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Cheap flights from Chicago Midway Airport to New York from $124

1 adult
1 adult, Economy, 0 bags

Find the cheapest flights from Chicago Midway Airport to New York

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
6:10 pm - 8:52 amMDW  Chicago Midway-SWF New Windsor Stewart
13h 42m1 stop Punta Gorda
Multiple Airlines Logo
12:16 pm - 8:42 pmSWF  New Windsor Stewart-MDW Chicago Midway
9h 26m2 stops Charleston Orlando
$412Multiple Airlines
Sun, Dec 6 - Mon, Dec 7
Multiple Airlines Logo
6:10 pm - 8:52 amMDW  Chicago Midway-SWF New Windsor Stewart
13h 42m1 stop Punta Gorda
Multiple Airlines Logo
12:16 pm - 8:42 pmSWF  New Windsor Stewart-MDW Chicago Midway
9h 26m2 stops Charleston Orlando
$414Multiple Airlines
Thu, Dec 3 - Mon, Dec 7
Multiple Airlines Logo
6:10 pm - 8:52 amMDW  Chicago Midway-SWF New Windsor Stewart
13h 42m1 stop Punta Gorda
Multiple Airlines Logo
12:16 pm - 8:42 pmSWF  New Windsor Stewart-MDW Chicago Midway
9h 26m2 stops Charleston Orlando
$419Multiple Airlines
Thu, Dec 3 - Mon, Dec 7
Multiple Airlines Logo
6:10 pm - 8:52 amMDW  Chicago Midway-SWF New Windsor Stewart
13h 42m1 stop Punta Gorda
Multiple Airlines Logo
12:16 pm - 8:42 pmSWF  New Windsor Stewart-MDW Chicago Midway
9h 26m2 stops Charleston Orlando
$423Multiple Airlines
Thu, Dec 3 - Mon, Dec 7
Multiple Airlines Logo
6:10 pm - 8:52 amMDW  Chicago Midway-SWF New Windsor Stewart
13h 42m1 stop Punta Gorda
Multiple Airlines Logo
12:16 pm - 8:42 pmSWF  New Windsor Stewart-MDW Chicago Midway
9h 26m2 stops Charleston Orlando
$425Multiple Airlines
Thu, Dec 3 - Mon, Dec 7
Multiple Airlines Logo
6:10 pm - 8:52 amMDW  Chicago Midway-SWF New Windsor Stewart
13h 42m1 stop Punta Gorda
Multiple Airlines Logo
12:16 pm - 8:42 pmSWF  New Windsor Stewart-MDW Chicago Midway
9h 26m2 stops Charleston Orlando
$426Multiple Airlines
Thu, Dec 10 - Mon, Dec 14
Multiple Airlines Logo
6:10 pm - 8:52 amMDW  Chicago Midway-SWF New Windsor Stewart
13h 42m1 stop Punta Gorda
Multiple Airlines Logo
12:16 pm - 8:42 pmSWF  New Windsor Stewart-MDW Chicago Midway
9h 26m2 stops Charleston Orlando
$431Multiple Airlines
Thu, Dec 3 - Mon, Dec 7
Multiple Airlines Logo
1:18 pm - 11:35 amMDW  Chicago Midway-SWF New Windsor Stewart
21h 17m2 stops Atlanta Hartsfield-Jackson Fort Lauderdale
Multiple Airlines Logo
10:56 am - 7:42 pmSWF  New Windsor Stewart-MDW Chicago Midway
9h 46m1 stop Orlando
$445Multiple Airlines
Wed, Jan 13 - Sun, Jan 17
Multiple Airlines Logo
6:10 pm - 8:52 amMDW  Chicago Midway-SWF New Windsor Stewart
13h 42m1 stop Punta Gorda
Multiple Airlines Logo
12:16 pm - 8:42 pmSWF  New Windsor Stewart-MDW Chicago Midway
9h 26m2 stops Charleston Orlando
$455Multiple Airlines
Thu, Dec 3 - Mon, Dec 7
Multiple Airlines Logo
5:26 pm - 10:11 amMDW  Chicago Midway-SWF New Windsor Stewart
15h 45m1 stop Punta Gorda
Multiple Airlines Logo
10:56 am - 7:42 pmSWF  New Windsor Stewart-MDW Chicago Midway
9h 46m1 stop Orlando
$466Multiple Airlines
Thu, Jan 14 - Thu, Jan 21

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Allegiant Air flights from Chicago Midway Airport to New Windsor

Our best Allegiant Air deals on Chicago Midway Airport to New Windsor flight tickets
Allegiant Air
Nov 12
MDW10:12 amChicago Midway
23h 07m
1 stop
SWF10:19 amNew Windsor Stewart
Nov 15
SWF5:37 pmNew Windsor Stewart
23h 04m
2 stops
MDW3:41 pmChicago Midway
$553
Allegiant Air
Nov 5
MDW10:12 amChicago Midway
23h 07m
1 stop
SWF10:19 amNew Windsor Stewart
Nov 8
SWF5:37 pmNew Windsor Stewart
23h 04m
2 stops
MDW3:41 pmChicago Midway
$640
Allegiant Air
Oct 15
MDW9:18 amChicago Midway
24h 11m
1 stop
SWF10:29 amNew Windsor Stewart
Oct 18
SWF11:53 amNew Windsor Stewart
25h 43m
2 stops
MDW12:36 pmChicago Midway
$753

momondo Fare Finder

 
Use the filters below to find and compare flights from Chicago Midway Airport to New Windsor that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

