Popular airlines from Swindon to Chicago, IL (MDW-Midway Intl.)
DeltaDelta
Southwest AirlinesSouthwest Airlines
Frontier AirlinesFrontier Airlines
Porter AirlinesPorter Airlines
Air TransatAir Transat
WestJetWestJet
AeromexicoAeromexico
Today's featured flight deals from Swindon to Chicago, IL (MDW-Midway Intl.)
- New York (LGA) to Chicago (MDW).Southwest Airlines, nonstop.Departing on Fri, Nov 14 at 7:15am from New York, arriving at 8:45am in Chicago.Returning on Mon, Nov 17 at 7:15pm from Chicago, arriving at 10:20pm in New York.Select Southwest Airlines flight departing on Fri, Nov 14 at 7:15am from New York, returning on Mon, Nov 17 at 7:15pm from Chicago priced at $14970% less than typical$149
- New York (LGA) to Chicago (MDW).Southwest Airlines, nonstop.Departing on Fri, Nov 14 at 9:00am from New York, arriving at 10:25am in Chicago.Returning on Mon, Nov 17 at 7:15pm from Chicago, arriving at 10:20pm in New York.Select Southwest Airlines flight departing on Fri, Nov 14 at 9:00am from New York, returning on Mon, Nov 17 at 7:15pm from Chicago priced at $14970% less than typical$149
- Boston (BOS) to Chicago (MDW).Southwest Airlines, nonstop.Departing on Fri, Nov 14 at 5:15am from Boston, arriving at 7:00am in Chicago.Returning on Mon, Nov 17 at 9:25am from Chicago, arriving at 9:40pm in Boston.Select Southwest Airlines flight departing on Fri, Nov 14 at 5:15am from Boston, returning on Mon, Nov 17 at 9:25am from Chicago priced at $13770% less than typical$137
- New York (LGA) to Chicago (MDW).Southwest Airlines, nonstop.Departing on Wed, Nov 19 at 9:55pm from New York, arriving at 11:20pm in Chicago.Returning on Sun, Nov 30 at 10:15pm from Chicago, arriving on Mon, Dec 1 at 1:21am in New York.Select Southwest Airlines flight departing on Wed, Nov 19 at 9:55pm from New York, returning on Sun, Nov 30 at 10:15pm from Chicago priced at $19765% less than typical$197
- New York (LGA) to Chicago (MDW).Southwest Airlines, nonstop.Departing on Sat, Nov 22 at 9:40pm from New York, arriving at 11:10pm in Chicago.Returning on Wed, Nov 26 at 8:25pm from Chicago, arriving at 11:25pm in New York.Select Southwest Airlines flight departing on Sat, Nov 22 at 9:40pm from New York, returning on Wed, Nov 26 at 8:25pm from Chicago priced at $14970% less than typical$149
- New York (LGA) to Chicago (MDW).Southwest Airlines, nonstop.Departing on Fri, Nov 21 at 9:00am from New York, arriving at 10:25am in Chicago.Returning on Mon, Nov 24 at 8:25pm from Chicago, arriving at 11:25pm in New York.Select Southwest Airlines flight departing on Fri, Nov 21 at 9:00am from New York, returning on Mon, Nov 24 at 8:25pm from Chicago priced at $20360% less than typical$203
- Boston (BOS) to Chicago (MDW).Southwest Airlines, nonstop.Departing on Sun, Nov 23 at 5:15am from Boston, arriving at 7:00am in Chicago.Returning on Wed, Nov 26 at 5:15pm from Chicago, arriving on Thu, Nov 27 at 12:45am in Boston.Select Southwest Airlines flight departing on Sun, Nov 23 at 5:15am from Boston, returning on Wed, Nov 26 at 5:15pm from Chicago priced at $13765% less than typical$137
- Boston (BOS) to Chicago (MDW).Southwest Airlines, nonstop.Departing on Sun, Nov 23 at 5:15am from Boston, arriving at 7:00am in Chicago.Returning on Fri, Nov 28 at 9:10am from Chicago, arriving at 6:10pm in Boston.Select Southwest Airlines flight departing on Sun, Nov 23 at 5:15am from Boston, returning on Fri, Nov 28 at 9:10am from Chicago priced at $20955% less than typical$209
- New York (LGA) to Chicago (MDW).Southwest Airlines, nonstop.Departing on Sat, Nov 22 at 9:40pm from New York, arriving at 11:10pm in Chicago.Returning on Sat, Nov 29 at 5:50am from Chicago, arriving at 8:55am in New York.Select Southwest Airlines flight departing on Sat, Nov 22 at 9:40pm from New York, returning on Sat, Nov 29 at 5:50am from Chicago priced at $30245% less than typical$302
Travel information
Origin airport | SWI-All Airports |
|---|---|
Destination airport | Midway Intl. |
Distance | 3889 mi |
Book with confidence
Swindon to Chicago Flights
The cheapest times to fly from Swindon to Chicago
On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Swindon to Chicago are during the month of . You can find some of the cheapest flights from Swindon to Chicago with Expedia's search tool and vast selection of airlines.
The best time to book a flight from Swindon to Chicago
Sunday is one of the best days to book for cheap flights from Swindon to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.
How to find cheap round-trip tickets from Swindon to Chicago
Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Swindon to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.
Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Swindon to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.
You could also save big by booking one of Expedia's vacation packages. Bundling together your Swindon to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.
*Terms apply.
Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.