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$52+ 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 4/24. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — HVN
Apr 20 — Apr 271
Mon 4/20
Mon 4/27
1 adult, Economy
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Cheap 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 March 21, 2026.

This Cheapflightsfares deal was found by Cheapflights users on 3/20. 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.
Fri 4/247:07 pm
ORD
-
HVN
Nonstop2h 32m
Avelo Airlines
Mon 4/274:20 pm
HVN
-
ORD
Nonstop2h 53m
Avelo Airlines
Deal found 3/20$103
This CheapOair deal was found by Cheapflights users on 3/17. 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.
Fri 5/17:07 pm
ORD
-
HVN
Nonstop2h 32m
Avelo Airlines
Sun 5/33:50 pm
HVN
-
ORD
Nonstop2h 53m
Avelo Airlines
Deal found 3/17$111
This Cheapflightsfares deal was found by Cheapflights users on 3/19. 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.
Fri 5/87:07 pm
ORD
-
HVN
Nonstop2h 32m
Avelo Airlines
Mon 5/114:20 pm
HVN
-
ORD
Nonstop2h 53m
Avelo Airlines
Deal found 3/19$123
This CheapOair deal was found by Cheapflights users on 3/17. 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 6/46:35 pm
ORD
-
HVN
Nonstop2h 32m
Avelo Airlines
Sun 6/73:50 pm
HVN
-
ORD
Nonstop2h 53m
Avelo Airlines
Deal found 3/17$152
This Super.com deal was found by Cheapflights users on 3/18. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/247:07 pm
ORD
-
HVN
Nonstop2h 32m
Avelo Airlines
Sun 4/263:50 pm
HVN
-
ORD
Nonstop2h 53m
Avelo Airlines
Deal found 3/18$159
This Mytrip deal was found by Cheapflights users on 3/19. 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 5/76:35 pm
ORD
-
HVN
Nonstop2h 32m
Multiple Airlines
Sat 5/910:55 am
HVN
-
ORD
1 stop7h 15m
Multiple Airlines
Deal found 3/19$173
This Travelocity deal was found by Cheapflights users on 3/20. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/26:35 pm
ORD
-
HVN
Nonstop2h 32m
Avelo Airlines
Mon 7/64:10 pm
HVN
-
ORD
Nonstop2h 53m
Avelo Airlines
Deal found 3/20$174
This CheapOair deal was found by Cheapflights users on 3/20. 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.
Fri 7/36:48 pm
ORD
-
HVN
Nonstop2h 31m
Avelo Airlines
Mon 7/64:10 pm
HVN
-
ORD
Nonstop2h 53m
Avelo Airlines
Deal found 3/20$175

Find 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 March 21, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$103
(Cheapflightsfares)

One-way from

$52
(Travelocity)

Popular in

June

Cheapest in

January

Average price

$160

Good round-trip deal

$142 or less

Good one-way deal

$130 or less
Provider with most accurate pricing for Chicago (CHI)-Tweed-New Haven flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Tweed-New Haven flights.
Search Deals
From Chicago (CHI) to Tweed-New Haven
Search Deals
One-way flight from Chicago (CHI) to Tweed-New Haven
Search Deals
Highest demand for flights based on searches. 24% potential increase in price ($64 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($12 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2026
Search Deals
Price to beat on a round-trip flight from Chicago (CHI) to Tweed-New Haven.
Search Deals
Price to beat on a one-way flight from Chicago (CHI) to Tweed-New Haven.
Search Deals

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 March 21, 2026.
Use the filters below to find and compare flights from Chicago to New Haven that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoNew Haven

