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Cheap flights from New Haven (HVN) to Chicago (CHI) from $292

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 6/6. 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
May 13 — May 201
From?
To?
Mon 5/13
Mon 5/20
1 adult, Economy
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The best prices from Tweed-New Haven to Chicago are usually found in March or February, booked 14 days in advance, depart on a Saturday 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 May 8, 2024.

Popular in

November

Cheapest in

March

Average price

$192

Round-trip from

$223
High demand for flights, 39% potential price rise
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Best time to find cheap flights, 70% potential price drop
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Average for round-trip flights in May 2024
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From Tweed-New Haven to Chicago (CHI)
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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 186% 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 56 days before your planned departure. Booking around this time can save you about 102% on the cost of this flight compared to booking a flight leaving this week. We have found prices from $276 if you need a flight within two weeks. For flights within the next 72 hours, you can find tickets from as low as $423.

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 $262 for the month, but tickets can be as low as $81. 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 May & June 2024

Find cheap flight options from New Haven to Chicago specifically for the months of May and June 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 2,749,864 searches. Prices were last updated on May 8, 2024.
Thu 6/612:20 pmHVN - ORD
1 stop9h 27mMultiple Airlines
Thu 6/135:20 amORD - HVN
2 stops8h 55mMultiple Airlines
Deal found 5/8$292
Thu 6/612:20 pmHVN - ORD
1 stop9h 27mMultiple Airlines
Thu 6/135:20 amORD - HVN
3 stops16h 25mMultiple Airlines
Deal found 5/8$300
Thu 6/67:35 pmHVN - ORD
2 stops13h 49mMultiple Airlines
Thu 6/135:20 amORD - HVN
3 stops16h 25mMultiple Airlines
Deal found 5/8$314
Thu 6/612:20 pmHVN - ORD
1 stop9h 27mMultiple Airlines
Thu 6/135:05 amORD - HVN
1 stop9h 10mMultiple Airlines
Deal found 5/8$318
Thu 6/67:35 pmHVN - ORD
2 stops13h 49mMultiple Airlines
Thu 6/139:24 amORD - HVN
2 stops12h 21mMultiple Airlines
Deal found 5/7$323
Thu 6/67:35 pmHVN - ORD
3 stops30h 20mMultiple Airlines
Thu 6/135:20 amORD - HVN
3 stops16h 25mMultiple Airlines
Deal found 5/8$333
Thu 6/67:35 pmHVN - ORD
3 stops30h 20mMultiple Airlines
Thu 6/139:24 amORD - HVN
2 stops12h 21mMultiple Airlines
Deal found 5/7$345
Thu 6/67:35 pmHVN - ORD
3 stops30h 20mMultiple Airlines
Thu 6/131:00 pmORD - HVN
3 stops24h 35mMultiple Airlines
Deal found 5/7$375
Sun 5/197:30 amHVN - ORD
2 stops12h 33mMultiple Airlines
Mon 5/207:30 amORD - HVN
1 stop5h 10mMultiple Airlines
Deal found 5/7$508

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 2,749,864 searches. Data last updated May 8, 2024.
Thu 6/612:20 pmHVN - ORD
1 stop9h 27mMultiple Airlines
Thu 6/135:20 amORD - HVN
2 stops8h 55mMultiple Airlines
Deal found 5/8$292
Thu 6/612:20 pmHVN - ORD
1 stop9h 27mMultiple Airlines
Thu 6/135:20 amORD - HVN
3 stops16h 25mMultiple Airlines
Deal found 5/8$300
Thu 6/67:35 pmHVN - ORD
2 stops13h 49mMultiple Airlines
Thu 6/135:20 amORD - HVN
3 stops16h 25mMultiple Airlines
Deal found 5/8$314
Thu 6/612:20 pmHVN - ORD
1 stop9h 27mMultiple Airlines
Thu 6/135:05 amORD - HVN
1 stop9h 10mMultiple Airlines
Deal found 5/8$318
Thu 6/67:35 pmHVN - ORD
2 stops13h 49mMultiple Airlines
Thu 6/139:24 amORD - HVN
2 stops12h 21mMultiple Airlines
Deal found 5/7$323
Thu 6/67:35 pmHVN - ORD
3 stops30h 20mMultiple Airlines
Thu 6/135:20 amORD - HVN
3 stops16h 25mMultiple Airlines
Deal found 5/8$333
Thu 6/67:35 pmHVN - ORD
3 stops30h 20mMultiple Airlines
Thu 6/139:24 amORD - HVN
2 stops12h 21mMultiple Airlines
Deal found 5/7$345
Thu 6/67:35 pmHVN - ORD
3 stops30h 20mMultiple Airlines
Thu 6/131:00 pmORD - HVN
3 stops24h 35mMultiple Airlines
Deal found 5/7$375
Sun 5/197:30 amHVN - ORD
2 stops12h 33mMultiple Airlines
Mon 5/207:30 amORD - HVN
1 stop5h 10mMultiple Airlines
Deal found 5/7$508

