HVN - CHI

$117 Find Cheap Flights from New Haven to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from New Haven to Chicago departing on 12/14. 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.
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0 bags

Search hundreds of travel sites at once for deals on flights to Chicago

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from New Haven to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from New Haven to Chicago, as well as popular online travel agencies
In the last 7 days travelers have searched 47,107,125 times on KAYAK, and here is why:

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Cheap Flight Deals from New Haven to Chicago (HVN-CHI)

 
These are the cheapest deals for flights from New Haven to Chicago currently on KAYAK along with options from the most popular airlines KAYAK users selected for this route. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.

Recent round-trip flight deals from New Haven to Chicago

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from New Haven to Chicago.

Recent one-way flight deals from New Haven to Chicago

Only flying one-way? Below are some of the best one-way flight deals from New Haven to Chicago found on KAYAK recently.

Recent last minute flight deals from New Haven to Chicago

Leaving soon but still want a bargain? Check out these latest deals for last minute flights from New Haven to Chicago.

Recent direct flight deals from New Haven to Chicago

The latest deals for direct flights from New Haven to Chicago so you can sit back and relax without the need for a layover.

Cheap bus & train deals from New Haven to Chicago

Find recent round-trip train or bus tickets from New Haven to Chicago.

All round-trip flight deals to Chicago

The cheapest plane tickets to Chicago found on KAYAK recently.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
10:40 am - 6:50 pmHVN-ORD
9h 10m1 stop
5:00 am - 9:38 amORD-HVN
27h 38m2 stops
Mon, Dec 16 - Tue, Dec 17
2:00 pm - 11:02 pmHVN-ORD
10h 02m1 stop
3:22 pm - 12:44 pmORD-HVN
20h 22m2 stops
Mon, Jan 13 - Wed, Jan 15
7:20 am - 12:33 amHVN-ORD
18h 13m2 stops
9:58 am - 9:38 amORD-HVN
22h 40m2 stops
Mon, Dec 16 - Tue, Dec 17
6:03 pm - 12:39 pmHVN-ORD
19h 36m2 stops
3:22 pm - 12:44 pmORD-HVN
20h 22m2 stops
Mon, Jan 13 - Wed, Jan 15
6:03 pm - 8:13 pmHVN-ORD
27h 10m3 stops
3:22 pm - 12:44 pmORD-HVN
20h 22m2 stops
Mon, Jan 13 - Wed, Jan 15
6:30 am - 2:17 pmHVN-ORD
8h 47m1 stop
5:10 am - 9:50 amORD-HVN
27h 40m3 stops
Mon, Jan 13 - Wed, Jan 15
6:30 am - 5:20 pmHVN-ORD
11h 50m1 stop
5:10 am - 1:25 pmORD-HVN
7h 15m1 stop
Mon, Jan 13 - Wed, Jan 15
6:30 am - 5:20 pmHVN-ORD
11h 50m1 stop
3:22 pm - 1:45 pmORD-HVN
21h 23m2 stops
Mon, Jan 13 - Wed, Jan 15
7:15 am - 12:39 pmHVN-ORD
30h 24m2 stops
5:10 am - 8:01 pmORD-HVN
13h 51m2 stops
Tue, Feb 4 - Fri, Feb 7
6:03 pm - 12:39 pmHVN-ORD
19h 36m2 stops
7:00 am - 9:50 amORD-HVN
25h 50m3 stops
Mon, Jan 13 - Wed, Jan 15
11:40 am - 11:11 pmHVN-ORD
12h 31m1 stop
Sat, Dec 14
6:30 am - 2:17 pmHVN-ORD
8h 47m1 stop
Fri, Jan 10
3:30 pm - 9:37 amHVN-ORD
19h 07m2 stops
Sat, Dec 14
11:40 am - 12:47 amHVN-ORD
14h 07m1 stop
Sat, Dec 21
7:30 am - 12:40 amHVN-ORD
18h 10m2 stops
Fri, Jan 10
4:35 pm - 11:04 amHVN-ORD
19h 29m2 stops
Sat, Dec 21
3:30 pm - 12:18 pmHVN-ORD
21h 48m3 stops
Sat, Dec 14
3:35 pm - 5:55 pmHVN-ORD
27h 20m3 stops
Mon, Nov 25
7:08 pm - 9:20 amHVN-ORD
15h 12m2 stops
Mon, Nov 25
6:45 am - 7:37 amHVN-ORD
25h 52m3 stops
Thu, Nov 28
6:45 am - 6:31 pmHVN-ORD
12h 46m1 stop
10:01 am - 10:55 pmORD-HVN
11h 54m1 stop
Fri, Nov 22 - Sun, Nov 24
3:45 pm - 9:20 amHVN-ORD
18h 35m2 stops
10:01 am - 10:55 pmORD-HVN
11h 54m1 stop
Fri, Nov 22 - Sun, Nov 24
8:54 pm - 6:31 pmHVN-ORD
22h 37m2 stops
10:25 am - 10:08 amORD-HVN
22h 43m2 stops
Fri, Nov 22 - Sun, Nov 24
8:54 pm - 2:31 pmHVN-ORD
18h 37m2 stops
3:26 pm - 10:15 pmORD-HVN
29h 49m3 stops
Fri, Nov 22 - Sun, Nov 24
6:45 am - 10:06 pmHVN-ORD
16h 21m3 stops
3:26 pm - 10:15 pmORD-HVN
29h 49m3 stops
Fri, Nov 22 - Sun, Nov 24

