Cheap flights from New Haven to Chicago (HVN - CHI)

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The best prices from New Haven to Chicago are usually found in June or July, booked 45 days in advance, depart on a Saturday or Friday and return on a Wednesday

How to find the cheapest flight from
New Haven (HVN) to Chicago (CHI)

All the information you need to plan the best HVN to CHI flight in 2021: compare New Haven to Chicago flight prices with the expected peak season, weather and rainfall in Chicago.
HVN - CHI
Price
$174 - $421
CHI
Temperature
33.8 - 84.2 °F
CHI
Rainfall
0.7 - 4.3 inches

Popular in

March

High demand for flights, 34% potential price rise

Cheapest in

June

Best time to find cheap flights, 37% potential price drop

Round-trip from

$174

From New Haven to Chicago

One-way from

$98

One-way flight from New Haven to Chicago

Flight route prices based on searches on Cheapflights within the last 3 days, monthly prices based on aggregated historical data.
What is the cheapest day to fly round-trip from New Haven to Chicago?

It’s generally more expensive to depart on a Friday, if you have to leave on this day you can still search on Cheapflights to find great options that meet your needs.

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

When searching for a good deal, it’s best to be prepared for potential fluctuations in price. We recommend booking at least 20 days in advance, which can save you up to 10% on flights from New Haven to Chicago compared to booking the week you need them. Waiting 20 days out may not be for everyone, so we have options available for flights within the next two weeks, with the lowest price starting at $137. For sooner than that we have options available in the next 3 days from $157.

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

Due to multiple factors, expect to potentially pay more when booking in December. For low rates, April can be a great choice for travel to Chicago. Flights to Chicago from New Haven in April are about $135 on average during April, but can be found for as low as $33.

When is the cheapest time to fly from New Haven to Chicago (HVN - CHI)?

One of the essential ways to save on airfare from New Haven to Chicago is to remain as flexible as possible. Flights that are in the afternoon tend to be the most expensive. A flight in the evening could potentially save you up to 29% on airfare.

Cheap flights from New Haven to Chicago in May, June 2021

The best prices found for HVN to CHI flights for May, June
11 Jun - 16 Jun
$333pp
HVN
New Haven Tweed-New Haven
American Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
 
1 STOP
HVN
New Haven Tweed-New Haven
4 Jun - 9 Jun
$335pp
HVN
New Haven Tweed-New Haven
American Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
   
2 STOPS
HVN
New Haven Tweed-New Haven
11 Jun - 12 Jun
$336pp
HVN
New Haven Tweed-New Haven
American Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
   
2 STOPS
HVN
New Haven Tweed-New Haven

New Haven to Chicago 2021 flight deals

Cheap flights to Chicago from New Haven found for this year
20 Aug - 28 Aug
$253pp
HVN
New Haven Tweed-New Haven
American Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
 
1 STOP
HVN
New Haven Tweed-New Haven
20 Aug - 30 Aug
$291pp
HVN
New Haven Tweed-New Haven
American Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
 
1 STOP
HVN
New Haven Tweed-New Haven
11 Jun - 16 Jun
$333pp
HVN
New Haven Tweed-New Haven
American Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
 
1 STOP
HVN
New Haven Tweed-New Haven

Last minute flights from New Haven to Chicago

Late deals on round-trip flights to Chicago from New Haven, departing today and this week
26 May - 30 May
$357pp
HVN
New Haven Tweed-New Haven
American Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
   
2 STOPS
HVN
New Haven Tweed-New Haven
23 May - 2 Jun
$387pp
HVN
New Haven Tweed-New Haven
American Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
   
2 STOPS
HVN
New Haven Tweed-New Haven

One-way flights to Chicago from New Haven

The cheapest one-way flights from New Haven to Chicago
2:03 am - 8:36 am
American Airlines
1 Stop
7h 33m
HVN - ORD
American Airlines
2:03 am - 7:01 pm
American Airlines
1 Stop
17h 58m
HVN - ORD
American Airlines
2:03 am - 6:50 am
American Airlines
1 Stop
5h 47m
HVN - ORD
American Airlines

Related info for your journey

Useful info, stats and facts about <span class="emphasized">New Haven</span> to <span class="emphasized">Chicago</span> flights.

Flight FAQs

From New Haven to Chicago

Are flight prices decreasing from New Haven to Chicago due to COVID-19 (coronavirus)?

At this time, Cheapflights has noticed price decreases for many domestic flights due to COVID-19. Travel is not necessarily recommended at this time, and flights may be prone to cancellation: please check with local authorities in both New Haven and Chicago for travel alerts, and be sure to review the airline's cancellation policy and travel advisories before booking. For more information, please view our post on what to know about COVID-19 (coronavirus) and travel.

Which airlines flying from New Haven Tweed-New Haven to Chicago have flexible cancellations due to COVID-19?

American Airlines, United Airlines, and Delta are some of the carriers that may have flexible cancellation policies. You can use our site to filter for other airlines that may also have this kind of flexibility.

What airport do you fly from for flights from New Haven to Chicago?

For a flight from New Haven to Chicago, you will be flying from Tweed-New Haven. New Haven Tweed-New Haven (HVN) is just 3.6 mi from the center of the city. Tweed-New Haven is the only New Haven airport and it handles 0 outbound flights to Chicago per day. 3 airlines have flights to Chicago from New Haven Tweed-New Haven on a regular basis.

Can I find flights from New Haven to Chicago for under $300 on Cheapflights?

Yes, there are multiple flights from New Haven to Chicago for under $300. The cheapest flight booked recently is on American Airlines for just $253, but on average you can expect to pay $341.

Are there nonstop flights from New Haven to Chicago for under $300 on Cheapflights?

There are no nonstop flights from New Haven to Chicago, but Cheapflights can provide you with all the information you need to find the fastest route with the fewest stops.

Are there last-minute flights available from New Haven to Chicago for under $400?

There are currently 2+ open flights from New Haven to Chicago within the next 7 days for less than $400.

What days are nonstop flights available from New Haven to Chicago?

Days when nonstop flights are available for this flight are: Tuesday.

Is New Haven weather warmer or cooler than Chicago?

Expect the weather to be around 84 °F on average in July. As the temperature peaks, try to get your plans done early, as flight price and availability will have an impact on your travels. The climate in Chicago is generally the same as in New Haven.

How long is the flight from New Haven to Chicago?

American Airlines can get you from New Haven to Chicago in just under 4h 51m. Your travel time can differ by up to .

What is the cheapest airline to fly from New Haven to Chicago round-trip?

Flying on American Airlines is currently your cheapest option to Chicago, with prices starting at $253. You may be able to fly from New Haven to Chicago for 8% less than the average price by searching for this airline.

What are the cheapest airlines to fly from New Haven to Chicago one-way?

$98 is the cheapest one-way deal found within the past few days, from American Airlines.

Alternative routes for New Haven to Chicago

See prices for flight routes from nearby airports that may be better suited for you.

Destination information for Chicago

Things to know before you go - useful duration and weather info for your trip from New Haven to Chicago.
Average temperature for May in Chicago
71.6 °F
Avg rainfall for May in Chicago
4.3 ″

Airports servicing New Haven

Airports servicing Chicago

Chicago Midway (MDW)
Rockford (RFD)
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