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Cheap Flights from New Haven (HVN) to Chicago Midway (MDW)

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Find the cheapest month or even day of the year to fly to Chicago Midway

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Flight deals from New Haven to Chicago Midway

Looking for a cheap last-minute deal or the best return flight from New Haven to Chicago Midway? Find the lowest prices on one-way and return tickets right here.
Chicago.£228 per passenger.Departing Sun, 8 Mar, returning Thu, 12 Mar.Return flight with Breeze Airways and Frontier Airlines.Outbound indirect flight with Breeze Airways, departs from New Haven on Sun, 8 Mar, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departs from Chicago Midway on Thu, 12 Mar, arriving in New Haven.Price includes taxes and charges.From £228, select.
Chicago.£232 per passenger.Departing Fri, 24 Apr, returning Sun, 26 Apr.Return flight with Breeze Airways and Frontier Airlines.Outbound indirect flight with Breeze Airways, departs from New Haven on Fri, 24 Apr, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departs from Chicago Midway on Sun, 26 Apr, arriving in New Haven.Price includes taxes and charges.From £232, select.
Chicago.£380 per passenger.Departing Sat, 28 Feb, returning Sat, 7 Mar.Return flight with Breeze Airways and Frontier Airlines.Outbound indirect flight with Breeze Airways, departs from New Haven on Sat, 28 Feb, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departs from Chicago Midway on Sat, 7 Mar, arriving in New Haven.Price includes taxes and charges.From £380, select.
Chicago.£615 per passenger.Departing Thu, 16 Jul, returning Sun, 19 Jul.Return flight with Breeze Airways and Frontier Airlines.Outbound indirect flight with Breeze Airways, departs from New Haven on Thu, 16 Jul, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departs from Chicago Midway on Sun, 19 Jul, arriving in New Haven.Price includes taxes and charges.From £615, select.
Chicago.£731 per passenger.Departing Wed, 25 Feb, returning Thu, 26 Feb.Return flight with Breeze Airways and Frontier Airlines.Outbound indirect flight with Breeze Airways, departs from New Haven on Wed, 25 Feb, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departs from Chicago Midway on Thu, 26 Feb, arriving in New Haven.Price includes taxes and charges.From £731, select.

Find the cheapest month to fly from New Haven to Chicago Midway

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like New Haven to Chicago Midway flights are currently cheapest in March.
Feb
from £731
Mar
from £228
Apr
from £232
May
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Jun
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Jul
from £615
Aug
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Sep
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Oct
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Nov
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Dec
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Jan
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New Haven to Chicago Midway: Alternative routes

Compare routes from New Haven to Chicago below. You may find an airport to fly into that's cheaper, faster, or easier than Chicago Midway.

Chicago Midway

9 miles from central Chicago
Closest
from £228
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Chicago O'Hare International

16 miles from central Chicago
Cheapest
from £150
Search flights

Chicago Dupage County

32 miles from central Chicago
Search flights

Chicago Rockford

78 miles from central Chicago
from £230
Search flights

New Haven to Chicago: Flight information

The things to know before you go.
Cheapest flight found£228
Cheapest month to flyMarch

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

The best price we found for a return flight from New Haven to Chicago Midway is £228. 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.
Currently, there are no airlines that fly direct from New Haven to Chicago Midway. But we found flights with one or more stops from £228.
As of February 2026, there are no flights flying from New Haven to Chicago Midway.
The cheapest month to fly from New Haven to Chicago Midway is usually March.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from New Haven Airport to Chicago Midway Airport on Sunday, 8 March 2026.
No airlines currently offer direct flights between New Haven Airport and Chicago Midway Airport. Most routes have one or more stops.
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 Midway 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.
Currently, Breeze Airways offers the cheapest flight tickets to Chicago Midway.

Flying from New Haven Airport (HVN) to Chicago Midway International Airport (MDW): what you need to know

  • Around 2 hours 25 minutes is how long you can expect to be in the air on a direct flight from New Haven Airport to Chicago Midway International Airport.

