HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Midway

$81+ Cheap flights from New York State 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 8/12. Fares are subject to change and may not be available on all flights or dates of travel.
JFK — MDW
Jun 20 — Jun 271
Sat 6/20
Sat 6/27
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from New York to Midway with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 May 21, 2026.

This Southwest deal was found by Cheapflights users on 5/18. 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.
Wed 6/176:00 am
LGA
-
MDW
Nonstop2h 20m
Southwest
Sat 6/205:00 am
MDW
-
LGA
Nonstop2h 00m
Southwest
Deal found 5/18$177
This Southwest deal was found by Cheapflights users on 5/18. 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 7/39:30 pm
LGA
-
MDW
Nonstop2h 25m
Southwest
Tue 7/77:45 pm
MDW
-
LGA
Nonstop2h 10m
Southwest
Deal found 5/18$182
This Southwest deal was found by Cheapflights users on 5/16. 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.
Sat 5/306:05 pm
LGA
-
MDW
Nonstop2h 25m
Southwest
Sat 6/65:25 pm
MDW
-
LGA
Nonstop2h 05m
Southwest
Deal found 5/16$184
This Southwest deal was found by Cheapflights users on 5/18. 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.
Tue 6/236:00 am
LGA
-
MDW
Nonstop2h 20m
Southwest
Tue 6/237:45 pm
MDW
-
LGA
Nonstop2h 10m
Southwest
Deal found 5/18$187
This Southwest deal was found by Cheapflights users on 5/19. 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 5/283:25 pm
LGA
-
MDW
1 stop6h 05m
Southwest
Tue 6/237:45 pm
MDW
-
LGA
Nonstop2h 10m
Southwest
Deal found 5/19$192
This Delta deal was found by Cheapflights users on 5/18. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/711:47 am
EWR
-
MDW
1 stop7h 31m
Delta
Wed 7/86:00 am
MDW
-
EWR
1 stop7h 16m
Delta
Deal found 5/18$197
This Southwest deal was found by Cheapflights users on 5/18. 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.
Wed 5/276:00 am
LGA
-
MDW
Nonstop2h 25m
Southwest
Fri 5/295:40 pm
MDW
-
LGA
1 stop4h 45m
Southwest
Deal found 5/18$197
This Southwest deal was found by Cheapflights users on 5/16. 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.
Sat 5/306:05 pm
LGA
-
MDW
Nonstop2h 25m
Southwest
Tue 6/24:40 pm
MDW
-
LGA
1 stop5h 20m
Southwest
Deal found 5/16$199
This Southwest deal was found by Cheapflights users on 5/16. 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 5/286:00 am
LGA
-
MDW
Nonstop2h 25m
Southwest
Sat 6/65:25 pm
MDW
-
LGA
Nonstop2h 05m
Southwest
Deal found 5/16$200
This Delta deal was found by Cheapflights users on 5/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/166:00 am
EWR
-
MDW
1 stop4h 14m
Delta
Fri 6/1912:50 pm
MDW
-
EWR
1 stop6h 54m
Delta
Deal found 5/17$202
This Southwest deal was found by Cheapflights users on 5/18. 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.
Sat 6/66:00 am
LGA
-
MDW
Nonstop2h 20m
Southwest
Tue 6/97:45 pm
MDW
-
LGA
Nonstop2h 10m
Southwest
Deal found 5/18$202
This Delta deal was found by Cheapflights users on 5/18. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/26:00 am
EWR
-
MDW
1 stop3h 42m
Delta
Wed 9/96:00 am
MDW
-
EWR
1 stop5h 23m
Delta
Deal found 5/18$207

Find flight deals from New York to Midway

Keep the following information in mind while searching for New York to Midway flight deals. Data was last updated May 21, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$177
(Southwest)

One-way from

$81
(Kiwi.com)

Popular in

May

Cheapest in

January

Average price

$292

Good round-trip deal

$274 or less

Good one-way deal

$173 or less
Provider with most accurate pricing for New York (NYC)-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for New York (NYC)-Chicago (CHI) flights.
Search Deals
From New York to Chicago Midway
Search Deals
One-way flight from New York to Chicago Midway
Search Deals
Highest demand for flights based on searches. 12% potential increase in price ($35 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
Search Deals
Price to beat on a round-trip flight from New York to Chicago Midway.
Search Deals
Price to beat on a one-way flight from New York 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 May 21, 2026.
Use the filters below to find and compare flights from New York State to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

