What is the cheapest airline that flies from Chicago Midway to New York?

Southwest and Delta are the most popular carriers operating from Chicago Midway to New York

How often are flights from Chicago to New York delayed?

Historically, on average around 20% of flights between Chicago and New York have experienced a delay on any given week. The average delay length over the past 12 months has been 127 minutes.

What is the most punctual flight time for Chicago to New York flights?

Generally, flights departing at night tend to experience fewer delays. Flights in the evening have, in the past, seen delays more frequently in comparison.

What day of the week experiences the fewest flight delays on this route?

Wednesday is statistically the day of the week which experiences the fewest number of delays on this flight route. Sunday has historically seen more delays on average compared to the rest of the week.

How many flights depart from Chicago Midway Airport to New York on average per week?

3 flights are operational weekly from Chicago Midway Airport to New York as of March 2026. The most popular departure day for this route is Sat, with 100% of flights per week taking off on this day.

What airlines fly to New York?

Southwest, Frontier and Delta are the top three most popular airlines that fly to New York from Chicago Midway Airport according to our data. Southwest is the first choice among our users, with 86% of people opting to fly with this airline when traveling to New York. Keep in mind that there are 3 different airlines that fly to New York on a routine basis, so you have a few additional options to choose from.

Which airline has the best punctuality record on Chicago to New York flights?

According to our data, Southwest have had the least number of delays on this route over the last 12 months; with about 20% of their flights experiencing any sort of delay.

How many operators does momondo search for flights from Chicago Midway Airport to New York?

As of March 2026, there are 3 operators available to choose from for flights from Chicago Midway Airport to New York.

How old do you have to be to fly from Chicago Midway Airport to New York?

The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago Midway Airport to New York.

What documentation or ID do you need to fly to New York?

The travel and health documents required for your trip to New York can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at New York. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

$56 Cheap Flights from Chicago Midway Airport to New York in 2026

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Find the cheapest flights from Chicago Midway Airport to New York

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Enter your travel dates to find the best prices.

