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

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 12/11. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — HVN
Nov 26 — Dec 31
Wed 11/26
Wed 12/3
1 adult, Economy
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Cheap flight deals from Chicago to New Haven

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to New Haven (HVN). 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 October 27, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$97
(Mytrip)

One-way from

$53
(CheapOair)

Popular in

January

Cheapest in

February

Average price

$137

Good round-trip deal

$108 or less
Provider with most accurate pricing for Chicago (CHI)-Tweed-New Haven flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Tweed-New Haven flights.
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From Chicago (CHI) to Tweed-New Haven
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One-way flight from Chicago (CHI) to Tweed-New Haven
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Highest demand for flights based on searches. 9% potential increase in price ($23 potential increase over avg. RT price).
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Cheapest flight prices on average. 9% potential price decrease ($21 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 round-trip flight from Chicago (CHI) to Tweed-New Haven.
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Find flight deals from Chicago to New Haven

Cheapest flights from Chicago to New Haven
Explore the most affordable flight options available from Chicago to New Haven. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 27, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 10/25. 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.
Thu 12/114:05 pmORD - HVN
Nonstop2h 05mAvelo Airlines
Wed 12/245:10 pmHVN - ORD
Nonstop2h 30mAvelo Airlines
Deal found 10/25$98
This CheapOair deal was found by Cheapflights users on 10/25. 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 12/114:05 pmORD - HVN
Nonstop2h 05mAvelo Airlines
Sun 12/141:50 pmHVN - ORD
Nonstop2h 30mAvelo Airlines
Deal found 10/25$101
This Cheapflightsfares deal was found by Cheapflights users on 10/26. 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.
Thu 11/66:20 pmORD - HVN
Nonstop2h 04mAvelo Airlines
Thu 11/133:50 pmHVN - ORD
Nonstop2h 30mAvelo Airlines
Deal found 10/26$148
This CheapOair deal was found by Cheapflights users on 10/26. 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 12/254:35 pmORD - HVN
Nonstop2h 05mAvelo Airlines
Tue 12/301:05 pmHVN - ORD
Nonstop2h 30mAvelo Airlines
Deal found 10/26$161
This eDestinos deal was found by Cheapflights users on 10/26. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/214:35 pmORD - HVN
Nonstop2h 05mAvelo Airlines
Sun 1/113:05 pmHVN - ORD
Nonstop2h 32mAvelo Airlines
Deal found 10/26$166
This CheapOair deal was found by Cheapflights users on 10/25. 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.
Tue 12/233:15 pmORD - HVN
Nonstop2h 05mAvelo Airlines
Wed 12/315:10 pmHVN - ORD
Nonstop2h 30mAvelo Airlines
Deal found 10/25$169
This Mytrip deal was found by Cheapflights users on 10/26. 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.
Thu 11/136:48 amORD - HVN
1 stop13h 31mMultiple Airlines
Sun 11/163:50 pmHVN - ORD
Nonstop2h 30mMultiple Airlines
Deal found 10/26$177
This CheapOair deal was found by Cheapflights users on 10/25. 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 12/214:35 pmORD - HVN
Nonstop2h 05mAvelo Airlines
Wed 12/315:10 pmHVN - ORD
Nonstop2h 30mAvelo Airlines
Deal found 10/25$184
This Trip.com deal was found by Cheapflights users on 10/27. 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.
Thu 12/184:35 pmORD - HVN
Nonstop2h 05mMultiple Airlines
Mon 1/197:00 amHVN - ORD
1 stop18h 12mMultiple Airlines
Deal found 10/27$192

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to New Haven 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 October 27, 2025.
Use the filters below to find and compare flights from Chicago to New Haven that are best for you.

