Skyscanner home

Cheap Flights from Chicago Midway (MDW) to New York (NYCA)

Compare Chicago Midway to New York flight deals

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

Book the best New York fare with no extra fees

Flight deals from Chicago Midway Airport 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 £56. Find the lowest prices on one-way and return tickets right here.
New York.£20 per passenger.Departing Thu, 30 Apr.One-way flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departs from Chicago Midway on Thu, 30 Apr, arriving in New York Newark.Price includes taxes and charges.From £20, select.
New York.£21 per passenger.Departing Fri, 1 May.One-way flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departs from Chicago Midway on Fri, 1 May, arriving in New York Newark.Price includes taxes and charges.From £21, select.
New York.£63 per passenger.Departing Wed, 3 Jun.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago Midway on Wed, 3 Jun, arriving in New York Newark.Price includes taxes and charges.From £63, select.
New York.£65 per passenger.Departing Wed, 2 Sep.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago Midway on Wed, 2 Sep, arriving in New York Newark.Price includes taxes and charges.From £65, select.
New York.£67 per passenger.Departing Wed, 1 Jul.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Wed, 1 Jul, arriving in New York LaGuardia.Price includes taxes and charges.From £67, select.
New York.£71 per passenger.Departing Tue, 11 Aug.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago Midway on Tue, 11 Aug, arriving in New York Newark.Price includes taxes and charges.From £71, select.
New York.£71 per passenger.Departing Mon, 1 Jun.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Mon, 1 Jun, arriving in New York LaGuardia.Price includes taxes and charges.From £71, select.
New York.£77 per passenger.Departing Tue, 23 Feb.One-way flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Tue, 23 Feb, arriving in New York Newark.Price includes taxes and charges.From £77, select.
New York.£77 per passenger.Departing Tue, 1 Dec.One-way flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Tue, 1 Dec, arriving in New York Newark.Price includes taxes and charges.From £77, select.
New York.£77 per passenger.Departing Tue, 10 Nov.One-way flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Tue, 10 Nov, arriving in New York Newark.Price includes taxes and charges.From £77, select.
New York.£78 per passenger.Departing Tue, 6 Oct.One-way flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Tue, 6 Oct, arriving in New York Newark.Price includes taxes and charges.From £78, select.
New York.£78 per passenger.Departing Fri, 8 Jan.One-way flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Fri, 8 Jan, arriving in New York Newark.Price includes taxes and charges.From £78, select.
New York.£101 per passenger.Departing Wed, 16 Sep.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Wed, 16 Sep, arriving in New York LaGuardia.Price includes taxes and charges.From £101, select.
New York.£101 per passenger.Departing Wed, 28 Oct.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Wed, 28 Oct, arriving in New York LaGuardia.Price includes taxes and charges.From £101, select.
New York.£104 per passenger.Departing Wed, 5 Aug.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Wed, 5 Aug, arriving in New York LaGuardia.Price includes taxes and charges.From £104, 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 April.
Apr
from £20
May
from £21
Jun
from £63
Jul
from £67
Aug
from £71
Sep
from £65
Oct
from £78
Nov
from £77
Dec
from £77
Jan
from £78
Feb
from £77
Mar
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

8 miles from central New York
Closest
from £51
Search flights

New York Newark

9 miles from central New York
Cheapest
from £20
Search flights

New York John F. Kennedy

13 miles from central New York
from £53
Search flights

Westchester County

29 miles from central New York
from £101
Search flights

Islip

48 miles from central New York
from £72
Search flights

Stewart International

55 miles from central New York
from £94
Search flights

Chicago to New York: Flight information

The things to know before you go.
Cheapest flight found£20
Cheapest month to flyApril
Average flight time2 hrs, 7 mins
Most popular airlineSouthwest Airlines
Average flights per week46

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 £41. 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 7 minutes is the average flight time from Chicago Midway to New York.
Southwest Airlines and Frontier Airlines fly direct from Chicago Midway to New York.
As of April 2026, there are 46 flights per week flying from Chicago Midway to New York.
The cheapest month to fly from Chicago Midway to New York is usually April.
If you're flying from Chicago Midway Airport, the cheapest airport near New York is New York Newark – which is 8.8 miles away from the centre of New York. We've found flights into this airport from £41.
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 Wednesday, 22 April 2026.
Yes – the average flight time is 2 hours and 7 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 April, the average temperature is usually around 9°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, Frontier Airlines offers the cheapest flight tickets to New York.

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

  • Chicago Midway International Airport is located in Chicago. Following the UTC-4 timezone, New York is one hour ahead of Chicago.

  • Chicago Midway International Airport (MDW) to LaGuardia Airport (LGA) is the most popular route, with 27 weekly flights to choose from. If you have things to do before leaving, the last flight from MDW to LGA is with Southwest Airlines at 20:20. Opt for the first departure operated by Southwest Airlines at 06:00 if you want to get on your way earlier.

  • To avoid rushing for your MDW to New York flight, allow plenty of time to check in and find your gate. Arriving two hours before international departures and an hour before domestic flights is the general rule.

  • Delays at check-in and security are more likely if you're flying during high season, so give yourself some extra breathing space. A good rule for peak times? Arrive up to four hours ahead for international flights and at least two hours for domestic departures.

