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

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

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

55 flights are operational weekly from Chicago Midway Airport to New York as of December 2025. The most popular departure day for this route is Fri, with 25% of flights per week taking off on this day.

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

As of December 2025, there are 7 flights per day flying from Chicago Midway Airport to New York. The most common time of day flights depart is 6:00AM, with 44% of flights taking off at noon.

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

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

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 125 minutes.

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 88% 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.

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.

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 19% 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 December 2025, 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.

$57 Cheap Flights from Chicago Midway Airport to New York in 2025/26

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One-way

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Cheap round-trip flights

Enter your travel dates to find the best prices.

7:44 am - 10:45 am

MDW

EWR

2h 01mnonstop

11:30 am - 1:01 pm

EWR

MDW

2h 31mnonstop

$104Frontier

Thu, Dec 18 - Thu, Dec 25

1:20 pm - 9:35 pm

MDW

EWR

7h 15m1 stop

6:10 am - 12:05 pm

EWR

MDW

6h 55m1 stop

$106Frontier

Wed, Jan 21 - Wed, Jan 28

5:10 pm - 1:10 am

MDW

EWR

7h 00m1 stop

10:30 pm - 12:02 am

EWR

MDW

2h 32mnonstop

$108Frontier

Wed, Jan 7 - Tue, Jan 13

4:21 pm - 10:00 am

MDW

EWR

16h 39m1 stop

10:30 pm - 12:02 am

EWR

MDW

2h 32mnonstop

$109Multiple Airlines

Sun, Jan 11 - Tue, Jan 13

1:20 pm - 9:35 pm

MDW

EWR

7h 15m1 stop

6:10 am - 12:05 pm

EWR

MDW

6h 55m1 stop

$110Frontier

Wed, Jan 21 - Wed, Jan 28

6:10 am - 9:14 pm

MDW

EWR

14h 04m2 stops

10:30 pm - 12:02 am

EWR

MDW

2h 32mnonstop

$113Multiple Airlines

Sat, Jan 10 - Thu, Jan 15

5:55 pm - 9:00 pm

MDW

LGA

2h 05mnonstop

9:00 am - 10:40 am

LGA

MDW

2h 40mnonstop

$114Southwest

Wed, Jan 14 - Thu, Jan 15

6:05 am - 9:10 am

MDW

LGA

2h 05mnonstop

9:45 pm - 11:15 pm

LGA

MDW

2h 30mnonstop

$116Southwest

Tue, Jan 27 - Wed, Feb 4

5:55 pm - 9:00 pm

MDW

LGA

2h 05mnonstop

8:20 am - 1:40 pm

LGA

MDW

6h 20m1 stop

$124Southwest

Wed, Jan 14 - Sat, Jan 17

6:05 pm - 9:10 pm

MDW

LGA

2h 05mnonstop

9:00 am - 10:40 am

LGA

MDW

2h 40mnonstop

$125Southwest

Thu, Jan 15 - Fri, Jan 16

Frontier flights from Chicago Midway Airport to New York

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

Frontier

Dec 18

MDW7:44 amChicago Midway

2h 01m

EWR10:45 amNewark

Dec 25

EWR11:30 amNewark

2h 31m

MDW1:01 pmChicago Midway

$104

Find similar

Frontier

Jan 21

MDW1:20 pmChicago Midway

7h 15m

1 stop

EWR9:35 pmNewark

Jan 28

EWR6:10 amNewark

6h 55m

1 stop

MDW12:05 pmChicago Midway

$106

Find similar

Frontier

Jan 7

MDW5:10 pmChicago Midway

7h 00m

1 stop

EWR1:10 amNewark

Jan 15

EWR10:30 pmNewark

2h 32m

MDW12:02 amChicago Midway

$108

Find similar

Delta flights from Chicago Midway Airport to New York

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

Delta

Jan 8

MDW6:14 pmChicago Midway

3h 59m

1 stop

EWR11:13 pmNewark

Jan 10

EWR6:00 amNewark

6h 05m

1 stop

MDW11:05 amChicago Midway

$183

Find similar

Delta

Jan 29

MDW10:48 amChicago Midway

4h 43m

1 stop

EWR4:31 pmNewark

Feb 2

EWR9:47 amNewark

3h 59m

1 stop

MDW12:46 pmChicago Midway

$187

Find similar

Delta

Dec 15

MDW6:40 pmChicago Midway

3h 41m

1 stop

EWR11:21 pmNewark

Jan 6

EWR6:00 amNewark

8h 09m

1 stop

MDW1:09 pmChicago Midway

$218

Find similar

momondo Fare Finder

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

Fly from

Fly to

Route

Depart

Return

Price

ChicagoNewark

MDW - EWR

MDWEWR

Chicago Midway

Thu 12/18

7:44 am-10:45 am

Nonstop2h 01m

Newark

Thu 12/25

11:30 am-1:01 pm

Nonstop2h 31m

$104

ChicagoNewark

MDW - EWR

MDWEWR

Chicago Midway

Wed 1/21

1:20 pm-9:35 pm

1 stop7h 15m

Newark

Wed 1/28

6:10 am-12:05 pm

1 stop6h 55m

$106

ChicagoNewark

MDW - EWR

MDWEWR

Chicago Midway

Wed 1/7

5:10 pm-1:10 am

1 stop7h 00m

Newark

Tue 1/13

10:30 pm-12:02 am

Nonstop2h 32m

$108

ChicagoNewark

MDW - EWR

MDWEWR

Chicago Midway

Sun 1/11

4:21 pm-10:00 am

1 stop16h 39m

Newark

Tue 1/13

10:30 pm-12:02 am

Nonstop2h 32m

$109

ChicagoNewark

MDW - EWR

MDWEWR

Chicago Midway

Wed 1/21

1:20 pm-9:35 pm

1 stop7h 15m

Newark

Wed 1/28

6:10 am-12:05 pm

1 stop6h 55m

$110

ChicagoNewark

MDW - EWR

MDWEWR

Chicago Midway

Sat 1/10

6:10 am-9:14 pm

2 stops14h 04m

Newark

Thu 1/15

10:30 pm-12:02 am

Nonstop2h 32m

$113

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Wed 1/14

5:55 pm-9:00 pm

Nonstop2h 05m

New York LaGuardia

Thu 1/15

9:00 am-10:40 am

Nonstop2h 40m

$114

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Tue 1/27

6:05 am-9:10 am

Nonstop2h 05m

New York LaGuardia

Wed 2/4

9:45 pm-11:15 pm

Nonstop2h 30m

$116

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Wed 1/14

5:55 pm-9:00 pm

Nonstop2h 05m

New York LaGuardia

Sat 1/17

8:20 am-1:40 pm

1 stop6h 20m

$124

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Thu 1/15

6:05 pm-9:10 pm

Nonstop2h 05m

