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

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The best prices from New Haven Tweed-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 2022: compare New Haven to Chicago flight prices with the expected peak season, weather and rainfall in Chicago.
HVN - CHI
Price
$174 - $421
CHI
Temperature
23 - 73.4 °F
CHI
Precipitation
1.7 - 4.9 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

Average price

$206

Average for round-trip flights in January 2022

Round-trip from

$174

From New Haven Tweed-New Haven to Chicago (CHI)

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

Our data shows that August tends to be the cheapest month to fly to Chicago from New Haven. Users have commonly found prices around $182 for the month, but tickets can be as low as $64. Due to multiple factors, prepare for potentially higher prices in December.

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 in the evening. Doing so could potentially save you 29% on the flight price compared to flying in the afternoon, which is usually more expensive.

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 20 days before your planned departure. Booking around this time can save you about 48% on the cost of this flight compared to booking a flight leaving this week. We have found prices from $213 if you need a flight within two weeks. For flights within the next 72 hours, you can find tickets from as low as $293.

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 31% on the overall cost on flights from New Haven to Chicago.

Cheap flights from New Haven to Chicago in January, February 2022

The best prices found for HVN to CHI flights for January, February
20 Jan - 27 Jan
$6,003pp
HVN
New Haven Tweed-New Haven
Multiple Airlines
     
3 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
   
2 STOPS
HVN
New Haven Tweed-New Haven
20 Jan - 27 Jan
$6,008pp
HVN
New Haven Tweed-New Haven
Multiple Airlines
     
3 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
     
3 STOPS
HVN
New Haven Tweed-New Haven
24 Feb - 1 Mar
$10,614pp
HVN
New Haven Tweed-New Haven
Multiple Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
     
3 STOPS
HVN
New Haven Tweed-New Haven

New Haven Tweed-New Haven to Chicago 2022 flight deals

Cheap flights to Chicago from New Haven found for this year
20 Jan - 27 Jan
$6,003pp
HVN
New Haven Tweed-New Haven
Multiple Airlines
     
3 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
   
2 STOPS
HVN
New Haven Tweed-New Haven
20 Jan - 27 Jan
$6,008pp
HVN
New Haven Tweed-New Haven
Multiple Airlines
     
3 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
     
3 STOPS
HVN
New Haven Tweed-New Haven
24 Feb - 1 Mar
$10,614pp
HVN
New Haven Tweed-New Haven
Multiple Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
     
3 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
11:00 am - 11:27 am
Multiple Airlines
2 Stops
25h 27m
HVN - ORD
Multiple Airlines
$1,609
Kiwi.com
1:17 pm - 1:43 pm
Multiple Airlines
2 Stops
25h 26m
HVN - ORD
Multiple Airlines
$3,289
Gotogate
9:26 am - 4:45 am
Linear Air Taxi
2 Stops
20h 19m
HVN - ORD
Linear Air Taxi
$7,605
Travelgenio

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

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.

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.

Can I find flights from New Haven to Chicago for under $10,700 on Cheapflights?

Yes, there are multiple flights from New Haven to Chicago for under $10,700. The cheapest flight booked recently is on Multiple Airlines for just $10,614, but on average you can expect to pay $14,209.

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

Currently priced at $15,156, Linear Air Taxi will fly you from New Haven to Chicago and back. In addition to Linear Air Taxi, many other airlines offer competitively priced options for your trip.

What are the most popular airlines that fly from New Haven to Chicago?

The most popular airlines flying from New Haven to Chicago are American Airlines, Delta and United Airlines. Something to consider prior to booking your flight.

What are the cheapest flights from New Haven to Chicago?

Looking at all options, your cheapest flight can be booked for $100. While the most popular route (New Haven Tweed-New Haven - Chicago O'Hare Intl) can be booked for $6,003 on average our data indicates $141 when flying from New Haven to Chicago.

COVID Restrictions

View COVID Travel Restrictions for Chicago, IL

Do I need a COVID test to fly to Chicago from New Haven?

Information is based on travel restrictions for travel to Chicago within the United States

Most visitors from New Haven Tweed-New Haven need to provide a negative COVID-19 test result and/or quarantine to enter Chicago.

COVID-19 testing requirements
Visitors from New Haven Tweed-New Haven must present a negative RT-PCR (NAAT) or Antigen (quick-test) test taken 24 hours before departing to Chicago.

Quarantine requirements
Visitors from New Haven Tweed-New Haven are not required to quarantine after entering Chicago.

Do I need a test to fly back to New Haven from Chicago?

Returning to New Haven Tweed-New Haven from Chicago

COVID-19 testing requirements
Visitors from Chicago must present a negative RT-PCR (NAAT) or Antigen (quick-test) test taken 24 hours before departing to New Haven Tweed-New Haven.

Quarantine requirements
Visitors from Chicago are not required to quarantine after entering New Haven Tweed-New Haven.

Hide COVID Travel Restrictions for Chicago, IL

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 January in Chicago
33.8 °F
Avg rainfall for January in Chicago
0.7 ″

Airports servicing New Haven

Airports servicing Chicago

Midway (MDW)
Rockford (RFD)
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