Southwest Airlines flights from Chicago to New York
Chicago to New York: 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 | New York weather | |
|---|---|---|---|---|---|
| October 2026 | 269 USD | Frontier Airlines | 1 stop | 14°C · 110 mm | Search → |
| November 2026 | 223 USD | Frontier Airlines | 1 stop | 7°C · 50 mm | Search → |
| December 2026 | 195 USD | Southwest Airlines | direct | 0°C · 80 mm | Search → |
| January 2027 | 158 USD | United Airlines | direct | -2°C · 28 mm | Search → |
| March 2027 | 322 USD | United Airlines | direct | 7°C · 164 mm | Search → |
| April 2027 | 323 USD | American Airlines | direct | 12°C · 71 mm | Search → |
Cheapest Southwest Airlines tickets found recently
About Southwest Airlines flights from Chicago to New York
Southwest Airlines (WN) operates flights from Chicago Midway International Airport (MDW) to LaGuardia Airport (LGA) in New York, covering a distance of 1,144 km. The typical flight duration is 147 minutes, though connections are common on this route, making it suitable for both business and leisure travelers.
Fares tend to be lowest in September. Note that Southwest does not include checked baggage in economy fares-your first checked bag costs extra and is limited to 22.7 kg. You can check in online up to 24 hours before departure, but must complete it at least 30 minutes before your flight takes off.
Airports on this route
| Departure | Chicago Midway International Airport (MDW) |
|---|---|
| Arrival | LaGuardia Airport (LGA) |
| Flight time | 2 h 13 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.