Nonstop flights from New York to Chicago

Southwest Airlines flies this route 4 to 7 times a day.

LGANew York LaGuardia

723 mi · 46 flights a week · about 2h 25m

MDWChicago Midway International

LGAMDW

When they leave

New York time

6:00a9:05pFirst departure 6:00 AM, last 9:05 PM

Seven in the morning, 6:00 AM to 10:55 AM, then five in the afternoon, 12:30 PM to 4:35 PM, then four in the evening, 5:45 PM to 9:05 PM.

Every flight

Earliest first

6:00 AM→7:30 AMSouthwest AirlinesBoeing 737-800 · 2h 30mSun
6:15 AM→7:45 AMSouthwest AirlinesBoeing 737 MAX 8 · 2h 30mSat
7:15 AM→8:35 AMSouthwest Airlines2h 20mMon, Tue, Wed, Thu, Fri, Sun
7:25 AM→8:45 AMSouthwest Airlines2h 20mTue, Wed
8:55 AM→10:25 AMSouthwest AirlinesBoeing 737 MAX 8 · 2h 30mMon, Thu, Fri
9:25 AM→10:55 AMSouthwest AirlinesBoeing 737 MAX 8 · 2h 30mSat
10:55 AM→12:15 PMSouthwest AirlinesBoeing 737 MAX 8 · 2h 20mMon, Tue, Wed, Thu, Fri, Sun
12:30 PM→1:50 PMSouthwest AirlinesBoeing 737-800 · 2h 20mMon, Tue, Wed, Thu, Fri, Sat
1:20 PM→2:40 PMSouthwest AirlinesBoeing 737 MAX 8 · 2h 20mSun
3:15 PM→4:35 PMSouthwest AirlinesBoeing 737 MAX 8 · 2h 20mSun
3:20 PM→4:40 PMSouthwest Airlines2h 20mMon, Tue, Wed, Thu, Fri
4:35 PM→5:55 PMSouthwest AirlinesBoeing 737-800 · 2h 20mSat
5:45 PM→7:15 PMSouthwest AirlinesBoeing 737-800 · 2h 30mMon, Thu, Fri, Sun
5:55 PM→7:25 PMSouthwest AirlinesBoeing 737 MAX 8 · 2h 30mTue, Wed
9:00 PM→10:25 PMSouthwest Airlines2h 25mMon, Thu, Fri
9:05 PM→10:30 PMSouthwest AirlinesBoeing 737-800 · 2h 25mTue, Wed, Sun

Schedules last checked Sep 30, 2026. Times are local.

Flying from New York to Chicago

Southwest Airlines is the only airline flying nonstop from New York to Chicago, 4 to 7 times a day on the Boeing 737 MAX 8 and Boeing 737-800.

Flights run every day of the week, from 4 on Saturdays to 7 on Mondays, Tuesdays, Wednesdays, Thursdays, Fridays and Sundays. The first arrival in Chicago is at 7:30 AM and the last at 10:30 PM. The flight covers 723 miles, and scheduled flight times run from 2h 20m to 2h 30m.

Flying back, Chicago to New York has 47 nonstop flights a week. From New York, O'Hare (ORD) is the other Chicago area airport with nonstop flights, 233 a week.