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Cheap flights from Chicago Midway Airport to New York from $139

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
10:38 am - 10:29 amMDW  Chicago Midway-SWF New Windsor Stewart
22h 51m1 stop Punta Gorda
Multiple Airlines Logo
12:39 pm - 11:43 pmSWF  New Windsor Stewart-MDW Chicago Midway
12h 04m2 stops Raleigh-Durham Atlanta Hartsfield-Jackson
$359Multiple Airlines
Thu, Oct 1 - Wed, Oct 14
Multiple Airlines Logo
10:08 am - 10:29 amMDW  Chicago Midway-SWF New Windsor Stewart
23h 21m1 stop Punta Gorda
Multiple Airlines Logo
7:01 pm - 9:53 pmSWF  New Windsor Stewart-MDW Chicago Midway
27h 52m2 stops Orlando Sanford Intl Atlanta Hartsfield-Jackson
$362Multiple Airlines
Thu, Oct 22 - Mon, Oct 26
Multiple Airlines Logo
10:38 am - 10:29 amMDW  Chicago Midway-SWF New Windsor Stewart
22h 51m1 stop Punta Gorda
Multiple Airlines Logo
12:39 pm - 11:43 pmSWF  New Windsor Stewart-MDW Chicago Midway
12h 04m2 stops Raleigh-Durham Atlanta Hartsfield-Jackson
$371Multiple Airlines
Thu, Oct 1 - Sat, Oct 10
Multiple Airlines Logo
10:38 am - 10:29 amMDW  Chicago Midway-SWF New Windsor Stewart
22h 51m1 stop Punta Gorda
Multiple Airlines Logo
10:56 am - 11:43 pmSWF  New Windsor Stewart-MDW Chicago Midway
13h 47m2 stops Orlando Atlanta Hartsfield-Jackson
$465Multiple Airlines
Thu, Oct 1 - Thu, Oct 15
Multiple Airlines Logo
4:53 pm - 9:50 amMDW  Chicago Midway-SWF New Windsor Stewart
15h 57m1 stop Punta Gorda
Multiple Airlines Logo
11:06 am - 7:02 pmSWF  New Windsor Stewart-MDW Chicago Midway
8h 56m1 stop Orlando
$591Multiple Airlines
Thu, Dec 24 - Thu, Dec 31
Allegiant Air Logo
10:38 am - 10:29 amMDW  Chicago Midway-SWF New Windsor Stewart
22h 51m1 stop Punta Gorda
Allegiant Air Logo
6:45 pm - 11:36 amSWF  New Windsor Stewart-MDW Chicago Midway
17h 51m2 stops Tampa St. Petersburg Knoxville McGhee Tyson
$609Allegiant Air
Thu, Oct 1 - Thu, Oct 8
Multiple Airlines Logo
8:07 pm - 11:36 amMDW  Chicago Midway-SWF New Windsor Stewart
14h 29m2 stops Orlando Charleston
Multiple Airlines Logo
11:06 am - 7:02 pmSWF  New Windsor Stewart-MDW Chicago Midway
8h 56m1 stop Orlando
$683Multiple Airlines
Thu, Dec 3 - Sun, Dec 6

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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

ChicagoNew Windsor

MDW Chicago Midway - SWF New Windsor Stewart

MDWSWF

Chicago Midway

Thu 10/1

10:38 am-10:29 am

1 stop22h 51m

New Windsor Stewart

Wed 10/14

12:39 pm-11:43 pm

2 stops12h 04m

$359

ChicagoNew Windsor

MDW Chicago Midway - SWF New Windsor Stewart

MDWSWF

Chicago Midway

Thu 10/22

10:08 am-10:29 am

1 stop23h 21m

New Windsor Stewart

Mon 10/26

7:01 pm-9:53 pm

2 stops27h 52m

$362

ChicagoNew Windsor

MDW Chicago Midway - SWF New Windsor Stewart

MDWSWF

Chicago Midway

Thu 10/1

10:38 am-10:29 am

1 stop22h 51m

New Windsor Stewart

Sat 10/10

12:39 pm-11:43 pm

2 stops12h 04m

$371

ChicagoNew Windsor

MDW Chicago Midway - SWF New Windsor Stewart

MDWSWF

Chicago Midway

Thu 10/1

10:38 am-10:29 am

1 stop22h 51m

New Windsor Stewart

Thu 10/15

10:56 am-11:43 pm

2 stops13h 47m

$465

ChicagoNew Windsor

MDW Chicago Midway - SWF New Windsor Stewart

MDWSWF

Chicago Midway

Thu 12/24

4:53 pm-9:50 am

1 stop15h 57m

New Windsor Stewart

Thu 12/31

11:06 am-7:02 pm

1 stop8h 56m

$591

ChicagoNew Windsor

MDW Chicago Midway - SWF New Windsor Stewart

MDWSWF

Chicago Midway

Thu 10/1

10:38 am-10:29 am

1 stop22h 51m

New Windsor Stewart

Thu 10/8

6:45 pm-11:36 am

2 stops17h 51m

$609
Quickest round-trip

ChicagoNew Windsor

MDW Chicago Midway - SWF New Windsor Stewart

MDWSWF

Chicago Midway

Thu 12/3

8:07 pm-11:36 am

2 stops14h 29m

New Windsor Stewart

Sun 12/6

11:06 am-7:02 pm

1 stop8h 56m

$683
Cheapest one-way

ChicagoNew Windsor

MDW Chicago Midway - SWF New Windsor Stewart

MDWSWF

Chicago Midway

Tue 10/13

6:15 am-9:28 am

2 stops50h 13m

$139

ChicagoNew Windsor

MDW Chicago Midway - SWF New Windsor Stewart

MDWSWF

Chicago Midway

Wed 9/16

6:25 am-11:36 am

3 stops52h 11m

$144

ChicagoNew Windsor

MDW Chicago Midway - SWF New Windsor Stewart

MDWSWF

Chicago Midway

Wed 9/16

6:25 am-11:36 am

3 stops52h 11m

$145

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 17 resultsSorted by cheapest first
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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 82% 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

$139

Fastest flight time

22h 51m

Direct flights

None
The best one-way flight to New Windsor from Chicago Midway Airport in the past 72 hours is $139. The best round-trip flight deal from Chicago Midway Airport to New Windsor found on momondo in the last 72 hours is $359.
The fastest flight from Chicago Midway Airport to New Windsor takes 22h 51m
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 22h 51m.

  • 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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