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$71+ 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 6/14. Fares are subject to change and may not be available on all flights or dates of travel.
HVN — CHI
Jun 6 — Jun 131
Sat 6/6
Sat 6/13
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 May 7, 2026.

This Super.com deal was found by Cheapflights users on 5/2. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/14:20 pm
HVN
-
ORD
Nonstop2h 53m
Avelo Airlines
Mon 6/87:07 pm
ORD
-
HVN
Nonstop2h 32m
Avelo Airlines
Deal found 5/2$141
This Cheapflightsfares deal was found by Cheapflights users on 5/2. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/14:20 pm
HVN
-
ORD
Nonstop2h 53m
Avelo Airlines
Thu 6/46:35 pm
ORD
-
HVN
Nonstop2h 32m
Avelo Airlines
Deal found 5/2$143
This Cheapflightsfares deal was found by Cheapflights users on 5/5. 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 5/294:20 pm
HVN
-
ORD
Nonstop2h 53m
Avelo Airlines
Mon 6/17:07 pm
ORD
-
HVN
Nonstop2h 32m
Avelo Airlines
Deal found 5/5$158
This Super.com deal was found by Cheapflights users on 5/2. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/254:20 pm
HVN
-
ORD
Nonstop2h 53m
Avelo Airlines
Mon 6/17:07 pm
ORD
-
HVN
Nonstop2h 32m
Avelo Airlines
Deal found 5/2$179
This Super.com deal was found by Cheapflights users on 5/4. 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.
Thu 6/43:50 pm
HVN
-
ORD
Nonstop2h 53m
Avelo Airlines
Mon 6/87:07 pm
ORD
-
HVN
Nonstop2h 32m
Avelo Airlines
Deal found 5/4$187
This Super.com deal was found by Cheapflights users on 5/4. 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 6/54:20 pm
HVN
-
ORD
Nonstop2h 53m
Avelo Airlines
Mon 6/87:07 pm
ORD
-
HVN
Nonstop2h 32m
Avelo Airlines
Deal found 5/4$188
This Super.com deal was found by Cheapflights users on 5/5. 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.
Thu 6/43:50 pm
HVN
-
ORD
Nonstop2h 53m
Avelo Airlines
Fri 6/57:07 pm
ORD
-
HVN
Nonstop2h 32m
Avelo Airlines
Deal found 5/5$191
This CheapOair deal was found by Cheapflights users on 5/4. 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 5/283:50 pm
HVN
-
ORD
Nonstop2h 53m
Avelo Airlines
Sun 5/316:35 pm
ORD
-
HVN
Nonstop2h 32m
Avelo Airlines
Deal found 5/4$196
This Super.com deal was found by Cheapflights users on 5/2. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/114:20 pm
HVN
-
ORD
Nonstop2h 53m
Avelo Airlines
Fri 5/157:07 pm
ORD
-
HVN
Nonstop2h 32m
Avelo Airlines
Deal found 5/2$199
This Cheapflightsfares deal was found by Cheapflights users on 5/3. 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 5/294:20 pm
HVN
-
ORD
Nonstop2h 53m
Avelo Airlines
Sun 5/316:35 pm
ORD
-
HVN
Nonstop2h 32m
Avelo Airlines
Deal found 5/3$203

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 May 7, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$141
(Super.com)

One-way from

$71
(Super.com)

Popular in

June

Cheapest in

January

Average price

$175

Good round-trip deal

$142 or less

Good one-way deal

$132 or less
Provider with most accurate pricing for Tweed-New Haven-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Tweed-New Haven-Chicago (CHI) flights.
Search Deals
From Tweed-New Haven to Chicago (CHI)
Search Deals
One-way flight from Tweed-New Haven to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 18% potential increase in price ($41 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
Search Deals
Price to beat on a round-trip flight from Tweed-New Haven to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Tweed-New Haven to Chicago (CHI).
Search Deals

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 May 7, 2026.
Use the filters below to find and compare flights from New Haven to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

