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Midway

$79+ 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 8/27. Fares are subject to change and may not be available on all flights or dates of travel.
NYC — MDW
Aug 5 — Aug 121
Tue 8/5
Tue 8/12
1 adult, Economy
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Cheapflights Tip: The best prices from New York to Chicago Midway are usually found in January or February, booked 73 days in advance, depart on a Wednesday or Thursday and return on a Wednesday

Cheap flight deals from New York to Midway

Discover tips and strategies to find the most affordable flight options for your journey from New York (NYC) to Midway (MDW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated July 31, 2025.

Round-trip from

$152
(Southwest)

One-way from

$79
(Southwest)

Popular in

December

Cheapest in

January

Average price

$263

Good round-trip deal

$210 or less

Good one-way deal

$159 or less
From New York (NYC) to Chicago Midway
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One-way flight from New York (NYC) to Chicago Midway
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High demand for flights, 0% potential price rise
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Cheapest flight prices on average. 3% potential price decrease ($11 potential savings vs. average RT price).
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Average for round-trip flights in July 2025
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Price to beat on a round-trip flight from New York (NYC) to Chicago Midway.
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Price to beat on a one-way flight from New York (NYC) to Chicago Midway.
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Find flight deals from New York to Midway

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 July 31, 2025.

This Southwest deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/316:00 amLGA - MDW
Nonstop2h 20mSouthwest
Wed 9/36:00 amMDW - LGA
Nonstop2h 00mSouthwest
Deal found 7/30$152
This Delta deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/203:30 pmEWR - MDW
1 stop6h 40mDelta
Wed 9/246:00 amMDW - EWR
1 stop5h 10mDelta
Deal found 7/31$167
This Frontier deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/1611:00 amEWR - MDW
1 stop8h 18mFrontier
Sun 10/195:56 pmMDW - EWR
Nonstop2h 04mFrontier
Deal found 7/31$170
This Frontier deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/138:47 pmLGA - MDW
1 stop13h 36mFrontier
Sat 9/2011:23 amMDW - LGA
1 stop7h 39mFrontier
Deal found 7/30$196
This eDestinos deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/16:15 amJFK - MDW
1 stop17h 54mFrontier
Wed 11/58:00 amMDW - JFK
1 stop15h 40mFrontier
Deal found 7/29$206
This Delta deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/239:35 pmJFK - MDW
1 stop12h 00mDelta
Wed 8/271:08 pmMDW - JFK
1 stop9h 30mDelta
Deal found 7/29$252

Cheapflights Fare Finder

 
Customize your flight search to find flights from New York to Midway that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 31, 2025.
Use the filters below to find and compare flights from New York to Chicago Midway Airport that are best for you.

Fly from

New York

Fly to

Midway

Route

Depart

Return

Price

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Sun 8/31

6:00 am-7:20 am

Nonstop2h 20m

Chicago Midway

Wed 9/3

6:00 am-9:00 am

Nonstop2h 00m

$152

NewarkChicago

EWR - MDW

EWRMDW

Newark

Sat 9/20

3:30 pm-9:10 pm

1 stop6h 40m

Chicago Midway

Wed 9/24

6:00 am-12:10 pm

1 stop5h 10m

$167

NewarkChicago

EWR - MDW

EWRMDW

Newark

Thu 10/16

11:00 am-6:18 pm

1 stop8h 18m

Chicago Midway

Sun 10/19

5:56 pm-9:00 pm

Nonstop2h 04m

$170

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Sat 9/13

8:47 pm-9:23 am

1 stop13h 36m

Chicago Midway

Sat 9/20

11:23 am-8:02 pm

1 stop7h 39m

$196

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Sat 11/1

6:15 am-11:09 pm

1 stop17h 54m

Chicago Midway

Wed 11/5

8:00 am-12:40 am

1 stop15h 40m

$206

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Sat 8/23

9:35 pm-8:35 am

1 stop12h 00m

Chicago Midway

Wed 8/27

1:08 pm-11:38 pm

1 stop9h 30m

$252

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Wed 8/27

9:00 am-10:25 am

Nonstop2h 25m

$79

NewarkChicago

EWR - MDW

EWRMDW

Newark

Wed 9/10

11:15 am-3:58 pm

1 stop5h 43m

$91

NewarkChicago

EWR - MDW

EWRMDW

Newark

Wed 8/27

1:00 pm-6:37 pm

1 stop6h 37m

$94

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Wed 9/3

9:00 am-2:01 pm

1 stop6h 01m

$98

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/31

Showing 1-10 of 17 results
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The best insider tips for New York to Chicago Midway Airport flights

Snippets provided in this section are AI-generated based on a summarization of Cheapflights-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
Cheapflights partnered with top experts to bring you the best recommendations for your New York to Chicago Midway Airport trip
Airports
LGA

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

Read more about LGAby Brandon Schultz
MDW

The Orange Line train connects MDW to downtown Chicago in under 30 minutes, offering a convenient and affordable transport option.

Read more about MDWby Ramsey Qubein
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on MDW

Ramsey Qubein

Ramsey Qubein

An avid traveler and aviation expert who has visited 173 countries, all 50 states and seven continents, Ramsey Qubein flies nearly 400,000 miles a year. As a North Carolina-based freelance journalist for publications including Conde Nast Traveler, Forbes, USA Today and Bloomberg among others, he explores the latest trends in aviation, hospitality, cruises and business.

Read more
Brandon Schultz

Brandon Schultz

Expert on LGA

Brandon Schultz

Brandon Schultz

Brandon Schultz is an award-winning food and travel writer based in New York City. His work has appeared in Forbes, AAA, Thrillist, Travel + Leisure, and The Daily Meal, among many others, and he is the author of 6 books, including 3 cookbooks.

Read more

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.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

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 July 25, 2025.

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 73 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 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 July 31, 2025.

It’s optimal to fly from New York to Chicago Midway Airport in the evening. By choosing this option you can save up to 26% on the cost of your flight, compared to a flight in the afternoon.

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.

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.

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Midway. Reviews last updated July 31, 2025.
Read through reviews of airlines operating flights from New York to Chicago Midway Airport, such as Southwest, Delta, and Allegiant Air. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Overall

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Overall

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Delta
8.0
Very good
7,981 reviews
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Overall

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Allegiant Air
7.2
Good
702 reviews
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Overall

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Frontier
5.9
Fair
3,239 reviews
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Overall

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

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.

  • 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 $152. Other airlines that can offer you cheap pricing are Delta, from $167, and Frontier, from $170. Southwest is priced at 46% 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 $79. Users have also found prices from $91 and $94 on Frontier and Delta, respectively.

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

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

  • 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.

  • 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.

See more FAQs

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Valparaiso
Chesterton

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Alternative routes for New York to Midway

See prices for flight routes from nearby airports that may be better suited for you.
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Binghamton to Midway flights
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Stewart to Midway flights

Top 3 airlines flying from New York to Midway

Discover the top 3 airlines that operate flights from New York to Midway. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$92Average$171FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$152Average$253FlexibilityNo cancel feeOn-time63%
DeltaCheapest$192Average$367FlexibilityNo cancel feeOn-timeN/A

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