ORD - HVN

ORDHVN

Chicago O'Hare Intl

Fri 4/24

7:07 pm-10:39 pm

Nonstop2h 32m

Tweed-New Haven

Mon 4/27

4:20 pm-6:13 pm

Nonstop2h 53m

$103

ChicagoNew Haven

ORD - HVN

ORDHVN

Chicago O'Hare Intl

Thu 4/30

6:35 pm-10:07 pm

Nonstop2h 32m

Tweed-New Haven

Mon 5/4

4:20 pm-6:13 pm

Nonstop2h 53m

$111

ChicagoNew Haven

ORD - HVN

ORDHVN

Chicago O'Hare Intl

Fri 5/1

7:07 pm-10:39 pm

Nonstop2h 32m

Tweed-New Haven

Sun 5/3

3:50 pm-5:43 pm

Nonstop2h 53m

$111

ChicagoNew Haven

ORD - HVN

ORDHVN

Chicago O'Hare Intl

Fri 5/8

7:07 pm-10:39 pm

Nonstop2h 32m

Tweed-New Haven

Mon 5/11

4:20 pm-6:13 pm

Nonstop2h 53m

$141

ChicagoNew Haven

ORD - HVN

ORDHVN

Chicago O'Hare Intl

Fri 4/24

7:07 pm-10:39 pm

Nonstop2h 32m

Tweed-New Haven

Sun 4/26

3:50 pm-5:43 pm

Nonstop2h 53m

$171

ChicagoNew Haven

ORD - HVN

ORDHVN

Chicago O'Hare Intl

Fri 6/5

7:07 pm-10:39 pm

Nonstop2h 32m

Tweed-New Haven

Sun 6/7

3:50 pm-5:43 pm

Nonstop2h 53m

$171
Quickest round-trip

ChicagoNew Haven

ORD - HVN

ORDHVN

Chicago O'Hare Intl

Fri 7/3

6:48 pm-10:19 pm

Nonstop2h 31m

Tweed-New Haven

Mon 7/6

4:10 pm-6:03 pm

Nonstop2h 53m

$182

ChicagoNew Haven

ORD - HVN

ORDHVN

Chicago O'Hare Intl

Fri 5/8

7:07 pm-10:39 pm

Nonstop2h 32m

Tweed-New Haven

Sun 5/10

3:50 pm-5:43 pm

Nonstop2h 53m

$199

ChicagoNew Haven

ORD - HVN

ORDHVN

Chicago O'Hare Intl

Fri 4/24

7:07 pm-10:39 pm

Nonstop2h 32m

Tweed-New Haven

Mon 4/27

11:05 am-10:23 am

3 stops24h 18m

$217

ChicagoNew Haven

ORD - HVN

ORDHVN

Chicago O'Hare Intl

Thu 8/13

6:35 pm-10:07 pm

Nonstop2h 32m

Tweed-New Haven

Sun 8/16

3:50 pm-5:43 pm

Nonstop2h 53m

$220

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/20

Showing 1-10 of 21 resultsSorted by cheapest first
1
2
3

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 March.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 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 Chicago-New Haven flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-New Haven flight deals on Cheapflights vs. FlightHub >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 FlightHub the most. FlightHub 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 March 21, 2026.

It’s typically best to fly out from Chicago to New Haven in the afternoon. Doing so could potentially save you 38% on the flight price compared to flying at noon, which is usually more expensive.

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 March 21, 2026.
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
7.6
Good

Overall

7.6

Entertainment

5.0

Food

5.1

Boarding

7.7

Crew

8.3

Comfort

7.1

Reviews

1 / 7
8.0
Excellent

Anonymous,Dec 2025

USA - ROC

The Customer Service department, particularly the baggage claim process, needs significant improvement. Currently, this department is only accessible via email, which makes resolving urgent issues difficult and frustrating. On December 8th, while traveling from Rochester, NY to Concord, NC, my elderly parent’s walker was never boarded onto the aircraft. This caused considerable frustration, stress, and disappointment during our travel. A mobility aid such as a walker is not optional—it is essential for my parent’s safety and independence. The failure to properly handle this item created a serious and avoidable issue. This situation significantly impacted our travel experience and highlights the need for better communication, accountability, and handling of mobility assistance devices. I hope this matter is taken seriously and that improvements are made to prevent similar incidents in the future.
Avelo Airlines
7.6
Good
Avelo Airlines
7.6
Good

Overall

7.6

Entertainment

5.0

Food

5.1

Boarding

7.7

Crew

8.3

Comfort

7.1

Reviews

1 / 7
8.0
Excellent

Anonymous,Dec 2025

USA - ROC

The Customer Service department, particularly the baggage claim process, needs significant improvement. Currently, this department is only accessible via email, which makes resolving urgent issues difficult and frustrating. On December 8th, while traveling from Rochester, NY to Concord, NC, my elderly parent’s walker was never boarded onto the aircraft. This caused considerable frustration, stress, and disappointment during our travel. A mobility aid such as a walker is not optional—it is essential for my parent’s safety and independence. The failure to properly handle this item created a serious and avoidable issue. This situation significantly impacted our travel experience and highlights the need for better communication, accountability, and handling of mobility assistance devices. I hope this matter is taken seriously and that improvements are made to prevent similar incidents in the future.

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 32m. 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 $78. Avelo Airlines is 60% 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 $99. While the most popular route (Chicago O'Hare Intl - Tweed-New Haven) can be booked for $103 on average, our data indicates $159 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

Browse thousands of different options on Cheapflights for your next trip

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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 March 21, 2026.
AirlineCheapestAverageFlexibilityOn-time
Avelo AirlinesCheapest$78Average$138FlexibilityNo cancel feeOn-timeN/A

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