HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Stewart

$122+ Cheap flights from Midway (MDW) to New Windsor (SWF)

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 5/29. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SWF
Feb 26 — Mar 51
Wed 2/26
Wed 3/5
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Midway to Stewart with Cheapflights

1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”
2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.
3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Midway to Stewart

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Stewart (SWF). 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 21, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Popular in

December

Cheapest in

September

Average price

$185
Provider with most accurate pricing for Chicago Midway-New Windsor Stewart flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago Midway-New Windsor Stewart flights.
Search Deals
Highest demand for flights based on searches. 9% potential increase in price ($18 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2025
Search Deals

Find flight deals from Midway to Stewart

Cheapest flights from Midway to Stewart
Explore the most affordable flight options available from Midway to Stewart. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 21, 2025.

This Mytrip deal was found by Cheapflights users on 2/21. 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 3/136:26 pmMDW - SWF
1 stop21h 05mAllegiant Air
Mon 3/245:41 pmSWF - MDW
1 stop25h 05mAllegiant Air
Deal found 2/21$353

Find flights from Midway to Stewart within your budget

Customize your flight search to find flights from Midway to Stewart 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 21, 2025.

Fly from

Midway

Fly to

Stewart

Route

Depart

Return

Price

ChicagoNew Windsor

MDW - SWF

MDWSWF

Chicago Midway

Thu 3/13

6:26 pm-4:31 pm

1 stop21h 05m

New Windsor Stewart

Mon 3/24

5:41 pm-5:46 pm

1 stop25h 05m

$353

ChicagoNew Windsor

MDW - SWF

MDWSWF

Chicago Midway

Thu 5/29

11:03 am-12:25 pm

1 stop24h 22m

$122

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/20

Compare providers for flights from Midway to Stewart

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Midway to Stewart in February.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago Midway Airport-New Windsor flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago Midway Airport-New Windsor flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-New Windsor flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago Midway Airport-New Windsor flights, Cheapflights users trust FlightHub the most. FlightHub 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 Chicago Midway Airport-New Windsor 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 Midway to Stewart

Have a flexible travel schedule? Discover the best time to fly to Stewart from Midway 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 Midway to Stewart

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

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

Currently, October is the cheapest month in which you can book a flight from Chicago Midway Airport to New Windsor (average of $109). Flying from Chicago Midway Airport to New Windsor in August is currently the most expensive (average of $226). 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 Stewart

Get insights into the airlines that provide service to Stewart. 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 Stewart. Reviews last updated February 21, 2025.
Allegiant Air
7.3
Good
765 reviews

Food

5.9

Crew

8.1

Entertainment

5.5

Boarding

7.6

Comfort

6.8

Overall

7.3

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
765 reviews
Allegiant Air
7.3
Good
765 reviews

Food

5.9

Crew

8.1

Entertainment

5.5

Boarding

7.6

Comfort

6.8

Overall

7.3

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 Midway to Stewart. 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 into for flights to New Windsor from Chicago Midway?

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

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Midway to Stewart 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 Chicago Midway Airport to New Windsor?

    Currently, October is the cheapest month in which you can book a flight from Chicago Midway Airport to New Windsor (average of $109). Flying from Chicago Midway Airport to New Windsor in August is currently the most expensive (average of $226). 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 Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Kingston

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Midway to Stewart

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to John F Kennedy Intl flights
O'Hare Intl to LaGuardia flights
O'Hare Intl to Newark flights
Midway to Newark flights
Midway to LaGuardia flights
Midway to John F Kennedy Intl flights
O'Hare Intl to Albany flights
O'Hare Intl to Syracuse flights
O'Hare Intl to Buffalo flights
O'Hare Intl to White Plains flights
Midway to Albany flights
O'Hare Intl to Stewart flights
O'Hare Intl to Rochester flights
Midway to Syracuse flights
O'Hare Intl to Islip flights
Midway to Buffalo flights
Midway to White Plains flights
Midway to Rochester flights
O'Hare Intl to Elmira flights
O'Hare Intl to Ithaca flights
Midway to Ithaca flights
O'Hare Intl to Rutland flights
O'Hare Intl to Binghamton flights
O'Hare Intl to Niagara Falls flights
O'Hare Intl to Saranac Lake flights
Midway to Binghamton flights
O'Hare Intl to Plattsburgh flights
O'Hare Intl to Watertown flights
100% Free
Cheapflights is completely free to use, so you can start saving the moment you arrive.
Book with Flexibility
Our users can plan ahead with confidence and find flights with no change fees
Travel Smart
Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.