7:30 am - 10:38 am

MDW

EWR

2h 08mnonstop

11:30 am - 1:00 pm

EWR

MDW

2h 30mnonstop

$95Frontier

Wed, Apr 22 - Wed, Apr 29

2:15 pm - 9:29 pm

MDW

EWR

6h 14m

1 stop

11:30 am - 1:00 pm

EWR

MDW

2h 30mnonstop

$96Frontier

Wed, Apr 22 - Wed, Apr 29

7:30 am - 10:38 am

MDW

EWR

2h 08mnonstop

11:30 am - 1:00 pm

EWR

MDW

2h 30mnonstop

$97Frontier

Wed, Apr 22 - Sun, Apr 26

2:15 pm - 9:29 pm

MDW

EWR

6h 14m

1 stop

11:30 am - 1:00 pm

EWR

MDW

2h 30mnonstop

$98Frontier

Wed, Apr 15 - Tue, Apr 21

2:15 pm - 9:29 pm

MDW

EWR

6h 14m

1 stop

11:30 am - 1:00 pm

EWR

MDW

2h 30mnonstop

$99Frontier

Wed, Apr 15 - Tue, Apr 21

7:30 am - 10:30 am

MDW

EWR

2h 00mnonstop

11:30 am - 1:02 pm

EWR

MDW

2h 32mnonstop

$100Frontier

Thu, Mar 19 - Thu, Mar 19

2:56 pm - 11:29 pm

MDW

EWR

7h 33m

1 stop

11:30 am - 1:00 pm

EWR

MDW

2h 30mnonstop

$101Multiple Airlines

Wed, Apr 8 - Tue, Apr 14

7:30 am - 10:38 am

MDW

EWR

2h 08mnonstop

11:30 am - 1:00 pm

EWR

MDW

2h 30mnonstop

$102Frontier

Wed, Apr 22 - Mon, May 4

7:30 am - 10:38 am

MDW

EWR

2h 08mnonstop

11:30 am - 1:00 pm

EWR

MDW

2h 30mnonstop

$103Frontier

Sun, May 10 - Tue, May 12

6:10 pm - 9:15 pm

MDW

LGA

2h 05mnonstop

9:45 pm - 11:10 pm

LGA

MDW

2h 25mnonstop

$137Southwest

Sat, Apr 25 - Mon, Apr 27

Delta flights from Chicago Midway Airport to New York

Our best Delta deals on Chicago Midway Airport to New York flight tickets

Delta

Mar 17

MDW1:10 pmChicago Midway

4h 20m

1 stop

JFK6:30 pmNew York John F Kennedy Intl

Apr 7

JFK7:25 amNew York John F Kennedy Intl

6h 04m

1 stop

MDW12:29 pmChicago Midway

$322

Delta

Mar 17

MDW12:47 pmChicago Midway

7h 42m

1 stop

JFK9:29 pmNew York John F Kennedy Intl

Mar 18

JFK5:35 pmNew York John F Kennedy Intl

5h 56m

1 stop

MDW10:31 pmChicago Midway

$327

Delta

Mar 17

MDW6:07 pmChicago Midway

5h 38m

1 stop

JFK12:45 amNew York John F Kennedy Intl

Mar 19

JFK7:25 amNew York John F Kennedy Intl

6h 04m

1 stop

MDW12:29 pmChicago Midway

$331

Frontier flights from Chicago Midway Airport to New York

Our best Frontier deals on Chicago Midway Airport to New York flight tickets

Frontier

Apr 22

MDW7:30 amChicago Midway

2h 08m

EWR10:38 amNewark

Apr 29

EWR11:30 amNewark

2h 30m

MDW1:00 pmChicago Midway

$95

Frontier

Apr 22

MDW2:15 pmChicago Midway

6h 14m

1 stop

EWR9:29 pmNewark

Apr 29

EWR11:30 amNewark

2h 30m

MDW1:00 pmChicago Midway

$96

Frontier

Apr 22

MDW7:30 amChicago Midway

2h 08m

EWR10:38 amNewark

Apr 26

EWR11:30 amNewark

2h 30m

MDW1:00 pmChicago Midway

$97

momondo Fare Finder

Use the filters below to find and compare flights from Chicago Midway Airport to New York that are best for you.

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Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoNewark

MDW - EWR

MDWEWR

Chicago Midway

Wed 4/22

7:30 am-10:38 am

Nonstop2h 08m

Newark

Wed 4/29

11:30 am-1:00 pm

Nonstop2h 30m

$95

ChicagoNewark

MDW - EWR

MDWEWR

Chicago Midway

Wed 4/22

2:15 pm-9:29 pm

1 stop6h 14m

Newark

Wed 4/29

11:30 am-1:00 pm

Nonstop2h 30m

$96

ChicagoNewark

MDW - EWR

MDWEWR

Chicago Midway

Wed 4/22

7:30 am-10:38 am

Nonstop2h 08m

Newark

Sun 4/26

11:30 am-1:00 pm

Nonstop2h 30m

$97

ChicagoNewark

MDW - EWR

MDWEWR

Chicago Midway

Wed 4/15

2:15 pm-9:29 pm

1 stop6h 14m

Newark

Tue 4/21

11:30 am-1:00 pm

Nonstop2h 30m

$98

ChicagoNewark

MDW - EWR

MDWEWR

Chicago Midway

Wed 4/15

2:15 pm-9:29 pm

1 stop6h 14m

Newark

Tue 4/21

11:30 am-1:00 pm

Nonstop2h 30m

$99

ChicagoNewark

MDW - EWR

MDWEWR

Chicago Midway

Thu 3/19

7:30 am-10:30 am

Nonstop2h 00m

Newark

Thu 3/19

11:30 am-1:02 pm

Nonstop2h 32m

$100

ChicagoNewark

MDW - EWR

MDWEWR

Chicago Midway

Wed 4/8

2:56 pm-11:29 pm

1 stop7h 33m

Newark

Tue 4/14

11:30 am-1:00 pm

Nonstop2h 30m

$101

ChicagoNewark

MDW - EWR

MDWEWR

Chicago Midway

Wed 4/22

7:30 am-10:38 am

Nonstop2h 08m

Newark

Mon 5/4

11:30 am-1:00 pm

Nonstop2h 30m

$102

ChicagoNewark

MDW - EWR

MDWEWR

Chicago Midway

Sun 5/10

7:30 am-10:38 am

Nonstop2h 08m

Newark

Tue 5/12

11:30 am-1:00 pm

Nonstop2h 30m

$103

Quickest round-trip

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Sat 4/25

6:10 pm-9:15 pm

Nonstop2h 05m

New York LaGuardia

Mon 4/27

9:45 pm-11:10 pm

Nonstop2h 25m

$137

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from Chicago Midway Airport to New York

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Airlines

Delays

Other information

What is the cheapest month to fly to New York?

The cheapest month to fly to New York from Chicago Midway Airport is in October. Flight prices, which tend to average around $167, are often lower during this time because this is during the off-season. The month of August is another great option to travel to New York, with average flight prices from Chicago Midway Airport averaging around $202.

What is the cheapest day to depart on your flight to New York?

The cheapest day to depart from Chicago Midway Airport to New York is on a Thursday when prices can be found for as low as $257. On the other hand, Sunday is the most expensive day to depart from Chicago Midway Airport because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $368.

What is the cheapest time of day to depart on your flight to New York?

Our most recent data shows that the best time of day to fly to New York is in the evening. Flights from Chicago Midway Airport to New York during this time can be as low as $229. Flights to New York are more costly at noon, with an average ticket price of $370. Departure times at noon fall within the peak daily travel times, which is why tickets can be more expensive.

What is the cheapest Chicago Midway to New York flight route?

Fly from Chicago Midway to Newark for the best Chicago Midway - New York flight prices

What cabin class options are available on Chicago Midway to New York flights?

There is only 1 cabin class available to choose from on Chicago Midway to New York flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Chicago Midway Airport to New York flights?

No. A direct flight is the cheapest option for a flight between Chicago Midway Airport to New York.

How have Chicago Midway Airport to New York flight prices changed over time?

As of March 2026, prices for Chicago Midway Airport to New York flights are approximately 2% more expensive when compared to flights at the same time last year.

