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HVN - CHI

$124 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 6/1. 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.
1 adult
0 bags
vie. 5/31
vie. 6/7

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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 43,740,974 times on KAYAK, and here is why:

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Cheap flight deals from New Haven to Chicago (HVN-CHI)

Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from New Haven to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
8:30 am - 5:40 pmHVN-ORD
10h 10m1 stop
5:05 am - 3:15 pmORD-HVN
9h 10m1 stop
mié., may. 29 - mié., jun. 5
9:15 am - 11:29 pmHVN-ORD
15h 14m2 stops
5:05 am - 3:15 pmORD-HVN
9h 10m1 stop
mié., may. 29 - mié., jun. 5
9:15 am - 11:29 pmHVN-ORD
15h 14m2 stops
4:32 pm - 10:45 pmORD-HVN
29h 13m3 stops
mié., may. 29 - mié., jun. 5
11:35 am - 4:28 pmHVN-ORD
5h 53m1 stop
6:40 pm - 1:45 pmORD-HVN
18h 05m1 stop
jue., may. 30 - jue., jun. 6
9:15 am - 11:29 pmHVN-ORD
15h 14m2 stops
4:32 pm - 9:45 amORD-HVN
16h 13m2 stops
mié., may. 29 - mié., jun. 5
11:35 am - 4:28 pmHVN-ORD
5h 53m1 stop
5:21 am - 10:45 pmORD-HVN
16h 24m2 stops
jue., may. 30 - jue., jun. 6
8:30 am - 12:12 pmHVN-ORD
28h 42m3 stops
5:45 pm - 10:45 pmORD-HVN
28h 00m3 stops
mié., may. 29 - mié., jun. 5
11:35 am - 12:12 pmHVN-ORD
25h 37m2 stops
5:21 am - 10:45 pmORD-HVN
16h 24m2 stops
jue., may. 30 - jue., jun. 6
8:30 am - 5:40 pmHVN-ORD
10h 10m1 stop
10:58 am - 9:45 amORD-HVN
21h 47m2 stops
mié., may. 22 - mar., may. 28
8:30 am - 5:40 pmHVN-ORD
10h 10m1 stop
5:36 pm - 9:45 amORD-HVN
15h 09m1 stop
mié., may. 22 - mar., may. 28

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 $72 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 $134.

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 Sundays and avoid leaving on a Thursday, as it's usually the priciest day. When flying back from Chicago, Saturday is the cheapest day to fly and Tuesday 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 February, where tickets cost $190 on average. On the other hand, the most expensive months are June and July, where the average cost of tickets is $361 and $316 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 2 weeks before departure. For the absolute cheapest price, our data suggests you should book 78 days before departure.

Which airlines fly non-stop between New Haven and Chicago?

Airline and price data is aggregated from results in KAYAK’s search results from the last 2 weeks for flights from New Haven to Chicago.
There is just one airline that flies from New Haven to Chicago direct and that is Avelo Airlines. The best one-way deal found from Avelo Airlines for the route is $131.

How many flights are there between New Haven and Chicago per day?

There is a maximum of 1 nonstop flight a day that takes off from New Haven and lands in Chicago, with an average flight time of 2h 25m. The most common departure time is 3:00 pm and most flights take off in the afternoon. Each week, there are 2 flights.

Which cabin class options are there for flights between New Haven and Chicago?

The average price of flights for each cabin class for the route found by users searching on KAYAK over the last 2 weeks.
There is only one cabin class option available for the route, which is Economy. Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.

What’s the earliest departure time from New Haven to Chicago?

Early birds can take the earliest flight from New Haven at 3:20 pm and will be landing in Chicago at 4:45 pm.

What’s the latest departure time from New Haven to Chicago?

If you prefer to fly at night, the latest flight from New Haven to Chicago jets off at 5:30 pm and lands at 6:55 pm.

Good to know

Low season

January

High season

September

Cheapest flight

$124
Best time to beat the crowds with an average 39% drop in price.
Most popular time to fly with an average 11% increase in price.
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 $124 for a one-way ticket and $205 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?

    Delta, JetBlue, 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 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 Monday, and Friday.

  • 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

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 $84 or less one-way and $178 or less round-trip.

