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Cheap Flights from Chicago Midway to New York

Compare Chicago Midway to New York flight deals

Find the cheapest month or even day of the year to fly to New York

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Flight deals from Chicago Midway to New York

Looking for a cheap last-minute deal or the best return flight from Chicago Midway Airport to New York? If you want to travel next month, return fares start from R 2,789. Find the lowest prices on one-way and return tickets right here.
New York.R 1,352 per passenger.Departing Tue, 1 Sep.One-way flight with KLM.Outbound indirect flight with KLM, departs from Chicago Midway on Tue, 1 Sep, arriving in New York Newark.Price includes taxes and charges.From R 1,352, select.
New York.R 1,371 per passenger.Departing Tue, 28 Jul.One-way flight with KLM.Outbound indirect flight with KLM, departs from Chicago Midway on Tue, 28 Jul, arriving in New York Newark.Price includes taxes and charges.From R 1,371, select.
New York.R 1,394 per passenger.Departing Tue, 15 Sep.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 15 Sep, arriving in New York LaGuardia.Price includes taxes and charges.From R 1,394, select.
New York.R 1,394 per passenger.Departing Sat, 1 Aug.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Sat, 1 Aug, arriving in New York LaGuardia.Price includes taxes and charges.From R 1,394, select.
New York.R 1,394 per passenger.Departing Tue, 6 Oct.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 6 Oct, arriving in New York LaGuardia.Price includes taxes and charges.From R 1,394, select.
New York.R 1,399 per passenger.Departing Wed, 22 Jul.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Wed, 22 Jul, arriving in New York LaGuardia.Price includes taxes and charges.From R 1,399, select.
New York.R 1,554 per passenger.Departing Wed, 2 Dec.One-way flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Wed, 2 Dec, arriving in New York Newark.Price includes taxes and charges.From R 1,554, select.
New York.R 1,554 per passenger.Departing Sat, 7 Nov.One-way flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Sat, 7 Nov, arriving in New York Newark.Price includes taxes and charges.From R 1,554, select.
New York.R 1,719 per passenger.Departing Fri, 1 Jan.One-way flight with KLM.Outbound indirect flight with KLM, departs from Chicago Midway on Fri, 1 Jan, arriving in New York Newark.Price includes taxes and charges.From R 1,719, select.
New York.R 1,842 per passenger.Departing Wed, 12 May.One-way flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Wed, 12 May, arriving in New York Newark.Price includes taxes and charges.From R 1,842, select.
New York.R 1,842 per passenger.Departing Wed, 10 Feb.One-way flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Wed, 10 Feb, arriving in New York Newark.Price includes taxes and charges.From R 1,842, select.
New York.R 1,846 per passenger.Departing Wed, 10 Mar.One-way flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Wed, 10 Mar, arriving in New York Newark.Price includes taxes and charges.From R 1,846, select.
New York.R 1,851 per passenger.Departing Mon, 11 Jan.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Mon, 11 Jan, arriving in New York LaGuardia.Price includes taxes and charges.From R 1,851, select.
New York.R 1,855 per passenger.Departing Thu, 1 Apr.One-way flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Thu, 1 Apr, arriving in New York Newark.Price includes taxes and charges.From R 1,855, select.
New York.R 1,858 per passenger.Departing Tue, 3 Nov.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 3 Nov, arriving in New York LaGuardia.Price includes taxes and charges.From R 1,858, select.
New York.R 1,859 per passenger.Departing Sat, 6 Feb.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Sat, 6 Feb, arriving in New York LaGuardia.Price includes taxes and charges.From R 1,859, select.

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

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Chicago Midway to New York flights are currently cheapest in September.
Jul
from R 1,371
Aug
from R 1,394
Sep
from R 1,352
Oct
from R 1,394
Nov
from R 1,554
Dec
from R 1,554
Jan
from R 1,719
Feb
from R 1,842
Mar
from R 1,846
Apr
from R 1,855
May
from R 1,842
Jun
Find prices

Direct flights from Chicago Midway to New York

Alternative Chicago Midway to New York routes

Looking for the cheapest, fastest or easiest route from Chicago Midway to New York? You could fly into the following airports instead.

New York LaGuardia

13km from central New York
Closest
from R 1,394
Search flights

New York Newark

14km from central New York
Cheapest
from R 1,352
Search flights

New York John F. Kennedy

21km from central New York
from R 2,035
Search flights

Westchester County

47km from central New York
from R 2,573
Search flights

Islip

77km from central New York
from R 2,544
Search flights

Stewart International

88km from central New York
from R 2,053
Search flights

Chicago to New York: Flight information

The things to know before you go.
Cheapest flight foundR 1,352
Cheapest month to flySeptember
Average flight time2 hrs, 23 mins
Most popular airlineSouthwest Airlines
Average flights per week48

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

There are 6 airports in New York: New York LaGuardia, New York Newark, New York John F. Kennedy, Westchester County, Islip, and Stewart International.
The best price we found for a return flight from Chicago Midway to New York is R 2,789. 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 23 minutes is the average flight time from Chicago Midway to New York.
Southwest Airlines and United fly direct from Chicago Midway to New York.
As of July 2026, there are 48 flights per week flying from Chicago Midway to New York.
The cheapest month to fly from Chicago Midway to New York is usually August.
If you're flying from Chicago Midway Airport, the cheapest airport near New York is New York LaGuardia – which is 13.2 km away from the centre of New York. We've found flights into this airport from R 2,789.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Chicago Midway Airport to New York on Saturday, 1 August 2026.
Yes – the average flight time is 2 hours and 23 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 New York 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 New York is around 40 days in advance, so don’t leave your flight to the last minute.

