HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news

Cheap flights from New Haven (HVN) to Chicago (CHI) from $115

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 5/12. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
HVN — CHI
Apr 29 — May 61
From?
To?
Mon 4/29
Mon 5/6
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

The best prices from Tweed-New Haven to Chicago are usually found in March or January, booked 86 days in advance, depart on a Friday or Tuesday and return on a Wednesday

Cheap 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 April 24, 2024.

Popular in

June

Cheapest in

March

Round-trip from

$222

One-way from

$157
High demand for flights, 27% potential price rise
Search Deals
Best time to find cheap flights, 46% potential price drop
Search Deals
From Tweed-New Haven to Chicago (CHI)
Search Deals
One-way flight from Tweed-New Haven to Chicago (CHI)
Search Deals

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

Leaving on a Friday is a viable option for saving on travel. Heavily demanded days of the week can typically drive up the prices you see. Booking your travel for a less competitive day can save up to 110% on the overall cost on flights from New Haven to Chicago.

How far in advance should I book a flight from New Haven to Chicago?

To save on the cost of your flight from New Haven to Chicago, book at least 48 days before your planned departure. Booking around this time can save you about 76% on the cost of this flight compared to booking a flight leaving this week. We have found prices from $302 if you need a flight within two weeks. For flights within the next 72 hours, you can find tickets from as low as $415.

What is the cheapest month to fly from New Haven to Chicago?

Our data shows that February tends to be the cheapest month to fly to Chicago from New Haven. Users have commonly found prices around $268 for the month, but tickets can be as low as $107. Due to multiple factors, prepare for potentially higher prices in June.

When is the cheapest time to fly from New Haven to Chicago (HVN - CHI)?

It’s typically best to fly out from New Haven to Chicago in the afternoon. Doing so could potentially save you 36% on the flight price compared to flying at noon, which is usually more expensive.

Cheap New Haven to Chicago flights in April & May 2024

Find cheap flight options from New Haven to Chicago specifically for the months of April and May 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 3,086,534 searches. Prices were last updated on April 24, 2024.
Wed 5/229:15 amHVN - ORD
2 stops9h 25mMultiple Airlines
Wed 5/297:27 pmORD - HVN
2 stops20h 33mMultiple Airlines
Deal found 4/23$249
Wed 5/229:15 amHVN - ORD
2 stops9h 25mMultiple Airlines
Wed 5/295:00 amORD - HVN
1 stop9h 15mMultiple Airlines
Deal found 4/23$252
Wed 5/229:15 amHVN - ORD
2 stops9h 25mMultiple Airlines
Wed 5/297:27 pmORD - HVN
3 stops26h 18mMultiple Airlines
Deal found 4/23$257
Sun 5/197:15 pmHVN - ORD
2 stops26h 20mMultiple Airlines
Tue 5/2110:58 amORD - HVN
2 stops21h 47mMultiple Airlines
Deal found 4/22$291
Sun 5/197:15 pmHVN - ORD
2 stops26h 20mMultiple Airlines
Tue 5/215:36 pmORD - HVN
1 stop15h 09mMultiple Airlines
Deal found 4/22$302
Sun 5/197:15 pmHVN - ORD
2 stops26h 20mMultiple Airlines
Tue 5/217:08 amORD - HVN
3 stops25h 37mMultiple Airlines
Deal found 4/22$303
Wed 5/229:15 amHVN - ORD
3 stops25h 59mMultiple Airlines
Wed 5/2910:57 pmORD - HVN
3 stops22h 48mMultiple Airlines
Deal found 4/23$308
Sun 5/197:15 pmHVN - ORD
3 stops26h 20mMultiple Airlines
Tue 5/217:08 amORD - HVN
3 stops25h 37mMultiple Airlines
Deal found 4/22$317
Wed 5/2210:25 amHVN - ORD
1 stop14h 27mMultiple Airlines
Wed 5/295:00 amORD - HVN
1 stop9h 15mMultiple Airlines
Deal found 4/23$341

