Title: Cheap Flights from Newburgh (SWF) to Chicago (MDW) - Expedia.ca ![City of Chicago. Image of Chicago downtown and Chicago River with bridges at sunny summer day](https://images.trvl-media.com/place/178248/e6aa83ce-7ad8-43a5-9d1d-b055eefa7e78.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/178248/e6aa83ce-7ad8-43a5-9d1d-b055eefa7e78.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Cheap Flights from Newburgh (SWF) to Chicago (MDW) - [Roundtrip](?flightType=roundtrip) - [One-way](?flightType=oneway) - [Multi-city](?flightType=multicity) ### Travellers Adults ChildrenAges 2 to 17 InfantsYounger than 2 EconomyPremium economyBusiness classFirst class Leaving from Going to Departing Returning Add a place to stay Add a car Direct flights only ## Popular airlines from Stewart Intl. Airport (SWF) to Chicago Midway Airport (MDW) - ![Air Canada](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_AC.svg) Air Canada [](https://www.expedia.ca/Flights-Search?leg1=from:swf,to:mdw,departure:03/10/2025TANYT&leg2=from:mdw,to:swf,departure:10/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AC"}}]) - ![WestJet](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_WS.svg) WestJet [](https://www.expedia.ca/Flights-Search?leg1=from:swf,to:mdw,departure:03/10/2025TANYT&leg2=from:mdw,to:swf,departure:10/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"WS"}}]) - ![Flair Airlines](https://a.travel-assets.com/air/airlines/f8_sq.svg) Flair Airlines [](https://www.expedia.ca/Flights-Search?leg1=from:swf,to:mdw,departure:03/10/2025TANYT&leg2=from:mdw,to:swf,departure:10/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"F8"}}]) - ![American Airlines](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_AA.svg) American Airlines [](https://www.expedia.ca/Flights-Search?leg1=from:swf,to:mdw,departure:03/10/2025TANYT&leg2=from:mdw,to:swf,departure:10/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AA"}}]) - ![United](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_UA.svg) United [](https://www.expedia.ca/Flights-Search?leg1=from:swf,to:mdw,departure:03/10/2025TANYT&leg2=from:mdw,to:swf,departure:10/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"UA"}}]) - ![Delta](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_DL.svg) Delta [](https://www.expedia.ca/Flights-Search?leg1=from:swf,to:mdw,departure:03/10/2025TANYT&leg2=from:mdw,to:swf,departure:10/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"DL"}}]) - ![Porter Airlines](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_PD.svg) Porter Airlines [](https://www.expedia.ca/Flights-Search?leg1=from:swf,to:mdw,departure:03/10/2025TANYT&leg2=from:mdw,to:swf,departure:10/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"PD"}}]) - ## Plan, book, fly with confidence - ### Be in the know Get alerts if flight prices drop or rise\* - ### Book smarter Save up to 30% on select hotels after you book a flight\* - ### Earn twice Earn your airline miles on top of our rewards [Sign in](https://www.expedia.ca/login) Flight from Newburgh to Chicago (SWF - MDW) route information | Origin airport | Stewart Intl. | | --- | --- | | Destination airport | Midway Intl. | | Distance | 1127 km | ## Newburgh to Chicago Flights **The easy way to book your flights from Newburgh to Chicago**  With Expedia, it’s simple to find and book flights to Chicago from Newburgh whether you’re traveling for business or pleasure. Enter your travel dates, hit search, and choose your flight from airlines that cover this route. There are nonstop flights to Midway Intl., too.   Choose your preferred carrier and cabin class with the advanced search tool and select your ideal departure time. Then, if you want, you can see just nonstop or refundable flights. And if you’re traveling last minute, just enter the date to check out flights from Newburgh to Chicago today, tomorrow, or this week.   **Save dollars with cheap flights from Stewart Intl., SWF to Midway Intl., MDW**  Sort your search results by price to find great deals on your flight from Newburgh to Chicago—you get all your cheapest options first. Grab yourself a bargain now—the lowest price on flights to Chicago from Newburgh currently is just rising to .   