Fly from

Chicago

Fly to

New Haven

Route

Depart

Return

Price

ChicagoNew Haven

ORD - HVN

ORDHVN

Chicago O'Hare Intl

Thu 12/11

4:05 pm-7:10 pm

Nonstop2h 05m

Tweed-New Haven

Wed 12/24

5:10 pm-6:40 pm

Nonstop2h 30m

$98

ChicagoNew Haven

ORD - HVN

ORDHVN

Chicago O'Hare Intl

Wed 12/17

7:25 pm-10:30 pm

Nonstop2h 05m

Tweed-New Haven

Sun 1/11

3:05 pm-4:37 pm

Nonstop2h 32m

$101

ChicagoNew Haven

ORD - HVN

ORDHVN

Chicago O'Hare Intl

Thu 11/13

6:05 pm-9:09 pm

Nonstop2h 04m

Tweed-New Haven

Sun 11/16

3:50 pm-5:20 pm

Nonstop2h 30m

$148

ChicagoNew Haven

ORD - HVN

ORDHVN

Chicago O'Hare Intl

Thu 1/29

5:20 pm-8:26 pm

Nonstop2h 06m

Tweed-New Haven

Mon 2/2

6:30 am-9:23 pm

1 stop15h 53m

$153

ChicagoNew Haven

ORD - HVN

ORDHVN

Chicago O'Hare Intl

Thu 12/25

4:35 pm-7:40 pm

Nonstop2h 05m

Tweed-New Haven

Tue 12/30

1:05 pm-2:35 pm

Nonstop2h 30m

$161

ChicagoNew Haven

ORD - HVN

ORDHVN

Chicago O'Hare Intl

Sun 12/21

4:35 pm-7:40 pm

Nonstop2h 05m

Tweed-New Haven

Sun 1/11

3:05 pm-4:37 pm

Nonstop2h 32m

$166

ChicagoNew Haven

ORD - HVN

ORDHVN

Chicago O'Hare Intl

Tue 12/23

3:15 pm-6:20 pm

Nonstop2h 05m

Tweed-New Haven

Wed 12/31

5:10 pm-6:40 pm

Nonstop2h 30m

$169

ChicagoNew Haven

ORD - HVN

ORDHVN

Chicago O'Hare Intl

Thu 11/13

6:48 am-9:19 pm

1 stop13h 31m

Tweed-New Haven

Sun 11/16

3:50 pm-5:20 pm

Nonstop2h 30m

$177

ChicagoNew Haven

ORD - HVN

ORDHVN

Chicago O'Hare Intl

Sun 12/21

4:35 pm-7:40 pm

Nonstop2h 05m

Tweed-New Haven

Wed 12/31

5:10 pm-6:40 pm

Nonstop2h 30m

$184

ChicagoNew Haven

ORD - HVN

ORDHVN

Chicago O'Hare Intl

Thu 12/11

4:05 pm-7:10 pm

Nonstop2h 05m

$53

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/25

Showing 1-10 of 18 results
1
2

Compare providers for flights from Chicago to New Haven

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 Chicago to New Haven in October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star

*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 Chicago-New Haven flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago-New Haven flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Chicago-New Haven flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-New Haven flights, Cheapflights users trust eDreams the most. eDreams 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 Chicago-New Haven 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 Chicago to New Haven

Have a flexible travel schedule? Discover the best time to fly to New Haven from Chicago 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 Chicago to New Haven

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

Currently, September is the cheapest month in which you can book a flight from Chicago to New Haven (average of $23). Flying from Chicago to New Haven in June is currently the most expensive (average of $107). 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 CHI to HVN?

Find hourly flight availability from Chicago to New Haven. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 27, 2025.

When flying from Chicago to New Haven, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Reviews of airlines servicing New Haven

Get insights into the airlines that provide service to New Haven. 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 New Haven. Reviews last updated October 27, 2025.
Read through reviews of airlines operating flights from Chicago to New Haven, such as Avelo Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Avelo Airlines
7.5
Good

Food

5.0

Comfort

7.1

Entertainment

5.0

Overall

7.5

Boarding

7.7

Crew

8.2

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

Food

5.0

Comfort

7.1

Entertainment

5.0

Overall

7.5

Boarding

7.7

Crew

8.2

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 Chicago to New Haven. 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 into for flights to New Haven from Chicago?

    If you book a flight to New Haven from Chicago, you will be flying to Tweed-New Haven, which is the city’s only airport. Tweed-New Haven (HVN) is located 3.6 mi from the center of New Haven. There are 0 flights from Chicago to Tweed-New Haven per day from 1 airline.

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

    Departing from Chicago to New Haven will take you 2h 05m. The distance between Chicago and New Haven is about 776 mi. Generally, flights for this route are nonstop.

  • What is the cheapest airline to fly from Chicago to New Haven round-trip?

    Cheapflights users have booked flights from Chicago to New Haven round-trip from $85. Avelo Airlines is 63% cheaper than the average price of flights available within the next 90 days to this destination.

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

    Looking at all options, your cheapest flight can be booked for $78. While the most popular route (Chicago O'Hare Intl - Tweed-New Haven) can be booked for $98 on average, our data indicates $158 when flying from Chicago to New Haven.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Chicago to New Haven 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 Chicago to New Haven?

    Currently, September is the cheapest month in which you can book a flight from Chicago to New Haven (average of $23). Flying from Chicago to New Haven in June is currently the most expensive (average of $107). 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 New Haven?

Book flights to New Haven if you plan to visit one of these locations
Wallingford

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Alternative routes for Chicago to New Haven

See prices for flight routes from nearby airports that may be better suited for you.
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Top airline flying from Chicago to New Haven

Discover the top airline that operate flights from Chicago to New Haven. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated October 27, 2025.
AirlineCheapestAverageFlexibilityOn-time
Avelo AirlinesCheapest$85Average$135FlexibilityNo cancel feeOn-timeN/A

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