HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
New York

$69+ Cheap flights from Midway (MDW) to New York State

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 5/24. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — JFK
Apr 20 — Apr 271
Sun 4/20
Sun 4/27
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Midway to New York 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 Midway to New York

Keep the following information in mind while searching for Midway to New York flight deals. Data was last updated April 15, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$137
(Southwest)

One-way from

$69
(Southwest)

Popular in

December

Cheapest in

September

Average price

$204

Good round-trip deal

$189 or less

Good one-way deal

$103 or less
Provider with most accurate pricing for Chicago (CHI)-New York (NYC) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-New York (NYC) flights.
Search Deals
From Chicago Midway to New York
Search Deals
One-way flight from Chicago Midway to New York
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($17 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($5 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2025
Search Deals
Price to beat on a round-trip flight from Chicago Midway to New York.
Search Deals
Price to beat on a one-way flight from Chicago Midway to New York.
Search Deals

Find flight deals from Midway to New York

Cheapest flights from Midway to New York
Explore the most affordable flight options available from Midway to New York. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 15, 2025.

This Southwest deal was found by Cheapflights users on 4/14. 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 5/246:15 pmMDW - LGA
Nonstop2h 10mSouthwest
Tue 5/276:10 amLGA - MDW
Nonstop2h 20mSouthwest
Deal found 4/14$137
This Delta deal was found by Cheapflights users on 4/13. 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 5/175:25 pmMDW - EWR
1 stop4h 04mDelta
Sun 5/256:05 amEWR - MDW
1 stop8h 10mDelta
Deal found 4/13$168
This Booking.com deal was found by Cheapflights users on 4/14. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/151:19 pmMDW - BUF
1 stop18h 42mFrontier
Sun 5/187:28 pmBUF - MDW
1 stop17h 56mFrontier
Deal found 4/14$170
This Cheapflightsfares deal was found by Cheapflights users on 4/14. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/139:34 amMDW - LGA
1 stop5h 55mFrontier
Wed 5/146:30 amLGA - MDW
1 stop5h 56mFrontier
Deal found 4/14$176
This Frontier deal was found by Cheapflights users on 4/14. 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.
Tue 5/139:34 amMDW - EWR
1 stop10h 32mFrontier
Sat 5/2411:00 amEWR - MDW
1 stop12h 02mFrontier
Deal found 4/14$178
This Frontier deal was found by Cheapflights users on 4/14. 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.
Wed 4/304:28 pmMDW - JFK
1 stop7h 05mFrontier
Wed 5/76:00 amJFK - MDW
1 stop6h 26mFrontier
Deal found 4/14$178
This Mytrip deal was found by Cheapflights users on 4/15. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/308:04 pmMDW - EWR
1 stop14h 01mAllegiant Air
Fri 6/69:55 amEWR - MDW
1 stop5h 08mAllegiant Air
Deal found 4/15$215
This Southwest deal was found by Cheapflights users on 4/14. 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 5/66:50 pmMDW - ALB
Nonstop1h 55mSouthwest
Thu 5/87:30 amALB - MDW
Nonstop2h 10mSouthwest
Deal found 4/14$239
This Delta deal was found by Cheapflights users on 4/14. 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 5/106:00 amMDW - ALB
1 stop5h 09mDelta
Sun 5/116:00 amALB - MDW
1 stop3h 40mDelta
Deal found 4/14$245
This Southwest deal was found by Cheapflights users on 4/15. 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 5/306:50 pmMDW - BUF
Nonstop1h 25mSouthwest
Sat 5/316:55 pmBUF - MDW
Nonstop1h 40mSouthwest
Deal found 4/15$249
This eDestinos deal was found by Cheapflights users on 4/15. 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.
Fri 5/308:04 pmMDW - EWR
1 stop14h 01mMultiple Airlines
Fri 6/65:59 amEWR - MDW
1 stop27h 48mMultiple Airlines
Deal found 4/15$263
This Frontier deal was found by Cheapflights users on 4/14. 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.
Fri 5/306:35 amMDW - SYR
1 stop7h 16mFrontier
Fri 6/612:46 pmSYR - MDW
1 stop11h 32mFrontier
Deal found 4/14$263

Cheapflights Fare Finder

Customize your flight search to find flights from Midway to New York 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 April 15, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to New York State that are best for you.

