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$206+ Cheap flights from New Windsor (SWF) to Midway (MDW)

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 6/8. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — MDW
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
1 adult, Economy
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Cheap flight deals from Stewart to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Stewart (SWF) to Midway (MDW). 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 February 20, 2025.

Most accurate provider

Expedia
1 star

Most trusted provider

Expedia
3 stars

Round-trip from

$305
(Mytrip)

One-way from

$206
(Mytrip)

Popular in

December

Cheapest in

September

Average price

$207
Provider with most accurate pricing for New Windsor Stewart-Chicago Midway flight deals.
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Provider most trusted by Cheapflights users for New Windsor Stewart-Chicago Midway flights.
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From New Windsor Stewart to Chicago Midway
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One-way flight from New Windsor Stewart to Chicago Midway
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Highest demand for flights based on searches. 3% potential increase in price ($8 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($5 potential savings vs. average RT price).
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Average for round-trip flights in February 2025
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Find flight deals from Stewart to Midway

Cheapest flights from Stewart to Midway
Explore the most affordable flight options available from Stewart to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 20, 2025.

This Mytrip deal was found by Cheapflights users on 2/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/2310:51 amSWF - MDW
1 stop24h 27mAllegiant Air
Sun 4/2710:08 amMDW - SWF
1 stop22h 03mAllegiant Air
Deal found 2/18$305
This Mytrip deal was found by Cheapflights users on 2/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/267:52 pmSWF - MDW
2 stops19h 11mMultiple Airlines
Sun 6/2911:45 amMDW - SWF
1 stop21h 46mMultiple Airlines
Deal found 2/19$388

Find flights from Stewart to Midway within your budget

Customize your flight search to find flights from Stewart to Midway 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 2,558,603 searches. Data last updated February 20, 2025.

Fly from

Stewart

Fly to

Midway

Route

Depart

Return

Price

New WindsorChicago

SWF - MDW

SWFMDW

New Windsor Stewart

Wed 4/23

10:51 am-10:18 am

1 stop24h 27m

Chicago Midway

Sun 4/27

10:08 am-9:11 am

1 stop22h 03m

$305

New WindsorChicago

SWF - MDW

SWFMDW

New Windsor Stewart

Thu 6/26

7:52 pm-2:03 pm

2 stops19h 11m

Chicago Midway

Sun 6/29

11:45 am-10:31 am

1 stop21h 46m

$388

New WindsorChicago

SWF - MDW

SWFMDW

New Windsor Stewart

Sun 6/8

11:11 am-7:46 pm

2 stops33h 35m

$206

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/19

  • Most accurate provider: When it comes to deals on New Windsor-Chicago Midway Airport flights, users find the pricing of Expedia to be most consistent on Cheapflights vs. Expedia Users can find the same prices on New Windsor-Chicago Midway Airport flight deals on Cheapflights vs. Expedia <90% of the time. Price accuracy is based on data collected from New Windsor-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on New Windsor-Chicago Midway Airport flights, Cheapflights users trust Expedia the most. Expedia has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for New Windsor-Chicago Midway Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Stewart to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Stewart with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Travel insights for flights from Stewart to Midway

Get recent, data-driven insights about flights from Stewart to Midway including ideal travel times, pricing trends, and more.

What is the cheapest month to book a flight from New Windsor to Chicago Midway Airport?

Currently, April is the cheapest month in which you can book a flight from New Windsor to Chicago Midway Airport (average of $160). Flying from New Windsor to Chicago Midway Airport in November is currently the most expensive (average of $249). 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.

Rainfall in Midway by month

Plan your trip to Midway by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago Midway Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 1.7 in.

Temperature in Midway by month

Plan your trip to Midway by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago Midway Airport, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Midway. Reviews last updated February 20, 2025.
Allegiant Air
7.3
Good
767 reviews

Overall

7.3

Boarding

7.6

Crew

8.1

Entertainment

5.5

Food

5.9

Comfort

6.8

Reviews

1 / 20

10.0
Excellent

Joellen,Aug 2024

LAS - GEG

Boarding was a hassle. I’ve had the same guy before. Never enjoy seeing him.

Allegiant Air
7.3
Good
767 reviews
Allegiant Air
7.3
Good
767 reviews

Overall

7.3

Boarding

7.6

Crew

8.1

Entertainment

5.5

Food

5.9

Comfort

6.8

Reviews

1 / 20

10.0
Excellent

Joellen,Aug 2024

LAS - GEG

Boarding was a hassle. I’ve had the same guy before. Never enjoy seeing him.

Related info for your journey

Find useful and relevant information for your journey from Stewart to Midway. 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 Midway?

    For a flight from New Windsor to Chicago Midway, you will be flying from Stewart. New Windsor Stewart (SWF) is just 4.3 mi from the center of the city. Stewart is the only New Windsor airport and it handles 0 outbound flights to Chicago Midway per day. 0 airlines have flights to Chicago Midway from New Windsor Stewart on a regular basis.

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

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

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

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

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

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

  • What is the cheapest month to book a flight from New Windsor to Chicago Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from New Windsor to Chicago Midway Airport (average of $160). Flying from New Windsor to Chicago Midway Airport in November is currently the most expensive (average of $249). 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.

See more FAQs

Traveling to a place near New Windsor?

Book flights to New Windsor if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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