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 2,749,864 searches. Data last updated May 8, 2024.
Fri 5/176:50 pmHVN - ORD
3 stops35h 30mMultiple Airlines
Sun 5/197:30 amORD - HVN
1 stop5h 10mMultiple Airlines
Deal found 5/7$513
Fri 5/176:50 pmHVN - ORD
2 stops22h 45mMultiple Airlines
Sun 5/197:30 amORD - HVN
1 stop5h 10mMultiple Airlines
Deal found 5/7$522
Fri 5/1710:25 amHVN - ORD
1 stop13h 45mMultiple Airlines
Sun 5/197:30 amORD - HVN
1 stop5h 10mMultiple Airlines
Deal found 5/7$535
Fri 5/176:50 pmHVN - ORD
3 stops24h 27mMultiple Airlines
Sun 5/195:41 pmORD - HVN
2 stops15h 04mMultiple Airlines
Deal found 5/7$547
Fri 5/176:50 pmHVN - ORD
3 stops24h 27mMultiple Airlines
Sun 5/197:30 amORD - HVN
3 stops25h 15mMultiple Airlines
Deal found 5/7$605

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 2,749,864 searches. Data last updated May 8, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$323 - $703

Route

Depart

Return

Price

Tweed-New HavenChicago O'Hare Intl

HVN - ORD

HVNORD

Tweed-New Haven

Thu 6/6

2 stops13h 49m

Chicago O'Hare Intl

Thu 6/13

2 stops12h 21m

$323

Tweed-New HavenChicago O'Hare Intl

HVN - ORD

HVNORD

Tweed-New Haven

Thu 6/6

3 stops30h 20m

Chicago O'Hare Intl

Thu 6/13

2 stops12h 21m

$345

Tweed-New HavenChicago O'Hare Intl

HVN - ORD

HVNORD

Tweed-New Haven

Thu 6/6

3 stops30h 20m

Chicago O'Hare Intl

Thu 6/13

3 stops24h 35m

$375

Tweed-New HavenChicago O'Hare Intl

HVN - ORD

HVNORD

Tweed-New Haven

Fri 5/17

3 stops35h 30m

Chicago O'Hare Intl

Sun 5/19

1 stop5h 10m

$513

Tweed-New HavenChicago O'Hare Intl

HVN - ORD

HVNORD

Tweed-New Haven

Fri 5/17

2 stops22h 45m

Chicago O'Hare Intl

Sun 5/19

1 stop5h 10m

$522

Tweed-New HavenChicago O'Hare Intl

HVN - ORD

HVNORD

Tweed-New Haven

Fri 5/17

1 stop13h 45m

Chicago O'Hare Intl

Sun 5/19

1 stop5h 10m

$535

Tweed-New HavenChicago O'Hare Intl

HVN - ORD

HVNORD

Tweed-New Haven

Fri 5/17

3 stops24h 27m

Chicago O'Hare Intl

Sun 5/19

2 stops15h 04m

$547

Tweed-New HavenChicago O'Hare Intl

HVN - ORD

HVNORD

Tweed-New Haven

Fri 5/17

3 stops24h 27m

Chicago O'Hare Intl

Sun 5/19

3 stops25h 15m

$605

Tweed-New HavenChicago O'Hare Intl

HVN - ORD

HVNORD

Tweed-New Haven

Fri 6/21

1 stop11h 56m

Chicago O'Hare Intl

Sun 6/23

2 stops18h 40m

$703

Flights are sorted by cheapest first

Deals found on 5/7

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 May 3, 2024.
The best time to book flights from New Haven to Chicago is 14 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.
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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 May 5, 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.
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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 $0 while a round-trip flight costs $496. Price data was last updated on May 5, 2024.

Currently, February is the cheapest month in which you can book a flight from New Haven to Chicago (average of $244). Flying from New Haven to Chicago in June is currently the most expensive (average of $348). 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

$244

March

$280

April

$258

May

$278

June

$348

July

$330

August

$274

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 $400 on Cheapflights?

    Yes, there are multiple flights from New Haven to Chicago for under $400. The cheapest flight booked recently is on Multiple Airlines for just $323, but on average you can expect to pay $564.

  • Are there last-minute flights available from New Haven to Chicago for under $600?

    There are currently 5+ open flights from New Haven to Chicago within the next 7 days for less than $600.

  • 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 5/8.

See more FAQs

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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 2,749,864 searches. Data last updated May 8, 2024.
AirlineCheapestAverageFlexibilityOn-time
Avelo AirlinesCheapest$131Average$327FlexibilityNo cancel feeOn-timeN/A
Search Avelo Airlines flights
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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.
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Business Class
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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.

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