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Cheap flights from New York to Chicago Midway

Compare New York 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

Map with a flight path from New York to Chicago Midway. A plane icon is halfway along the route with a label that says "Direct flight."
Direct flight

Your route at a glance

Cheapest dealC$124
Cheapest monthSeptember
Average flight duration2 hours and 29 minutes
Most popular airlineSouthwest Airlines

Flight deals from New York to Chicago Midway

Looking for a cheap last-minute deal or the best round-trip flight from New York to Chicago Midway? Find the lowest prices on one-way and round-trip tickets right here.
Chicago.C$124 per passenger.Departing Thu, Oct 9, returning Wed, Oct 15.Round-trip flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departing from New York LaGuardia on Thu, Oct 9, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departing from Chicago Midway on Wed, Oct 15, arriving in New York LaGuardia.Price includes taxes and charges.From C$124, select.
Chicago.C$124 per passenger.Departing Tue, Sep 30, returning Thu, Oct 2.Round-trip flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departing from New York Newark on Tue, Sep 30, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departing from Chicago Midway on Thu, Oct 2, arriving in New York Newark.Price includes taxes and charges.From C$124, select.
Chicago.C$132 per passenger.Departing Tue, Nov 11, returning Tue, Nov 18.Round-trip flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departing from New York Newark on Tue, Nov 11, arriving in Chicago Midway.Inbound direct flight with Frontier Airlines departing from Chicago Midway on Tue, Nov 18, arriving in New York Newark.Price includes taxes and charges.From C$132, select.
Chicago.C$132 per passenger.Departing Tue, Oct 7, returning Tue, Oct 14.Round-trip flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departing from New York Newark on Tue, Oct 7, arriving in Chicago Midway.Inbound direct flight with Frontier Airlines departing from Chicago Midway on Tue, Oct 14, arriving in New York Newark.Price includes taxes and charges.From C$132, select.
Chicago.C$132 per passenger.Departing Tue, Nov 18, returning Tue, Dec 9.Round-trip flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departing from New York Newark on Tue, Nov 18, arriving in Chicago Midway.Inbound direct flight with Frontier Airlines departing from Chicago Midway on Tue, Dec 9, arriving in New York Newark.Price includes taxes and charges.From C$132, select.
Chicago.C$132 per passenger.Departing Tue, Oct 21, returning Tue, Nov 4.Round-trip flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departing from New York Newark on Tue, Oct 21, arriving in Chicago Midway.Inbound direct flight with Frontier Airlines departing from Chicago Midway on Tue, Nov 4, arriving in New York Newark.Price includes taxes and charges.From C$132, select.
Chicago.C$160 per passenger.Departing Thu, Dec 4, returning Sun, Dec 14.Round-trip flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departing from New York Newark on Thu, Dec 4, arriving in Chicago Midway.Inbound direct flight with Frontier Airlines departing from Chicago Midway on Sun, Dec 14, arriving in New York Newark.Price includes taxes and charges.From C$160, select.
Chicago.C$171 per passenger.Departing Tue, Aug 26, returning Tue, Sep 9.Round-trip flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departing from New York LaGuardia on Tue, Aug 26, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departing from Chicago Midway on Tue, Sep 9, arriving in New York LaGuardia.Price includes taxes and charges.From C$171, select.

Find the cheapest month to fly from New York 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 to Chicago Midway flights are currently cheapest in October.
Aug
from C$287
Sep
from C$171
Oct
from C$124
Nov
from C$132
Dec
from C$160
Jan
from C$202
Feb
from C$284
Mar
from C$307
Apr
from C$300
May
from C$332
Jun
from C$323
Jul
Find prices

Direct flights from New York to Chicago Midway

New York to Chicago Midway: Alternative routes

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

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

The best price we found for a round-trip flight from New York to Chicago Midway is C$124. 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 29 minutes is the average flight time from New York to Chicago Midway.
Southwest Airlines, Frontier Airlines and United fly direct from New York to Chicago Midway.
There are 60 flights per week flying from New York to Chicago Midway, as of August 2025.
The cheapest month to fly from New York to Chicago Midway is usually September.
After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from New York to Chicago Midway Airport on Tuesday, September 30, 2025.
Yes – the average flight time is 2 hours and 29 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 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.
The cheapest airline that flies to Chicago Midway is Frontier Airlines.

Travelling from New York to Chicago Midway International Airport (MDW): What you need to know

  • Start your journey at one of New York's main airports, John F. Kennedy International Airport (JFK) or Newark Liberty International Airport (EWR). Check out your options for booking a flight from New York to Chicago Midway International Airport (MDW) jetting off from either of these.

  • Chicago Midway International Airport is located in Chicago. The city operates on the UTC-5 timezone and is one hour behind New York.

  • Arrive at the airport on time so you don't miss your flight from New York to MDW. Be there at least two hours ahead for international flights and an hour early for domestic departures to avoid the mad dash to your gate.

  • Planning to travel during a peak time like school or public holidays? Expect longer queues at check-in and security. To be on the safe side, arrive up to four hours before international flights and two hours ahead of domestic departures.

