Cheap Flights from Colorado Springs to Chicago
Cheap Flights from Colorado Springs to Chicago
Looking for cheap flights from Colorado Springs to Chicago? PointsYeah scans award availability across major airline and bank transfer programs in one place, so travelers can compare the lowest points and cash routes faster. Instead of searching each airline separately, users can see pricing from programs like Chase, Amex, Capital One, Citi, and Bilt side by side.
Award prices from Colorado Springs to Chicago vary by season, cabin, and date, but available award flights can start around 7,500 points one way, with premium cabins available at higher mileage levels. The live search above allows filtering by cabin, airline, stops, or maximum points to find the best award flights from Colorado Springs to Chicago for specific travel dates.
2026-11-10
COS - ORD
Economy | Non stop | 9+ left
From 7,500 Pts + $25.6
2026-11-11
COS - ORD
Economy | Non stop | 9+ left
From 7,500 Pts + $25.6
2026-11-17
COS - ORD
Economy | Non stop | 9+ left
From 7,500 Pts + $25.6
2026-11-18
COS - ORD
Economy | Non stop | 9+ left
From 7,500 Pts + $25.6
2026-12-02
COS - ORD
Economy | Non stop | 2 left
From 7,500 Pts + $25.6
2026-12-05
COS - ORD
Economy | Non stop | 9+ left
From 7,500 Pts + $25.6
Colorado Springs to Chicago flight facts
Distance
905 mi
1,456 km in a straight line
Estimated flight time
about 2h 15m
In the air, for the straight-line distance
Time difference
+1h
Chicago is 1 hour ahead of Colorado Springs.
Airports in Colorado Springs
COS · City of Colorado Springs Municipal
Airports in Chicago
DPA · Dupage
MDW · Chicago Midway Intl
ORD · Chicago O'Hare Intl
Nearby airport alternatives
Flights Denver - Chicago · Denver is 73 mi from Colorado Springs
Flights Aspen - Chicago · Aspen is 120 mi from Colorado Springs
Flights Gunnison - Chicago · Gunnison is 122 mi from Colorado Springs
Flights Vail - Chicago · Vail is 132 mi from Colorado Springs
Flights Colorado Springs - Grand Rapids · Grand Rapids is 142 mi from Chicago
Flights Montrose CO - Chicago · Montrose CO is 173 mi from Colorado Springs
Premium cabin flights from Colorado Springs to Chicago
Premium cabin
2026-11-06
COS - ORD
First | Non stop | 1 left
From 15,000 Pts + $25.6
Premium cabin
2026-11-07
COS - ORD
First | Non stop | 5 left
From 15,000 Pts + $25.6
Premium cabin
2026-11-09
COS - ORD
First | Non stop | 3 left
From 15,000 Pts + $25.6
Premium cabin
2026-11-12
COS - ORD
First | Non stop | 3 left
From 15,000 Pts + $25.6
Premium cabin
2026-12-03
COS - ORD
First | Non stop | 1 left
From 15,000 Pts + $25.6
Premium cabin
2026-12-04
COS - ORD
First | Non stop | 6 left
From 15,000 Pts + $25.6
Selected hotels for your next stay
Chicago (United States)
Chicago Athletic Association
From 15,000 Pts or $236
Chicago (USA)
ACME Hotel Chicago, Outset Collection by Hilton
From 28,000 Pts or $75
Chicago, IL (USA)
Waldorf Astoria Chicago
From 95,000 Pts or $407
Frequently Asked Questions
The cheapest route from Colorado Springs to Chicago depends on award space, transfer bonuses, and travel dates. PointsYeah compares bank and airline programs in one place so you can find the best points and cash combinations faster.
Yes. Transferable points from Chase, Amex, Capital One, Citi, and Bilt can often be moved to airline partners for flights from Colorado Springs to Chicago.
Yes. Searching metro codes when available helps compare nearby airport combinations for flights from Colorado Springs to Chicago.
Colorado Springs and Chicago are about 905 miles (1,456 km) apart in a straight line.
Flying the 905-mile straight-line distance takes about 2h 15m in the air, estimated from typical cruising speed. Actual travel time depends on the routing; itineraries with connections take longer.
Chicago is 1 hour ahead of Colorado Springs.
Departures from Colorado Springs: City of Colorado Springs Municipal (COS). Arrivals in Chicago: Dupage (DPA), Chicago Midway Intl (MDW), Chicago O'Hare Intl (ORD).
Travelers searching this route also look at other popular routes into Chicago, plus the return trip when we track it. Fares and award space change daily.
Our mission is to provide
the simplest and best
points travel planning
experience. Yeah!
Our mission is to provide the simplest and best
points travel planning experience. Yeah!