In July, the average temperature is usually around 23°C. July is typically the warmest month in New York, when it usually averages around 27°C. You can expect the least rain in February. The coldest month is January, with temperatures averaging -4°C. The rainiest month is August.
Currently, Southwest Airlines offers the cheapest flight tickets to New York.

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

  • New York is one hour ahead of Chicago, where Chicago Midway International Airport is located. New York observes the UTC-5 timezone.

  • With 35 flights a week between the two airports, Chicago Midway International Airport (MDW) to New York LaGuardia Airport (LGA) is the most popular route. Southwest Airlines operates the earliest flight at 06:00. If you prefer to get more out of your day before flying, the last departure from MDW to LGA is with Southwest Airlines at 20:20.

  • To avoid rushing for your MDW to New York flight, leave plenty of time to check in and drop off your luggage. Arriving two hours ahead of international departures and one hour before domestic flights is the standard rule.

  • During popular months like July, it's wise to get to the airport even earlier. Plan to arrive two hours before domestic departures and four hours ahead for an international flight when you fly during high season in general.

  • Begin your trip at MDW and fly straight to Newark Liberty International Airport (EWR). That will be your arrival point when searching for Chicago Midway International Airport to New York tickets.

  • Southwest Airlines is a popular carrier that offers direct flights from Chicago Midway International Airport to New York.

  • Travelling from central Chicago to MDW takes around 30 minutes on public transport. If you drive, ride-share or get a taxi, you'll cover the 14 kilometres in 25 minutes or so, depending on traffic.

  • Searching for a hotel close to MDW? If you're catching an early flight from Chicago Midway International Airport to New York, these stays will put you moments from check-in:

  • Of all flights departing from Chicago Midway International Airport, 76% arrive on time at their destination.

  • MDW's address is 5700 South Cicero.

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

  • The best price we've found for a one-way Chicago Midway International Airport to New York flight is R 1,352. The cheapest price for a return flight is R 2,799. Remember fares may change due to demand at the time of booking.

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

  • The 'Whole month' search tool will show you the cheapest tickets from Chicago Midway International Airport to New York across the month. It's a great way to find a bargain if your travel dates aren't set in stone.

  • Stay on top of deals for cheap flights from MDW to New York by setting up a Price Alert. We'll send you an email or push notification on the app when fares go down.

  • Tailor your flights with filters. Choose your preferred departure and arrival times, total journey duration and airlines. You can also sort your results by 'Best,' 'Cheapest' or 'Fastest' flights from Chicago Midway International Airport to New York.

Airports in New York

New York John F. Kennedy International Airport (JFK)

  • New York John F. Kennedy International Airport (JFK) to central New York takes about 45 minutes by car. The centre is roughly 24 kilometres away.

  • If you're using public transport, expect a journey time of about 50 minutes.

  • The last thing you want is a lengthy journey to your hotel if you're arriving on a late flight from Chicago Midway International Airport to New York. Stay at one of these accommodation options near JFK instead:

  • For the lowest price, book your vehicle from New York John F. Kennedy International Airport around two weeks in advance of your flight from MDW to New York.

  • You'll find JFK at JFK Airport.

Newark Liberty International Airport (EWR)

  • After your flight from Chicago Midway International Airport to New York has landed, you can make your way to the city centre in around 35 minutes by car. Central New York is roughly 24 kilometres from Newark Liberty International Airport (EWR).

  • The trip will take roughly 1 hour on public transport.

  • There are some comfortable places to call home for the night near EWR. Unwind and get cosy after your MDW to New York flight at one of these well-located options:

  • Get exactly what you want. Reserving your ride from EWR three weeks in advance often means better prices and a wider selection of vehicles.

  • You can find Newark Liberty International Airport at Building 1, Conrad Road.

New York LaGuardia Airport (LGA)

  • Set your sights on the city centre after your flight from Chicago Midway International Airport to New York has arrived. Central New York is about 13 kilometres from New York LaGuardia Airport (LGA) and takes roughly 30 minutes to reach by taxi or ride-share.

  • The journey takes around 55 minutes using public transport.

  • If you don't want to make the journey to the centre, find a hotel close to LGA. Get comfortable at one of these stays after your MDW to New York flight:

  • Plan ahead and put that extra money in your pocket. Book your ride from LGA two weeks before your flight from Chicago Midway International Airport to New York for the most affordable rates.

  • New York LaGuardia Airport's official address is Hangar 7 Centre.

Best time to go to New York

  • It's time to figure out your travel dates for your flight from Chicago Midway International Airport to New York. July is the most popular month for a trip to New York. If you prefer a quieter vibe, go in December.

  • Before locking in your Chicago Midway International Airport to New York plane ticket, think about the type of weather you enjoy. July is the warmest month in New York, with temperatures ranging from 18ºC (64ºF) to 30ºC (86ºF).

  • If you want to travel in cooler conditions, search for a cheap ticket from MDW to New York in January when temperatures average between -6ºC (21ºF) and 8ºC (46ºF).

More about New York

  • Start your New York trip right by choosing the ideal place to stay. Once you've booked your flight from Chicago Midway International Airport to New York, explore our range of accommodation options including:

  • There are so many things to do and see in this city it can be difficult to know where to start. Statue of Liberty, Central Park and Metropolitan Museum of Art are major attractions which should feature on every New York itinerary.

Explore more of the United States

  • New York is always a good idea, but there are so many other corners of the United States you'll want to see. Around 129 kilometres southwest of New York, a trip to Philadelphia will keep your itinerary busy. Start with popular sights like Independence Hall, Liberty Bell and Philadelphia Museum of Art.

  • Boston is another well-known destination in the United States and is around 306 kilometres northeast of New York. No trip is complete without a visit to Museum of Fine Arts Boston, Freedom Trail and USS Constitution Museum.

Plan the rest of your trip from Chicago to New York

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