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$49+ 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 1/8. Fares are subject to change and may not be available on all flights or dates of travel.
HVN — CHI
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
1 adult, Economy
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Cheap 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 December 18, 2025.

This Booking.com deal was found by Cheapflights users on 12/16. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/315:10 pmHVN - ORD
Nonstop2h 30mAvelo Airlines
Sun 1/44:35 pmORD - HVN
Nonstop2h 05mAvelo Airlines
Deal found 12/16$372
This Mytrip deal was found by Cheapflights users on 12/16. 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.
Wed 12/315:10 pmHVN - ORD
Nonstop2h 30mMultiple Airlines
Sun 1/47:57 pmORD - HVN
2 stops25h 32mMultiple Airlines
Deal found 12/16$379
This Mytrip deal was found by Cheapflights users on 12/16. 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 12/182:20 pmHVN - ORD
Nonstop2h 30mMultiple Airlines
Sun 12/217:30 amORD - HVN
1 stop11h 54mMultiple Airlines
Deal found 12/16$471
This eDestinos deal was found by Cheapflights users on 12/15. 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.
Wed 12/175:10 pmHVN - ORD
Nonstop2h 30mMultiple Airlines
Sat 1/36:17 pmORD - HVN
1 stop20h 28mMultiple Airlines
Deal found 12/15$478
This Mytrip deal was found by Cheapflights users on 12/16. 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 12/182:20 pmHVN - ORD
Nonstop2h 30mMultiple Airlines
Fri 12/191:15 pmORD - HVN
2 stops25h 17mMultiple Airlines
Deal found 12/16$501
This Booking.com deal was found by Cheapflights users on 12/16. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/182:20 pmHVN - ORD
Nonstop2h 30mAvelo Airlines
Sun 12/214:35 pmORD - HVN
Nonstop2h 05mAvelo Airlines
Deal found 12/16$607

Find 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 December 18, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$110
(Super.com)

One-way from

$49
(Super.com)

Popular in

June

Cheapest in

February

Average price

$158

Good round-trip deal

$95 or less

Good one-way deal

$45 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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One-way flight from Tweed-New Haven to Chicago (CHI)
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Highest demand for flights based on searches. 14% potential increase in price ($30 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($7 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 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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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 December 18, 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

Thu 1/15

3:05 pm-4:37 pm

Nonstop2h 32m

Chicago O'Hare Intl

Fri 4/17

5:55 pm-9:29 pm

Nonstop2h 34m

$110

New HavenChicago

HVN - ORD

HVNORD

Tweed-New Haven

Thu 1/22

3:20 pm-11:46 pm

1 stop9h 26m

Chicago O'Hare Intl

Sun 1/25

5:20 pm-8:26 pm

Nonstop2h 06m

$182

New HavenChicago

HVN - ORD

HVNORD

Tweed-New Haven

Tue 2/3

2:46 pm-9:44 pm

1 stop7h 58m

Chicago O'Hare Intl

Wed 2/4

4:38 pm-10:58 am

1 stop17h 20m

$193

New HavenChicago

HVN - ORD

HVNORD

Tweed-New Haven

Thu 1/8

3:05 pm-4:37 pm

Nonstop2h 32m

Chicago O'Hare Intl

Sat 1/10

5:15 am-2:27 pm

1 stop8h 12m

$196

New HavenChicago

HVN - ORD

HVNORD

Tweed-New Haven

Mon 1/12

12:07 pm-8:18 am

2 stops21h 11m

Chicago O'Hare Intl

Wed 1/14

7:21 pm-10:58 am

1 stop14h 37m

$207

New HavenChicago

HVN - ORD

HVNORD

Tweed-New Haven

Sat 1/17

8:00 am-5:52 pm

1 stop10h 52m

Chicago O'Hare Intl

Thu 1/22

5:20 pm-8:26 pm

Nonstop2h 06m

$217

New HavenChicago

HVN - ORD

HVNORD

Tweed-New Haven

Sat 1/24

8:00 am-7:41 pm

1 stop12h 41m

Chicago O'Hare Intl

Mon 1/26

12:44 pm-10:39 pm

1 stop8h 55m

$242

New HavenChicago

HVN - ORD

HVNORD

Tweed-New Haven

Mon 3/30

3:25 pm-5:10 pm

Nonstop2h 45m

$51

New HavenChicago

HVN - ORD

HVNORD

Tweed-New Haven

Wed 4/8

4:40 pm-6:25 pm

Nonstop2h 45m

$70

New HavenChicago

HVN - ORD

HVNORD

Tweed-New Haven

Sun 1/18

3:05 pm-4:37 pm

Nonstop2h 32m

$70

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/17

Showing 1-10 of 17 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 December.
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 December 18, 2025.

It’s typically best to fly out from New Haven to Chicago in the evening. Doing so could potentially save you 45% 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 December 18, 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

Boarding

7.7

Overall

7.5

Comfort

7.1

Crew

8.2

Entertainment

5.0

Food

5.0

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
7.5
Good
Avelo Airlines
7.5
Good

Boarding

7.7

Overall

7.5

Comfort

7.1

Crew

8.2

Entertainment

5.0

Food

5.0

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 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. 1 airline has 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 32m. 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 is the cheapest airline to fly from New Haven to Chicago round-trip?

    Currently priced at $104, Avelo Airlines will fly you from New Haven to Chicago and back. In addition to Avelo Airlines, many other airlines offer competitively priced options for your trip. You may be able to fly from New Haven to Chicago for 42% less than the average price by searching for this airline.

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

    Looking at all options, your cheapest flight can be booked for $39. While the most popular route (Tweed-New Haven - Chicago O'Hare Intl) can be booked for $110 on average, our data indicates $110 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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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Top airline flying from New Haven to Chicago

Discover the top airline that operate flights from New Haven to Chicago. 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 December 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
Avelo AirlinesCheapest$104Average$199FlexibilityNo cancel feeOn-timeN/A

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