New Haven to Chicago 2024 flight deals

Discover exclusive flight deals for travel between New Haven and Chicago in 2024. Find excellent offers based on user searches. Over the last 7 days, Cheapflights users made 3,086,534 searches. Data last updated April 24, 2024.
Wed 5/229:15 amHVN - ORD
2 stops9h 25mMultiple Airlines
Wed 5/297:27 pmORD - HVN
2 stops20h 33mMultiple Airlines
Deal found 4/23$249
Wed 5/229:15 amHVN - ORD
2 stops9h 25mMultiple Airlines
Wed 5/295:00 amORD - HVN
1 stop9h 15mMultiple Airlines
Deal found 4/23$252
Wed 5/229:15 amHVN - ORD
2 stops9h 25mMultiple Airlines
Wed 5/297:27 pmORD - HVN
3 stops26h 18mMultiple Airlines
Deal found 4/23$257
Sun 5/197:15 pmHVN - ORD
2 stops26h 20mMultiple Airlines
Tue 5/2110:58 amORD - HVN
2 stops21h 47mMultiple Airlines
Deal found 4/22$291
Sun 5/197:15 pmHVN - ORD
2 stops26h 20mMultiple Airlines
Tue 5/215:36 pmORD - HVN
1 stop15h 09mMultiple Airlines
Deal found 4/22$302
Sun 5/197:15 pmHVN - ORD
2 stops26h 20mMultiple Airlines
Tue 5/217:08 amORD - HVN
3 stops25h 37mMultiple Airlines
Deal found 4/22$303
Wed 5/229:15 amHVN - ORD
3 stops25h 59mMultiple Airlines
Wed 5/2910:57 pmORD - HVN
3 stops22h 48mMultiple Airlines
Deal found 4/23$308
Sun 5/197:15 pmHVN - ORD
3 stops26h 20mMultiple Airlines
Tue 5/217:08 amORD - HVN
3 stops25h 37mMultiple Airlines
Deal found 4/22$317
Wed 5/2210:25 amHVN - ORD
1 stop14h 27mMultiple Airlines
Wed 5/295:00 amORD - HVN
1 stop9h 15mMultiple Airlines
Deal found 4/23$341

New Haven to Chicago flights leaving soon

Find last-minute flight options from New Haven to Chicago for spontaneous travel. Discover available flights and compare prices based on user searches. Secure great deals and offers for spontaneous trips with quick booking options. Over the last 7 days, Cheapflights users made 3,086,534 searches. Data last updated April 24, 2024.
Wed 5/17:30 amHVN - ORD
1 stop12h 35mMultiple Airlines
Wed 5/19:25 pmORD - HVN
2 stops22h 05mMultiple Airlines
Deal found 4/23$380
Wed 5/17:30 amHVN - ORD
1 stop12h 35mMultiple Airlines
Wed 5/110:00 pmORD - HVN
3 stops21h 30mMultiple Airlines
Deal found 4/23$416
Wed 5/17:30 amHVN - ORD
1 stop12h 35mMultiple Airlines
Wed 5/19:25 pmORD - HVN
1 stop16h 45mMultiple Airlines
Deal found 4/23$448

One-way flights to Chicago from New Haven

Search for one-way flight options from New Haven to Chicago. Find affordable one-way fares based on user searches. Compare prices and availability to plan your one-way journey according to your preferred dates and budget. Over the last 7 days, Cheapflights users made 3,086,534 searches. Data last updated April 24, 2024.
Sun 5/127:00 pmHVN - ORD
2 stops26h 35mMultiple Airlines
Deal found 4/23$115
Wed 5/222:45 pmHVN - ORD
2 stops9h 44mMultiple Airlines
Deal found 4/22$130
Sun 5/127:00 pmHVN - ORD
3 stops26h 35mMultiple Airlines
Deal found 4/23$148
Sat 6/18:30 amHVN - ORD
1 stop9h 05mMultiple Airlines
Deal found 4/23$157
Wed 5/228:30 amHVN - ORD
1 stop10h 10mMultiple Airlines
Deal found 4/22$158
Wed 5/222:45 pmHVN - ORD
3 stops21h 23mMultiple Airlines
Deal found 4/22$179
Sat 6/19:15 amHVN - ORD
2 stops15h 14mMultiple Airlines
Deal found 4/23$182
Sat 6/19:15 amHVN - ORD
3 stops25h 59mMultiple Airlines
Deal found 4/23$225
Mon 7/2911:55 amHVN - ORD
1 stop9h 50mMultiple Airlines
Deal found 4/23$237

Find flights from New Haven to Chicago within your budget

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 3,086,534 searches. Data last updated April 24, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$249 - $341

