Cheap flights from New Haven to Chicago

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Flight deals from New Haven to Chicago

Looking for a cheap last-minute deal or the best round-trip flight from New Haven Airport to Chicago? If you want to travel next month, round-trip fares start from $221. Find the lowest prices on one-way and round-trip tickets right here.

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 August.

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$221
Cheapest month to flyAugust
Average flight time2 hrs, 51 mins
Most popular airlineAvelo Airlines
Average flights per week4

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

There are 3 airports in Chicago: Chicago Midway, Chicago O'Hare International and Chicago Rockford.
The best price we found for a round-trip flight from New Haven to Chicago is $221. 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 51 minutes is the average flight time from New Haven to Chicago.
Avelo Airlines flies direct from New Haven to Chicago.
There are 4 flights per week flying from New Haven to Chicago, as of July 2026.
The cheapest month to fly from New Haven to Chicago is usually August.
If you're flying from New Haven Airport, the cheapest airport near Chicago is Chicago O'Hare International – which is 25.5 km away from the center of Chicago. We've found flights to this airport from $221.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from New Haven Airport to Chicago on Monday, August 24, 2026.
Yes – the average flight time is 2 hours and 51 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 July, the average temperature is usually around 22°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.

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

  • The average length of a direct flight from Tweed New Haven Airport to Chicago is 2 hours 30 minutes.

  • Tweed New Haven Airport is located in New Haven. Based in the UTC-6 timezone, Chicago is one hour behind New Haven.

  • For a smooth journey, turn up at the airport two hours ahead of international flights and an hour before domestic departures. This leaves you with plenty of time to board your HVN to Chicago flight.

  • During popular months like March, you'll want to get to the airport even earlier. Arrive two hours before a domestic departure and four hours ahead of international flights whenever you're traveling during high season in general.

  • Direct Tweed New Haven Airport to Chicago tickets are available for booking. Chicago O'Hare International Airport (ORD) will be your arrival point.

  • Avelo Airlines is a well-known airline that operates direct flights from Tweed New Haven Airport to Chicago.

  • HVN is around 6 kilometers from central New Haven. If you're catching a cab, driving or ride-sharing from the center, it'll take 10 minutes or so to get there, depending on traffic. If you're planning to take public transport, expect the trip time to be around 20 minutes.

  • Looking for a hotel near HVN? If you're boarding an early flight from Tweed New Haven Airport to Chicago, these stays set you up for a seamless send-off:

  • When it comes to Tweed New Haven Airport's on-time performance, 76% of flights complete their journey on time.

  • You'll find HVN at 155 Burr Street.

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

  • The best price we've seen for a one-way Tweed New Haven Airport to Chicago flight is $128. The cheapest price for a return flight is $221. Bear in mind fares can change due to demand at the time of booking.

  • To pick up cheap flights from HVN to Chicago, book in advance. Airlines usually offer lower fares when flights first go on sale.

  • Landing cheap tickets from Tweed New Haven Airport to Chicago is easier if you're flexible with your dates. Try using the 'Whole month' search function to get the lowest prices across each month and land an epic deal.

  • Locking in a cheap flight from HVN to Chicago is a breeze with Price Alerts. All you need to do is create one of these automatic notifications and we'll get in touch as soon as a deal gets even better.

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

Airports in Chicago

Chicago O'Hare International Airport (ORD)

  • The distance from Chicago O'Hare International Airport (ORD) to central Chicago is roughly 27 kilometers. It takes around 30 minutes to get to the center driving.

  • It takes around 45 minutes if you're traveling by public transport.

  • The last thing you need is a long journey to your hotel if you're landing late on a flight from Tweed New Haven Airport to Chicago. Reserve one of these accommodation options near ORD instead:

  • For the lowest price, reserve your vehicle from Chicago O'Hare International Airport about four weeks ahead of your flight from HVN to Chicago.

  • You'll find ORD at 10000 West O'Hare.

Chicago Midway International Airport (MDW)

  • Central Chicago is about 16 kilometers from Chicago Midway International Airport (MDW). After your flight from Tweed New Haven Airport to Chicago has touched down and you've navigated your way to arrivals, the drive should take about 25 minutes.

  • Public transport will get you there in around 30 minutes.

  • Place the 'Do not disturb' sign on your door and unwind at a hotel close to MDW. Here are a few options where you can settle in after your HVN to Chicago flight:

  • Lock in the best price by booking your ride from MDW four weeks in advance. You can also expect to have a wider selection of vehicles.

  • Chicago Midway International Airport is located at 5700 South Cicero.

Chicago Rockford International Airport (RFD)

  • Head to the city center after your flight from Tweed New Haven Airport to Chicago has arrived. Central Chicago is around 145 kilometers from Chicago Rockford International Airport (RFD) and takes roughly 1 hour 40 minutes to get to by car.

  • Public transport will get you there in about 2 hours.

  • Enjoy a restful, unhurried start to your break by staying at a hotel near RFD after your HVN to Chicago flight. Take a load off after a long travel day or just give yourself time to find your footing in a new city at:

  • Rental agencies sometimes offer promotions for early bookings, so secure your ride from RFD ahead of your flight from Tweed New Haven Airport to Chicago. A bit of planning goes a long way in savings.

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

Best time to go to Chicago

  • July is the most popular month for flights from Tweed New Haven Airport to Chicago. To steer clear of the crowds, visit Chicago in January.

  • Book a Tweed New Haven Airport to Chicago plane ticket with a departure in July to experience the city during its warmest month. You can expect temperatures to range from 16ºC (61ºF) to 28ºC (82ºF).

  • Search for cheap tickets from HVN to Chicago in January if you like traveling in cooler conditions. Temperatures are at their lowest then, ranging between -12ºC (10ºF) and 3ºC (37ºF) on average.

More about Chicago

Explore more of the United States

  • You've visited Chicago, now it's time to explore more of the United States. Travel about 451 kilometers southeast to Columbus to tick off its leading sights. From Franklin Park Conservatory and Botanical Gardens to Whetstone Park / Park of Roses and Ohio Theater, you'll have a packed itinerary ahead.

  • Indianapolis is another must-experience destination in the United States and is around 257 kilometers southeast of Chicago. No trip is complete without a visit to Lucas Oil Stadium, Eiteljorg Museum and The Children's Museum of Indianapolis.

Prices shown on this page are estimated lowest prices only. Found in the last 12 days.