Cheap Flights from Chicago to New Haven

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Flight deals from Chicago to New Haven

Looking for a cheap last-minute deal or the best return flight from Chicago to New Haven? Find the lowest prices on one-way and return tickets right here.

Find the cheapest month to fly from Chicago to New Haven

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Chicago to New Haven flights are currently cheapest in February.

Direct flights from Chicago to New Haven

Chicago to New Haven: Flight information

The things to know before you go.
Cheapest flight foundR 1,199
Cheapest month to flyFebruary
Average flight time2 hrs, 33 mins
Most popular airlineAvelo Airlines
Average flights per week4

Finding cheap flights from Chicago to New Haven: Frequently asked questions

The best price we found for a return flight from Chicago to New Haven is R 2,421. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
2 hours and 33 minutes is the average flight time from Chicago to New Haven.
Avelo Airlines flies direct from Chicago to New Haven.
As of February 2026, there are 4 flights per week flying from Chicago to New Haven.
The cheapest month to fly from Chicago to New Haven is usually March.
After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Chicago to New Haven Airport on Thursday, 5 March 2026.
Yes – the average flight time is 2 hours and 33 minutes.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to New Haven but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.
We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to New Haven is around 40 days in advance, so don’t leave your flight to the last minute.
The cheapest airline that flies to New Haven is Avelo Airlines .

Travelling from Chicago to New Haven Airport (HVN): What you need to know

  • Your travel plans take shape at one of Chicago's main airports, O'Hare International Airport (ORD) or Chicago Midway International Airport (MDW). Explore the options for booking a flight from Chicago to New Haven Airport (HVN) leaving from either of these bases.

  • New Haven is one hour ahead of Chicago. New Haven Airport is located in New Haven, which follows the UTC-4 timezone.

  • Arriving two hours before an international flight and one hour ahead of a domestic departure are golden rules for stress-free travel. Be at the airport on time to board your flight from Chicago to HVN.

  • During peak travel periods, allow for longer wait times and be there earlier. Aim for at least two hours ahead for domestic flights and as much as four hours for international journeys.

Airports in Chicago

O'Hare International Airport (ORD)

  • The journey from central Chicago to ORD takes about 55 minutes by public transport. If you ride-share, drive or take a cab, you'll cover the 40 kilometres in 35 minutes or so, depending on traffic conditions.

  • Planning to catch an early flight from Chicago to New Haven Airport? Avoid the hassle of rushing to the terminal (and sneak in some bonus sleep) by choosing one of these hotels close to O'Hare International Airport:

  • When it comes to O'Hare International Airport's on-time performance, 74.85% of flights complete their journey on time.

  • ORD is located at 10000 West O'Hare.

Chicago Midway International Airport (MDW)

  • You can book a direct Chicago to New Haven Airport (HVN) plane ticket out of Chicago Midway International Airport (MDW). Work out whether departing from MDW makes the most sense for you.

  • Take a direct flight from Chicago to HVN with Avelo Airlines. This is one of the top carriers flying this route out of MDW.

  • On the MDW to HVN route, Avelo Airlines is the airline most travellers rely on.

  • Among the carriers operating flights between Chicago Midway International Airport and New Haven Airport, Avelo Airlines has the best track record for timeliness.

  • You can reach MDW from central Chicago in about 20 minutes by car (depending on traffic). The journey by public transport takes roughly 45 minutes to travel the 19 kilometres or so.

  • Want to treat yourself to an extra night away before catching your Chicago to HVN flight? Check in to a hotel near Chicago Midway International Airport before your break officially starts. Here's where you can stay:

  • Looking at how often flights stay on schedule, Chicago Midway International Airport has an on-time arrival rate of 77.88%.

  • The address for MDW is 5700 South Cicero.

Chicago Rockford International Airport (RFD)

  • The journey to RFD from the centre of Chicago is around 4 hours 15 minutes by public transport. If you're in a car, it'll take you about 1 hour 25 minutes to cover the 137 kilometres or so.

  • Make departure day worry-free — stay close to Chicago Rockford International Airport and know you'll reach the terminal with time to spare. Get settled at one of these hotels the day before if you're catching an early Chicago to New Haven Airport flight:

  • Airports have an on-time performance rating that monitors how often flights touch down as expected. At RFD, that rate is 76.19%.

  • Chicago Rockford International Airport is located at 2 Airport Cir.

About New Haven Airport (HVN)

Getting from New Haven Airport (HVN) to central New Haven

  • New Haven Airport is about 6 kilometres from central New Haven. How long it'll take to get to the centre in a cab or car hire will depend on the time of day. Do some research before you go.

  • It typically takes 35 minutes to get there using public transport.

How to find the cheapest flights from Chicago to New Haven Airport (HVN)

  • The cheapest price we've found for a one-way ticket from Chicago to New Haven Airport is R 1,199. For a return flight on this route, the best price is R 2,421. Depending on when you book and the availability, these fares could change.

  • Snap up cheap flights from Chicago to HVN by booking one month ahead. Based on our research, that's the ideal time frame for finding a bargain.

  • Schedule your trip for June. That's the best month for landing an awesome deal on Chicago to New Haven Airport tickets. If your travel dates are flexible, use the 'Whole month' tool to find the cheapest price across every month.

  • Never miss a deal on plane tickets from Chicago to HVN by creating a Price Alert. We'll send you an email or notification on the app when fares go down.

  • Lock in a cheap flight from Chicago to New Haven Airport by using the search filters. Choose your ideal times, airlines and number of stops, then sort the results by 'Cheapest' for the best deals.

The best time to fly from Chicago to New Haven Airport (HVN)

  • August is the busiest month for flights from Chicago to New Haven Airport (HVN). Visit New Haven in May if you'd rather avoid peak season.

  • Book a Chicago to HVN plane ticket departing in July if you want to experience the city during its warmest month. Expect temperatures in New Haven to range from 17ºC (63ºF) to 29ºC (84ºF).

  • January has temperatures of between -6ºC (21ºF) and 7ºC (45ºF). Search for cheap tickets from Chicago to New Haven Airport around that time if you'd rather travel in cooler conditions.

More about New Haven

  • Once you've booked your flight from Chicago to New Haven Airport, choose a hotel that puts you where you want to be. Make one of these accommodation options your base for exploring New Haven:

  • All great adventures should include a little sightseeing. Yale Peabody Museum of Natural History, Shubert Theatre and Yale University Art Gallery are essential stops on your New Haven itinerary.

Explore more of the United States

  • New York is just one of the many cities in the United States waiting to be discovered once you've seen the sights of New Haven. Around 113 kilometres away to the south-west, its top attractions include Central Park, Manhattan Skyline and Statue of Liberty.

  • Around 241 kilometres south-west of New Haven, Philadelphia is another essential stop in the United States. Start your sightseeing at Independence Hall, Liberty Bell and Philadelphia Museum of Art.

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.