Route

Depart

Return

Price

Tweed-New HavenChicago O'Hare Intl

HVN - ORD

HVNORD

Tweed-New Haven

Wed 5/22

2 stops9h 25m

Chicago O'Hare Intl

Wed 5/29

2 stops20h 33m

$249

Tweed-New HavenChicago O'Hare Intl

HVN - ORD

HVNORD

Tweed-New Haven

Wed 5/22

2 stops9h 25m

Chicago O'Hare Intl

Wed 5/29

1 stop9h 15m

$252

Tweed-New HavenChicago O'Hare Intl

HVN - ORD

HVNORD

Tweed-New Haven

Wed 5/22

2 stops9h 25m

Chicago O'Hare Intl

Wed 5/29

3 stops26h 18m

$257

Tweed-New HavenChicago O'Hare Intl

HVN - ORD

HVNORD

Tweed-New Haven

Sun 5/19

2 stops26h 20m

Chicago O'Hare Intl

Tue 5/21

2 stops21h 47m

$291

Tweed-New HavenChicago O'Hare Intl

HVN - ORD

HVNORD

Tweed-New Haven

Sun 5/19

2 stops26h 20m

Chicago O'Hare Intl

Tue 5/21

1 stop15h 09m

$302

Tweed-New HavenChicago O'Hare Intl

HVN - ORD

HVNORD

Tweed-New Haven

Sun 5/19

2 stops26h 20m

Chicago O'Hare Intl

Tue 5/21

3 stops25h 37m

$303

Tweed-New HavenChicago O'Hare Intl

HVN - ORD

HVNORD

Tweed-New Haven

Wed 5/22

3 stops25h 59m

Chicago O'Hare Intl

Wed 5/29

3 stops22h 48m

$308

Tweed-New HavenChicago O'Hare Intl

HVN - ORD

HVNORD

Tweed-New Haven

Sun 5/19

3 stops26h 20m

Chicago O'Hare Intl

Tue 5/21

3 stops25h 37m

$317

Tweed-New HavenChicago O'Hare Intl

HVN - ORD

HVNORD

Tweed-New Haven

Wed 5/22

1 stop14h 27m

Chicago O'Hare Intl

Wed 5/29

1 stop9h 15m

$341

Flights are sorted by cheapest first

Deals found on 4/23

When is the best time to book a flight from New Haven to Chicago?

Use this chart to determine the optimal time to book a round-trip flight from New Haven to Chicago. Price data was last updated on January 28, 2024.
The best time to book flights from New Haven to Chicago is 70 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
Search Deals

When is the cheapest time to fly from New Haven to Chicago?

Use this chart to determine the cheapest time to fly round-trip from New Haven to Chicago. Price data was last updated on April 21, 2024.
Morning
Noon
Afternoon
Evening
All times are departure.
Travelers seeking maximum savings on their New Haven to Chicago flight should consider departing on Saturday afternoons when fares are most often at their lowest. Thursday mornings flights should be avoided if possible as fares are typically the most expensive at this time.
Search Deals

Average price of flights to Chicago by month

Plan your trip from New Haven to Chicago by taking into account the cheapest months to travel. The average price of a one-way flight from New Haven to Chicago is currently $170 while a round-trip flight costs $291. Price data was last updated on April 21, 2024.

Currently, February is the cheapest month in which you can book a flight from New Haven to Chicago (average of $245). Flying from New Haven to Chicago in June is currently the most expensive (average of $356). 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.

January

$248

February

$245

March

$280

April

$273

May

$282

June

$356

July

$336

August

$276

September

$258

October

$248

November

$270

December

$248

Temperature and rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average temperature and rainfall totals by month.

CHI

Temperature

23 - 73.4 °F

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.

  • Can I find flights from New Haven to Chicago for under $300 on Cheapflights?

    Yes, there are multiple flights from New Haven to Chicago for under $300. The cheapest flight booked recently is on Multiple Airlines for just $249, but on average you can expect to pay $355.

  • Are there last-minute flights available from New Haven to Chicago for under $400?

    There are currently 3+ open flights from New Haven to Chicago within the next 7 days for less than $400.

  • What does HVN to ORD mean?

    Great question - HVN to ORD just means Tweed-New Haven Airport to Chicago O'Hare Intl Airport. Now you’ll know what these unique codes when you look for flights! Chicago Midway Airport (MDW), Chicago Greater Rockford Airport (RFD) are some additional IATA codes for airports related to your trip.

