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Midway

$94+ 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 7/14. Fares are subject to change and may not be available on all flights or dates of travel.
NYC — MDW
Jul 20 — Jul 271
Mon 7/20
Mon 7/27
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 45 days in advance, depart on a Tuesday or Thursday and return on a Thursday

Cheap 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 June 20, 2026.

This Southwest deal was found by Cheapflights users on 6/17. 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.
Wed 7/1510:55 am
LGA
-
MDW
Nonstop2h 20m
Southwest
Wed 7/227:45 pm
MDW
-
LGA
Nonstop2h 15m
Southwest
Deal found 6/17$187
This Southwest deal was found by Cheapflights users on 6/17. 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.
Tue 9/225:40 pm
LGA
-
MDW
Nonstop2h 30m
Southwest
Sat 9/267:50 am
MDW
-
LGA
Nonstop2h 10m
Southwest
Deal found 6/17$192
This Southwest deal was found by Cheapflights users on 6/17. 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.
Mon 8/108:55 pm
LGA
-
MDW
Nonstop2h 20m
Southwest
Sat 8/156:00 am
MDW
-
LGA
Nonstop2h 00m
Southwest
Deal found 6/17$195
This Southwest deal was found by Cheapflights users on 6/17. 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.
Sat 7/116:00 am
LGA
-
MDW
Nonstop2h 20m
Southwest
Tue 7/147:45 pm
MDW
-
LGA
Nonstop2h 15m
Southwest
Deal found 6/17$197
This Southwest deal was found by Cheapflights users on 6/16. 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.
Thu 8/136:00 am
LGA
-
MDW
Nonstop2h 15m
Southwest
Sat 8/156:00 am
MDW
-
LGA
Nonstop2h 00m
Southwest
Deal found 6/16$200
This Southwest deal was found by Cheapflights users on 6/17. 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.
Sat 8/19:10 pm
LGA
-
MDW
Nonstop2h 40m
Southwest
Tue 8/47:10 pm
MDW
-
LGA
Nonstop2h 05m
Southwest
Deal found 6/17$202
This Southwest deal was found by Cheapflights users on 6/16. 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.
Thu 8/206:00 am
LGA
-
MDW
Nonstop2h 15m
Southwest
Mon 8/247:50 pm
MDW
-
LGA
Nonstop2h 05m
Southwest
Deal found 6/16$203
This Southwest deal was found by Cheapflights users on 6/18. 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.
Fri 8/286:00 am
LGA
-
MDW
Nonstop2h 15m
Southwest
Mon 8/317:50 pm
MDW
-
LGA
Nonstop2h 05m
Southwest
Deal found 6/18$205
This Delta deal was found by Cheapflights users on 6/16. 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.
Wed 8/56:00 am
EWR
-
MDW
1 stop4h 17m
Delta
Tue 8/116:42 pm
MDW
-
EWR
1 stop3h 43m
Delta
Deal found 6/16$207
This Southwest deal was found by Cheapflights users on 6/16. 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.
Mon 8/39:30 pm
LGA
-
MDW
Nonstop2h 30m
Southwest
Tue 8/45:10 am
MDW
-
LGA
Nonstop2h 00m
Southwest
Deal found 6/16$207
This Southwest deal was found by Cheapflights users on 6/16. 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.
Thu 8/206:00 am
LGA
-
MDW
Nonstop2h 15m
Southwest
Thu 8/275:00 am
MDW
-
LGA
Nonstop2h 00m
Southwest
Deal found 6/16$208
This Southwest deal was found by Cheapflights users on 6/16. 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.
Thu 8/136:00 am
LGA
-
MDW
Nonstop2h 15m
Southwest
Sun 8/165:25 am
MDW
-
LGA
Nonstop2h 00m
Southwest
Deal found 6/16$210

Find 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 June 20, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$187
(Southwest)

One-way from

$94
(Southwest)

Popular in

August

Cheapest in

January

Average price

$355

Good round-trip deal

$202 or less

Good one-way deal

$150 or less
Provider with most accurate pricing for New York (NYC)-Chicago Midway flight deals.
Search Deals
Provider most trusted by Cheapflights users for New York (NYC)-Chicago Midway flights.
Search Deals
From New York (NYC) to Chicago Midway
Search Deals
One-way flight from New York (NYC) to Chicago Midway
Search Deals
Highest demand for flights based on searches. 12% potential increase in price ($41 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 2026
Search Deals
Price to beat on a round-trip flight from New York (NYC) to Chicago Midway.
Search Deals
Price to beat on a one-way flight from New York (NYC) to Chicago Midway.
Search Deals

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 June 20, 2026.
Use the filters below to find and compare flights from New York to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Wed 9/9