Flights from New Haven to Chicago - Travel Insights & Trends

Get data-powered insights and trends into flights from New Haven to Chicago to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest New Haven to Chicago flight route?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for one-way flights from New Haven to Chicago.
Our data shows that the cheapest route for a one-way flight from New Haven to Chicago cost $59 and was between New Haven and Chicago Midway Airport. On average, the best prices are found if you fly this route. The average price for a return flight for this route is $78.

What’s the cheapest day of the week to fly from New Haven to Chicago?

The average price of all flights from New Haven to Chicago clicked on KAYAK for each day over the last 12 months.
If you are looking for a flight deal from New Haven to Chicago, look for departures on Tuesdays and avoid leaving on a Wednesday, as it's usually the priciest day. When flying back from Chicago, Wednesday is the cheapest day to fly and Sunday is the most expensive.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights from New Haven to Chicago, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.
The cheapest month for flights from New Haven to Chicago is September, where tickets cost $176 on average. On the other hand, the most expensive months are December and May, where the average cost of tickets is $286 and $263 respectively.

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

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights from New Haven to Chicago, removes the top 0.1% to account for outliers, and then takes the average of all the values for each month.
To get a below average price on the flight from New Haven to Chicago, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 160 days before departure.

Good to know

Low season

January

High season

November

Cheapest flight

$117
Best time to beat the crowds but there is an average 44% increase in price.
Most popular time to fly and prices are also 4% lower on average.
Flight from New Haven to Chicago O'Hare Airport

When to book flights from New Haven to Chicago

Are your dates flexible? Find out the best times to travel from New Haven to Chicago based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking flights from New Haven to Chicago

  • What is the cheapest flight from New Haven to Chicago?

    In the last 3 days, the lowest price for a flight from New Haven to Chicago was $117 for a one-way ticket and $253 for a round-trip.

  • Do I need a passport to fly between New Haven and Chicago?

    No

  • Which airlines offer Wi-Fi service onboard planes from New Haven to Chicago?

    JetBlue, Delta, and American Airlines offer inflight Wi-Fi service on the New Haven to Chicago flight route.

  • Which aircraft models fly most regularly from New Haven to Chicago?

    The Boeing 737-800 Passenger/BBJ2 (winglets) is the aircraft model that flies most regularly on the New Haven to Chicago flight route.

  • On which days can I fly direct from New Haven to Chicago?

    You can catch a nonstop flight from New Haven to Chicago on on Tuesday, Wednesday, Thursday, and Sunday.

  • How does KAYAK find such low prices on flights from New Haven to Chicago?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from New Haven to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from New Haven to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from New Haven is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from New Haven to Chicago?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to New Haven with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from New Haven to Chicago?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from New Haven up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

KAYAK’s top tips for finding a cheap flight from New Haven to Chicago

  • Looking for a cheap flight? 25% of our users found flights on this route for $93 or less one-way and $135 or less round-trip.

Prefer to fly non-stop from New Haven to Chicago?

