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$49+ 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 7/31. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — HVN
jul. 8 — jul. 151
mar. 7/8
mar. 7/15
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 julio 3, 2025.

Round-trip from

$93
(Expedia)

One-way from

$49
(Orbitz)

Popular in

January

Cheapest in

February

Average price

$132

Good round-trip deal

$178 or less

Good one-way deal

$115 or less
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. 17% potential increase in price ($45 potential increase over avg. RT price).
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Cheapest flight prices on average. 11% potential price decrease ($22 potential savings vs. average RT price).
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Average for round-trip flights in July 2025
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Price to beat on a round-trip flight from Chicago (CHI) to Tweed-New Haven.
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Price to beat on a one-way 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 julio 3, 2025.

This Expedia deal was found by Cheapflights users on 7/2. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 8/283:55 pmORD - HVN
Nonstop2h 10mAvelo Airlines
dom. 8/311:45 pmHVN - ORD
Nonstop2h 20mAvelo Airlines
Deal found 7/2$93
This Trip.com deal was found by Cheapflights users on 7/1. 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.
vie. 8/299:32 amORD - HVN
1 stop9h 13mMultiple Airlines
dom. 8/311:45 pmHVN - ORD
Nonstop2h 20mMultiple Airlines
Deal found 7/1$150

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 julio 3, 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

jue. 8/28

3:55 pm-7:05 pm

Nonstop2h 10m

Tweed-New Haven

dom. 8/31

1:45 pm-3:05 pm

Nonstop2h 20m

$93

ChicagoNew Haven

ORD - HVN

ORDHVN

Chicago O'Hare Intl

vie. 8/29

9:32 am-7:45 pm

1 stop9h 13m

Tweed-New Haven

dom. 8/31

1:45 pm-3:05 pm

Nonstop2h 20m

$150

ChicagoNew Haven

ORD - HVN

ORDHVN

Chicago O'Hare Intl

jue. 7/31

3:55 pm-7:05 pm

Nonstop2h 10m

$49

ChicagoNew Haven

ORD - HVN

ORDHVN

Chicago O'Hare Intl

vie. 8/1

12:35 pm-9:19 pm

1 stop7h 44m

$91

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/1

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, February is the cheapest month in which you can book a flight from Chicago to New Haven (average of $91). Flying from Chicago to New Haven in December is currently the most expensive (average of $185). 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 julio 3, 2025.

It’s typically best to fly out from Chicago to New Haven at noon. Doing so could potentially save you 26% on the flight price compared to flying in the morning, 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 julio 3, 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
7.4
Good

Comfort

7.1

Entertainment

5.0

Boarding

7.6

Food

5.1

Overall

7.4

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
7.4
Good
Avelo Airlines
7.4
Good

Comfort

7.1

Entertainment

5.0

Boarding

7.6

Food

5.1

Overall

7.4

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.

  • 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 $93. Avelo Airlines is 57% 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 $69. While the most popular route (Chicago O'Hare Intl - Tweed-New Haven) can be booked for $93 on average our data indicates $183 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, February is the cheapest month in which you can book a flight from Chicago to New Haven (average of $91). Flying from Chicago to New Haven in December is currently the most expensive (average of $185). 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.

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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 julio 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
Avelo AirlinesCheapest$84Average$169FlexibilityNo cancel feeOn-timeN/A

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