Here are more money-saving tips:  - Fly in when flight prices are normally at their lowest  - Book about a month to 6 weeks before you travel for the best prices to Chicago   - Avoid peak season and weekends when flights can cost more - Early morning and late-night flights are sometimes cheaper, so try varying your travel times  - One surefire way to save money on your flight is to book your flight and hotel together with Expedia. Sometimes, the savings are so large that the flight is basically free!  **Reasons to choose Expedia for your flight to Chicago from Newburgh**  Whatever your destination, budget, or reason to travel, in just one quick search, you can choose from loads of flights, airlines, and cabin classes. The filters make it quick and easy to find your ideal flights, and if you choose one of the flexible options, you won’t be charged to change your flight. So book your flight to Chicago with Expedia today. ## Frequently asked questions ### How much is a flight from Stewart Intl. Airport to Midway Intl. Airport (MDW)? > The lowest price advertised for a round-trip journey from Stewart Intl. Airport (SWF) to Chicago Airport is . But you better act quick. This figure is taken from fares available within the last 7 days on Expedia for flights departing within the next year. Prices and availability are subject to change. Additional terms apply. ### Do I need to pay a cancellation fee if I cancel my flight from SWF to Chicago Airport? > Each air carrier has its own terms and conditions. If you do decide to cancel, follow the simple instructions on our [Customer Service Portal](https://www.expedia.ca/helpcenter). ### How do I find cheap flights from SWF to Midway Intl. Airport (MDW) that have flexible change policies? > Use our "No change fees" filter to find flexible travel options for your flight from SWF to Midway Intl. Airport (MDW). This allows you to snag a low rate in advance and still have the freedom to make changes without any extra fees. Keep in mind that you'll need to cover the fare difference. ### How far is the flight from Stewart Intl. Airport to Chicago Airport? > With a flight distance of 1,150 kilometres, it's just a short hop from Stewart Intl. Airport to Midway Airport. It might be a quick flight, but it's still worth bringing something to read. ### Which airlines fly direct from Stewart Intl. Airport to Chicago Airport? > At the moment, no airlines offer direct flights from Stewart Intl. Airport to Chicago Airport. You'll need to book a flight with one or more stops. To get the best price and connections, lock in your fare well in advance. ### Are Stewart Intl. Airport to Chicago Airport flight tickets cheaper when they're purchased at the last minute? > Fares from Stewart Intl. Airport to Midway Airport are available up to 12 months before departure on Expedia. And although you may pick up great last-minute deal, it's never something you can count on. Also, booking your flights in advance means you'll have more choices — and you can avoid landing the dreaded middle seat! We regularly update our fares to bring you the biggest bargains, so check back often for all the latest specials. ## Explore a world of travel with Expedia - Flights ### Flights - [Flights from Lincoln to Rush Street](https://www.expedia.ca/lp/flights/602964/6175183/lincoln-to-rush-street) - [Flights from Waterloo (ALO) to Chicago (ORD)](https://www.expedia.ca/lp/flights/alo/ord/waterloo-to-chicago) - [Flights from Ahmedabad (AMD) to Chicago (ORD)](https://www.expedia.ca/lp/flights/amd/ord/ahmedabad-to-chicago) - [Flights from Atlanta (ATL) to Chicago (ORD)](https://www.expedia.ca/lp/flights/atl/ord/atlanta-to-chicago) - [Flights from Austin (AUS) to Chicago (ORD)](https://www.expedia.ca/lp/flights/aus/ord/austin-to-chicago) - [Flights from Bangor (BGR) to Chicago (ORD)](https://www.expedia.ca/lp/flights/bgr/ord/bangor-to-chicago) - [Flights from Bellingham (BLI) to Chicago (ORD)](https://www.expedia.ca/lp/flights/bli/ord/bellingham-to-chicago) - [Flights from Nashville (BNA) to Chicago (ORD)](https://www.expedia.ca/lp/flights/bna/ord/nashville-to-chicago) - [Flights from Mumbai (BOM) to Chicago (ORD)](https://www.expedia.ca/lp/flights/bom/ord/mumbai-to-chicago) - [Flights from Burlington (BTV) to Chicago (ORD)](https://www.expedia.ca/lp/flights/btv/ord/burlington-to-chicago) - [Flights from Buffalo (BUF) to Chicago (ORD)](https://www.expedia.ca/lp/flights/buf/ord/buffalo-to-chicago) - [Flights from Baltimore (BWI) to Chicago (ORD)](https://www.expedia.ca/lp/flights/bwi/ord/baltimore-to-chicago) - [Flights from Sault Ste. 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