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Cheap flights from New Windsor to Chicago from $109

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from New Windsor to Chicago departing on 12/7. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from New Windsor to Chicago

Cheap round-trip flights

These are some of the best round-trip flight deals from New Windsor to Chicago that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from New Windsor to Chicago.

Cheap last minute flights

Planning a quick getaway from New Windsor to Chicago? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to Chicago, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from New Windsor to Chicago

Find recent round-trip train or bus tickets from New Windsor to Chicago.

All round-trip flight deals to Chicago

The cheapest plane tickets to Chicago found on KAYAK recently.
5:59 pm - 9:39 amSWF-ORD
16h 40m1 stop
5:35 am - 5:19 pmORD-SWF
10h 44m1 stop
Wed, Jan 15 - Wed, Jan 22
12:55 pm - 9:07 pmSWF-ORD
9h 12m1 stop
6:05 am - 6:50 pmORD-SWF
11h 45m1 stop
Fri, Dec 13 - Wed, Dec 18
12:55 pm - 9:07 pmSWF-ORD
9h 12m1 stop
5:11 pm - 12:05 pmORD-SWF
17h 54m1 stop
Fri, Dec 13 - Sun, Dec 15
11:40 am - 11:11 pmSWF-ORD
12h 31m1 stop
8:20 am - 6:50 pmORD-SWF
9h 30m1 stop
Sat, Dec 7 - Wed, Dec 11
12:55 pm - 9:07 pmSWF-ORD
9h 12m1 stop
5:11 pm - 12:05 pmORD-SWF
17h 54m1 stop
Fri, Dec 13 - Sun, Dec 15
6:44 pm - 11:12 amSWF-ORD
17h 28m1 stop
6:06 pm - 11:20 amORD-SWF
16h 14m2 stops
Thu, Jan 9 - Sun, Jan 12
12:55 pm - 9:07 pmSWF-ORD
9h 12m1 stop
5:11 pm - 12:05 pmORD-SWF
17h 54m1 stop
Fri, Dec 13 - Sun, Dec 15
12:55 pm - 9:07 pmSWF-ORD
9h 12m1 stop
7:45 pm - 12:05 pmORD-SWF
15h 20m2 stops
Fri, Dec 13 - Sun, Dec 15
5:57 pm - 9:17 amSWF-RFD
16h 20m1 stop
10:30 am - 7:10 pmRFD-SWF
7h 40m1 stop
$472Allegiant Air
Find Deal
Sat, Dec 21 - Mon, Dec 30
8:00 pm - 9:54 amSWF-RFD
14h 54m1 stop
10:30 am - 7:10 pmRFD-SWF
7h 40m1 stop
$482Allegiant Air
Find Deal
Mon, Dec 23 - Mon, Dec 30
11:40 am - 11:11 pmSWF-ORD
12h 31m1 stop
Sat, Dec 7
2:10 pm - 11:02 pmSWF-ORD
9h 52m1 stop
Mon, Feb 10
10:57 am - 6:50 pmSWF-ORD
8h 53m1 stop
Fri, Dec 6
12:55 pm - 9:07 pmSWF-ORD
9h 12m1 stop
Fri, Dec 13
11:40 am - 11:11 pmSWF-ORD
12h 31m1 stop
Sat, Dec 7
7:54 pm - 9:52 amSWF-RFD
14h 58m1 stop
Thu, Feb 6
10:57 am - 6:50 pmSWF-ORD
8h 53m1 stop
Mon, Dec 9
11:46 am - 9:37 amSWF-ORD
22h 51m2 stops
Mon, Dec 16
5:57 pm - 9:17 amSWF-RFD
16h 20m1 stop
$183Allegiant Air
Find Deal
Sat, Dec 21
7:41 pm - 8:18 amSWF-RFD
13h 37m1 stop
$186Allegiant Air
Find Deal
Sun, Mar 23
10:10 am - 8:03 pmSWF-ORD
10h 53m1 stop
7:39 pm - 1:10 pmORD-SWF
16h 31m1 stop
Fri, Nov 22 - Sun, Nov 24
7:50 pm - 6:31 pmSWF-ORD
23h 41m2 stops
9:10 pm - 5:21 pmORD-SWF
19h 11m2 stops
Sun, Nov 24 - Tue, Nov 26
10:10 am - 7:37 amSWF-ORD
22h 27m2 stops
7:39 pm - 1:10 pmORD-SWF
16h 31m1 stop
Fri, Nov 22 - Sun, Nov 24
7:50 pm - 8:26 pmSWF-ORD
25h 36m3 stops
9:10 pm - 5:21 pmORD-SWF
19h 11m2 stops
Sun, Nov 24 - Tue, Nov 26
7:50 pm - 10:56 amSWF-ORD
16h 06m1 stop
9:10 pm - 5:21 pmORD-SWF
19h 11m2 stops
Sun, Nov 24 - Tue, Nov 26
10:10 am - 6:31 pmSWF-ORD
9h 21m1 stop
7:39 pm - 1:10 pmORD-SWF
16h 31m1 stop
Fri, Nov 22 - Sun, Nov 24
7:50 pm - 8:26 pmSWF-ORD
25h 36m3 stops
11:51 am - 5:21 pmORD-SWF
28h 30m3 stops
Sun, Nov 24 - Tue, Nov 26
10:10 am - 7:37 amSWF-ORD
22h 27m2 stops
7:39 pm - 1:10 pmORD-SWF
16h 31m1 stop
Fri, Nov 22 - Sun, Nov 24
11:46 am - 8:15 pmSWF-ORD
9h 29m2 stops
5:41 pm - 11:00 amORD-SWF
16h 19m2 stops
Fri, Nov 22 - Mon, Nov 25
11:46 am - 8:15 pmSWF-ORD
9h 29m2 stops
4:45 pm - 11:06 amORD-SWF
17h 21m3 stops
Fri, Nov 22 - Sun, Nov 24