NewarkChicago

EWR - MDW

EWRMDW

Newark

Tue 9/1

9:39 am-12:30 pm

1 stop3h 51m

Chicago Midway

Wed 9/2

10:35 am-4:43 pm

1 stop5h 08m

$197

NewarkChicago

EWR - MDW

EWRMDW

Newark

Wed 6/10

6:00 am-9:14 am

1 stop4h 14m

Chicago Midway

Fri 6/19

6:00 am-2:20 pm

1 stop7h 20m

$212

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Tue 6/2

6:00 am-7:25 am

Nonstop2h 25m

Chicago Midway

Fri 6/5

1:00 pm-6:55 pm

1 stop4h 55m

$217

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Wed 8/19

6:00 am-7:15 am

Nonstop2h 15m

Chicago Midway

Sun 8/23

5:25 am-8:25 am

Nonstop2h 00m

$227

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Sat 8/22

5:50 pm-7:15 pm

Nonstop2h 25m

Chicago Midway

Sun 8/23

5:25 am-8:25 am

Nonstop2h 00m

$227

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Thu 7/9

6:00 am-7:20 am

Nonstop2h 20m

Chicago Midway

Mon 7/13

6:00 pm-11:20 pm

1 stop4h 20m

$237

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Thu 7/2

6:00 am-7:20 am

Nonstop2h 20m

Chicago Midway

Tue 7/7

7:45 pm-10:55 pm

Nonstop2h 10m

$242

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Thu 6/25

9:30 pm-10:55 pm

Nonstop2h 25m

Chicago Midway

Sat 6/27

5:25 pm-8:30 pm

Nonstop2h 05m

$247

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Wed 7/22

5:45 pm-10:35 pm

1 stop5h 50m

Chicago Midway

Sun 7/26

5:20 am-8:20 am

Nonstop2h 00m

$247

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Mon 7/20

5:30 pm-9:55 pm

1 stop5h 25m

Chicago Midway

Tue 7/21

7:45 pm-10:55 pm

Nonstop2h 10m

$252

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/16

Showing 1-10 of 60 resultsSorted by cheapest first
1
2
3
...
6

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 State to Chicago Midway Airport

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

Currently, December is the cheapest month in which you can book a flight from State of New York to Chicago Midway Airport (average of $39). Flying from State of New York to Chicago Midway Airport in June is currently the most expensive (average of $156). 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 NY 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 May 21, 2026.

One of the essential ways to save on airfare from State of New York to Chicago Midway Airport is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the evening could potentially save you up to 11% on airfare.

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

The best time to book flights from State of New York to Chicago Midway Airport is 33 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

What is the cheapest day to fly from State of 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 May 16, 2026.

Travelers seeking maximum savings on their State of 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.

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 State of New York to Chicago Midway Airport?

    Delta and Southwest can get you from State of New York to Chicago Midway Airport in just under 2h 25m. Your travel time can differ by up to 1h 26m. The distance from State of New York to Chicago Midway Airport is about 722 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

    To fly one-way, consider booking your trip with Frontier, which is currently one of the cheapest options available, starting at $35. Southwest flights start at $78 while deals on Delta start at $89 one-way.

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

    Currently, December is the cheapest month in which you can book a flight from State of New York to Chicago Midway Airport (average of $39). Flying from State of New York to Chicago Midway Airport in June is currently the most expensive (average of $156). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for New York to Midway

See prices for flight routes from nearby airports that may be better suited for you.
Dallas/Fort Worth to O'Hare Intl flights
Los Angeles to O'Hare Intl flights
Newark to O'Hare Intl flights
John F Kennedy Intl to O'Hare Intl flights
LaGuardia to O'Hare Intl flights
Seattle to O'Hare Intl flights
Baltimore to O'Hare Intl flights
Newark to Midway flights
San Francisco to O'Hare Intl flights
Hobby to O'Hare Intl flights
Denver to O'Hare Intl flights
Philadelphia to O'Hare Intl flights
Dallas/Fort Worth to Midway flights
Ontario to O'Hare Intl flights
George Bush Intcntl to O'Hare Intl flights
Dulles Intl to O'Hare Intl flights
Orlando to O'Hare Intl flights
Boston to O'Hare Intl flights
Reagan-National to O'Hare Intl flights
John F Kennedy Intl to Midway flights
Los Angeles to Midway flights
Atlanta to O'Hare Intl flights
Dulles Intl to Midway flights
Fort Lauderdale to O'Hare Intl flights
Sky Harbor Intl to O'Hare Intl flights
Austin to O'Hare Intl flights
Tampa to O'Hare Intl flights
Santa Ana to O'Hare Intl flights
LaGuardia to Midway flights
San Diego to O'Hare Intl flights
Atlanta to Midway flights
Hobby to Midway flights
Raleigh to O'Hare Intl flights
Miami to O'Hare Intl flights
San Francisco to Midway flights
Charlotte to O'Hare Intl flights
San Jose to O'Hare Intl flights
Reagan-National to Midway flights
Minneapolis to O'Hare Intl flights
Minneapolis to Midway flights
Baltimore to Midway flights
Seattle to Midway flights
Hartford to O'Hare Intl flights
George Bush Intcntl to Midway flights
Philadelphia to Midway flights
Portland to O'Hare Intl flights
Sacramento to O'Hare Intl flights
Oakland to O'Hare Intl flights
Salt Lake City to O'Hare Intl flights
Las Vegas to O'Hare Intl flights

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 May 21, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$55Average$164FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$148Average$306FlexibilityNo cancel feeOn-time69%
DeltaCheapest$153Average$303FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$168Average$364FlexibilityNo cancel feeOn-time63%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.