Cheap flights from New Haven (HVN) to Chicago (CHI) from $113

This is the cheapest one-way flight price, found on 9/19. Prices may vary by date and flight preferences.
HVN — CHI
sep. 26 — oct. 31

The best prices from Tweed-New Haven to Chicago are usually found in August or May, booked 60 days in advance, depart on a Monday or Tuesday and return on a Monday

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 2023: compare New Haven to Chicago flight prices with the expected peak season, weather and rainfall in Chicago.

Popular in

November

Cheapest in

August

Round-trip from

$207

One-way from

$113
High demand for flights, 14% potential price rise
Best time to find cheap flights, 18% potential price drop
From Tweed-New Haven to Chicago (CHI)
One-way flight from Tweed-New Haven to Chicago (CHI)

HVN - CHI

Price

$207 - $364

CHI

Temperature

23 - 73.4 °F

CHI

Rainfall

1.7 - 4.9 inches

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

Leaving on a Tuesday is a viable option for saving on travel. Heavily demanded days of the week can typically drive up the prices you see. Booking your travel for a less competitive day can save up to 144% on the overall cost on flights from New Haven to Chicago.

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

To save on the cost of your flight from New Haven to Chicago, book at least 28 days before your planned departure. Booking around this time can save you about 32% on the cost of this flight compared to booking a flight leaving this week. We have found prices from $277 if you need a flight within two weeks. For flights within the next 72 hours, you can find tickets from as low as $344.

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

Our data shows that February tends to be the cheapest month to fly to Chicago from New Haven. Users have commonly found prices around $265 for the month, but tickets can be as low as $166. Due to multiple factors, prepare for potentially higher prices in June.

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

It’s typically best to fly out from New Haven to Chicago at noon. Doing so could potentially save you 41% on the flight price compared to flying in the morning, which is usually more expensive.

Cheap New Haven to Chicago flights in September & October 2023

The best prices found for HVN to CHI flights for September, October

New Haven to Chicago 2023 flight deals

Cheap flights to Chicago from New Haven found for this year

New Haven to Chicago flights leaving soon

Late deals on return flights to Chicago from New Haven, departing today and this week

One-way flights to Chicago from New Haven

The cheapest one-way flights from New Haven to Chicago

Find flights from New Haven to Chicago within your budget

Use the slider to find flights from New Haven to Chicago that fit your budget.

Fly from

Any airport

Fly to

Any airport

Budget

$186 - $272

Route

Depart

Return

Price

Tweed-New HavenChicago O'Hare Intl

HVN - ORD

HVNORD

Tweed-New Haven

mar. 10/17

2 stops20h 13m

Chicago O'Hare Intl

jue. 10/19

2 stops15h 13m

Tweed-New HavenChicago O'Hare Intl

HVN - ORD

HVNORD

Tweed-New Haven

mar. 10/17

2 stops20h 13m

Chicago O'Hare Intl

jue. 10/19

1 stop17h 27m

Tweed-New HavenChicago O'Hare Intl

HVN - ORD

HVNORD

Tweed-New Haven

mar. 10/17

3 stops27h 58m

Chicago O'Hare Intl

jue. 10/19

2 stops15h 13m

Tweed-New HavenChicago O'Hare Intl

HVN - ORD

HVNORD

Tweed-New Haven

mar. 10/10

2 stops20h 13m

Chicago O'Hare Intl

sáb. 10/14

2 stops18h 15m

Tweed-New HavenChicago O'Hare Intl

HVN - ORD

HVNORD

Tweed-New Haven

mar. 10/10

3 stops30h 28m

Chicago O'Hare Intl

sáb. 10/14

2 stops18h 15m

Tweed-New HavenChicago O'Hare Intl

HVN - ORD

HVNORD

Tweed-New Haven

vie. 10/20

1 stop13h 25m

Chicago O'Hare Intl

lun. 10/23

2 stops17h 28m

Tweed-New HavenChicago O'Hare Intl

HVN - ORD

HVNORD

Tweed-New Haven

vie. 10/20

3 stops33h 50m

Chicago O'Hare Intl

lun. 10/23

2 stops17h 28m

Tweed-New HavenChicago O'Hare Intl

HVN - ORD

HVNORD

Tweed-New Haven

mar. 10/10

2 stops20h 13m

Chicago O'Hare Intl

sáb. 10/14

1 stop14h 45m

Tweed-New HavenChicago O'Hare Intl

HVN - ORD

HVNORD

Tweed-New Haven

vie. 10/20

2 stops24h 53m

Chicago O'Hare Intl

lun. 10/23

2 stops17h 28m

Flights are sorted by cheapest first

Deals found on 9/19

Related info for your journey

Useful info, stats and facts about New Haven to Chicago flights.

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. 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. 1 airline has flights to Chicago from Tweed-New Haven on a regular basis.

Can I find flights from New Haven to Chicago for under $200 on Cheapflights?

Yes, there are multiple flights from New Haven to Chicago for under $200. The cheapest flight booked recently is on Multiple Airlines for just $186, but on average you can expect to pay $275.

Are there last-minute flights available from New Haven to Chicago for under $300?

There are currently 16+ open flights from New Haven to Chicago within the next 7 days for less than $300.

What does HVN to ORD mean?

Great question - HVN to ORD just means Tweed-New Haven Airport to Chicago O'Hare Intl Airport. Now you’ll know what these unique codes when you look for flights! Chicago Midway Airport (MDW), Chicago Greater Rockford Airport (RFD) are some additional IATA codes for airports related to your trip.

Top airline flying from New Haven to Chicago

The chart below displays the airlines Cheapflights users traveling from New Haven to Chicago choose most often. Cheapest and average prices are based on aggregated data from the past 12 months.
AirlineCheapestAverageFlexibilityOn-time
Avelo AirlinesCheapest$115Average$247FlexibilityNo cancel feeOn-timeN/A
Search Avelo Airlines flights

Hourly flight availability from New Haven to Chicago

See what time of day planes typically take off from New Haven to Chicago
1%of flight departuresEarly morningMidnight to 6 am
33%of flight departuresMorning6 am to noon
66%of flight departuresAfternoonNoon to 6 pm
0%of flight departuresEvening6 pm to midnight
Midnight
6 AM
Noon
6 PM
100% Free
Cheapflights is completely free to use, so you can start saving the moment you arrive.
Book with Flexibility
Our users can plan ahead with confidence and find flights with no change fees
Travel Smart
Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.