ChicagoNew Windsor

MDW Chicago Midway - SWF New Windsor Stewart

MDWSWF

Chicago Midway

Sun 12/6

6:10 pm-8:52 am

1 stop13h 42m

New Windsor Stewart

Mon 12/7

12:16 pm-8:42 pm

2 stops9h 26m

$412

ChicagoNew Windsor

MDW Chicago Midway - SWF New Windsor Stewart

MDWSWF

Chicago Midway

Thu 12/3

6:10 pm-8:52 am

1 stop13h 42m

New Windsor Stewart

Mon 12/7

12:16 pm-8:42 pm

2 stops9h 26m

$414

ChicagoNew Windsor

MDW Chicago Midway - SWF New Windsor Stewart

MDWSWF

Chicago Midway

Thu 12/3

6:10 pm-8:52 am

1 stop13h 42m

New Windsor Stewart

Mon 12/7

12:16 pm-8:42 pm

2 stops9h 26m

$419

ChicagoNew Windsor

MDW Chicago Midway - SWF New Windsor Stewart

MDWSWF

Chicago Midway

Thu 12/3

6:10 pm-8:52 am

1 stop13h 42m

New Windsor Stewart

Mon 12/7

12:16 pm-8:42 pm

2 stops9h 26m

$423

ChicagoNew Windsor

MDW Chicago Midway - SWF New Windsor Stewart

MDWSWF

Chicago Midway

Thu 12/3

6:10 pm-8:52 am

1 stop13h 42m

New Windsor Stewart

Mon 12/7

12:16 pm-8:42 pm

2 stops9h 26m

$425

ChicagoNew Windsor

MDW Chicago Midway - SWF New Windsor Stewart

MDWSWF

Chicago Midway

Thu 12/10

6:10 pm-8:52 am

1 stop13h 42m

New Windsor Stewart

Mon 12/14

12:16 pm-8:42 pm

2 stops9h 26m

$426

ChicagoNew Windsor

MDW Chicago Midway - SWF New Windsor Stewart

MDWSWF

Chicago Midway

Thu 12/3

6:10 pm-8:52 am

1 stop13h 42m

New Windsor Stewart

Mon 12/7

12:16 pm-8:42 pm

2 stops9h 26m

$431

ChicagoNew Windsor

MDW Chicago Midway - SWF New Windsor Stewart

MDWSWF

Chicago Midway

Wed 1/13

1:18 pm-11:35 am

2 stops21h 17m

New Windsor Stewart

Sun 1/17

10:56 am-7:42 pm

1 stop9h 46m

$445

ChicagoNew Windsor

MDW Chicago Midway - SWF New Windsor Stewart

MDWSWF

Chicago Midway

Thu 12/3

6:10 pm-8:52 am

1 stop13h 42m

New Windsor Stewart

Mon 12/7

12:16 pm-8:42 pm

2 stops9h 26m

$455

ChicagoNew Windsor

MDW Chicago Midway - SWF New Windsor Stewart

MDWSWF

Chicago Midway

Thu 1/14

5:26 pm-10:11 am

1 stop15h 45m

New Windsor Stewart

Thu 1/21

10:56 am-7:42 pm

1 stop9h 46m

$466

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to New York from

How to get the cheapest flight ticket from Chicago Midway Airport to New Windsor

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest airline that flies from Chicago Midway to New Windsor Stewart?

Allegiant Air is the most popular carrier operating from Chicago Midway to New Windsor Stewart

What airlines fly to New Windsor?

Southwest, Frontier and Delta are the top three most popular airlines that fly to New Windsor from Chicago Midway Airport according to our data. Southwest is the first choice among our users, with 85% of people opting to fly with this airline when traveling to New Windsor. Keep in mind that there are 3 different airlines that fly to New Windsor on a routine basis, so you have a few additional options to choose from.

When to book flights from Chicago Midway Airport to New Windsor

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago Midway Airport to New Windsor according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago Midway Airport to New Windsor (MDW to SWF) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to New Windsor

Best Price Found

$124

Fastest flight time

12h 34m

Direct flights

None
The best one-way flight to New Windsor from Chicago Midway Airport in the past 72 hours is $124. The best round-trip flight deal from Chicago Midway Airport to New Windsor found on momondo in the last 72 hours is $412.
The fastest flight from Chicago Midway Airport to New Windsor takes 12h 34m
There are no direct flights from Chicago Midway Airport to New Windsor. There are no popular flight routes from Chicago Midway Airport to New Windsor.
Search flight deals

Frequently asked questions about flying from Chicago Midway Airport to New Windsor

  • How far is Chicago Midway to New Windsor Stewart by plane?

    There are 707.7 mi between Chicago Midway and New Windsor Stewart. In terms of flight time, this usually takes a little over 12h 34m.

  • When did momondo last update prices for flights from Chicago Midway Airport to New Windsor Stewart Airport?

    Prices for flights from Chicago Midway Airport to New Windsor Stewart Airport are refreshed on a daily basis.

  • How old do you have to be to fly from Chicago Midway Airport to New Windsor Stewart Airport?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago Midway Airport to New Windsor Stewart Airport.

  • What documentation or ID do you need to fly to New Windsor Stewart Airport?

    The necessary travel and health documents for your New Windsor Stewart Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

Traveling to a place near New York?

Book flights to New York if you plan to visit one of these locations
Newburgh
Kingston
Woodstock
Saugerties

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to New Windsor?

Finding the right flight to New Windsor from Chicago is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to New Windsor quick and easy, saving you time and money.

Can I find flights from Chicago to New Windsor with flexible booking policies on momondo?

All flight searches from Chicago to New Windsor on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights from Chicago to New Windsor?

Once you have performed a search for Chicago to New Windsor flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

I’m not ready to book a flight from Chicago to New Windsor right now. Can momondo alert me if prices change?

Price alerts on flights to New Windsor from Chicago are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

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