  • Direct Chicago Midway International Airport to New York tickets are available for booking. LaGuardia Airport (LGA) is where you'll complete your journey.

  • Get on board with Southwest Airlines. This well-known carrier offers direct flights from Chicago Midway International Airport to New York.

  • Located around 9 miles from the centre of Chicago, MDW can be reached in about 20 minutes by car. The journey on public transport takes roughly 45 minutes.

  • Want a hassle-free start to your journey? Stay near MDW. Whether you're boarding an early flight from Chicago Midway International Airport to New York or don't want departure day to feel hectic, these hotels are worth a look:

  • When it comes to Chicago Midway International Airport's on-time performance, 77.88% of flights arrive within the expected time frame.

  • The address for MDW is 5700 South Cicero.

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

  • £20 is the lowest price we've seen for a one-way Chicago Midway International Airport to New York flight. A return ticket right now is £41. Depending on when you want to go and the availability, these fares could change.

  • Book one month before you want to fly. Research on pricing trends suggests this is the ideal window for finding cheap flights from MDW to New York.

  • Plan your trip for May. That's the best month for landing an incredible deal on Chicago Midway International Airport to New York tickets. If you're flexible with your travel dates, use the 'Whole month' tool to find the cheapest price across each month.

  • Cut down on the time spent looking for cheap flights from MDW to New York by setting up a Price Alert. You'll receive an email or push notification on the app when a special offer becomes available.

  • Select your ideal arrival and departure times, number of stops and airlines with our filters. Then, sort the results for your flight from Chicago Midway International Airport to New York by 'Fastest,' 'Cheapest' or 'Best.'

Airports in New York

John F. Kennedy International Airport (JFK)

  • John F. Kennedy International Airport (JFK) to the centre of New York takes about 50 minutes by car. The centre is roughly 30 miles away.

  • Travelling by public transport takes about 1 hour 20 minutes.

  • If you're arriving on a late flight from Chicago Midway International Airport to New York, few things beat the convenience of staying near the terminal. Collect your bags from the carousel and then be showered and sleeping soon after at one of these accommodation options near JFK:

  • Pick up a John F. Kennedy International Airport rental car and discover New York and beyond with your own set of wheels. Budget, Dollar and Sixt are well-known companies to choose from here.

  • Lock in the best deal by booking your ride from John F. Kennedy International Airport about two weeks ahead of your flight from MDW to New York.

  • JFK is located at JFK Airport.

Newark Liberty International Airport (EWR)

  • The centre of New York is about 15 miles from Newark Liberty International Airport (EWR). After your flight from Chicago Midway International Airport to New York has hit the runway and you've made your way out of the airport, the drive should be around 30 minutes.

  • You can expect the journey to take about 1 hour 10 minutes on public transport.

  • There are some comfortable places to drop your things at near EWR. Kick back and get cosy after your MDW to New York flight at any of these perfectly located options:

  • Forget about inconvenient public transport timetables or cab lines. Pick up a Newark Liberty International Airport rental car and take your trip in whatever direction you choose. Compare rates and availability from Dollar, Budget and Thrifty.

  • Avoid paying extra. Securing your ride three weeks ahead of your arrival at EWR will help you stay within budget.

  • Newark Liberty International Airport is located at Building 1, Conrad Road.

LaGuardia Airport (LGA)

  • Step off your flight from Chicago Midway International Airport to New York and make your way to your hotel or start taking in the sights right away. Central New York is around 11 miles from LaGuardia Airport (LGA) and typically takes 25 minutes to reach driving.

  • If you go by public transport, the journey will take you about 1 hour.

  • Check in to a hotel close to LGA and get from baggage claim to bedtime in a flash. Whether you're coming in on a late MDW to New York flight or just want to keep your travel plans simple, these stays put comfort right within reach:

  • Start your trip without stressing over how to get to your next stop with a LaGuardia Airport rental car. Book your ideal wheels with reliable companies here like Dollar, Ace Rent a Car and Thrifty.

  • About two weeks before your flight from Chicago Midway International Airport to New York is a good time to secure your ride from LGA. You're more likely to lock in a better rate or catch some early booking discounts.

  • The street address for LaGuardia Airport is Hangar 7 Centre.

Best time to go to New York

  • Carefully consider your trip dates before locking in your flight from Chicago Midway International Airport to New York. The city comes alive during peak season, but hotel prices are typically higher and attractions can be busy. Visit New York in low season if you want a quieter vibe.

  • The warmest month in New York is July, with temperatures ranging between 18ºC (64ºF) and 30ºC (86ºF). Book your Chicago Midway International Airport to New York plane ticket then if that's the weather you find most pleasant.

  • If you want 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. After booking your flight from Chicago Midway International Airport to New York, browse our range of hotels including:

  • There are so many things to explore in this city it can be tricky to work out where to start. Central Park, Statue of Liberty and Empire State Building are major attractions which should be on every New York itinerary.

Explore more of United States

  • You've visited New York, now it's time to discover other corners of United States. Travel about 80 miles south-west to Philadelphia to tick off its top sights. From Liberty Bell to Independence Hall and Philadelphia Museum of Art, you'll have a packed itinerary ahead.

  • Boston is another well-known destination in United States and is around 190 miles north-east of New York. No journey is complete without a visit to Freedom Trail, Museum of Fine Arts Boston and Boston Tea Party Ships & 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 45 days.