Skip to main content
Beginning of main content

Cheap Flights from Colorado Springs to Chicago $431.75

Search over 282,000 hotels worldwide and 400 airlines worldwide.
Secure incredible value with Expedia’s Price Pledge
No Expedia cancellation fee to change or cancel almost any hotel reservation.

Cheapest Flights from Colorado Springs to Chicago (COS to MDW)

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Interesting Facts About Flights from Colorado Springs to Chicago (COS to MDW)

Question : Interested in traveling in the next 30 days and want to get the lowest fare?
Answer : As of November 28th, the best day for booking to Chicago (MDW) from Colorado Springs (COS) is December 8th. Bookings have been made roughly 35% below the average price for this route.

Question : How long do most people stay in Chicago when they fly in from Colorado Springs?
Answer : The average time spent in Chicago by travelers flying from COS is seven days.

Question : Can you cut down on flight costs by changing the day of the week you travel to Chicago?
Answer : For the month of December, the cheapest day to fly is Sunday. Flexibility is paramount when booking travel plans in order to keep costs down.

Question : Who's offering the cheapest round-trip flight to Chicago Midway International Airport (MDW) over the coming months?
Answer : Delta Air Lines is booking the cheapest flights for its customers over the next three months.

Question : Should you be aware of any airlines that have a reputation of delays for this route?
Answer : NetJets Aviation flights from COS to MDW are late 25% of the time. If you're on NetJets Aviation, be sure to sign up for the delay notifications to stay up to date with your flight's status.

Question : Which airline has been on time to Chicago Midway International Airport (MDW) from Colorado Springs Airport (COS) the most?
Answer : Executive Jet Management will have you to MDW on schedule 100% of the time. Spend as little time in an airport as necessary by flying with Executive Jet Management. Hopefully they keep that perfect record alive.