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Cheap Flights from New York (JFK) to Chicago (MDW)

Compare New York John F. Kennedy to Chicago Midway flight deals

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

Book the best Chicago Midway fare with no extra fees

Flight deals from New York John F. Kennedy to Chicago Midway

Looking for a cheap last-minute deal or the best return flight from New York John F. Kennedy to Chicago Midway? Find the lowest prices on one-way and return tickets right here.
Chicago.$225 per passenger.Departing Sat, 4 Oct, returning Mon, 6 Oct.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from New York John F. Kennedy on Sat, 4 Oct, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departs from Chicago Midway on Mon, 6 Oct, arriving in New York John F. Kennedy.Price includes taxes and charges.From $225, select.
Chicago.$225 per passenger.Departing Wed, 29 Oct, returning Sat, 1 Nov.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from New York John F. Kennedy on Wed, 29 Oct, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departs from Chicago Midway on Sat, 1 Nov, arriving in New York John F. Kennedy.Price includes taxes and charges.From $225, select.
Chicago.$225 per passenger.Departing Sat, 1 Nov, returning Sat, 8 Nov.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from New York John F. Kennedy on Sat, 1 Nov, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departs from Chicago Midway on Sat, 8 Nov, arriving in New York John F. Kennedy.Price includes taxes and charges.From $225, select.
Chicago.$225 per passenger.Departing Fri, 5 Sep, returning Mon, 15 Sep.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from New York John F. Kennedy on Fri, 5 Sep, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departs from Chicago Midway on Mon, 15 Sep, arriving in New York John F. Kennedy.Price includes taxes and charges.From $225, select.
Chicago.$225 per passenger.Departing Fri, 26 Sep, returning Thu, 23 Oct.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from New York John F. Kennedy on Fri, 26 Sep, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departs from Chicago Midway on Thu, 23 Oct, arriving in New York John F. Kennedy.Price includes taxes and charges.From $225, select.
Chicago.$259 per passenger.Departing Wed, 27 Aug, returning Thu, 4 Sep.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from New York John F. Kennedy on Wed, 27 Aug, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departs from Chicago Midway on Thu, 4 Sep, arriving in New York John F. Kennedy.Price includes taxes and charges.From $259, select.
Chicago.$395 per passenger.Departing Sat, 23 Aug, returning Sun, 24 Aug.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from New York John F. Kennedy on Sat, 23 Aug, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departs from Chicago Midway on Sun, 24 Aug, arriving in New York John F. Kennedy.Price includes taxes and charges.From $395, select.
Chicago.$450 per passenger.Departing Sat, 6 Dec, returning Sat, 6 Dec.Return flight with Delta.Outbound indirect flight with Delta, departs from New York John F. Kennedy on Sat, 6 Dec, arriving in Chicago Midway.Inbound indirect flight with Delta, departs from Chicago Midway on Sat, 6 Dec, arriving in New York John F. Kennedy.Price includes taxes and charges.From $450, select.

Find the cheapest month to fly from New York John F. Kennedy to Chicago Midway

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like New York John F. Kennedy to Chicago Midway flights are currently cheapest in September.
Aug
from $395
Sep
from $225
Oct
from $225
Nov
from $225
Dec
from $450
Jan
from $456
Feb
from $455
Mar
from $501
Apr
from $455
May
from $456
Jun
Find prices
Jul
from $455

New York John F. Kennedy to Chicago Midway: Alternative routes

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

New York to Chicago: Flight information

The things to know before you go.
Cheapest flight found$225
Cheapest month to flySeptember

Finding cheap flights from New York John F. Kennedy to Chicago Midway: Frequently asked questions

The best price we found for a return flight from New York John F. Kennedy to Chicago Midway is $225. 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 York John F. Kennedy to Chicago Midway. But we found flights with one or more stops from $225.
As of August 2025, there are no flights flying from New York John F. Kennedy to Chicago Midway.
The cheapest month to fly from New York John F. Kennedy to Chicago Midway is usually September.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from New York John F. Kennedy Airport to Chicago Midway Airport on Friday, 26 September 2025.
No airlines currently offer direct flights between New York John F. Kennedy 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, Frontier Airlines offers the cheapest flight tickets to Chicago Midway.

