Q: What is the typical price of a round-trip flight between New York and Chicago Midway Airport?

Prices are currently low for flights on this route. Typical prices usually range from $222 to $399. The lowest price recently found on this route was $89.

Question 1

How often are flights from New York to Chicago delayed?

Accepted Answer

Historically, on average around 21% of flights between New York and Chicago have experienced a delay on any given week. The average delay length over the past 12 months has been 139 minutes.

Question 2

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

Accepted Answer

Saturday 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.

Question 3

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

Accepted Answer

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

Question 4

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

Accepted Answer

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

Question 5

What is the cheapest day to depart on your flight to Chicago Midway Airport?

Accepted Answer

According to our data, Tuesday is the cheapest day to fly to Chicago Midway Airport from New York. The lowest ticket price found for a Tuesday departure recently was $256. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Monday is the most expensive day to depart from New York because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $396.

Question 6

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

Accepted Answer

As of February 2026, prices for New York to Chicago Midway Airport flights are approximately 151% more expensive when compared to flights at the same time last year.

Question 7

What is the typical price of a round-trip flight between New York and Chicago Midway Airport?

Accepted Answer

Prices are currently low for flights on this route.Typical prices usually range from $222 to $399.
The lowest price recently found on this route was $89.

Question 8

How long does it take to fly to Chicago Midway Airport?

Accepted Answer

On average, it takes 2h 28m to fly from New York to Chicago Midway Airport if you fly out of Newark (the most popular airport in New York) and into Chicago O'Hare Intl Airport (the most popular airport in Chicago Midway Airport). If you’re flying out of New York and into Chicago O'Hare Intl Airport, then the flight time is around 2h 34m.

Question 9

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

Accepted Answer

The number of flights available between New York and Chicago Midway Airport is 35 per week as of February 2026. The most frequent departure day is Fri, with 23% of weekly flights leaving on this day.

Question 10

What is the cheapest month to fly to Chicago Midway Airport?

Accepted Answer

The month of January is, on average, the cheapest month to fly to Chicago Midway Airport from New York, with most prices found around $149. If you are unable to visit Chicago Midway Airport during the month of January, then departing from New York during the month July is also very affordable. Most momondo users find prices during this month for around $253.

Question 11

What airlines fly to Chicago Midway Airport?

Accepted Answer

Southwest, Delta and Frontier are the top three most popular airlines that fly to Chicago Midway Airport from New York according to our data. Southwest is the first choice among our users, with 66% of people opting to fly with this airline when traveling to Chicago Midway Airport. Keep in mind that there are 3 different airlines that fly to Chicago Midway Airport on a routine basis, so you have a few additional options to choose from.

Question 12

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

Accepted Answer

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

Question 13

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

Accepted Answer

According to our data, Southwest have had the least number of delays on this route over the last 12 months; with about 21% of their flights experiencing any sort of delay.

Question 14

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

Accepted Answer

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

Question 15

What is the cheapest time of day to depart on your flight to Chicago Midway Airport?

Accepted Answer

Flying to Chicago Midway Airport from New York in the evening is the least expensive time of day to depart. momondo users have found prices as low as $223 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $354. Of course, these prices can vary depending on the time of year and what airport you fly to.

Question 16

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

Accepted Answer

As of February 2026, 5 flights take off from New York and land in Chicago Midway Airport each day. The most common flight departure time for this route is 11:00AM, with 45% of daily flights taking off at noon.

Question 17

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

Accepted Answer

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

Question 18

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

Accepted Answer

Prices for flights from New York to Chicago Midway Airport were last updated today.

Question 19

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

Accepted Answer

There are 3 operators available for flights from New York to Chicago Midway Airport as of February 2026.

Question 20

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

Accepted Answer

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 New York to Chicago Midway Airport.

Question 21

What documentation or ID do you need to fly to Chicago Midway Airport?

Accepted Answer

The travel and health documents you'll need for your trip to Chicago Midway Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago Midway Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

Best Price Found	$72
Fastest flight time	2h 15m
Direct flights	Every day

Airline	Rating	Free Cancellation	Price
Frontier	PriceFrom $58	Free Cancellation	Rating 5.7 3,051 reviews	Search Frontier flights
Southwest	PriceFrom $158	Free Cancellation	Rating 8.0 4,281 reviews	Search Southwest flights
Delta	PriceFrom $186	Free Cancellation	Rating 7.9 8,174 reviews	Search Delta flights

Cheap flights from New York to Chicago from $62

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from New York to Chicago departing on 4/25. 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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How to get the cheapest flight ticket from New York to Chicago Midway Airport

What is the typical price of a round-trip flight between New York and Chicago Midway Airport?

What is the cheapest month to fly to Chicago Midway Airport?

What is the cheapest day to depart on your flight to Chicago Midway Airport?

What is the cheapest time of day to depart on your flight to Chicago Midway Airport?

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

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

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

There is only 1 cabin class available to choose from on New York to Chicago Midway 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 New York to Chicago Midway Airport flights?

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

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

As of February 2026, prices for New York to Chicago Midway Airport flights are approximately 151% more expensive when compared to flights at the same time last year.

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

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

What airlines fly to Chicago Midway Airport?

How often are flights from New York to Chicago delayed?

Historically, on average around 21% of flights between New York and Chicago have experienced a delay on any given week. The average delay length over the past 12 months has been 139 minutes.

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

Generally, flights departing in the morning tend to experience fewer delays. Flights at night 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. Sunday has historically seen more delays on average compared to the rest of the week.

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

According to our data, Southwest have had the least number of delays on this route over the last 12 months; with about 21% of their flights experiencing any sort of delay.

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

As of February 2026, 5 flights take off from New York and land in Chicago Midway Airport each day. The most common flight departure time for this route is 11:00AM, with 45% of daily flights taking off at noon.

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

The number of flights available between New York and Chicago Midway Airport is 35 per week as of February 2026. The most frequent departure day is Fri, with 23% of weekly flights leaving on this day.

How long does it take to fly to Chicago Midway Airport?

When to book flights from New York to Chicago Midway Airport

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

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How far is New York to Chicago Midway by plane?

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

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

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

What documentation or ID do you need to fly to Chicago Midway Airport?

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

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