Allegiant Air flights from New Windsor to Chicago

Our best Allegiant Air deals on New Windsor to Chicago flight tickets
Allegiant Air
Dec 21
SWF5:57 pmNew Windsor Stewart
16h 20m
1 stop
RFD9:17 amChicago Greater Rockford
Dec 30
RFD10:30 amChicago Greater Rockford
7h 40m
1 stop
SWF7:10 pmNew Windsor Stewart
Allegiant Air
Dec 23
SWF8:00 pmNew Windsor Stewart
14h 54m
1 stop
RFD9:54 amChicago Greater Rockford
Dec 30
RFD10:30 amChicago Greater Rockford
7h 40m
1 stop
SWF7:10 pmNew Windsor Stewart

See travel insights to Chicago from

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

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 month to fly to Chicago?

The month of September is, on average, the cheapest month to fly to Chicago from New Windsor, with most prices found around $176. If you’re not able to fly to Chicago in September, then January is your next best option. Flight prices from New Windsor to Chicago during January average around $196.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Tuesday when prices can be found for as low as $201. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from New Windsor to Chicago for around $272.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from New Windsor to Chicago during this time can be as low as $213. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $265.

How far in advance should I book a flight to Chicago?

The best time to book a flight to Chicago from New Windsor is 30 days out, which is when prices tend to be around $228. Don’t hesitate to check prices now though because momondo users recently found tickets for as low as $165.

Can stopping save me money on New Windsor to Chicago flights?

You could potentially save up to 21% on your flight if you consider stops on a New Windsor to Chicago flight.

When to book flights from New Windsor to Chicago

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

Cheap New Windsor to Chicago (SWF to CHI) flight deals and tips

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

Best Price Found

$109

Fastest flight time

7h 16m

Direct flights

None

Airports in Chicago

2 airports
The best one-way flight to Chicago from New Windsor in the past 72 hours is $109. The best round-trip flight deal from New Windsor to Chicago found on momondo in the last 72 hours is $229.
The fastest flight from New Windsor to Chicago takes 7h 16m
There are no direct flights from New Windsor to Chicago. Popular non-direct routes for this connection are New Windsor Stewart Airport - Chicago O'Hare Intl Airport and New Windsor Stewart Airport - Chicago Greater Rockford Airport.
There are 2 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Greater Rockford (RFD)

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

    There are 701.4 mi between New Windsor Stewart and Chicago. Flights usually cover this in 9h 12m, depending on flying conditions and air traffic around both airports.

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

    Prices for flights from New Windsor Stewart Airport to Chicago are updated daily.

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

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from New Windsor Stewart Airport to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The required travel and health documents for your Chicago trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

  • What is the most popular airline from New Windsor to Chicago?


Why use momondo?

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

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from New Windsor to Chicago. Millions of users trust and use momondo every year so you are in good hands.

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

Yes. momondo allows you to filter the results for New Windsor to Chicago flights to just show those with flexible booking policies.

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

Once all potential New Windsor to Chicago flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

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

Of course. momondo tracks the price of New Windsor to Chicago flights. All you need is a valid email address and we will do the rest; it is that quick and easy.


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Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago