HVN - CHI

$90 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 5/15. 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
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Cheap Flights from New Haven to Chicago

 
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

KAYAK's recommended round-trip deals from the most popular airlines that fly from New Haven to Chicago.
Discover the best prices for you by selecting your travel dates on KAYAK.
Choose your dates
Avelo Airlines Logo
2:05 pm - 3:26 pmHVN-ORD
2h 21mnonstop
Avelo Airlines Logo
4:26 pm - 7:27 pmORD-HVN
2h 01mnonstop
$188Avelo Airlines
Find Deal
Thu, May 15 - Sun, May 18
Avelo Airlines Logo
4:50 pm - 6:11 pmHVN-ORD
2h 21mnonstop
Avelo Airlines Logo
6:26 pm - 9:27 pmORD-HVN
2h 01mnonstop
$198Avelo Airlines
Find Deal
Thu, Jun 5 - Sun, Jun 8
Avelo Airlines Logo
2:05 pm - 3:26 pmHVN-ORD
2h 21mnonstop
Avelo Airlines Logo
4:26 pm - 7:27 pmORD-HVN
2h 01mnonstop
$208Avelo Airlines
Find Deal
Thu, May 15 - Sun, May 18
Avelo Airlines Logo
4:50 pm - 6:11 pmHVN-ORD
2h 21mnonstop
Avelo Airlines Logo
6:26 pm - 9:27 pmORD-HVN
2h 01mnonstop
$209Avelo Airlines
Find Deal
Thu, Jun 5 - Sun, Jun 8
 Logo
3:35 pm - 11:29 pmHVN-ORD
8h 54m1 stop
 Logo
6:26 pm - 9:27 pmORD-HVN
2h 01mnonstop
Thu, Jun 5 - Sun, Jun 8
 Logo
10:30 am - 4:25 pmHVN-ORD
6h 55m1 stop
 Logo
7:47 am - 1:59 pmORD-HVN
29h 12m1 stop
Mon, May 12 - Tue, May 13
 Logo
10:30 am - 4:25 pmHVN-ORD
6h 55m1 stop
 Logo
12:41 pm - 8:59 pmORD-HVN
31h 18m2 stops
Mon, May 12 - Tue, May 13
 Logo
6:30 am - 8:55 amHVN-ORD
27h 25m1 stop
 Logo
12:26 pm - 4:01 pmORD-HVN
26h 35m1 stop
Sun, May 11 - Fri, May 16
 Logo
3:35 pm - 4:25 pmHVN-ORD
25h 50m2 stops
 Logo
6:26 pm - 9:27 pmORD-HVN
2h 01mnonstop
Thu, Jun 5 - Sun, Jun 8
 Logo
6:30 am - 11:29 pmHVN-ORD
17h 59m2 stops
 Logo
4:26 pm - 7:27 pmORD-HVN
2h 01mnonstop
Thu, May 15 - Sun, May 18

KAYAK's insights & trends for New Haven to Chicago flights

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 $134 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 $134.

Good to know

High season

November

Cheapest flight

$90
Most popular time to fly and prices are also 28% 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

  • 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 21m. The most common departure time is 2:00 pm and most flights take off in the afternoon. Each week, there are 2 flights.

  • 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 $90 for a one-way ticket and $188 for a round-trip.

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

    No

  • Which airports will I be using when flying from New Haven to Chicago?

    On your way to Chicago, you’ll fly out from Tweed-New Haven. You’ll be landing in one of Chicago’s 2 airports: Chicago Midway or Chicago O'Hare Intl.

  • 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 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 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

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

Thursday

Avelo Airlines

Avelo Airlines

Sunday

Avelo Airlines

Avelo Airlines

See more direct flights

Direct returns

Chicago to Tweed-New Haven

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

It’s what we expected from Spirit..reasonable cost, good for a 2-3 hour flight. Disappointed that we had a 2 hour delay in departure from DFW for a maintenance issue, but the pilot handled it well once we were outbound on a different Airbus.

Worst airline ever! The guy weighing my bag had his foot on the metal plate and when I called him out on it, I got this stupid little smirk. La is a scam and so is Spirit Airlines. All the flight attendants looked like they hated our flight just as much as we did.

My experience with Spirit went pretty much as expected. It's a no frills airline, and you get what you pay for. I don't require much, so I was grateful to have an inexpensive way to travel. It is sad to me that the gate agents and flight crew don't smile much or seem very friendly or helpful. They are competent and efficient, and that's really all I need.

My experience was okay. The flight did not offer even water without a fee. Also had to pay extra for my carry on, as I was told I had to check my bag, even though it said I had the option to carry on a bag when booking. This costed me an extra $100. Would likely not fly with Spirit again.

The flight was rescheduled several times without a reason for the schedule changes. I had to be in New Orleans at a certain time and it was just easier to drive at a certain point. I don’t know if the flight ever left. This is my first experience with Spirit Airlines and is also the last.

It was fast but uncomfortable seats. Had to pay a bit extra not sure why? Maybe in selection of all my 4 tix together ? Just knew I had a balance before getting boarding pass online when departing from satx ? And flight was delayed..

Terrible-extreme delay with very little communication, plane was overfull, luggage was returned on baggage claim in filthy condition.

Lower cost is the reason to fly Spirit. Should give free baggage with credit card.

Very difficult. Flew out on Dec 24th and it was a mess. They know it is going to be the busiest time of the year and they had no organization. Finally they called for people going on certiam flights so they could get them thru thw line then we had to rush to our gate to get in li e to board.We missed our flight do to being stuck at the border of Mexico. They would not work with us to make an affordable price so we had to wait a day with no where to go and pay 280 more for our flights. I would think that a complimentary drink would be nice. But we had to pay 4.49 for a coke. Not an overall good experience

I very late and supose be in home at 12 pm from yesterday but I stiill in detroi airport

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

Information on your arrival and departure airports

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