HVN - CHI

$224 Find Cheap Flights from New Haven to Chicago

This is the cheapest round-trip flight price found by a KAYAK user in the last 72 hours by searching for a flight from New Haven to Chicago departing on 2/7. 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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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 41,299,237 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.

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.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
6:30 am - 2:23 pmHVN-ORD
8h 53m1 stop
6:06 pm - 9:45 amORD-HVN
14h 39m1 stop
Fri, Feb 7 - Sun, Feb 9
7:15 am - 4:10 pmHVN-ORD
9h 55m1 stop
11:12 am - 12:54 pmORD-HVN
24h 42m2 stops
Thu, Jan 9 - Sun, Jan 12
7:05 am - 8:49 pmHVN-ORD
14h 44m1 stop
11:12 am - 12:54 pmORD-HVN
24h 42m2 stops
Wed, Jan 8 - Sun, Jan 12
4:25 pm - 8:13 pmHVN-ORD
28h 48m2 stops
6:06 pm - 9:45 amORD-HVN
14h 39m1 stop
Sun, Feb 2 - Sun, Feb 9
10:23 am - 11:32 pmHVN-ORD
14h 09m2 stops
11:12 am - 12:54 pmORD-HVN
24h 42m2 stops
Thu, Jan 9 - Sun, Jan 12
7:15 am - 4:10 pmHVN-ORD
9h 55m1 stop
5:35 am - 2:05 pmORD-HVN
7h 30m1 stop
Thu, Jan 9 - Sun, Jan 12
7:05 am - 8:49 pmHVN-ORD
14h 44m1 stop
5:35 am - 2:05 pmORD-HVN
7h 30m1 stop
Wed, Jan 8 - Sun, Jan 12
4:25 pm - 8:13 pmHVN-ORD
28h 48m3 stops
6:06 pm - 9:45 amORD-HVN
14h 39m1 stop
Sun, Feb 2 - Sun, Feb 9
7:05 am - 12:33 amHVN-ORD
18h 28m2 stops
11:12 am - 12:54 pmORD-HVN
24h 42m2 stops
Wed, Jan 8 - Sun, Jan 12
4:25 pm - 8:13 pmHVN-ORD
28h 48m3 stops
1:35 pm - 9:45 amORD-HVN
19h 10m2 stops
Sun, Feb 2 - Sun, Feb 9

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 round-trip flights from New Haven to Chicago.
Our data shows that the cheapest route for a return flight from New Haven to Chicago cost $143 and was between New Haven (HVN) and Chicago Midway Airport (MDW). On average, the best prices are found if you fly this route. The average price for a return flight for this route is $143.

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 round-trip 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 (return) on average. On the other hand, the most expensive months are December and May, where the average cost of round-trip tickets is $300 and $263 respectively.

Good to know

Low season

January

High season

November

Cheapest flight

$224
Best time to beat the crowds but there is an average 45% increase in price.
Most popular time to fly and prices are also 27% 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 $224 for a round-trip ticket.

  • 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?

    American Airlines, Delta, and JetBlue 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, 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 $68 or less one-way and $144 or less round-trip.

Prefer to fly direct 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.

Direct 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

Direct 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
7.8Boarding
8.4Crew
5.2Food
7.1Comfort
5.1Entertainment
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!!

I was comfortable because I upgraded. I would not have been comfortable in economy. It was a short flight so there was limited food service and no inflight entertainment.

I thought since I upgraded my seat I would get some perks. Free water, free snacks. Free carry on luggage.

Seats were surprisingly comfortable, and crew was polite. I did not like the baggage fee prices, the minimal amount of flight choices for my area and the difficulty of the self service bag drop.

I’ve now flown Spirit a few times and while the general perception of Spirit I feel is poor, I’ve had a great experience each time. They do charge extra for everything but you should know that going in

Horrible. Take off was delayed by an hour. They were letting people board d the plane right before takeoff. I was delayed an hour when I arrived and late for my meeting. Spirit is NEVER on time.

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

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

Information on your arrival and departure airports

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