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$53+ Cheap flights from New Haven (HVN) to Chicago (CHI)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 2/20. Fares are subject to change and may not be available on all flights or dates of travel.
HVN — CHI
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
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Cheap flight deals from New Haven to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from New Haven (HVN) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated September 15, 2025.

Round-trip from

$193
(Kiwi.com)

One-way from

$99
(Cheapflightsfares)

Popular in

December

Cheapest in

January

Average price

$177

Good round-trip deal

$199 or less

Good one-way deal

$77 or less
From Tweed-New Haven to Chicago (CHI)
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One-way flight from Tweed-New Haven to Chicago (CHI)
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High demand for flights, 16% potential price rise
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Cheapest flight prices on average. 4% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from Tweed-New Haven to Chicago (CHI).
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Price to beat on a one-way flight from Tweed-New Haven to Chicago (CHI).
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Find flight deals from New Haven to Chicago

Cheapest flights from New Haven to Chicago
Explore the most affordable flight options available from New Haven to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 15, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/146:26 pmHVN - ORD
1 stop6h 02mMultiple Airlines
Sun 11/161:50 pmORD - HVN
1 stop26h 56mMultiple Airlines
Deal found 9/13$193
This CheapOair deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/213:50 pmHVN - ORD
Nonstop2h 21mAvelo Airlines
Sun 9/286:02 pmORD - HVN
Nonstop2h 08mAvelo Airlines
Deal found 9/14$201
This Kiwi.com deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/146:26 pmHVN - ORD
1 stop6h 02mMultiple Airlines
Mon 11/1710:18 amORD - HVN
1 stop26h 39mMultiple Airlines
Deal found 9/13$215
This CheapOair deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/253:50 pmHVN - ORD
Nonstop2h 21mAvelo Airlines
Sun 9/286:02 pmORD - HVN
Nonstop2h 08mAvelo Airlines
Deal found 9/11$220
This Kiwi.com deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/135:52 pmHVN - ORD
2 stops20h 46mMultiple Airlines
Sun 11/161:50 pmORD - HVN
1 stop26h 56mMultiple Airlines
Deal found 9/13$235
This Trip.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/217:30 amHVN - ORD
1 stop10h 10mMultiple Airlines
Fri 10/242:41 pmORD - HVN
2 stops21h 27mMultiple Airlines
Deal found 9/14$247
This Trip.com deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/278:00 amHVN - ORD
1 stop15h 48mMultiple Airlines
Wed 10/111:57 amORD - HVN
1 stop26h 43mMultiple Airlines
Deal found 9/12$252
This Kiwi.com deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/135:52 pmHVN - ORD
2 stops20h 46mMultiple Airlines
Mon 11/1710:18 amORD - HVN
1 stop26h 39mMultiple Airlines
Deal found 9/13$253
This Kiwi.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/212:42 pmHVN - ORD
1 stop25h 26mMultiple Airlines
Sat 10/257:43 pmORD - HVN
1 stop22h 03mMultiple Airlines
Deal found 9/14$257

Cheapflights 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, Cheapflights users made 2,558,603 searches. Data last updated September 15, 2025.
Use the filters below to find and compare flights from New Haven to Chicago that are best for you.

