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

HVN — CHI
Oct 11 — Oct 181

The best prices from Tweed-New Haven to Chicago are usually found in January or February, booked 50 days in advance, depart on a Saturday or Wednesday and return on a Friday

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

Leaving on a Friday 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 91% 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 24% on the cost of this flight compared to booking a flight leaving this week. We have found prices from $260 if you need a flight within two weeks. For flights within the next 72 hours, you can find tickets from as low as $304.

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

Our data shows that January tends to be the cheapest month to fly to Chicago from New Haven. Users have commonly found prices around $236 for the month, but tickets can be as low as $117. 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 40% on the flight price compared to flying in the morning, which is usually more expensive.

Cheap flights from New Haven to Chicago in October, November 2022

The best prices found for HVN to CHI flights for October, November
Nov 28 - Nov 30
HVN

Tweed-New Haven

ORD

Chicago O'Hare Intl

1 stop

13h 28m
ORD

Chicago O'Hare Intl

HVN

Tweed-New Haven

2 stops

17h 05m
$270

Multiple Airlines

Pick Dates

Deal found 6/10/22

Nov 2 - Nov 5
HVN

Tweed-New Haven

ORD

Chicago O'Hare Intl

2 stops

11h 10m
ORD

Chicago O'Hare Intl

HVN

Tweed-New Haven

1 stop

6h 35m
$275

Multiple Airlines

Pick Dates

Deal found 6/10/22

Nov 2 - Nov 9
HVN

Tweed-New Haven

ORD

Chicago O'Hare Intl

2 stops

11h 10m
ORD

Chicago O'Hare Intl

HVN

Tweed-New Haven

2 stops

10h 10m
$276

Multiple Airlines

Pick Dates

Deal found 5/10/22

New Haven to Chicago 2022 flight deals

Cheap flights to Chicago from New Haven found for this year
Nov 28 - Nov 30
HVN

Tweed-New Haven

ORD

Chicago O'Hare Intl

1 stop

13h 28m
ORD

Chicago O'Hare Intl

HVN

Tweed-New Haven

2 stops

17h 05m
$270

Multiple Airlines

Pick Dates

Deal found 6/10/22

Nov 2 - Nov 5
HVN

Tweed-New Haven

ORD

Chicago O'Hare Intl

2 stops

11h 10m
ORD

Chicago O'Hare Intl

HVN

Tweed-New Haven

1 stop

6h 35m
$275

Multiple Airlines

Pick Dates

Deal found 6/10/22

Nov 2 - Nov 9
HVN

Tweed-New Haven

ORD

Chicago O'Hare Intl

2 stops

11h 10m
ORD

Chicago O'Hare Intl

HVN

Tweed-New Haven

2 stops

10h 10m
$276

Multiple Airlines

Pick Dates

Deal found 5/10/22

Last minute flights from New Haven to Chicago

Late deals on return flights to Chicago from New Haven, departing today and this week
Oct 13 - Oct 17
HVN

Tweed-New Haven

ORD

Chicago O'Hare Intl

1 stop

7h 18m
ORD

Chicago O'Hare Intl

HVN

Tweed-New Haven

1 stop

8h 52m
$362

Multiple Airlines

Pick Dates

Deal found 4/10/22

Oct 13 - Oct 17
HVN

Tweed-New Haven

ORD

Chicago O'Hare Intl

2 stops

13h 10m
ORD

Chicago O'Hare Intl

HVN

Tweed-New Haven

1 stop

8h 52m
$418

Multiple Airlines

Pick Dates

Deal found 4/10/22

Oct 13 - Oct 16
HVN

Tweed-New Haven

ORD

Chicago O'Hare Intl

1 stop

7h 18m
ORD

Chicago O'Hare Intl

HVN

Tweed-New Haven

1 stop

13h 45m
$434

Multiple Airlines

Pick Dates

Deal found 4/10/22

One-way flights to Chicago from New Haven

The cheapest one-way flights from New Haven to Chicago
Oct 24
HVN

Tweed-New Haven

ORD

Chicago O'Hare Intl

2 stops

28h 08m
$107

Multiple Airlines

Pick Dates

Deal found 3/10/22

Oct 24
HVN

Tweed-New Haven

ORD

Chicago O'Hare Intl

1 stop

13h 19m
$112

Multiple Airlines

Pick Dates

Deal found 3/10/22

Oct 17
HVN

Tweed-New Haven

ORD

Chicago O'Hare Intl

1 stop

13h 19m
$121

Multiple Airlines

Pick Dates

Deal found 3/10/22

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. 2 airlines have flights to Chicago from Tweed-New Haven on a regular basis.

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

Linear Air Taxi is one of the carriers that may have flexible change policies. You can use our site to filter for other airlines that may also have this kind of flexibility.

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 Multiple Airlines for just $275, but on average you can expect to pay $312.

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

There are currently 14+ open flights from New Haven to Chicago within the next 7 days for less than $400.

What are the cheapest flights from New Haven to Chicago?

Looking at all options, your cheapest flight can be booked for $211. While the most popular route (Tweed-New Haven - Chicago O'Hare Intl) can be booked for $276 on average our data indicates $211 when flying from New Haven to Chicago.

Alternative routes for New Haven to Chicago

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

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-timeCOVID-19 safety
Avelo AirlinesCheapest$120Average$237FlexibilityNo cancel feeOn-timeN/ACOVID-19 safety
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
0%of flight departuresEarly morningMidnight to 6 am
0%of flight departuresMorning6 am to noon
100%of flight departuresAfternoonNoon to 6 pm
0%of flight departuresEvening6 pm to midnight
Midnight
6 AM
Noon
6 PM

Weekly flight availability from New Haven to Chicago

See how many times per day planes take to the skies headed from New Haven to Chicago
Sunday1daily flight
Monday1daily flight
Tuesday0daily flights
Wednesday0daily flights
Thursday1daily flight
Friday1daily flight
Saturday0daily flights