New HavenChicago

HVN - ORD

HVNORD

Tweed-New Haven

Mon 6/1

4:20 pm-6:13 pm

Nonstop2h 53m

Chicago O'Hare Intl

Mon 6/8

7:07 pm-10:39 pm

Nonstop2h 32m

$155

New HavenChicago

HVN - ORD

HVNORD

Tweed-New Haven

Fri 5/29

4:20 pm-6:13 pm

Nonstop2h 53m

Chicago O'Hare Intl

Mon 6/1

7:07 pm-10:39 pm

Nonstop2h 32m

$173

New HavenChicago

HVN - ORD

HVNORD

Tweed-New Haven

Fri 6/5

4:20 pm-6:13 pm

Nonstop2h 53m

Chicago O'Hare Intl

Mon 6/8

7:07 pm-10:39 pm

Nonstop2h 32m

$188

New HavenChicago

HVN - ORD

HVNORD

Tweed-New Haven

Mon 5/11

4:20 pm-6:13 pm

Nonstop2h 53m

Chicago O'Hare Intl

Fri 5/15

7:07 pm-10:39 pm

Nonstop2h 32m

$199

New HavenChicago

HVN - ORD

HVNORD

Tweed-New Haven

Mon 6/1

4:20 pm-6:13 pm

Nonstop2h 53m

Chicago O'Hare Intl

Thu 6/4

12:20 pm-10:31 pm

2 stops9h 11m

$229
Quickest round-trip

New HavenChicago

HVN - ORD

HVNORD

Tweed-New Haven

Thu 7/9

3:45 pm-5:38 pm

Nonstop2h 53m

Chicago O'Hare Intl

Mon 7/13

6:48 pm-10:19 pm

Nonstop2h 31m

$281

New HavenChicago

HVN - ORD

HVNORD

Tweed-New Haven

Fri 7/24

4:10 pm-6:03 pm

Nonstop2h 53m

Chicago O'Hare Intl

Mon 7/27

6:48 pm-10:19 pm

Nonstop2h 31m

$284

New HavenChicago

HVN - ORD

HVNORD

Tweed-New Haven

Mon 6/1

4:20 pm-6:13 pm

Nonstop2h 53m

Chicago O'Hare Intl

Mon 6/8

12:20 pm-9:31 pm

2 stops8h 11m

$309

New HavenChicago

HVN - ORD

HVNORD

Tweed-New Haven

Fri 6/12

4:20 pm-6:13 pm

Nonstop2h 53m

Chicago O'Hare Intl

Sun 6/14

6:35 pm-10:07 pm

Nonstop2h 32m

$319

New HavenChicago

HVN - ORD

HVNORD

Tweed-New Haven

Fri 7/17

4:10 pm-6:03 pm

Nonstop2h 53m

Chicago O'Hare Intl

Mon 7/20

6:48 pm-10:19 pm

Nonstop2h 31m

$321

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/2

Showing 1-10 of 20 resultsSorted by cheapest first
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 May.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice 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 New Haven-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on New Haven-Chicago flight deals on Cheapflights vs. FlightHub >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 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 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, September is the cheapest month in which you can book a flight from New Haven to Chicago (average of $51). Flying from New Haven to Chicago in July is currently the most expensive (average of $198). 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 May 7, 2026.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from New Haven to Chicago as you normally would.

How much does it cost to fly round-trip from New Haven to Chicago?

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 May 7, 2026.
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
7.6
Good

Overall

7.6

Comfort

7.1

Food

5.1

Entertainment

5.0

Crew

8.3

Boarding

7.7

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

Comfort

7.1

Food

5.1

Entertainment

5.0

Crew

8.3

Boarding

7.7

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 53m. 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 $77, 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 58% 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 $51. While the most popular route (Tweed-New Haven - Chicago O'Hare Intl) can be booked for $158 on average, our data indicates $213 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, September is the cheapest month in which you can book a flight from New Haven to Chicago (average of $51). Flying from New Haven to Chicago in July is currently the most expensive (average of $198). 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
Benton Harbor
Lansing
Merrillville
Hammond
Porter

Browse thousands of different options on Cheapflights for your next trip

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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 May 7, 2026.
AirlineCheapestAverageFlexibilityOn-time
Avelo AirlinesCheapest$77Average$188FlexibilityNo cancel feeOn-timeN/A

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