When to book flights from Chicago Midway Airport to New York

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago Midway Airport to New York according to our flight data. Find out which month and days have the cheapest flights.

Estimated round-trip price

Cheap Chicago Midway Airport to New York (MDW to NYC) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to New York

Best Price Found	$27
Fastest flight time	2h 00m
Direct flights	Every day
Airports in New York	3 airports

The best one-way flight to New York from Chicago Midway Airport in the past 72 hours is $27. The best round-trip flight deal from Chicago Midway Airport to New York found on momondo in the last 72 hours is $56.

The fastest flight from Chicago Midway Airport to New York takes 2h 00m

Direct flights go from Chicago Midway Airport to New York every day.

There are 3 airports in New York. From Chicago Midway Airport there are direct flights to New York LaGuardia (LGA).

Search flight deals

How far is Chicago Midway to New York by plane?
The distance between Chicago Midway and New York is about 716.7 mi. Flights usually cover this in 2h 00m, depending on flying conditions and air traffic around both airports.
When did momondo last update prices for flights from Chicago Midway Airport to New York?
Prices for flights from Chicago Midway Airport to New York refresh daily.
How many operators does momondo search for flights from Chicago Midway Airport to New York?
As of March 2026, there are 3 operators available to choose from for flights from Chicago Midway Airport to New York.
How old do you have to be to fly from Chicago Midway Airport to New York?
The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago Midway Airport to New York.
What documentation or ID do you need to fly to New York?
The travel and health documents required for your trip to New York can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at New York. We always recommend checking with your airline or a trusted third party such as IATA to get advice.
What is the most popular plane model from Chicago Midway Airport to New York?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Chicago Midway Airport to New York is Boeing 737 MAX 8 (14.22% of total bookings). The next most popular plane models are Boeing 737-800 (12.78%), Airbus A320-100/200 (10.66%), and Airbus A321neo (8.45%).
What is the most popular airline from Chicago Midway Airport to New York?
momondo data reveals that the most frequently booked airline on the route from Chicago Midway Airport to New York is Southwest, representing 85% of all bookings. The subsequent popular airlines are Frontier at 10% and United Airlines at 5%.

Best airlines flying from Chicago Midway Airport to New York

Compare and see reviews for airlines that fly from Chicago Midway Airport to New York with momondo

Airline	Rating	Free Cancellation	Price
Frontier	PriceFrom $56	Free Cancellation	Rating 5.7 3,039 reviews	Search Frontier flights
Southwest	PriceFrom $163	Free Cancellation	Rating 8.0 4,311 reviews	Search Southwest flights
Delta	PriceFrom $176	Free Cancellation	Rating 7.9 8,270 reviews	Search Delta flights

Southwest Flights From Chicago Midway Airport to New York
Across 3 Southwest flights from Chicago Midway Airport to New York this week, the average price was $302, with the best Southwest deals starting from $163 round-trip. 4,311 users have rated Southwest on momondo, with an average score of 8.0/10.

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Why use momondo?

Why should I use momondo to find a flight deal from Chicago to New York?

It is quick and easy to find Chicago to New York flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to New York that suits you.

Can I find flights from Chicago to New York with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to New York from Chicago with this policy.

How can momondo help me find flights from Chicago to New York?

momondo helps you find the best flight between Chicago and New York by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

I’m not ready to book a flight from Chicago to New York right now. Can momondo alert me if prices change?

Of course. momondo tracks the price of Chicago to New York flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

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Delta flights from Chicago Midway Airport to New York

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Our best Frontier deals on Chicago Midway Airport to New York flight tickets

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Use the filters below to find and compare flights from Chicago Midway Airport to New York that are best for you.

See travel insights to New York from

How to get the cheapest flight ticket from Chicago Midway Airport to New York

What is the cheapest month to fly to New York?

What is the cheapest day to depart on your flight to New York?

What is the cheapest time of day to depart on your flight to New York?

What is the cheapest Chicago Midway to New York flight route?

What cabin class options are available on Chicago Midway to New York flights?

Can stopping save me money on Chicago Midway Airport to New York flights?

How have Chicago Midway Airport to New York flight prices changed over time?

What is the cheapest airline that flies from Chicago Midway to New York?

What airlines fly to New York?

How often are flights from Chicago to New York delayed?

What is the most punctual flight time for Chicago to New York flights?

What day of the week experiences the fewest flight delays on this route?

Which airline has the best punctuality record on Chicago to New York flights?

How many flights depart from Chicago Midway Airport to New York on average per week?

When to book flights from Chicago Midway Airport to New York

Cheap Chicago Midway Airport to New York (MDW to NYC) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to New York

Best Price Found

Fastest flight time

Direct flights

Airports in New York

Best airlines flying from Chicago Midway Airport to New York

Compare and see reviews for airlines that fly from Chicago Midway Airport to New York with momondo

Southwest Flights From Chicago Midway Airport to New York

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Airports listed have a maximum distance of 13.6 mi from New York

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List of cabin classes available on flights landing in New York. Availability may vary depending on flight origin and airline.

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