5:40 pm-7:10 pm

Nonstop2h 30m

Chicago Midway

Wed 9/23

7:10 pm-10:15 pm

Nonstop2h 05m

$197

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Tue 7/7

3:55 pm-5:45 pm

Nonstop2h 50m

Chicago Midway

Tue 7/7

7:45 pm-11:00 pm

Nonstop2h 15m

$212

NewarkChicago

EWR - MDW

EWRMDW

Newark

Sat 9/5

6:00 am-9:17 am

1 stop4h 17m

Chicago Midway

Sat 9/26

9:30 am-3:59 pm

1 stop5h 29m

$215

NewarkChicago

EWR - MDW

EWRMDW

Newark

Fri 8/14

1:00 pm-6:33 pm

1 stop6h 33m

Chicago Midway

Sat 8/15

9:24 am-3:59 pm

1 stop5h 35m

$217
Quickest round-trip

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Fri 8/14

6:00 am-7:15 am

Nonstop2h 15m

Chicago Midway

Mon 8/17

5:00 am-8:00 am

Nonstop2h 00m

$225

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Mon 8/10

6:00 am-7:15 am

Nonstop2h 15m

Chicago Midway

Fri 8/14

5:00 am-8:00 am

Nonstop2h 00m

$227

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Sat 7/4

6:35 am-7:55 am

Nonstop2h 20m

Chicago Midway

Sat 7/4

11:10 am-6:30 pm

1 stop6h 20m

$237

NewarkChicago

EWR - MDW

EWRMDW

Newark

Sat 7/25

6:00 am-9:13 am

1 stop4h 13m

Chicago Midway

Tue 7/28

6:00 am-12:21 pm

1 stop5h 21m

$242

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Sun 7/5

6:00 am-7:20 am

Nonstop2h 20m

Chicago Midway

Tue 7/7

7:45 pm-11:00 pm

Nonstop2h 15m

$242

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Thu 7/9

7:25 am-8:50 am

Nonstop2h 25m

Chicago Midway

Tue 7/14

11:25 am-6:55 pm

1 stop6h 30m

$247

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/19

Showing 1-10 of 60 resultsSorted by cheapest first
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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 June.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
Super.comPrice Accuracy-Trust Score*3 stars
OvagoPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on New York-Chicago Midway Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on New York-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >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 FlightHub the most. FlightHub 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.

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

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

Currently, December is the cheapest month in which you can book a flight from New York to Chicago Midway Airport (average of $39). Flying from New York to Chicago Midway Airport in June is currently the most expensive (average of $182). 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 June 20, 2026.

It’s optimal to fly from New York to Chicago Midway Airport in the evening. By choosing this option you can save up to 38% on the cost of your flight, compared to a flight in the afternoon.

Weekly flight availability from New York to Chicago Midway Airport

Explore weekly flight availability from New York to Midway. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated June 20, 2026.

The most flights from NYC to MDW are scheduled on a Monday (8 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (1 on average).

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

How often are flights from New York to Chicago delayed?

About 23% of weekly flights between New York and Chicago have experienced delays in the past year, with the average delay time being 140 minutes.

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

Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving at night tend to experience delays more often.

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

Saturday tends to have the lowest number of delays on this route, whereas Sunday has historically faced a higher average of delays compared to other days of the week.

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

Over the last year, Southwest have had the lowest number of delays on this route, with just 23% of flights being delayed.

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 58 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

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 June 13, 2026.

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. Sunday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

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

AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your New York to Chicago Midway Airport trip
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on MDW

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 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

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 June 20, 2026.
Read through reviews of airlines operating flights from New York to Chicago Midway Airport, such as Southwest,United Airlines, andFrontier. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
7.9
Good
4,241 reviews

Entertainment

7.5

Food

7.0

Overall

7.9

Comfort

8.0

Crew

8.6

Boarding

8.1

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
Southwest
7.9
Good
4,241 reviews
Southwest
7.9
Good
4,241 reviews

Entertainment

7.5

Food

7.0

Overall

7.9

Comfort

8.0

Crew

8.6

Boarding

8.1

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
United Airlines
7.4
Good
9,865 reviews
Southwest
7.9
Good
4,241 reviews

Entertainment

7.5

Food

7.0

Overall

7.9

Comfort

8.0

Crew

8.6

Boarding

8.1

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
Frontier
5.6
Fair
2,877 reviews
Southwest
7.9
Good
4,241 reviews

Entertainment

7.5

Food

7.0

Overall

7.9

Comfort

8.0

Crew

8.6

Boarding

8.1

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers

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?

    There are many flights that can get you from New York to Chicago Midway Airport in 2h 30m. Fly via 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 $55. Other airlines that can offer you cheap pricing are United Airlines, from $148, and Southwest, from $164. Frontier is priced at 80% 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 $33. Users have also found prices from $78 and $88 on Southwest 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, December is the cheapest month in which you can book a flight from New York to Chicago Midway Airport (average of $39). Flying from New York to Chicago Midway Airport in June is currently the most expensive (average of $182). 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
Benton Harbor
Lansing
Merrillville
Hammond
Porter

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Top 4 airlines flying from New York to Midway

Discover the top 4 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 June 20, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$55Average$168FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$148Average$306FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$164Average$313FlexibilityNo cancel feeOn-time63%
DeltaCheapest$186Average$306FlexibilityNo cancel feeOn-timeN/A

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