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

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

Nonstop departures

Tweed-New Haven to Chicago

Monday

Avelo Airlines

Avelo Airlines

Friday

Avelo Airlines

Avelo Airlines

See more direct flights

Nonstop returns

Chicago to Tweed-New Haven

Monday

Avelo Airlines

Avelo Airlines

Friday

Avelo Airlines

Avelo Airlines

See more direct flights
See more direct flights

Top 4 airlines serving 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 67 reviews
5.2Entertainment
5.2Food
7.6Boarding
8.3Crew
7.1Comfort
Airline reviews

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 .

10.0 ExcellentMaurice, Oct 2023DAB - HVN
Read more about Avelo Airlines reviews

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!!

Barely room for the tray table to come down. Clearly a budget airline that overcharges for every additional service.

I was told we'd have a hot breakfast option in first class, so I chose not get a hot breakfast. It was a very strange meal, but the fresh fruit was very good quality. Service was excellent from ORD to ELP. No service from MBS to ORD, not even water. However, when flying American from FNT to ORD, which is a shorter flight, they at least pass out snacks and offer water.

The delays (5 hrs) were a comedy of errors, and the multiple safety issues encountered were very concerning.

The flight was delayed instead of leaving at 11 it left at 12.20

United WiFi is consistently unusable (it can take 10 mins to load a single web page). If you need Wifi to do work, be prepared to lose half a day of productivity.

Good movies, iffy pay WiFi, food ok- on time though and that was great!

Awful…flight was delayed more than 12hrs, missed all connections to Fort Wayne, IN, had to get flight to another city 2 hours from my destination, flight was again delayed by 40 mins because they did not have enough fuel, again missed a connection, finally arrived in Indiana at 11pm…but before my 2 hour drive home, ay, no Five That Our Luggage Never Made On The plane and Still In Chicago

Boarding was friendly and quick. While the plane model was older with no live tv, the entertainment was full of movies and tv shows. All food was available. Pilots were very communicative with status of the flight. Flight landed on time.

The Palm Springs to Chicago O’Hare was on Time and Palm Springs airport is easier navigate. As our connection was only an approximately 50 minutes, we asked staff for insights for the Chicago airport in terms of transferring into the other terminal from which our flight left, and they were unhelpful. However, the United App was very helpful in terms of notifications and even providing directions. The Chicago to Detroit flight was significantly delayed which we all know does happen. However, there were very few updates or notifications as to why this was happening when we would actually arrive. It took nearly 30 minutes for bags to make it to baggage claim. We arrived nearly 1 hour late on a 40 minute flight.

Flight cancelled due to fog. No other flights available for 36 hours. Directed by United to book passage on another carrier, and submit receipts for reimbursement. Did that. United now states they will not reimburse. Currently out 2 grand.

The flight was delayed by 4 hours !!!!! It was very uncomfortable , and they told us only one our before departure

This flight is frequently delayed. The connections seemingly are more frequently delayed. I’ve missed connections as a result twice on the same route to charlotte then Charleston. Final destination arrival has been the next day, twice in a row. No pilots, no crew. Too many excuses. Unfortunately, my days with American are over.

Entertainment was okay not because anything was wrong but it is a short flight so having no wifi is annoying but understandable. Crew was outstanding as usual

Those seats were way too narrow. I had the middle seat, one person was a very skinny person and we still couldn’t avoid touching each other anytime one of us moved. The other person was larger and we were basically sitting in each others lap the entire flight. There was zero entertainment. The flight was long enough to justify tvs, but no. Gotta sit there in your infant seat and twiddle your thumbs.

Flight was fine. It took an unusually long time to have baggage delivered to the carousel in ORD.

Average - flew with Jet Blue internal and it was far more comfortable and better food and entertainment. Notable difference

The flight got canceled due to mechanical issues, and he to be rebooked and missed my appointments for that day

The flight was scheduled to depart DCA at 12:30 pm but was delayed twice on the ground so that we were finally scheduled to depart at around 4:00 pm. Once we boarded, it was announced that takeoff would be delayed again to fix a hydraulic problem which delayed our eventual takeoff until around 5:00 pm. Once we departed, it was a smooth flight back to ORD. We did not get any explanation about what caused the original significant delay. In my experience, this happens frequently with AA.

