How much does it cost to fly round-trip from New York to Chicago Midway Airport?

Airfare is below average for this route at the moment. New York to Chicago Midway Airport flights typically cost between $221 and $334 in October. The cheapest round-trip price found within the last 3 days was $137 on Southwest (Oct 7-Oct 8).

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 35m. Fly via Southwest, Frontier, 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 $91. Other airlines that can offer you cheap pricing are Spirit Airlines, from $92, and Southwest, from $154. Frontier is priced at 68% 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 Southwest. According to our data, you can fly for as low as $70. Users have also found prices from $82 and $89 on Frontier 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, April is the cheapest month in which you can book a flight from New York to Chicago Midway Airport (average of $160). Flying from New York to Chicago Midway Airport in November is currently the most expensive (average of $249). 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 Tuesday 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 is the cheapest day to fly round-trip from New York to Chicago Midway Airport?

Users have found that leaving on a Tuesday can be a cost-effective option. It’s possible to save up to 47% on your flight compared to booking on days when demand is much higher.

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

Travelers have found it’s best to book a flight 36 days in advance to save up to 97% compared to booking the same week of travel. As your travel date approaches, the cost of this flight route may potentially increase. While opting to book 36 days out may not be an option for all, there are still additional ways to secure a deal in the near future. You might find a flight from New York to Chicago Midway Airport 1-2 weeks in advance for as low as $254, or $445 for flights within the next 24 hours.

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

Our data shows that January tends to be the cheapest month to fly to Chicago Midway Airport from New York. Users have commonly found prices around $239 for the month, but tickets can be as low as $86. Due to multiple factors, prepare for potentially higher prices in August.

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 28% on the cost of your flight, compared to a flight at noon.

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.

$70+ Flights from New York, NY to Chicago Midway Airport

Round-trip from	$137 (Southwest)
One-way from	$71 (Kiwi.com)
Popular in	December
Cheapest in	January
Average price	$297
Good round-trip deal	$71 or less
Good one-way deal	$68 or less

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$91	Average$225	FlexibilityNo cancel fee	On-time62%
Spirit Airlines	Cheapest$92	Average$174	FlexibilityNo cancel fee	On-time65%
Southwest	Cheapest$154	Average$259	FlexibilityNo cancel fee	On-time63%
Delta	Cheapest$192	Average$351	FlexibilityNo cancel fee	On-timeN/A

$70+ 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 10/29. 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 Wednesday

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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 septiembre 15, 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 septiembre 15, 2025.

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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.

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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 September 12, 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 septiembre 15, 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.

How much does it cost to fly round-trip from New York to Chicago Midway Airport?

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 septiembre 15, 2025.