Travelling from John F. Kennedy International Airport (JFK) to Chicago Midway International Airport (MDW): what you need to know

  • The timezone in Chicago is UTC-5, which is one hour behind New York.

  • Your JFK to MDW flight won't wait if you're late, so show up at the airport on time. Arrive up to one hour in advance for domestic flights and two hours ahead when you're travelling internationally.

  • Travelling during a peak month such as July? Public holidays and other popular periods can result in longer lines at security. Play it safe and get there up to four hours before an international flight and two hours before domestic departures.

  • If you'd like to break up your flight, simply uncheck 'Direct flights only' when searching for your ticket from John F. Kennedy International Airport to Chicago Midway International Airport. Here are the most popular stopovers between JFK and MDW:

    • Pittsburgh International Airport

    • Buffalo Niagara International Airport

    • Detroit Metropolitan Wayne County Airport

How to find the cheapest flights from John F. Kennedy International Airport (JFK) to Chicago Midway International Airport (MDW)

  • The cheapest price we've found for a one-way John F. Kennedy International Airport to Chicago Midway International Airport flight is $107. A round-trip plane ticket is currently $225. Depending on the availability when you book, these fares could change.

  • Don't leave everything to the last minute. You're more likely to get cheap tickets from JFK to MDW if you book ahead. Airlines often have some terrific early bird rates.

  • Getting cheap flights from John F. Kennedy International Airport to Chicago Midway International Airport is easier if you're flexible with your trip dates. Use the 'Whole month' function to see the lowest fares across the month and bag a great deal.

  • Landing cheap flights from JFK to MDW is a cinch with Price Alerts. Simply create one of these automatic alerts and we'll notify you as soon as a new deal comes up.

  • Tailor your flights using filters. Select your departure and arrival times, airlines and total journey duration. You can also sort the results by 'Cheapest,' 'Fastest' or 'Best' flights from John F. Kennedy International Airport to Chicago Midway International Airport.

Handy information about John F. Kennedy International Airport (JFK)

  • JFK's address is JFK Airport.

  • When it comes to the on-time performance of John F. Kennedy International Airport, 74.1% of flights stick to their scheduled arrival time.

  • To reach John F. Kennedy International Airport from central New York, it takes about 50 minutes by car. This depends on traffic though. It's approximately 48 kilometres from the airport to the city centre.

  • The trip on public transport takes roughly 1 hour 20 minutes.

  • Get your journey off to a stress-free start by staying near JFK. Whether you're boarding an early flight from John F. Kennedy International Airport to Chicago Midway International Airport or just don't like being rushed, these hotels are the answer:

Arriving at Chicago Midway International Airport (MDW)

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

  • The street address for MDW is 5700 South Cicero.

  • From Chicago Midway International Airport, Chicago is approximately 19 kilometres away. It takes around 20 minutes to reach the centre by car.

  • If you're travelling on public transport, expect a journey of around 45 minutes.

When to fly to Chicago Midway International Airport (MDW)

  • It's time to work out your travel dates for your flight from John F. Kennedy International Airport to Chicago Midway International Airport. July is the most popular month to head to Chicago. If you're after a more relaxed vibe, go in May.

  • Book your flight from John F. Kennedy International Airport to Chicago Midway International Airport for July if you'd like to go to Chicago during its warmest month. You can expect temperatures of between 15ºC (59ºF) and 29ºC (84ºF).

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

Explore more of United States

  • Chicago has plenty to offer, but there are so many other parts of United States you'll want to see. About 451 kilometres south-east of Chicago, a trip to Columbus will fill your itinerary to the brim. Start with attractions like Franklin Park Conservatory and Botanical Gardens, Ohio Statehouse and German Village.

  • Around 257 kilometres south-east of Chicago, Indianapolis is another essential stop in United States. Start your sightseeing at The Children's Museum of Indianapolis, Indianapolis Museum of Art and Indianapolis Zoo.

More travel options

Plan the rest of your trip from New York to Chicago

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