Is Southwest the cheapest airline to fly with from New York to Chicago Midway Airport?

With an average price of $274 return, Southwest is not the cheapest airline to fly from New York to Chicago Midway Airport with. Instead, for the lowest price, our data suggests flying with Spirit Airlines, where a return flight costs $161 on average.

Does Southwest fly direct to Chicago Midway Airport from New York?

Yes, Southwest does offer direct flights for the route, with around 32 flights per week.

What’s the cheapest day of the week to fly from New York to Chicago Midway Airport with Southwest?

On average, the cheapest day of the week to fly from New York to Chicago Midway Airport with Southwest is Tuesday, when prices are around $77. The most expensive day is generally Sunday, where the average price is around $162.

What’s the cheapest month to fly from New York to Chicago Midway Airport with Southwest?

The cheapest month for Southwest flights to Chicago Midway Airport from New York is generally November, where plane tickets cost $114 on average. If possible, try to avoid the most expensive months of December and April, where tickets cost $239 and $277 respectively.

$69 Cheap Southwest Flights from New York to Chicago Midway Airport

NYC - MDW

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Flight Deals

Cheap Southwest Flight Deals from New York to Chicago Midway Airport

Here are some of the best deals found on KAYAK recently from Southwest for round-trip flights from New York to Chicago Midway Airport that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.

Discover the best prices for you by selecting your travel dates on KAYAK.

Round-trip

One-way

Last minute

Direct

Recent round-trip Southwest flight deals from New York to Chicago Midway Airport

Tue, Dec 9 - Wed, Dec 17

9:10 am - 10:40 amLGA-MDW

2h 30mnonstop

6:00 am - 9:00 amMDW-LGA

2h 00mnonstop

$130Southwest

Find Deal

Thu, Jan 15 - Sat, Jan 17

9:40 pm - 11:10 pmLGA-MDW

2h 30mnonstop

3:55 pm - 9:05 pmMDW-LGA

4h 10m1 stop

$133Southwest

Find Deal

Thu, Nov 13 - Mon, Nov 17

7:15 am - 8:45 amLGA-MDW

2h 30mnonstop

7:15 pm - 10:20 pmMDW-LGA

2h 05mnonstop

$137Southwest

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Sun, Nov 2 - Mon, Nov 3

7:15 am - 8:45 amLGA-MDW

2h 30mnonstop

5:55 pm - 9:00 pmMDW-LGA

2h 05mnonstop

$138Southwest

Find Deal

Sat, Nov 22 - Fri, Nov 28

9:40 pm - 11:10 pmLGA-MDW

2h 30mnonstop

6:10 am - 9:15 amMDW-LGA

2h 05mnonstop

$139Southwest

Find Deal

Tue, Dec 9 - Wed, Dec 17

8:30 am - 1:05 pmLGA-MDW

5h 35m1 stop

9:25 am - 4:10 pmMDW-LGA

5h 45m1 stop

$140Southwest

Find Deal

Sat, Dec 6 - Tue, Dec 9

2:15 pm - 3:45 pmLGA-MDW

2h 30mnonstop

7:15 pm - 10:20 pmMDW-LGA

2h 05mnonstop

$149Southwest

Find Deal

Sat, Nov 8 - Mon, Nov 10

2:15 pm - 3:45 pmLGA-MDW

2h 30mnonstop

8:25 pm - 11:25 pmMDW-LGA

2h 00mnonstop

$157Southwest

Find Deal

Thu, Nov 13 - Mon, Nov 17

7:15 am - 8:45 amLGA-MDW

2h 30mnonstop

2:15 pm - 9:25 pmMDW-LGA

6h 10m1 stop

$158Southwest

Find Deal

Wed, Dec 3 - Sat, Dec 6

9:10 am - 10:40 amLGA-MDW

2h 30mnonstop

12:40 pm - 10:20 pmMDW-LGA

8h 40m1 stop

$159Southwest

Find Deal

Useful Info

Low season	January
High season	May
Cheapest flight	$69
Average price round-trip	$309
Good deal one-way	$156

Best time to beat the crowds with an average 30% drop in price.

Most popular time to fly and prices are also 1% lower on average.

