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Midway

$172+ 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 8/7. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — MDW
Jul 5 — Jul 121
Sat 7/5
Sat 7/12
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 June 30, 2025.

Popular in

December

Cheapest in

September

Average price

$277
Highest demand for flights based on searches. 1% potential increase in price ($3 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
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Average for round-trip flights in June 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 June 30, 2025.

This Mytrip deal was found by Cheapflights users on 6/28. 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.
Sun 6/297:52 pmSWF - MDW
2 stops19h 11mMultiple Airlines
Fri 7/42:54 pmMDW - SWF
2 stops20h 24mMultiple Airlines
Deal found 6/28$1,290

Cheapflights Fare Finder

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 June 30, 2025.
Use the filters below to find and compare flights from New Windsor to Chicago Midway Airport that are best for you.

Fly from

Stewart

Fly to

Midway

Route

Depart

Return

Price

New WindsorChicago

SWF - MDW

SWFMDW

New Windsor Stewart

Thu 8/7

8:03 pm-1:56 pm

2 stops18h 53m

$172

New WindsorChicago

SWF - MDW

SWFMDW

New Windsor Stewart

Sun 7/20

7:52 pm-2:04 pm

2 stops19h 12m

$259

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/28

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.

Cheapflights Insights

Everything you need to know about your flight from New Windsor to Chicago Midway Airport

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.

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 June 30, 2025.
Read through reviews of airlines operating flights from New Windsor to Chicago Midway Airport, such as Allegiant Air. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Allegiant Air
7.2
Good
710 reviews

Boarding

7.6

Entertainment

5.5

Overall

7.2

Comfort

6.8

Food

5.9

Crew

8.1

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
7.2
Good
710 reviews
Allegiant Air
7.2
Good
710 reviews

Boarding

7.6

Entertainment

5.5

Overall

7.2

Comfort

6.8

Food

5.9

Crew

8.1

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
Lansing
Benton Harbor
Porter
Hammond
Valparaiso
Chesterton

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