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Cheap flights from New Windsor (SWF) to Chicago (CHI) from $114

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 6/3. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
SWF — CHI
May 13 — May 201
From?
To?
Mon 5/13
Mon 5/20
1 adult, Economy
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Cheap flight deals from Stewart to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Stewart (SWF) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated May 8, 2024.

Round-trip from

$223

One-way from

$114
From New Windsor Stewart to Chicago (CHI)
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One-way flight from New Windsor Stewart to Chicago (CHI)
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How far in advance should I book a flight from New Windsor to Chicago?

Users have found that booking a flight from New Windsor to Chicago at least 56 days early can save you up to 102% on average compared to booking a flight this week. If booking 56 days before your flight isn’t an option for you, users have found flights from New Windsor to Chicago for as little as $276 when booking for a departure date within the next two weeks. You can also check prices now. Some users have found airline tickets as low as $423 for flights departing within the next 3 days.

What is the cheapest month to fly from New Windsor to Chicago?

February can be a great time to fly to Chicago from New Windsor with a flight ticket averaging about $262. Cheapflights users have found deals in the month of February for as cheap as $81. The most expensive prices can be found in the month of June.

When is the cheapest time to fly from New Windsor to Chicago (SWF - CHI)?

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

Cheap Stewart to Chicago flights in May & June 2024

Find cheap flight options from Stewart to Chicago specifically for the months of May and June 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 2,752,338 searches. Prices were last updated on May 8, 2024.
Sat 6/229:41 amSWF - ORD
1 stop14h 40mMultiple Airlines
Sun 6/307:18 amORD - SWF
1 stop9h 09mMultiple Airlines
Deal found 5/7$316
Mon 6/1012:46 pmSWF - ORD
2 stops20h 48mMultiple Airlines
Thu 6/135:18 pmORD - SWF
2 stops17h 48mMultiple Airlines
Deal found 5/7$347
Mon 6/1012:46 pmSWF - ORD
2 stops20h 48mMultiple Airlines
Thu 6/135:20 amORD - SWF
3 stops29h 46mMultiple Airlines
Deal found 5/7$350
Fri 5/175:54 pmSWF - ORD
1 stop25h 23mMultiple Airlines
Sun 5/196:12 amORD - SWF
1 stop28h 01mMultiple Airlines
Deal found 5/7$358
Mon 6/1012:46 pmSWF - ORD
3 stops28h 42mMultiple Airlines
Thu 6/135:20 amORD - SWF
3 stops29h 46mMultiple Airlines
Deal found 5/7$374
Mon 5/1312:46 pmSWF - ORD
2 stops35h 43mMultiple Airlines
Sun 5/196:12 amORD - SWF
1 stop28h 01mMultiple Airlines
Deal found 5/7$380
Fri 5/175:54 pmSWF - ORD
1 stop25h 23mMultiple Airlines
Sun 5/196:12 amORD - SWF
1 stop28h 01mMultiple Airlines
Deal found 5/7$420
Thu 5/1610:25 amSWF - ORD
2 stops25h 43mMultiple Airlines
Sun 5/1910:58 amORD - SWF
2 stops24h 08mMultiple Airlines
Deal found 5/7$430
Mon 6/1012:46 pmSWF - ORD
2 stops20h 48mMultiple Airlines
Thu 6/135:20 amORD - SWF
1 stop13h 37mMultiple Airlines
Deal found 5/7$478

