Cheap Flights from New Haven (HVN) to Chicago (CHIA)

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Find the cheapest month to fly from New Haven to Chicago

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

Direct flights from New Haven to Chicago

Alternative New Haven to Chicago routes

Looking for the cheapest, fastest or easiest route from New Haven to Chicago? You could fly into the following airports instead.

New Haven to Chicago: Flight information

The things to know before you go.
Cheapest flight found$329
Cheapest month to flyJune
Average flight time2 hrs, 23 mins
Most popular airlineAvelo Airlines
Average flights per week3

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

There are 4 airports in Chicago: Chicago Midway, Chicago O'Hare International, Chicago Dupage County, and Chicago Rockford.
The best price we found for a return flight from New Haven to Chicago is $329. 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 23 minutes is the average flight time from New Haven to Chicago.
Avelo Airlines flies direct from New Haven to Chicago.
As of May 2025, there are 3 flights per week flying from New Haven to Chicago.
The cheapest month to fly from New Haven to Chicago is usually May 2025.
If you're flying from New Haven Airport, the cheapest airport near Chicago is Chicago O'Hare International – which is 25.4 km away from the centre of Chicago. We've found flights into this airport from $329.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from New Haven Airport to Chicago on Sunday, 15 June 2025.
Yes – the average flight time is 2 hours and 23 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 Chicago 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 Chicago is around 40 days in advance, so don’t leave your flight to the last minute.
In May, the average temperature is usually around 13°C. July is typically the warmest month in Chicago, when it usually averages around 26°C. You can expect the least rain in January. The coldest month is January, with temperatures averaging -8°C. The rainiest month is August.
Currently, Avelo Airlines offers the cheapest flight tickets to Chicago.

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

  • Chicago is one hour behind New Haven, where New Haven Airport is located. Chicago follows the UTC-5 timezone.

  • For hassle-free travel, turn up at the airport two hours ahead of international flights and an hour before domestic departures. This will give you enough time to catch your HVN to Chicago flight.

  • If you're jetting off during a bank holiday or another peak period, give yourself extra time. A good general rule is two hours before domestic flights and up to four hours before international departures. Check-in and security lines will be longer.

  • You can book a direct New Haven Airport to Chicago ticket. Begin your trip at HVN and arrive at Chicago Midway International Airport (MDW).

  • Check out the offers from Avelo Airlines. This carrier operates direct flights from New Haven Airport to Chicago.

  • Located around 6 kilometres from the centre of New Haven, HVN can be reached in about 15 minutes by car. Travelling on public transport will take roughly 35 minutes.

  • Catching an early flight from New Haven Airport to Chicago? Avoid the hassle of rushing to the airport (and enjoy a little extra shut-eye) by choosing one of these stays near HVN:

  • When it comes to New Haven Airport's on-time performance, data shows 59.1% of flights arrive within the scheduled time frame.

  • You'll find HVN at 155 Burr Street.

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

  • $181 is the cheapest price we've found for a one-way New Haven Airport to Chicago flight. A return ticket right now is $329. Depending on the availability when you book, these fares may change.

  • Book four months before you want to travel. Pricing trends show that this is the ideal window for finding cheap flights from HVN to Chicago.

  • Organise your trip for August. That's the best month for scoring an awesome deal on New Haven Airport to Chicago tickets. If you're flexible on when you fly, use the 'Whole month' tool to access the lowest price across each month.

  • Save time looking for cheap flights from HVN to Chicago by creating a Price Alert. We'll send you an email or push notification on the app when a lower fare pops up.

  • Pick your preferred arrival and departure times, airlines and number of stops with our filters. Then, sort the results for your flight from New Haven Airport to Chicago by 'Fastest,' 'Cheapest' or 'Best.'

Airports in Chicago

O'Hare International Airport (ORD)

  • The distance from O'Hare International Airport (ORD) to central Chicago is roughly 40 kilometres. It'll take you about 35 minutes to get to the centre driving.

  • Getting there on public transport takes about 55 minutes.

  • If you're arriving on a late flight from New Haven Airport to Chicago, few things beat the convenience of staying close to the terminal. Grab your suitcases from the carousel and then be showered and snoozing not long after at one of these hotels near ORD:

  • Follow your own route with an O'Hare International Airport rental car. Pick up a set of wheels from Routes Car Rentals, Dollar or Budget and experience more of Chicago and beyond.

  • Lock in the lowest price by reserving your ride from O'Hare International Airport about four weeks before your flight from HVN to Chicago.

  • The street address for ORD is 10000 West O'Hare.

Chicago Midway International Airport (MDW)

  • Chicago Midway International Airport (MDW) is around 19 kilometres from the centre of Chicago. After your flight from New Haven Airport to Chicago, it'll take you around 20 minutes to get to the heart of the city in a ride-share or cab.

  • The trip will take roughly 45 minutes on public transport.

  • You'll find some great places to drop your things at near MDW. Unwind and get cosy after your HVN to Chicago flight at one of these perfectly located options:

  • Forget about inconvenient public transport schedules or waiting forever for a cab. Grab a Chicago Midway International Airport rental car and let the journey unfold your way. Compare rates and availability from Dollar, Hertz and Budget.

  • Secure your first choice, not your last resort. Reserving your ride from MDW four weeks ahead of time often means more savings and a wider range of vehicles.

  • You'll find Chicago Midway International Airport at 5700 South Cicero.

Chicago Rockford International Airport (RFD)

  • Chicago Rockford International Airport (RFD) is about 137 kilometres from the centre of Chicago. It takes about 1 hour 25 minutes to get to the city centre in a ride-share or cab once you've hopped off your flight from New Haven Airport to Chicago.

  • The journey will take you about 4 hours 15 minutes on public transport.

  • Stay at a hotel close to RFD and get from baggage claim to your bed in a snap. Whether you have a late HVN to Chicago flight or just want a stress-free arrival, these accommodation options put comfort right within reach:

  • Put yourself in the driver's seat of the next leg of your trip with a Chicago Rockford International Airport rental car. Budget, Alamo and National are dependable companies for booking.

  • Booking at least a few weeks ahead of your flight from New Haven Airport to Chicago is always smart. As well as better deals, you'll be able to choose the vehicle make and model you prefer at RFD.

  • Chicago Rockford International Airport's official address is 2 Airport Cir.

Best time to go to Chicago

  • Visit Chicago in peak season if you like a bustling atmosphere, but remember that hotel prices are generally higher. Alternatively, book your flights from New Haven Airport to Chicago in the off-season when prices are cheaper and it's less crowded.

  • Before booking a New Haven Airport to Chicago flight ticket, think about what kind of weather you prefer. July is the warmest month in Chicago, with temperatures ranging from 15ºC (59ºF) to 29ºC (84ºF).

  • For cooler conditions, search for a cheap ticket from HVN to Chicago in January when temperatures average between -12ºC (10ºF) and 3ºC (37ºF).

More about Chicago

Explore more of United States

  • Chicago will leave a lasting impression, but there are so many other parts of United States just waiting to be discovered. Around 451 kilometres south-east of Chicago, a visit to Columbus will keep you on the go. Start with attractions like Franklin Park Conservatory and Botanical Gardens, Ohio Statehouse and German Village.

  • If there's time to check out another corner of United States, head for Indianapolis, about 257 kilometres south-east of Chicago. The Children's Museum of Indianapolis, Indianapolis Museum of Art and Indianapolis Zoo are the start of reasons to visit.

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