New York LaGuardia

Fri 1/16

9:00 am-10:40 am

Nonstop2h 40m

$125

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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 January is another great option to travel to New York, with average flight prices from Chicago Midway Airport averaging around $191.

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 $261. 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 $377.

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 $367. 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 December 2025, prices for Chicago Midway Airport to New York flights are approximately 19% cheaper 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	$69
Fastest flight time	2h 00m
Direct flights	Every day
Airports in New York	2 airports

The best one-way flight to New York from Chicago Midway Airport in the past 72 hours is $69. The best round-trip flight deal from Chicago Midway Airport to New York found on momondo in the last 72 hours is $62.

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 2 airports near New York: Newark (EWR), 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 December 2025, 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 737-800 (14.93% of total bookings). The next most popular plane models are Boeing 737 MAX 8 (12.41%), Airbus A321neo (9.11%), and Airbus A320neo (8.89%).
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 93% of all bookings. The subsequent popular airline is Frontier at 7%.

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 $59	Free Cancellation	Rating 5.8 3,089 reviews	Search Frontier flights
Southwest	PriceFrom $157	Free Cancellation	Rating 8.0 4,253 reviews	Search Southwest flights
Delta	PriceFrom $294	Free Cancellation	Rating 7.9 8,013 reviews	Search Delta flights

Southwest Flights From Chicago Midway Airport to New York
Across 53 Southwest flights from Chicago Midway Airport to New York this week, the average price was $302, with the best Southwest deals starting from $157 round-trip. 4,252 users have rated Southwest on momondo, with an average score of 8.0/10.
Frontier Flights From Chicago Midway Airport to New York
Frontier is also a popular choice for this route. Frontier flight deals for Chicago Midway Airport to New York start from as low as $59 round-trip, depending on your selected dates, with average Frontier deals seen on momondo around $162. Frontier operates 2 flights to New York from Chicago Midway Airport in an average week. Users have rated it 5.8/10 across 3,088 reviews.

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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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Cheap flights from Chicago Midway Airport to New York from $57

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to New York departing on 2/4. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

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Frontier flights from Chicago Midway Airport to New York

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

Delta flights from Chicago Midway Airport to New York

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

momondo Fare Finder

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

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

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?

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 December 2025, prices for Chicago Midway Airport to New York flights are approximately 19% cheaper when compared to flights at the same time last year.

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

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

What airlines fly 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 125 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?

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

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 19% of their flights experiencing any sort of delay.

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

As of December 2025, there are 7 flights per day flying from Chicago Midway Airport to New York. The most common time of day flights depart is 6:00AM, with 44% of flights taking off at noon.

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

55 flights are operational weekly from Chicago Midway Airport to New York as of December 2025. The most popular departure day for this route is Fri, with 25% of flights per week taking off on this day.

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

How far is Chicago Midway to New York by plane?

When did momondo last update prices for flights from Chicago Midway Airport to New York?

How many operators does momondo search 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?

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

What is the most popular plane model from Chicago Midway Airport to New York?

What is the most popular airline from Chicago Midway Airport to 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

Frontier Flights From Chicago Midway Airport to New York

Traveling to a place near New York?

Why use momondo?

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

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

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

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

An easier way to manage your New York trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to the United States

Fly into one of these airports located in New York