Find which airlines fly direct from Tweed-New Haven Airport to Chicago, which days they fly and book direct flights.

Nonstop departures

Tweed-New Haven to Chicago

Tuesday

Avelo Airlines

Avelo Airlines

Thursday

Avelo Airlines

Avelo Airlines

Sunday

Avelo Airlines

Avelo Airlines

See more direct flights

Nonstop returns

Chicago to Tweed-New Haven

Tuesday

Avelo Airlines

Avelo Airlines

Thursday

Avelo Airlines

Avelo Airlines

Sunday

Avelo Airlines

Avelo Airlines

See more direct flights
See more direct flights

Top airlines flying from New Haven to Chicago

 
See real verified KAYAK customer reviews for airlines flying from New Haven to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from New Haven to Chicago? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.5
Avelo AirlinesOverall score based on 74 reviews
8.4Crew
5.1Entertainment
5.2Food
7.1Comfort
7.8Boarding
Airline reviews

Terrible landing. Uncomfortable seats. Great cabin crew-helpful and pleasant!

6.0 GoodMaurice, Jun 2024HVN - DAB
Read more Avelo Airlines reviews

Terrible landing. Uncomfortable seats. Great cabin crew-helpful and pleasant!

Tight fit in middle seat but OK for short flight. Crew was more interested in talking to each other than helping passengers - strickingly dissappointing. DAB is a great airport. New Haven sucks! Excellent value for the .

Avelo is definitely a budget airline and you get what you pay for. The plane was packed and the seats were not particularly comfortable. Staff was very nice and both of our flights were on time. The one thing I wish I had known was that the staff does not show up at the airport desk to check your bags until two hours before the flight. We had a 4:30 flight and had to check out of our hotel at noon. Since we have lounge passes we planned to check our bag, go through security and hang out at the lounge until we had to board. But because we could not check our bag until 2:30, when the staff showed up, we could not go through security and access the lounge. Passengers with boarding passes and carry on luggage would not have this issue. I might fly Avelo again but would only do carry on or plan to get to the airport no sooner than two hours before check in. And I would not recommend a long flight on Avelo since there is no food or entertainment and the seats are not comfortable.

No food or entertainment, but flight very comfortable and on time.

Baggage claim was barbaric at Wilmington. I realize that this is a startup airline but if they hope to grow or even survive they need to upgrade this airport. There is no automated luggage carousel and at times you are not only fighting your fellow passengers to get to your bags but also passengers coming in from other flights who cross right in front of you

No frills, i.e., no drinks or snacks. One is charged for everything. The cost really adds up. The crew and flight attendants were excellent and very pleasant.

I always walk by a pallet of Avelo branded mini bottles of water on the tarmac, but I’ve never seen them in flight. Yup, not even water offered on a 3 hour flight. No wi-fi onboard. We just watch the flight crew on their phone for 3 hours every flight. At least a mid-flight trash pickup would be great. Better than my last flight, but they only could have gone up from there. Don’t use for business or ticketed vacation like Disney… too unreliable.

You get what you pay for. The plane was dirty and the seats were awful.

Nightmare airline. Avoid Avelo. Understaffed at check-in with long, slow lines. Inexplicably had two flights and only one plane. Not weather or maintenance related apparently. One was supposed to go to Myrtle Beach and one to Orlando. I imagine someone thought it would be better to fly the available plane to Myrtle Beach and back and then go to Orlando since that round-trip was shorter. This didn’t account for the human factor of an end-of-week Orlando flight being 85% Disney passengers and putting the flight on a six-hour delay in New Haven airport… which, if you’ve been there, is tiny and has nothing to do for 50 kids excited to get to Disney. This delay was announced at the time of departure. No one realized before the time of departure there was no plane on the ground? And no one thought… hey I think the Myrtle Beach crowd might be a better one to have wait if we’re going to make a choice here (mind you the initial inbound plane was coming from Orlando and supposed to be out aircraft… they literally said let just grab this plane because it’s here to get this other group out at the last second). There is/was zero customer service desk for Avelo in HVN and there were no updates/announcements throughout the day. Plane still gets back late and we finally leave. No wi-fi on these planes, no snack or even water. I know this is budget airline, but expected at least a water after 8 hours of travel day. This should have been offered in terminal too. We land… hooray. Would you believe there is no ground crew to get the plane in to the gate… for 27 minutes. 27 minutes!!! At this point the rental car center is closing in 10 minutes, kids on the plane are crying again, and everyone is talking about how they’re never flying Avelo again. Finally get off. Bags are out at baggage claim right away (finally something right?), but they’ve stopped the carousel immediately and there is no baggage service rep. People are climbing over the carousel to get to the far side (if you’ve ever been to MCO you’ve seen it) because obviously they just stopped it immediately once all the bags were out. This airline is a dumpster fire. Icing on the cake was that while everyone was stuck in HVN, they were setting up for a celebration of their millionth passenger tomorrow. I bet 995,000 of those will never fly the airline again. Don’t fly Avelo. You’ve been warned.