Flight from New York LaGuardia Airport to Chicago Midway Airport

(avg. price over the last 2 weeks)

or less

When to Book Flights with Southwest from New York to Chicago Midway Airport

Average price per month

Flight prices as travel date approaches

Is Southwest the cheapest airline to fly with from New York to Chicago Midway Airport?
With an average price of $274 return, Southwest is not the cheapest airline to fly from New York to Chicago Midway Airport with. Instead, for the lowest price, our data suggests flying with Spirit Airlines, where a return flight costs $161 on average.
What is the cheapest Southwest flight from New York to Chicago Midway Airport?
In the last 3 days, the lowest price for a flight with Southwest from New York to Chicago Midway Airport was $49 for a return flight and $34 for a one-way flight.
Does Southwest fly direct to Chicago Midway Airport from New York?
Yes, Southwest does offer direct flights for the route, with around 32 flights per week.
What’s the cheapest day of the week to fly from New York to Chicago Midway Airport with Southwest?
On average, the cheapest day of the week to fly from New York to Chicago Midway Airport with Southwest is Tuesday, when prices are around $77. The most expensive day is generally Sunday, where the average price is around $162.
What’s the cheapest month to fly from New York to Chicago Midway Airport with Southwest?
The cheapest month for Southwest flights to Chicago Midway Airport from New York is generally November, where plane tickets cost $114 on average. If possible, try to avoid the most expensive months of December and April, where tickets cost $239 and $277 respectively.

8.0

Very good4,239 verified ratings

8.6Crew

8.1Boarding

7.5Entertainment

7.0Food

8.0Comfort

Pros +

Cons -

Show reviews that mention

2.0 Poor

Verified traveler, Oct 2025

DAL-LIT

Delayed 5.5 hours

10.0 Wonderful

Verified traveler, Oct 2025

BOS-BWI

Great flight. Outstanding Service. Southwest was able to put us on a direct flight to Denver when the connection could have been affected by a later arrival to Baltimore. The direct flight was less expensive that the flight with the connection in Baltimore.

8.0 Very good

Verified traveler, Oct 2025

MHT-MDW

Getting worse with new changes.

4.0 Mediocre

Jeff, Oct 2025

MCI-SAN

Delays delays delays. Late taking off, late landing, wait for a gate, etc.

4.0 Mediocre

Thomas, Oct 2025

STL-CMH

Internet was not functioning.

2.0 Poor

Thomas, Oct 2025

SAT-STL

Boarded on time but once we were ready for take off, the crew determined that, although every seat was taken, somehow someone was on the wrong flight. Delay, delay delay, announcements and ended up with one person checking EVERY ID against their passenger Manifest only to figure out it was a "clerical error." We departed 54 minutes late causing me to run in the St. Louis Airport to make my connection and lose the priority boarding spot I had paid for. Unnecessary delay.

10.0 Wonderful

Lynda, Oct 2025

VPS-BNA

On time. Communication good. Smooth flight

2.0 Poor

Princess, Oct 2025

MSY-DAL

I was re-booked onto another flight because my original flight was delayed and I would have missed my connector. I ended up in the “C” group after paying extra to be in the “A “ group on the original flight. At least if you’re going to re-book people, re-book them into the same group.

6.0 Okay

Thomas, Oct 2025

DAL-SAT

Late again.

6.0 Okay

Thomas, Oct 2025

CMH-DAL

Just the usual delays

Everything you need to know for your flight from New York to Chicago Midway Airport

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NYC - MDW

$69 Find Cheap Southwest Flights from New York to Chicago Midway Airport

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Cheap Southwest Flight Deals from New York to Chicago Midway Airport

Recent round-trip Southwest flight deals from New York to Chicago Midway Airport

Recent one-way Southwest flight deals from New York to Chicago Midway Airport

Recent last minute Southwest flight deals from New York to Chicago Midway Airport

Recent direct Southwest flight deals from New York to Chicago Midway Airport

Good to know

When to Book Flights with Southwest from New York to Chicago Midway Airport

FAQs for flying to Chicago Midway Airport with Southwest

Is Southwest the cheapest airline to fly with from New York to Chicago Midway Airport?

What is the cheapest Southwest flight from New York to Chicago Midway Airport?

Does Southwest fly direct to Chicago Midway Airport from New York?

What’s the cheapest day of the week to fly from New York to Chicago Midway Airport with Southwest?

What’s the cheapest month to fly from New York to Chicago Midway Airport with Southwest?

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Everything you need to know for your flight from New York to Chicago Midway Airport

Cabin class types available on flights to Chicago Midway Airport

Cabin classes available on flights to New York. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.

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The most popular flights on KAYAK according to clicks in the last 2 weeks. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.

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Top Southwest flights

The most popular destinations for flights with Southwest according to clicks from KAYAK users. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.