Southwest Airlines flights from New York to Chicago
New York to Chicago: prices by month
Lowest one-way fares found by travellers for each month. Prices change daily; the link opens live search results for that date. Weather: average temperature and total rainfall for that month last year.
| Month | Lowest fare | Airline | Stops | Chicago weather | |
|---|---|---|---|---|---|
| October 2026 | 265 USD | Frontier Airlines | 1 stop | 14°C · 56 mm | Search → |
| November 2026 | 218 USD | United Airlines | direct | 6°C · 74 mm | Search → |
| December 2026 | 238 USD | Frontier Airlines | 1 stop | -3°C · 81 mm | Search → |
| January 2027 | 270 USD | Frontier Airlines | 1 stop | -5°C · 60 mm | Search → |
| February 2027 | 281 USD | Frontier Airlines | 1 stop | -3°C · 24 mm | Search → |
| March 2027 | 340 USD | Frontier Airlines | 1 stop | 6°C · 94 mm | Search → |
| April 2027 | 323 USD | American Airlines | direct | 10°C · 65 mm | Search → |
| September 2027 | 396 USD | American Airlines | direct | 20°C · 38 mm | Search → |
Cheapest Southwest Airlines tickets found recently
About Southwest Airlines flights from New York to Chicago
Southwest Airlines operates flights from LaGuardia Airport (LGA) in New York to Chicago Midway International Airport (MDW), covering a distance of 1,144 kilometers. With a typical flight time of 3 hours and 3 minutes, connections are common on this route, making it suitable for both business and leisure travelers between these major cities.
Fares tend to be lowest in September. Note that checked baggage is not included in economy fares; the first checked bag costs extra and is limited to 22.7 kg. Online check-in opens 24 hours before departure and closes 30 minutes before your flight.
Airports on this route
| Departure | LaGuardia Airport (LGA) |
|---|---|
| Arrival | Chicago Midway International Airport (MDW) |
| Flight time | 2 h 53 min |
| Distance | 1144 km |
Checked bag in Economy: not included in the basic fare (from 45 USD).
| Item | Allowance | Details |
|---|---|---|
| Cabin bag | 1 piece | |
| Personal item | included | small bag under the seat |
| Checked baggage - Economy | 1 piece · 22.7 kg (50 lb) | paid option, from 45 USD · max total dimensions 157 cm (62 in) |
| Checked baggage - Economy | 1 piece · 22.7 kg (50 lb) | paid option |
| Extra bag | from 55 USD | cheaper when added online in advance |
Basic Economy allowance on most routes; premium fares and some destinations get more. Weights are shown in kilograms with pounds in brackets, sizes in centimetres with inches in brackets. Always confirm on the official website before travelling.
Southwest Airlines online check-in opens 24 h before departure and closes 30 min before departure. Online check-in is free.
| Online check-in opens | 24 h before departure |
|---|---|
| Online check-in closes | 30 min before departure |
| Airport counters close | 30 min before departure |
| Check-in fee | online check-in is free |
| Boarding pass | mobile boarding pass, print at home |
| Mobile app check-in | available |
| Self-service kiosks | available |
Times apply to most routes; long-haul, US and some airport-specific deadlines differ. Confirm on the official website before travelling.