operators does momondo search for flights from Tweed-New Haven Airport to Chicago?

  • 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?

Best airlines flying from New Haven to Chicago

Compare and see reviews for airlines that fly from New Haven to Chicago with momondo
Airline
Rating
Free Cancellation
Price
Avelo AirlinesPriceFrom $76Free CancellationRating
7.6
88 reviews
Search Avelo Airlines flights

  • Avelo Airlines Flights From New Haven to Chicago

    The lowest priced Avelo Airlines flight from New Haven to Chicago from the last 72 hours was $76. Generally, Avelo Airlines has 2 flights on this route every week with an average price of $178. Avelo Airlines is rated 7.6/10 by our users.

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
Munster
Crown Point
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.

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Sun 3/8
Sun 3/15
By creating a price alert you accept our terms of use and privacy policy.

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