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Fares from $79 One Way, $142 Round Trip from New Haven to Chicago

Prices starting at $142 for return flights and $79 for one-way flights to Chicago were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

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More About Flying To Chicago from New Haven

Flights from New Haven to Chicago - Frequently Asked Questions

What is the shortest flight from New Haven to Chicago?

The shortest flight from New Haven, CT (HVN-Tweed - New Haven Regional) to Chicago, IL (MDW-Midway Intl.) is 3 hours and 1 minute. Order your favorite wine from the drink cart, get stuck into your travel journal or listen to that podcast — you'll have plenty of time on this medium-haul journey.

Route Information for Flights from New Haven to Chicago

Origin Airport IATA CodeHVN
Destination Airport IATA CodeCHI
Distance780 mi
Direct Flight AirlinesAmerican Airlines, Qatar Airways, Alaska Airlines, ANA, Air New Zealand, United Airlines
Earliest Flight Arrival12:00PM UTC
Latest Flight Arrival8:52PM UTC

Find Cheap Flights from New Haven to Chicago

Tweed New Haven Regional Airport

Use Orbtiz.com to find cheap flights from New Haven to any destination. The website searches all domestic and international flights departing from New Haven to find you discount tickets. The Tweed New Haven Airport is located at 155 Burr Street, approximately four miles from downtown New Haven. Thirteen airlines service the airport-including Air Canada, American Airlines, British Airways and US Airways-taking passengers to over 130 destinations worldwide.

Parking and Transportation

If you need to leave your car at the airport while you travel, you can park it in the long-term parking lot for $7.50 per day or $37.50 per week. Payments for parking can be made with all major credit cards, cash or check. The CT Transit buses run from downtown New Haven to the airport, and the bus fare costs $3.25 per person. If you want access to a vehicle when you arrive at your destination, you can purchase a package on Orbitz.com that contains both your flight and a rental car.

Dining at the Airport

There is a small breakfast café at the airport, but it is only open between 6:30 a.m. and 11:30 a.m. If you do need to grab a snack or a drink after this time, the airport does have vending areas in the terminal. When you use Orbtiz.com to find cheap flights from New Haven, you can save money by purchasing all of the services you need in a vacation package. The website has packages available that include hotel rooms, rental vehicles and flights.

Airports in Chicago

Chicago O'Hare International Airport is located on West O'Hare, approximately 18 miles from downtown Chicago. It has hubs for every major airline that offers flights to Chicago, including American Airlines, British Airways and JetBlue. The Chicago Midway International Airport is located on South Cicero Avenue, approximately 12 miles from downtown Chicago. Seven airlines service Midway airport, including Air Tran, Delta and Southwest Airlines. Orbitz.com searches flights arriving at both airports so you get the best prices.

Transportation from the Airport

Both airports offer public transportation via Chicago's elevated train system. The tickets cost $2.25, or you can purchase an all-day pass for $5.75. Taxi services are also available from both airports. Cab fares to downtown Chicago range from $35 to $45. If you want to rent a car for the duration of your stay, Orbitz.com can reserve a vehicle for you. Both airports have onsite rental car facilities.

Weather in Chicago

Summer temperatures in Chicago range from 66 to 84 degrees Fahrenheit, and the temperatures during the winter months range from 18 to 35 degrees Fahrenheit. Chicago is prone to heavy snowfall during the winter months, so most vacationers travel to Chicago during the summer. However, if you use Orbitz.com and schedule your trip during the off-peak travel season, it's easy to find cheap flights to Chicago.

Highlights and Attractions

Orbitz.com not only helps you find cheap flights to Chicago, but can also help you purchase tickets to the Sears Tower or make reservations for guided city tours.

^Savings based on all package bookings with Flight + Hotel made on Orbitz.com from January 1, 2019 to December 31, 2019 as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.