Fly from

Midway

Fly to

New York

Route

Depart

Return

Price

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Sat 5/24

6:15 pm-9:25 pm

Nonstop2h 10m

New York LaGuardia

Tue 5/27

6:10 am-7:30 am

Nonstop2h 20m

$137

ChicagoNewark

MDW - EWR

MDWEWR

Chicago Midway

Sat 5/17

5:25 pm-10:29 pm

1 stop4h 04m

Newark

Sun 5/25

6:05 am-1:15 pm

1 stop8h 10m

$168

ChicagoBuffalo

MDW - BUF

MDWBUF

Chicago Midway

Thu 5/15

1:19 pm-9:01 am

1 stop18h 42m

Buffalo

Sun 5/18

7:28 pm-12:24 pm

1 stop17h 56m

$170

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Tue 5/13

9:34 am-4:29 pm

1 stop5h 55m

New York LaGuardia

Wed 5/14

6:30 am-11:26 am

1 stop5h 56m

$176

ChicagoNewark

MDW - EWR

MDWEWR

Chicago Midway

Tue 5/13

9:34 am-9:06 pm

1 stop10h 32m

Newark

Sat 5/24

11:00 am-10:02 pm

1 stop12h 02m

$178

ChicagoNew York

MDW - JFK

MDWJFK

Chicago Midway

Wed 4/30

4:28 pm-12:33 am

1 stop7h 05m

New York John F Kennedy Intl

Wed 5/7

6:00 am-11:26 am

1 stop6h 26m

$178

ChicagoNewark

MDW - EWR

MDWEWR

Chicago Midway

Fri 5/30

8:04 pm-11:05 am

1 stop14h 01m

Newark

Fri 6/6

9:55 am-2:03 pm

1 stop5h 08m

$215

ChicagoAlbany

MDW - ALB

MDWALB

Chicago Midway

Tue 5/6

6:50 pm-9:45 pm

Nonstop1h 55m

Albany Intl

Thu 5/8

7:30 am-8:40 am

Nonstop2h 10m

$239

ChicagoAlbany

MDW - ALB

MDWALB

Chicago Midway

Sat 5/10

6:00 am-12:09 pm

1 stop5h 09m

Albany Intl

Sun 5/11

6:00 am-8:40 am

1 stop3h 40m

$245

ChicagoBuffalo

MDW - BUF

MDWBUF

Chicago Midway

Fri 5/30

6:50 pm-9:15 pm

Nonstop1h 25m

Buffalo

Sat 5/31

6:55 pm-7:35 pm

Nonstop1h 40m

$249

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/14

Showing 1-10 of 45 results
1
2
3
...
5

Best time to book a flight from Midway to New York

Have a flexible travel schedule? Discover the best time to fly to New York from Midway 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 Chicago Midway Airport to New York State

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

Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to State of New York (average of $236). Flying from Chicago Midway Airport to State of New York in June is currently the most expensive (average of $351). 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 MDW to NY?

Find hourly flight availability from Midway to New York. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 15, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago Midway Airport to State of New York as you normally would.

Rainfall in New York by month

Plan your trip to New York by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in State of New York ranges from 2.8 - 4.5 inches per month. July is typically the wettest month, when rainfall can reach 4.5 in. February is typically the driest time to visit State of New York when rainfall is around 2.8 in.

Temperature in New York by month

Plan your trip to New York by taking into account the average temperature totals by month.

If weather is an important factor for your trip to State of New York, 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 77.0 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 33.8 F).

Reviews of airlines servicing New York

Get insights into the airlines that provide service to New York. 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 New York. Reviews last updated April 15, 2025.
Get a feel of what it's like to fly with Southwest, Delta and Allegiant Air from Chicago to New York by reading reviews from past customers. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,279 reviews

Boarding

8.2

Crew

8.6

Overall

8.0

Comfort

8.0

Entertainment

7.6

Food

7.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Southwest
8.0
Very good
4,279 reviews
Southwest
8.0
Very good
4,279 reviews

Boarding

8.2

Crew

8.6

Overall

8.0

Comfort

8.0

Entertainment

7.6

Food

7.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Delta
8.0
Very good
7,918 reviews
Southwest
8.0
Very good
4,279 reviews

Boarding

8.2

Crew

8.6

Overall

8.0

Comfort

8.0

Entertainment

7.6

Food

7.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Allegiant Air
7.3
Good
734 reviews
Southwest
8.0
Very good
4,279 reviews

Boarding

8.2

Crew

8.6

Overall

8.0

Comfort

8.0

Entertainment

7.6

Food

7.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Frontier
6.0
Okay
3,281 reviews
Southwest
8.0
Very good
4,279 reviews

Boarding

8.2

Crew

8.6

Overall

8.0

Comfort

8.0

Entertainment

7.6

Food

7.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

Related info for your journey

Find useful and relevant information for your journey from Midway to New York. 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 to fly from Chicago Midway Airport to State of New York one-way?

    The cheapest airline one-way is Southwest, with whom users have recently found tickets for as low as $69. However, be on the lookout for offers from Delta and Frontier, as they are both options that can get you from Chicago Midway Airport to State of New York for a low price.

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

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

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Midway to New York 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 Chicago Midway Airport to State of New York?

    Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to State of New York (average of $236). Flying from Chicago Midway Airport to State of New York in June is currently the most expensive (average of $351). 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

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 Midway to New York

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

Top 3 airlines flying from Midway to New York

Discover the top 3 airlines that operate flights from Midway to New York. 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 April 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$63Average$131FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$149Average$318FlexibilityNo cancel feeOn-time63%
DeltaCheapest$162Average$443FlexibilityNo cancel feeOn-timeN/A

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.