Stewart to Chicago 2024 flight deals

Discover exclusive flight deals for travel between Stewart and Chicago in 2024. Find excellent offers based on user searches. Over the last 7 days, Cheapflights users made 2,752,338 searches. Data last updated May 8, 2024.
Sat 6/229:41 amSWF - ORD
1 stop14h 40mMultiple Airlines
Sun 6/307:18 amORD - SWF
1 stop9h 09mMultiple Airlines
Deal found 5/7$316
Mon 6/1012:46 pmSWF - ORD
2 stops20h 48mMultiple Airlines
Thu 6/135:18 pmORD - SWF
2 stops17h 48mMultiple Airlines
Deal found 5/7$347
Mon 6/1012:46 pmSWF - ORD
2 stops20h 48mMultiple Airlines
Thu 6/135:20 amORD - SWF
3 stops29h 46mMultiple Airlines
Deal found 5/7$350
Fri 5/175:54 pmSWF - ORD
1 stop25h 23mMultiple Airlines
Sun 5/196:12 amORD - SWF
1 stop28h 01mMultiple Airlines
Deal found 5/7$358
Mon 6/1012:46 pmSWF - ORD
3 stops28h 42mMultiple Airlines
Thu 6/135:20 amORD - SWF
3 stops29h 46mMultiple Airlines
Deal found 5/7$374
Mon 5/1312:46 pmSWF - ORD
2 stops35h 43mMultiple Airlines
Sun 5/196:12 amORD - SWF
1 stop28h 01mMultiple Airlines
Deal found 5/7$380
Fri 5/175:54 pmSWF - ORD
1 stop25h 23mMultiple Airlines
Sun 5/196:12 amORD - SWF
1 stop28h 01mMultiple Airlines
Deal found 5/7$420
Thu 5/1610:25 amSWF - ORD
2 stops25h 43mMultiple Airlines
Sun 5/1910:58 amORD - SWF
2 stops24h 08mMultiple Airlines
Deal found 5/7$430
Fri 7/2611:59 amSWF - ORD
1 stop7h 27mMultiple Airlines
Sat 7/277:18 amORD - SWF
1 stop9h 09mMultiple Airlines
Deal found 5/8$458

Stewart to Chicago flights leaving soon

Find last-minute flight options from Stewart to Chicago for spontaneous travel. Discover available flights and compare prices based on user searches. Secure great deals and offers for spontaneous trips with quick booking options. Over the last 7 days, Cheapflights users made 2,752,338 searches. Data last updated May 8, 2024.
Fri 5/175:54 pmSWF - ORD
1 stop25h 23mMultiple Airlines
Sun 5/196:12 amORD - SWF
1 stop28h 01mMultiple Airlines
Deal found 5/7$358
Mon 5/1312:46 pmSWF - ORD
2 stops35h 43mMultiple Airlines
Sun 5/196:12 amORD - SWF
1 stop28h 01mMultiple Airlines
Deal found 5/7$380
Fri 5/175:54 pmSWF - ORD
1 stop25h 23mMultiple Airlines
Sun 5/196:12 amORD - SWF
1 stop28h 01mMultiple Airlines
Deal found 5/7$420
Thu 5/1610:25 amSWF - ORD
2 stops25h 43mMultiple Airlines
Sun 5/1910:58 amORD - SWF
2 stops24h 08mMultiple Airlines
Deal found 5/7$430
Thu 5/1610:25 amSWF - ORD
2 stops25h 43mMultiple Airlines
Sun 5/197:30 amORD - SWF
3 stops27h 36mMultiple Airlines
Deal found 5/7$486
Thu 5/1610:25 amSWF - ORD
3 stops25h 43mMultiple Airlines
Sun 5/197:30 amORD - SWF
3 stops27h 36mMultiple Airlines
Deal found 5/7$574
Thu 5/1610:25 amSWF - ORD
1 stop12h 47mMultiple Airlines
Sun 5/1910:58 amORD - SWF
2 stops24h 08mMultiple Airlines
Deal found 5/7$692
Sat 5/187:15 pmSWF - ORD
3 stops39h 40mMultiple Airlines
Wed 5/225:00 amORD - SWF
2 stops27h 45mMultiple Airlines
Deal found 5/8$1,143
Sat 5/187:15 pmSWF - ORD
3 stops39h 40mMultiple Airlines
Wed 5/2210:58 amORD - SWF
3 stops21h 47mMultiple Airlines
Deal found 5/8$1,166

