Nonstop flights from Colorado Springs to Chicago

3 airlines fly from Colorado Springs (COS) to 2 Chicago airports (ORD and MDW), with up to 4 flights a day.

COSORD

Routes

2 airport pairs

When they leave

Colorado Springs time

7:55a1:15pFirst departure 7:55 AM, last 1:15 PM

Four in the morning, 7:55 AM to 11:55 AM, then two in the afternoon, 12:37 PM to 1:15 PM.

Every flight

Earliest first

7:55 AM→11:59 AMCOS to ORDUnited AirlinesEmbraer 175Daily
10:00 AM→1:20 PMCOS to MDWSouthwest AirlinesUntil Oct 30, back Nov 21Boeing 737-700Sun
10:40 AM→2:00 PMCOS to MDWSouthwest AirlinesUntil Oct 30, back Nov 21Boeing 737-700Sat
11:55 AM→3:38 PMCOS to ORDUnited AirlinesBoeing 737 MAX 9Daily
12:37 PM→4:30 PMCOS to ORDAmerican AirlinesCRJ 700Daily
1:15 PM→4:35 PMCOS to MDWSouthwest AirlinesUntil Oct 30, back Nov 21Boeing 737 MAX 8Mon, Thu, Fri
1:15 PM→4:35 PMCOS to MDWSouthwest 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

United Airlines flies most often, twice a day on the Boeing 737 MAX 9 and Embraer 175. American Airlines flies daily on the CRJ 700. Southwest Airlines flies daily on the Boeing 737 MAX 8 and Boeing 737-700.

There are 4 flights every day of the week. The first arrival in Chicago is at 11:59 AM and the last at 4:35 PM.

COS to ORD is the busiest airport pair, with 21 flights a week, then COS to MDW with 7.

On COS to MDW, Southwest Airlines flies it until Oct 30 and is back on Nov 21.

Flying back, Chicago to Colorado Springs has 28 nonstop flights a week.

Return flights

Chicago to Colorado SpringsView

Find the cheapest day to fly from Colorado Springs to Chicago.

Schedules as of Oct 9, 2026.