HVN - CHI

$49 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 11/28. 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
1 adult, Economy, 0 bags

KAYAK searches 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
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Flight Deals

Cheap Flights 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 for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from New Haven to Chicago

Mon, Mar 2 - Mon, Mar 9
Avelo Airlines Logo
2:40 pm - 3:57 pmHVN-ORD
2h 17mnonstop
Avelo Airlines Logo
5:10 pm - 8:29 pmORD-HVN
2h 19mnonstop
$98Avelo Airlines
Find Deal
Sat, Feb 21 - Sat, Feb 28
Avelo Airlines Logo
7:00 am - 8:17 amHVN-ORD
2h 17mnonstop
Avelo Airlines Logo
9:15 am - 12:34 pmORD-HVN
2h 19mnonstop
$101Avelo Airlines
Find Deal
Mon, Mar 2 - Tue, Mar 3
Multiple Airlines Logo
2:40 pm - 3:57 pmHVN-ORD
2h 17mnonstop
Multiple Airlines Logo
6:05 am - 3:16 pmORD-HVN
8h 11m1 stop
$164Multiple Airlines
Find Deal
Sun, Nov 16 - Sun, Nov 23
Avelo Airlines Logo
3:50 pm - 5:20 pmHVN-ORD
2h 30mnonstop
Avelo Airlines Logo
4:25 pm - 7:30 pmORD-HVN
2h 05mnonstop
$178Avelo Airlines
Find Deal
Thu, Dec 4 - Sun, Dec 7
Avelo Airlines Logo
1:50 pm - 3:20 pmHVN-ORD
2h 30mnonstop
Avelo Airlines Logo
4:05 pm - 7:10 pmORD-HVN
2h 05mnonstop
$181Avelo Airlines
Find Deal
Thu, Nov 13 - Sun, Nov 16
Avelo Airlines Logo
3:50 pm - 5:20 pmHVN-ORD
2h 30mnonstop
Avelo Airlines Logo
6:05 pm - 9:09 pmORD-HVN
2h 04mnonstop
$182Avelo Airlines
Find Deal
Thu, Nov 20 - Mon, Nov 24
Multiple Airlines Logo
1:35 pm - 3:05 pmHVN-ORD
2h 30mnonstop
Multiple Airlines Logo
6:48 am - 10:29 pmORD-HVN
14h 41m1 stop
$192Multiple Airlines
Find Deal
Thu, Nov 20 - Sun, Nov 23
Avelo Airlines Logo
1:35 pm - 3:05 pmHVN-ORD
2h 30mnonstop
Avelo Airlines Logo
4:25 pm - 7:30 pmORD-HVN
2h 05mnonstop
$195Avelo Airlines
Find Deal
Mon, Mar 2 - Tue, Mar 3
Multiple Airlines Logo
2:40 pm - 3:57 pmHVN-ORD
2h 17mnonstop
Multiple Airlines Logo
5:05 am - 8:48 pmORD-HVN
14h 43m2 stops
$203Multiple Airlines
Find Deal
Mon, Nov 10 - Thu, Nov 13
Multiple Airlines Logo
6:26 pm - 11:28 pmHVN-ORD
6h 02m1 stop
Multiple Airlines Logo
1:36 pm - 5:46 pmORD-HVN
27h 10m2 stops
$204Multiple Airlines
Find Deal

Everything you should know

Top routes
HVN-MDW
Cheapest • 24% average savings
HVN-ORD
Most popular
Insights
Insights
Insights
Insights
Nonstop flights
6 days a week
There are direct flights from New Haven to Chicago 6 days a week: Mon, Tue, Wed, Thu, Fri, Sun.
Direct flights
Direct flights
Direct flights
Direct flights
Cheapest round-trip
$98
Avelo Airlines
Mon 3/2Mon 3/9
HVN - ORD • Non-stop
Cheapest one-way
$49
Avelo Airlines
Fri 11/28
HVN - ORD • Non-stop
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Chicago!
Booking Insights

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?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest return flight from New Haven to Chicago costs $136 on the route between New Haven (HVN) and Chicago Midway Airport (MDW). Over the past month, this route was, on average, 24% cheaper than other New Haven-Chicago routes. The most popular route is between New Haven (HVN) and Chicago O'Hare Intl Airport (ORD).

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

The average price of all round-trip flights from New Haven to Chicago clicked on KAYAK for each day over the last 12 months.

Your flight ticket price will generally be cheaper if you fly to Chicago on a Thursday and more expensive on a Sunday. On your return trip to New Haven, you should consider flying back on a Friday, and avoid Thursdays for better deals.

Good to know

Cheapest flight$49
Most popular time to fly and prices are also 3% lower on average.
Flight from New Haven to Chicago

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 $49 for a one-way ticket and $98 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?

    Delta, American Airlines, 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 Monday, Tuesday, Wednesday, Thursday, Friday, 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.

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 $49 or less one-way.

Prefer to fly direct from New Haven to Chicago?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Tweed-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

Monday

Avelo Airlines

Avelo Airlines

Tuesday

Avelo Airlines

Avelo Airlines

Wednesday

Avelo Airlines

Avelo Airlines

Thursday

Avelo Airlines

Avelo Airlines

Friday

Avelo Airlines

Avelo Airlines

Sunday

Avelo Airlines

Avelo Airlines

See more direct flights

Direct returns

Chicago to Tweed-New Haven

Monday

Avelo Airlines

Avelo Airlines

Tuesday

Avelo Airlines

Avelo Airlines

Wednesday

Avelo Airlines

Avelo Airlines

Thursday

Avelo Airlines

Avelo Airlines

Friday

Avelo Airlines

Avelo Airlines

Sunday

Avelo Airlines

Avelo Airlines

See more direct flights

Reviews of the top airline 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 82 reviews
7.7Boarding
7.1Comfort
8.2Crew
5.0Entertainment
5.0Food
Airline reviews

Short 2-hour flight, we took off on time, ETA was earlier than stated, no interaction needed with stewards, no food, no entertainment on such a short flight.

10.0 ExcellentChristina, Sep 2025EUG - BUR
Read more Avelo Airlines reviews

Short 2-hour flight, we took off on time, ETA was earlier than stated, no interaction needed with stewards, no food, no entertainment on such a short flight.

Avelo provided exactly what I expected. They are a low-cost option with no frills but the experience was comfortable and the staff was great! I will be using them in the future for trips when cost is a priority for me.

Expect nothing and you will be fine. Seats are crammed.

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.

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

Information on your arrival and departure airports

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