  • Can I find deals for flights from New Haven to Chicago that include extra baggage allowance?

    The amount of baggage you can bring on your New Haven to Chicago flight depends on the airline and the type of fare you've chosen. After entering your flight details, you'll be able to view the specific baggage policies for each deal in the search results. Keep in mind that certain deals may offer additional baggage allowance.

  • Can I find deals on flights from New Haven to Chicago with specific airlines?

    Yes, Cheapflights allows you to browse and filter New Haven to Chicago flight deals by airline. After entering your origin and destination, use the available filters to view flights offered by airlines.

  • 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.

  • Can I find deals for flights from New Haven to Chicago that allow pets onboard?

    Many airlines flying from New Haven to Chicago offer the option to travel with pets. After selecting a flight deal, you can find more information about the airline's pet policy on their official website or by contacting the airline directly. Please note that additional fees and restrictions may apply.

  • Can I find deals on last-minute flights from New Haven to Chicago?

    Yes, you can often find last-minute deals on New Haven to Chicago flights on Cheapflights. However, these deals can vary and may not always be available. We recommend checking back frequently or signing up for price alerts for the most up-to-date deals.

  • How recently were the New Haven to Chicago flight deals updated?

    The New Haven to Chicago flight deals you see on this page were last updated on 4/23.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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

Hartford to O'Hare Intl flights
Hartford to Midway flights
Hartford to St. Louis flights
New Haven to O'Hare Intl flights
New Haven to St. Louis flights
Hartford to Peoria flights
Hartford to Moline flights
Hartford to Bloomington flights
Hartford to Rockford flights

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 3,086,534 searches. Data last updated April 24, 2024.
AirlineCheapestAverageFlexibilityOn-time
Avelo AirlinesCheapest$131Average$318FlexibilityNo cancel feeOn-timeN/A
Search Avelo Airlines flights
Philadelphia to Phoenix flights
San Juan to Orlando flights
USA to Maldives flights
Los Angeles to San Diego flights
Newark Airport to Tampa flights
Los Angeles to Barcelona flights
Dallas to Hawaii flights
Baltimore to Los Angeles flights
Austin to Dallas flights
San Diego to Hawaii flights
Boston to Toronto flights
New Haven to Charlottesville flights

Search flights from New Haven to Chicago by cabin class

Find flights from New Haven to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
First Class
Business Class
Prem Econ Class
Economy Class

Book a flight to one of these trending destinations

User searches for flights to these destinations increased 20% or more in the past 90 days compared to other destinations
Flights to Bodø
Flights to Bar Harbor
Flights to Bastia Poretta
Flights to Dharamshala Kangra
Flights to Biarritz Parme
Flights to Menorca/Mahon
Flights to Milas–Bodrum
Flights to Dipolog
Flights to Kagoshima
Flights to Edremit/Korfez
Flights to Bourgas
Flights to Ordu/Giresun
Flights to Chios
Flights to Argostoli Cephalonia
Flights to Barrow Wiley Post/W.Rogers
Flights to Kristiansand Kjevik
Flights to Zakynthos Dionsios Salomos
Flights to Batumi
Flights to Guilin
Flights to Pau Pyrénées
Flights to Fez Sais
Flights to Kos
Flights to Mytilene
Flights to Norwich Arpt

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.

How does Cheapflights help users find flights from New Haven to Chicago?

Cheapflights makes it easy to find New Haven to Chicago flights by helping our users search from 900+ travel sites for deals. We also provide you with filters for cabin, price, airline, airports, number of stops, and many more to narrow down that perfect flight.

Why should you use Cheapflights to find cheap flight tickets from New Haven to Chicago?

It’s simple! Cheapflights, which is free to use for everyone, saves millions of users time and money every year by helping them find the cheapest and most suitable flights from New Haven to Chicago.

Can Cheapflights find flights from New Haven to Chicago with no change fees?

Yes! Cheapflights helps users easily find flights from New Haven to Chicago with no change fees.

Can Cheapflights notify me if prices for flights from New Haven to Chicago become cheaper?

Yes, Cheapflights has a feature called Price Alert, which notifies users when flight prices change. Track prices for your flight to Chicago from New Haven today and book when prices fit your budget.

100% Free
Cheapflights is completely free to use, so you can start saving the moment you arrive.
Book with Flexibility
Our users can plan ahead with confidence and find flights with no change fees
Travel Smart
Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.
View all available airlines