  • Chicago's timezone is UTC-5, which makes Chicago one hour behind New Haven.

  • Leave plenty of time to catch your HVN to MDW flight. It's generally best to arrive two hours before international departures and an hour ahead for domestic flights.

  • You'll likely experience bigger queues in popular months such as August. Arriving up to four hours ahead of international flights and two hours for domestic departures is a wise move.

  • Avelo Airlines is your gateway to exploring Chicago (and maybe even some other great corners of United States!). Browse the direct flights from New Haven Airport to Chicago Midway International Airport offered by this popular airline.

  • The airline that serves the most passengers on this route is Avelo Airlines.

  • The carrier with the most consistent on-time arrivals for HVN to MDW flights is Avelo Airlines.

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

  • £70 is currently the best price for a one-way New Haven Airport to Chicago Midway International Airport flight. Return flights start at £228. These prices may change based on availability and demand.

  • To score cheap tickets from HVN to MDW, book your journey nine months before your departure date.

  • The cheapest month for flights from New Haven Airport to Chicago Midway International Airport is August. Use the 'Whole month' tool to see the lowest prices if you have a flexible travel schedule.

  • Snapping up cheap flights from HVN to MDW is a breeze with Price Alerts. Simply set up one of these automatic alerts and we'll get in touch when there's a better deal.

  • Choose your ideal arrival and departure times, airlines and number of stops with the filters. Alternatively, sort your results by 'Cheapest' to see the best deals on flights from New Haven Airport to Chicago Midway International Airport.

Handy information about New Haven Airport (HVN)

  • HVN is located at 155 Burr Street.

  • Of the departures from New Haven Airport, 59.1% land on time at their destination.

  • Central New Haven to New Haven Airport is around 6 miles. Depending on traffic, it'll take about 15 minutes to get there if you're driving, catching a cab or ride-sharing.

  • The journey on public transport will take about 35 minutes.

  • Get your break off to a stress-free start by staying near HVN. Whether you've booked an early flight from New Haven Airport to Chicago Midway International Airport or just don't want to be rushed, these stays have you covered:

Arriving at Chicago Midway International Airport (MDW)

  • If you're landing on a late New Haven Airport to Chicago Midway International Airport flight, nothing tops the convenience of staying near the terminal. Pick up your bags from the carousel and then be showered and sleeping not long after at one of these accommodation options near MDW:

  • Pick up a Chicago Midway International Airport rental car and explore Chicago and beyond with your own set of wheels. Dollar, Hertz and Budget are popular outlets to choose from here.

  • Lock in the best rate by booking your vehicle from Chicago Midway International Airport about four weeks before your departure date.

Getting from Chicago Midway International Airport (MDW) to central Chicago

  • You'll find MDW at 5700 South Cicero.

  • From Chicago Midway International Airport, Chicago is approximately 12 miles away. It takes around 20 minutes to get to the centre driving.

  • When travelling by public transport, expect a journey of roughly 45 minutes.

When to fly to Chicago Midway International Airport (MDW)

  • The quietest month for a flight from New Haven Airport to Chicago Midway International Airport is May, while July is the most popular. Choose the best time to go to Chicago based on whether you prefer a faster pace or a more relaxed vibe.

  • Book your flight from New Haven Airport to Chicago Midway International Airport for July if you want to visit Chicago during its warmest month. Expect temperatures of between 15ºC (59ºF) and 29ºC (84ºF).

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

Explore more of United States

  • Columbus is just one of the many cities in United States waiting to be explored once you've taken in the sights of Chicago. Around 280 miles away to the south-east, popular attractions include Franklin Park Conservatory and Botanical Gardens, Ohio Statehouse and German Village.

  • Around 160 miles south-east of Chicago, Indianapolis is another favourite stop in United States. Experience major highlights starting with The Children's Museum of Indianapolis, Indianapolis Museum of Art and Indianapolis Zoo.

Plan the rest of your trip from New Haven to Chicago

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