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$98+ Cheap flights from New Haven (HVN) to Chicago (CHI)

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/14. Fares are subject to change and may not be available on all flights or dates of travel.
HVN — CHI
Nov 29 — Dez 61
Sa 11/29
Sa 12/6
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 Oktober 30, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$98
(Mytrip)

Popular in

December

Cheapest in

January

Average price

$184

Good one-way deal

$49 or less
Provider with most accurate pricing for Tweed-New Haven-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Tweed-New Haven-Chicago (CHI) flights.
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From Tweed-New Haven to Chicago (CHI)
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High demand for flights, 11% potential price rise
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Cheapest flight prices on average. 2% potential price decrease ($6 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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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 Oktober 30, 2025.

This Mytrip deal was found by Cheapflights users on 10/29. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
So 12/141:50 pmHVN - ORD
Nonstop2h 30mAvelo Airlines
Do 12/184:35 pmORD - HVN
Nonstop2h 05mAvelo Airlines
Deal found 10/29$98
This Mytrip deal was found by Cheapflights users on 10/28. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Di 11/2511:05 amHVN - ORD
Nonstop2h 30mAvelo Airlines
Fr 11/281:20 pmORD - HVN
Nonstop2h 05mAvelo Airlines
Deal found 10/28$138
This Cheapflightsfares deal was found by Cheapflights users on 10/29. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mo 12/111:05 amHVN - ORD
Nonstop2h 30mAvelo Airlines
Do 12/44:05 pmORD - HVN
Nonstop2h 05mAvelo Airlines
Deal found 10/29$158
This Cheapflightsfares deal was found by Cheapflights users on 10/28. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Do 12/182:20 pmHVN - ORD
Nonstop2h 30mAvelo Airlines
So 12/214:35 pmORD - HVN
Nonstop2h 05mAvelo Airlines
Deal found 10/28$183
This Trip.com deal was found by Cheapflights users on 10/28. 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.
Do 11/201:35 pmHVN - ORD
Nonstop2h 30mAvelo Airlines
So 11/234:25 pmORD - HVN
Nonstop2h 05mAvelo Airlines
Deal found 10/28$201
This Mytrip deal was found by Cheapflights users on 10/29. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
So 12/141:50 pmHVN - ORD
Nonstop2h 30mMultiple Airlines
Do 12/187:20 amORD - HVN
1 stop14h 39mMultiple Airlines
Deal found 10/29$211
This Mytrip deal was found by Cheapflights users on 10/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
So 12/71:50 pmHVN - ORD
Nonstop2h 30mMultiple Airlines
Mo 12/87:20 amORD - HVN
1 stop14h 10mMultiple Airlines
Deal found 10/30$216
This Mytrip deal was found by Cheapflights users on 10/28. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
So 11/238:00 amHVN - ORD
1 stop16h 13mMultiple Airlines
Fr 11/281:20 pmORD - HVN
Nonstop2h 05mMultiple Airlines
Deal found 10/28$218
This Mytrip deal was found by Cheapflights users on 10/29. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Do 11/133:50 pmHVN - ORD
Nonstop2h 30mMultiple Airlines
Fr 11/147:34 pmORD - HVN
2 stops16h 40mMultiple Airlines
Deal found 10/29$220
This Mytrip deal was found by Cheapflights users on 10/29. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mo 12/111:05 amHVN - ORD
Nonstop2h 30mMultiple Airlines
Do 12/48:15 amORD - HVN
1 stop13h 11mMultiple Airlines
Deal found 10/29$244

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 Oktober 30, 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

Di 11/25

11:05 am-12:35 pm

Nonstop2h 30m

Chicago O'Hare Intl

Fr 11/28

1:20 pm-4:25 pm

Nonstop2h 05m

$138

New HavenChicago

HVN - ORD

HVNORD

Tweed-New Haven

Mo 12/1

11:05 am-12:35 pm

Nonstop2h 30m

Chicago O'Hare Intl

Do 12/4

4:05 pm-7:10 pm

Nonstop2h 05m

$158

New HavenChicago

HVN - ORD

HVNORD

Tweed-New Haven

So 12/14

1:50 pm-3:20 pm

Nonstop2h 30m

Chicago O'Hare Intl

Do 12/18

7:20 am-10:59 pm

1 stop14h 39m

$211

New HavenChicago

HVN - ORD

HVNORD

Tweed-New Haven

So 12/7

1:50 pm-3:20 pm

Nonstop2h 30m

Chicago O'Hare Intl

Mo 12/8

7:20 am-10:30 pm

1 stop14h 10m

$216

New HavenChicago

HVN - ORD

HVNORD

Tweed-New Haven

So 11/23

8:00 am-11:13 pm

1 stop16h 13m

Chicago O'Hare Intl

Fr 11/28

1:20 pm-4:25 pm

Nonstop2h 05m

$218

New HavenChicago

HVN - ORD

HVNORD

Tweed-New Haven

Mo 12/1

11:05 am-12:35 pm

Nonstop2h 30m

Chicago O'Hare Intl

Do 12/4

8:15 am-10:26 pm

1 stop13h 11m

$244

New HavenChicago

HVN - ORD

HVNORD

Tweed-New Haven

Fr 11/14

3:35 pm-11:06 pm

1 stop8h 31m

Chicago O'Hare Intl

Di 11/18

4:57 pm-4:05 pm

2 stops22h 08m

$259

New HavenChicago

HVN - ORD

HVNORD

Tweed-New Haven

Mo 11/24

4:15 pm-11:06 pm

1 stop7h 51m

$103

New HavenChicago

HVN - ORD

HVNORD

Tweed-New Haven

Mi 11/19

3:55 pm-5:13 pm

1 stop26h 18m

$107

New HavenChicago

HVN - ORD

HVNORD

Tweed-New Haven

Fr 11/7

3:15 pm-11:28 pm

1 stop9h 13m

$176

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/27

Showing 1-10 of 13 results
1
2

Compare providers for flights from New Haven to Chicago

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from New Haven to Chicago in October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
MytripPrice Accuracy3 starsTrust Score*3 stars
Trip.comPrice Accuracy2 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on New Haven-Chicago flights, users find the pricing of Mytrip to be most consistent on Cheapflights vs. Mytrip Users can find the same prices on New Haven-Chicago flight deals on Cheapflights vs. Mytrip >95% of the time. Price accuracy is based on data collected from New Haven-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on New Haven-Chicago flights, Cheapflights users trust Mytrip the most. Mytrip has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for New Haven-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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, May is the cheapest month in which you can book a flight from New Haven to Chicago (average of $55). Flying from New Haven to Chicago in July is currently the most expensive (average of $126). 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 Oktober 30, 2025.

It’s typically best to fly out from New Haven to Chicago in the evening. Doing so could potentially save you 41% on the flight price compared to flying in the afternoon, which is usually more expensive.

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 Oktober 30, 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

Crew

8.2

Overall

7.5

Comfort

7.1

Entertainment

5.0

Food

5.0

Boarding

7.7

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

Crew

8.2

Overall

7.5

Comfort

7.1

Entertainment

5.0

Food

5.0

Boarding

7.7

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 30m. 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 $49. While the most popular route (Tweed-New Haven - Chicago O'Hare Intl) can be booked for $98 on average, our data indicates $88 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, May is the cheapest month in which you can book a flight from New Haven to Chicago (average of $55). Flying from New Haven to Chicago in July is currently the most expensive (average of $126). 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
Porter
Benton Harbor

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