The only problem experienced was a ground stop in Chicago due to weather. But the crew handled everything professionally. They prioritized rebooking those passengers who had connecting flights and then deplaning the other passengers. When the hold was lifted, they efficiently re-boarded all the passengers so that we could depart before our departure limit expired.

Our second leg to Jackson WY was unable to land due to weather. We were flown back to Dallas after stopping in SLC. We were given hotel rooms and vouchers. We were told that we would be back on the same plane in the morning. Instead we were given a different flight with different seats. Not a good experience. No one knew what was going on.

Turn on the heat. Flight was way too cold from Arizona to Chicago.

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.

I had a death in my family and booked my flight on Spirit. My flight was cancelled the morning of my flight, no explanation, no help to rebook, nobody to talk to. The next available flight was 2days later !!!! Terrible airline, will NEVER fly with them again!

They took a horrible route with a lot of turbulence and I eneded up getting sick. Even if the flight takes longer. Don't put people life at risk just to get to the airport on time.

Every thing was fine ,low price,easy on time ,clean, good staff, really no issues

Had to board plan 2x due to lack of security check after 1st boarding

Miserable. The crew was rude, the flight was delayed 5 hours for mechanical reasons and then “weather” even though other planes were leaving.

They kept Changing the flight times. It was delayed several times and at one point it was supposed to depart at 3.40am! At which point we ended up staying overnight and booked long a separate United flight for early morning departure. The spirit flight then got moved up and left at 1.30 in the morning when it was supposed to leave at 9.40pm the night before.

Flight was delayed...not horribly late. Just before push back engine shut down for a quick replacement item that took about five minutes. After that, everything was smooth and the pilot was able to make up time in the air so that our arrival time was not too far off the original anticipated arrival time.

Only inflight purchases for food and water. Nothing comes with ticket price. Have to purchase bags, food...

The flight was delayed almost two hours on the front end, and an hour on the backend once we landed and waited for a gate to open up. We were told to remain in our seats during that whole delay and I had to go to the bathroom badly. I was unable to hold it and was forced to urinate in my pants while in my seat. I then had to sit in it until we finally deboarded and I was able to change my clothes.

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.
6/1sáb.
1 stop
10h 10mHVN-ORD
$124
6/1sáb.
2 stops
15h 14mHVN-ORD
$129
5/8mié.
3 stops
23h 58mHVN-ORD
$169
6/30dom.
2 stops
12h 52mHVN-ORD
$179
6/1sáb.
3 stops
15h 53mHVN-ORD
$182
6/30dom.
1 stop
10h 44mHVN-ORD
$194
7/4jue.
1 stop
10h 10mHVN-ORD
$216
7/22lun.
2 stops
26h 15mHVN-ORD
$224
5/8mié.
1 stop
9h 05mHVN-ORD
$231
5/8mié.
2 stops
9h 44mHVN-ORD
$236

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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.
5/3vie.
multi-stop
22h 55mHVN-ORD
5/10vie.
multi-stop
14h 25mORD-HVN
$501
5/3vie.
multi-stop
13h 02mHVN-ORD
5/10vie.
multi-stop
14h 25mORD-HVN
$504
5/3vie.
multi-stop
22h 20mHVN-ORD
5/10vie.
multi-stop
14h 25mORD-HVN
$513
5/3vie.
multi-stop
22h 20mHVN-ORD
5/10vie.
multi-stop
27h 45mORD-HVN
$584
5/2jue.
multi-stop
13h 20mHVN-ORD
5/5dom.
multi-stop
18h 55mORD-HVN
$608
5/3vie.
multi-stop
22h 20mHVN-ORD
5/10vie.
multi-stop
25h 15mORD-HVN
$613
5/3vie.
multi-stop
9h 48mHVN-ORD
5/5dom.
multi-stop
18h 55mORD-HVN
$625
5/3vie.
multi-stop
22h 55mHVN-ORD
5/5dom.
multi-stop
18h 55mORD-HVN
$629
5/2jue.
multi-stop
15h 18mHVN-ORD
5/5dom.
multi-stop
18h 55mORD-HVN
$647
5/2jue.
multi-stop
13h 20mHVN-ORD
5/5dom.
multi-stop
5h 10mORD-HVN
$696

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New Haven - Chicago Flights

Departure:

New Haven (HVN)United States

Cabin classes:

$134