Airports in New York

John F. Kennedy International Airport (JFK)

  • Located around 48 kilometres from central New York, JFK can be reached in about 50 minutes by car, depending on traffic. The journey by public transport is roughly 1 hour 20 minutes.

  • Want a stress-free start to your trip? Stay near John F. Kennedy International Airport. Whether you're boarding an early flight from New York to Chicago Midway International Airport or want to avoid feeling rushed, these hotels offer the perfect solution:

  • Of all flights leaving John F. Kennedy International Airport, 74.1% arrive as scheduled at their destination.

  • You'll find JFK at JFK Airport.

Newark Liberty International Airport (EWR)

  • On public transport, you can travel from central New York to EWR in about 1 hour 10 minutes. The airport is roughly 24 kilometres away, and making the trip by car will take approximately 30 minutes.

  • Catching an early morning flight? You might like to check in to one of these hotels near Newark Liberty International Airport the day before your New York to MDW flight:

  • Newark Liberty International Airport has an on-time performance of 73.3%. This figure provides insight into how frequently flights departing from this airport land at their destination on schedule.

  • You'll find EWR at Building 1, Conrad Road.

LaGuardia Airport (LGA)

  • Board once and be on your way from LaGuardia Airport (LGA). Direct flights from New York to Chicago Midway International Airport can be booked from here.

  • Get ready to jet away with Southwest Airlines. It offers direct New York to MDW flight tickets from LGA.

  • The preferred airline for passengers flying between LGA and MDW is Southwest Airlines.

  • The carrier with the best on-time performance on this route is Southwest Airlines. Its services land as scheduled 75.91% of the time.

  • The journey time to LGA from the centre of New York is around 1 hour on public transport. If you're in a car, it'll take you roughly 25 minutes to cover the 18 kilometres or so.

  • Rest a little longer, move a little slower, and still make your New York to Chicago Midway International Airport flight with plenty of time to spare. These accommodation options near LaGuardia Airport make it a breeze to get to the terminal if you're jetting off early:

  • LGA has a solid on-time arrivals rating of 80.0%, so you can rely on your flight to stay on track and reach your final stop as expected.

  • You'll find LaGuardia Airport at Hangar 7 Centre.

About Chicago Midway International Airport (MDW)

  • The last thing you need is a lengthy journey to your hotel if you're getting in late on a flight from New York to Chicago Midway International Airport. Book one of these accommodation options near MDW instead:

  • Go where the road takes you with a Chicago Midway International Airport rental car. Pick up your wheels from Dollar, Hertz or Budget and see more of Chicago and beyond.

  • Booking your vehicle around four weeks in advance of your New York to Chicago Midway International Airport flight can help you secure the lowest rate.

  • You'll find MDW at 5700 South Cicero.

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

  • Chicago Midway International Airport to the centre of Chicago is around 14 kilometres. If you're taking a cab or renting a car, do some research to make your trip as smooth as possible. Journey times may vary based on traffic conditions and the time of day.

  • Travelling by public transport takes about 45 minutes.

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

  • C$80 is currently the lowest price for a one-way ticket from New York to Chicago Midway International Airport. Return flights start at C$124. These fares can change depending on demand.

  • To pick up cheap flights from New York to MDW, book in advance. Airlines typically offer lower fares when flights are first released.

  • Cheap New York to Chicago Midway International Airport tickets are easier to find when you have flexibility in your schedule. Try using the 'Whole month' search function to compare fares throughout the month and then fly out on the cheapest day.

  • Be the first to know about deals for flight tickets from New York to MDW by setting up a Price Alert. We'll send you an email or notification on the app when a lower fare pops up.

  • Nail down a great price on a flight from New York to Chicago Midway International Airport with the help of the filters. Pick your preferred departure and arrival times, airlines and number of stops. You can also sort your results by 'Best,' 'Fastest' or 'Cheapest.'

The best time to fly from New York to Chicago Midway International Airport (MDW)

  • It's time to work out your travel dates for your flight from New York to Chicago Midway International Airport (MDW). July is the most popular month to visit Chicago. If a slower pace sounds more appealing, go in May.

  • When booking your New York to MDW flight ticket, consider the weather you're most comfortable in. July is the warmest month in Chicago, with temperatures ranging from 15ºC (59ºF) to 29ºC (84ºF).

  • Search for cheap tickets from New York to Chicago Midway International Airport in January if you like travelling in cooler conditions. Temperatures are at their lowest then, ranging between -12ºC (10ºF) and 3ºC (37ºF).

More about Chicago

Explore more of the United States

  • You've done Chicago, now it's time to discover other parts of the United States. Travel about 257 kilometres south-east to Indianapolis to check off its leading sights. From 9-11 Memorial to Lucas Oil Stadium and Eiteljorg Museum, you've got a jam-packed schedule ahead.

  • If you're looking to explore another side of the United States, consider Milwaukee, about 137 kilometres north of Chicago. Richards Duplex Apartments by Frank Lloyd Wright, Miller Park and Milwaukee County Zoo are the start of reasons to visit.

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.