Airline was the only available airline during the Southwest cancellation. It was easy to book. Lowest available fair. Convenient airports. Everything was great. Problem was, they didn’t release what gate flight was departing. The woman at the ticket booth didn’t know which terminal they were boarding and wanted me to wait in 30+ minute line versus telling me to look for flight kiosk. Burbank gate was packed. Otherwise the flight was perfect!!

Average, boarding was ok, the eye scanner broken mid way through boarding they ahd to do it manually. Did not eat any food, Not even water was offered for free.

Boarding attendant was rude. Crew on the plan were more interested in talking amongst themselves and did not ask parentage if they needed anything or even walk down the isles.

Flight was ok with exception of the multiple delays. As with all Spirit flights, the sights are extremely uncomfortable and lack leg space. However, the price savings is the plus.

The flight landed with a delay and we had to wait almost an hour to be off boarded. So typical of spirit.

The gate employees and the flight crew were friendly and professional. Afterboarding we waited 20 minutes for another flight; a complimentary beverage would have ben appreciated for the inconvenience.

You get what you pay for, but those tickets weren't cheap, so I expected better, but Spirit is just one of those airlines.

Cancelled the return flight moments before boarding, horrible customer service in assisting with any rebooking. Never again will I fly Spirit.

Flight got diwngraded last minute and left us stranded. I was told I’ll be given credit for my luggage and seat upgrades but haven’t got anything yet

Crew was nice, explained emergency protocol very well. Flight took off and arrived on time. Pilot explained the small delay that occurred with docking and providing updates. I would definitely fly spirit again.

The seat are terrible. Don’t even think of sleeping on a Spirit flight. The kids that run the plane aka flight attendants are pretty rude and straight forward. They get the job done but without class.

Book cheap flights from New Haven to Chicago

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from New Haven to Chicago found on KAYAK in the last 72 hours.
12/14Sat
1 stop
12h 31mHVN-ORD
$117
1/10Fri
1 stop
8h 47mHVN-ORD
$140
12/14Sat
2 stops
19h 07mHVN-ORD
$146
12/21Sat
1 stop
14h 07mHVN-ORD
$149
1/10Fri
2 stops
18h 10mHVN-ORD
$154
12/21Sat
2 stops
19h 29mHVN-ORD
$177
12/14Sat
3 stops
21h 48mHVN-ORD
$181
11/25Mon
3 stops
27h 20mHVN-ORD
$198
11/25Mon
2 stops
15h 12mHVN-ORD
$206
11/28Thu
3 stops
25h 52mHVN-ORD
$226

Search by stops

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Last minute flights from New Haven to Chicago

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from New Haven to Chicago that are departing in the next 10 days.
11/22Fri
multi-stop
12h 46mHVN-ORD
11/24Sun
multi-stop
11h 54mORD-HVN
$464
11/22Fri
multi-stop
18h 35mHVN-ORD
11/24Sun
multi-stop
11h 54mORD-HVN
$473
11/22Fri
multi-stop
22h 37mHVN-ORD
11/24Sun
multi-stop
22h 43mORD-HVN
$482
11/22Fri
multi-stop
18h 37mHVN-ORD
11/24Sun
multi-stop
29h 49mORD-HVN
$538
11/22Fri
multi-stop
16h 21mHVN-ORD
11/24Sun
multi-stop
29h 49mORD-HVN
$603

Search by stops

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Everything you need to know for your flight from New Haven to Chicago

Information on your arrival and departure airports

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