How long is the flight from New York to Chicago Midway Airport?

There are many flights that can get you from New York to Chicago Midway Airport in 2h 25m. Fly via Frontier, Southwest, or Delta to get the fastest option. New York and Chicago Midway Airport are separated by a distance of 722 mi. This flight may include one or multiple stops.

What are the cheapest airlines flying from New York to Chicago Midway Airport round-trip?

Cheapflights users have booked flights from New York to Chicago Midway Airport round-trip from $80. Other airlines that can offer you cheap pricing are Spirit Airlines, from $92, and Southwest, from $156. Frontier is priced at 73% lower than the current average price of a flight leaving 3 months from now.

What are the cheapest airlines to fly from New York to Chicago Midway Airport one-way?

For one-way options, check prices for Frontier. According to our data, you can fly for as low as $65. Users have also found prices from $69 and $89 on Southwest and Delta, respectively.

How far ahead should I book a flight from New York to Chicago Midway Airport?

The price you pay for your flight from New York to Chicago Midway Airport may vary depending on when you book. For the best chance of a lower fare, look to book 57 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

What is the cheapest month to book a flight from New York to Chicago Midway Airport?

Currently, November is the cheapest month in which you can book a flight from New York to Chicago Midway Airport (average of $54). Flying from New York to Chicago Midway Airport in August is currently the most expensive (average of $194). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest day to fly from New York to Chicago Midway Airport?

Travelers seeking maximum savings on their New York to Chicago Midway Airport flight should consider departing on Wednesday evenings when fares are most often at their lowest. Saturday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

In terms of precipitation, rainfall in Chicago Midway Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 1.7 in.

If weather is an important factor for your trip to Chicago Midway Airport, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

What are the most popular routes from New York to Chicago Midway Airport?

While some choose either New York LaGuardia - Chicago Midway or Newark - Chicago Midway, New York John F Kennedy Intl - Chicago Midway is the most popular route from New York to Chicago Midway Airport.

What are the most popular airlines that fly from New York to Chicago Midway Airport?

Before booking your flight from New York to Chicago Midway Airport check out the most popular airlines for this route: Southwest, Delta or Frontier.

What is the cheapest time of day to fly from NYC to MDW?

It’s optimal to fly from New York to Chicago Midway Airport in the evening. By choosing this option you can save up to 52% on the cost of your flight, compared to a flight at noon.

Most accurate provider : When it comes to deals on New York-Chicago Midway Airport flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on New York-Chicago Midway Airport flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from New York-Chicago Midway Airport flight searches over the past month and is updated monthly.

Most trusted provider : When it comes to deals on New York-Chicago Midway Airport flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for New York-Chicago Midway Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Can I find deals for flights from New York to Midway that include hotel bookings?

Yes. In addition to deals on New York to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

How can I find direct flights from New York to Midway?

After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from New York to Midway.

Can I find deals for business class flights from New York to Midway?

Yes. Cheapflights offers flight deals from New York to Midway by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

$64+ Flights from New York, NY to Chicago Midway Airport

Most accurate provider	eDreams 3 stars
Most trusted provider	eDreams 3 stars
Round-trip from	$110 (Mytrip)
One-way from	$64 (Trip.com)
Popular in	December
Cheapest in	January
Average price	$309
Good round-trip deal	$82 or less
Good one-way deal	$58 or less

Provider	Price Accuracy	Trust Score*
Expedia	Price Accuracy2 stars	Trust Score*3 stars
eDreams	Price Accuracy3 stars	Trust Score*3 stars
FlightHub	Price Accuracy3 stars	Trust Score*1 star
Ovago	Price Accuracy2 stars	Trust Score*2 stars
Cheapflightsfares	Price Accuracy3 stars	Trust Score*2 stars

LGA offers free Wi-Fi with a strong signal throughout, perfect for accessing digital boarding passes and staying connected from check-in to boarding.

Airline	Cheapest	Average	Flexibility	On-time
Frontier	Cheapest$80	Average$221	FlexibilityNo cancel fee	On-time62%
Spirit Airlines	Cheapest$92	Average$161	FlexibilityNo cancel fee	On-time65%
Southwest	Cheapest$156	Average$275	FlexibilityNo cancel fee	On-time63%
Delta	Cheapest$187	Average$368	FlexibilityNo cancel fee	On-timeN/A

$64+ Cheap flights from New York, NY (NYC) to Midway (MDW)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/13. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from New York to Midway with Cheapflights

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Cheapflights Tip: The best prices from New York to Chicago Midway are usually found in January or February, booked 57 days in advance, depart on a Wednesday or Tuesday and return on a Thursday

Cheap flight deals from New York to Midway

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Find flight deals from New York to Midway

Cheapest flights from New York to MidwayExplore the most affordable flight options available from New York to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 30, 2025.

Explore the most affordable flight options available from New York to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 30, 2025.

Cheapflights Fare Finder

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

Compare providers for flights from New York to Midway

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.

Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from New York to Midway in October.

Best time to book a flight from New York to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from New York with our price prediction graph.

Cheapflights Insights

Everything you need to know about your flight from New York to Chicago Midway Airport

How far ahead should I book a flight from New York to Chicago Midway Airport?

Use this chart to determine the optimal time to book a round-trip flight from New York to Midway. Price data was last updated on October 24, 2025.

What is the cheapest month to book a flight from New York to Chicago Midway Airport?

What is the cheapest time of day to fly from NYC to MDW?

Find hourly flight availability from New York to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 30, 2025.

What is the cheapest day to fly from New York to Chicago Midway Airport?

Use this chart to determine the cheapest time to fly round-trip from New York to Midway. Price data was last updated on December 16, 2024.

The best insider tips for New York to Chicago Midway Airport flights

Cheapflights partnered with top experts to bring you the best recommendations for your New York to Chicago Midway Airport trip

Airports

LGA

MDW

Our travel experts

Reviews of airlines servicing Midway

Read through reviews of airlines operating flights from New York to Chicago Midway Airport, such as Southwest, Delta, and United Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.

Related info for your journey

Find useful and relevant information for your journey from New York to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

How long is the flight from New York to Chicago Midway Airport?

What are the cheapest airlines flying from New York to Chicago Midway Airport round-trip?

What are the cheapest airlines to fly from New York to Chicago Midway Airport one-way?

What are the most popular routes from New York to Chicago Midway Airport?

Can I find deals for flights from New York to Midway that include hotel bookings?

How can I find direct flights from New York to Midway?

Can I find deals for business class flights from New York to Midway?

What is the cheapest month to book a flight from New York to Chicago Midway Airport?

Traveling to a place near Chicago Midway Airport?

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Cheapest flights from New York to Midway
Explore the most affordable flight options available from New York to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 30, 2025.