One-way flights to Chicago from Stewart

Search for one-way flight options from Stewart to Chicago. Find affordable one-way fares based on user searches. Compare prices and availability to plan your one-way journey according to your preferred dates and budget. Over the last 7 days, Cheapflights users made 2,752,338 searches. Data last updated May 8, 2024.
Mon 6/310:38 amSWF - ORD
1 stop10h 07mMultiple Airlines
Deal found 5/6$114
Fri 5/3110:38 amSWF - ORD
1 stop10h 07mMultiple Airlines
Deal found 5/7$140
Mon 5/2012:03 pmSWF - ORD
1 stop12h 07mMultiple Airlines
Deal found 5/7$169
Mon 6/1012:46 pmSWF - ORD
2 stops20h 48mMultiple Airlines
Deal found 5/7$172
Fri 5/175:54 pmSWF - ORD
1 stop25h 23mMultiple Airlines
Deal found 5/7$181
Fri 7/1911:59 amSWF - ORD
1 stop7h 27mMultiple Airlines
Deal found 5/7$193
Mon 6/1012:46 pmSWF - ORD
3 stops29h 54mMultiple Airlines
Deal found 5/7$195
Mon 7/811:59 amSWF - ORD
1 stop7h 13mMultiple Airlines
Deal found 5/7$200
Fri 7/2611:59 amSWF - ORD
1 stop7h 27mMultiple Airlines
Deal found 5/7$201

Find flights from Stewart to Chicago within your budget

Customize your flight search to find flights from Stewart to Chicago 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 2,752,338 searches. Data last updated May 8, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$316 - $458

Route

Depart

Return

Price

New Windsor StewartChicago O'Hare Intl

SWF - ORD

SWFORD

New Windsor Stewart

Sat 6/22

1 stop14h 40m

Chicago O'Hare Intl

Sun 6/30

1 stop9h 09m

$316

New Windsor StewartChicago O'Hare Intl

SWF - ORD

SWFORD

New Windsor Stewart

Mon 6/10

2 stops20h 48m

Chicago O'Hare Intl

Thu 6/13

2 stops17h 48m

$347

New Windsor StewartChicago O'Hare Intl

SWF - ORD

SWFORD

New Windsor Stewart

Mon 6/10

2 stops20h 48m

Chicago O'Hare Intl

Thu 6/13

3 stops29h 46m

$350

New Windsor StewartChicago O'Hare Intl

SWF - ORD

SWFORD

New Windsor Stewart

Fri 5/17

1 stop25h 23m

Chicago O'Hare Intl

Sun 5/19

1 stop28h 01m

$358

New Windsor StewartChicago O'Hare Intl

SWF - ORD

SWFORD

New Windsor Stewart

Mon 6/10

3 stops28h 42m

Chicago O'Hare Intl

Thu 6/13

3 stops29h 46m

$374

New Windsor StewartChicago O'Hare Intl

SWF - ORD

SWFORD

New Windsor Stewart

Mon 5/13

2 stops35h 43m

Chicago O'Hare Intl

Sun 5/19

1 stop28h 01m

$380

New Windsor StewartChicago O'Hare Intl

SWF - ORD

SWFORD

New Windsor Stewart

Fri 5/17

1 stop25h 23m

Chicago O'Hare Intl

Sun 5/19

1 stop28h 01m

$420

New Windsor StewartChicago O'Hare Intl

SWF - ORD

SWFORD

New Windsor Stewart

Thu 5/16

2 stops25h 43m

Chicago O'Hare Intl

Sun 5/19

2 stops24h 08m

$430

New Windsor StewartChicago O'Hare Intl

SWF - ORD

SWFORD

New Windsor Stewart

Fri 7/26

1 stop7h 27m

Chicago O'Hare Intl

Sat 7/27

1 stop9h 09m

$458

Flights are sorted by cheapest first

Deals found on 5/7

No data available for this route at this time. Please check back soon.

Average price of flights to Chicago by month

Plan your trip from Stewart to Chicago by taking into account the cheapest months to travel. The average price of a one-way flight from Stewart to Chicago is currently $174 while a round-trip flight costs $381. Price data was last updated on May 5, 2024.

Currently, February is the cheapest month in which you can book a flight from New Windsor to Chicago (average of $244). Flying from New Windsor to Chicago in June is currently the most expensive (average of $348). 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.

January

$248

February

$244

March

$280

April

$258

May

$278

June

$348

July

$330

August

$274

September

$258

October

$248

November

$270

December

$248

Temperature and rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average temperature and rainfall totals by month.

CHI

Temperature

23 - 73.4 °F

Related info for your journey

Find useful and relevant information for your journey from Stewart to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from New Windsor to Chicago?

