Nonstop flights from Colorado Springs to Chicago

Southwest Airlines flies this route daily until Oct 30, then again from Nov 21.

COSColorado Springs

916 mi · 7 flights a week

MDWChicago Midway International

COSMDW

When they leave

Colorado Springs time

10:00a1:15pFirst departure 10:00 AM, last 1:15 PM

Two in the morning, 10:00 AM to 10:40 AM, then one afternoon flight at 1:15 PM.

Every flight

Earliest first

10:00 AM→1:20 PMSouthwest AirlinesUntil Oct 30, back Nov 21Boeing 737-700Sun
10:40 AM→2:00 PMSouthwest AirlinesUntil Oct 30, back Nov 21Boeing 737-700Sat
1:15 PM→4:35 PMSouthwest AirlinesUntil Oct 30, back Nov 21Boeing 737 MAX 8Mon, Thu, Fri
1:15 PM→4:35 PMSouthwest AirlinesUntil Oct 30, back Nov 21Boeing 737 MAX 8Tue, Wed

Schedules last checked Sep 22, 2026. Times are local.

Flying from Colorado Springs to Chicago

Southwest Airlines is the only airline flying nonstop from Colorado Springs to Chicago, daily on the Boeing 737 MAX 8 and Boeing 737-700.

The first arrival in Chicago is at 1:20 PM and the last at 4:35 PM. The flight covers 916 miles.

Flying back, Chicago to Colorado Springs has 7 nonstop flights a week. From Colorado Springs, O'Hare (ORD) is the other Chicago area airport with nonstop flights, 21 a week.