Fly from

New Haven

Fly to

Chicago

Route

Depart

Return

Price

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

$193

New HavenChicago

HVN - ORD

HVNORD

Tweed-New Haven

Fri 11/14

6:26 pm-11:28 pm

1 stop6h 02m

Chicago O'Hare Intl

Mon 11/17

10:18 am-1:57 pm

1 stop26h 39m

$215

New HavenChicago

HVN - ORD

HVNORD

Tweed-New Haven

Thu 9/25

3:50 pm-5:11 pm

Nonstop2h 21m

Chicago O'Hare Intl

Sun 9/28

6:02 pm-9:10 pm

Nonstop2h 08m

$220

New HavenChicago

HVN - ORD

HVNORD

Tweed-New Haven

Thu 11/13

5:52 pm-1:38 pm

2 stops20h 46m

Chicago O'Hare Intl

Sun 11/16

1:50 pm-5:46 pm

1 stop26h 56m

$235

New HavenChicago

HVN - ORD

HVNORD

Tweed-New Haven

Tue 10/21

7:30 am-4:40 pm

1 stop10h 10m

Chicago O'Hare Intl

Fri 10/24

2:41 pm-1:08 pm

2 stops21h 27m

$247

New HavenChicago

HVN - ORD

HVNORD

Tweed-New Haven

Sat 9/27

8:00 am-10:48 pm

1 stop15h 48m

Chicago O'Hare Intl

Wed 10/1

11:57 am-3:40 pm

1 stop26h 43m

$252

New HavenChicago

HVN - ORD

HVNORD

Tweed-New Haven

Fri 10/3

3:02 pm-9:58 pm

2 stops31h 56m

Chicago O'Hare Intl

Mon 10/6

8:49 pm-1:57 pm

1 stop16h 08m

$260

New HavenChicago

HVN - ORD

HVNORD

Tweed-New Haven

Fri 2/20

2:40 pm-3:57 pm

Nonstop2h 17m

$53

New HavenChicago

HVN - ORD

HVNORD

Tweed-New Haven

Sun 1/18

3:05 pm-4:37 pm

Nonstop2h 32m

$63

New HavenChicago

HVN - ORD

HVNORD

Tweed-New Haven

Sat 10/4

8:00 am-10:48 pm

1 stop15h 48m

$92

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/13

Showing 1-10 of 16 results
1
2

Best time to book a flight from New Haven to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from New Haven with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from New Haven to Chicago

What is the cheapest month to book a flight from New Haven to Chicago?

Currently, August is the cheapest month in which you can book a flight from New Haven to Chicago (average of $245). Flying from New Haven to Chicago in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from HVN to CHI?

Find hourly flight availability from New Haven to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 15, 2025.

It’s typically best to fly out from New Haven to Chicago in the morning. Doing so could potentially save you 39% on the flight price compared to flying in the evening, which is usually more expensive.

How much does it cost to fly round-trip from New Haven to Chicago?

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated September 15, 2025.
Peruse reviews from past customers who have flown with Avelo Airlines from New Haven to Chicago to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Avelo Airlines
7.5
Good

Entertainment

5.0

Crew

8.2

Boarding

7.6

Comfort

7.1

Overall

7.5

Food

5.1

Reviews

1 / 6
2.0
Mediocre

Cindy,Sep 2023

MCO - DAY

I was emailed and told that if I check my luggage early I get a 10 dollar discount, also on the website, if it's under 50 lbs. it would be $40.00 I was charged $65.00 on first flight and $60.00 on second flight (second flight I checked in early, did not receive the discount, both flights my luggage was under 40 lbs.). Avelo destroyed my luggage, wheels were tore off, and plastic was ripped off.
Avelo Airlines
7.5
Good
Avelo Airlines
7.5
Good

Entertainment

5.0

Crew

8.2

Boarding

7.6

Comfort

7.1

Overall

7.5

Food

5.1

Reviews

1 / 6
2.0
Mediocre

Cindy,Sep 2023

MCO - DAY

I was emailed and told that if I check my luggage early I get a 10 dollar discount, also on the website, if it's under 50 lbs. it would be $40.00 I was charged $65.00 on first flight and $60.00 on second flight (second flight I checked in early, did not receive the discount, both flights my luggage was under 40 lbs.). Avelo destroyed my luggage, wheels were tore off, and plastic was ripped off.

Related info for your journey

Find useful and relevant information for your journey from New Haven to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from New Haven to Chicago?

    For a flight from New Haven to Chicago, you will be flying from Tweed-New Haven. Tweed-New Haven (HVN) is just 3.6 mi from the center of the city. Tweed-New Haven is the only New Haven airport and it handles 0 outbound flights to Chicago per day. 0 airlines have flights to Chicago from Tweed-New Haven on a regular basis.

  • How long is the flight from New Haven to Chicago?

    There are many flights that can get you from New Haven to Chicago in 2h 21m. Fly via Avelo Airlines to get the fastest option. The distance between New Haven and Chicago is about 776 mi. All flights are typically nonstop.

  • What are the cheapest flights from New Haven to Chicago?

    Looking at all options, your cheapest flight can be booked for $46. While the most popular route (Tweed-New Haven - Chicago O'Hare Intl) can be booked for $112 on average, our data indicates $185 when flying from New Haven to Chicago.

  • Can I find deals for flights from New Haven to Chicago that include hotel bookings?

    Yes. In addition to deals on New Haven to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from New Haven to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from New Haven to Chicago.

  • Can I find deals for business class flights from New Haven to Chicago?

    Yes. Cheapflights offers flight deals from New Haven to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from New Haven to Chicago?

    Currently, August is the cheapest month in which you can book a flight from New Haven to Chicago (average of $245). Flying from New Haven to Chicago in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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