    Located just 4.3 mi from the city center, New Windsor Stewart is the airport most travelers will use when flying to Chicago from New Windsor. Booking flights from Stewart (SWF) to Chicago should be relatively easy as there are 0 daily outbound flights to Chicago from 0 different airlines.

  • Can I find flights from New Windsor to Chicago for under $400 on Cheapflights?

    Yes, there are multiple flights from New Windsor to Chicago for under $400. The cheapest flight booked recently is on Multiple Airlines for just $316, but on average you can expect to pay $483.

  • Are there last-minute flights available from New Windsor to Chicago for under $400?

    There are currently 10+ open flights from New Windsor to Chicago within the next 7 days for less than $400.

  • What are the most popular routes from New Windsor to Chicago?

    While some choose either New Windsor Stewart - Chicago Midway or New Windsor Stewart - Chicago Greater Rockford, New Windsor Stewart - Chicago O'Hare Intl is the most popular route from New Windsor to Chicago.

  • What does SWF to ORD mean?

    This is defined as New Windsor Stewart Airport (SWF) and Chicago O'Hare Intl Airport (ORD). Codes like Chicago O'Hare Intl Airport are often used to just call airports uniquely. Ready for more IATA code knowledge? These are related airports for your current travel destination: Chicago Midway Airport (MDW), Chicago Greater Rockford Airport (RFD).

  • Can I find deals for flights from Stewart to Chicago that include extra baggage allowance?

    The amount of baggage you can bring on your Stewart to Chicago flight depends on the airline and the type of fare you've chosen. After entering your flight details, you'll be able to view the specific baggage policies for each deal in the search results. Keep in mind that certain deals may offer additional baggage allowance.

  • Can I find deals on flights from Stewart to Chicago with specific airlines?

    Yes, Cheapflights allows you to browse and filter Stewart to Chicago flight deals by airline. After entering your origin and destination, use the available filters to view flights offered by airlines.

  • Can I find deals for flights from Stewart to Chicago that include hotel bookings?

    Yes. In addition to deals on Stewart to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Stewart to Chicago?

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

  • Can I find deals for business class flights from Stewart to Chicago?

    Yes. Cheapflights offers flight deals from Stewart to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • Can I find deals for flights from Stewart to Chicago that allow pets onboard?

    Many airlines flying from Stewart to Chicago offer the option to travel with pets. After selecting a flight deal, you can find more information about the airline's pet policy on their official website or by contacting the airline directly. Please note that additional fees and restrictions may apply.

  • Can I find deals on last-minute flights from Stewart to Chicago?

    Yes, you can often find last-minute deals on Stewart to Chicago flights on Cheapflights. However, these deals can vary and may not always be available. We recommend checking back frequently or signing up for price alerts for the most up-to-date deals.

  • How recently were the New Windsor to Chicago flight deals updated?

    The New Windsor to Chicago flight deals you see on this page were last updated on 5/8.

See more FAQs

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Alternative routes for Stewart to Chicago
See prices for flight routes from nearby airports that may be better suited for you.

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Search flights from Stewart to Chicago by cabin class

Find flights from Stewart to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
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Fly with Cheapflights

Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.

How does Cheapflights help users find flights from Stewart to Chicago?

900+ travel sites are searched through when a user searches for a flight using Cheapflights. From the search interface, users can use filters to choose airlines, airports, flight times, cabin classes and more to their preference. Book your flight to Chicago from Stewart today with Cheapflights!

Why should you use Cheapflights to find cheap flight tickets from Stewart to Chicago?

By finding flights from multiple airlines and providers at completely no cost, Cheapflights helps millions of users like you annually find the best flights to Chicago from Stewart.

Can Cheapflights find flights from Stewart to Chicago with no change fees?

Yes! Cheapflights helps users easily find flights from Stewart to Chicago with no change fees.

Can Cheapflights notify me if prices for flights from Stewart to Chicago become cheaper?

Yes, Cheapflights offers price alerts on Stewart to Chicago flights so you can book your travel at the perfect time. Price Alerts can be enabled by clicking the bell icon next to the flight deals above and providing your email address where you want to receive the alerts.

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