Cheap Flights from Denver to Chicago
Cheap Flights from Denver to Chicago
Looking for cheap flights from Denver 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 Denver 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 Denver to Chicago for specific travel dates.
2026-11-05
DEN - ORD
Economy | Non stop | 9+ left
From 7,500 Pts + $25.6
2026-11-06
DEN - ORD
Economy | Non stop | 9+ left
From 7,500 Pts + $25.6
2026-11-07
DEN - ORD
Economy | Non stop | 9+ left
From 7,500 Pts + $25.6
2026-11-08
DEN - ORD
Economy | Non stop | 9+ left
From 7,500 Pts + $25.6
2026-11-09
DEN - ORD
Economy | Non stop | 9+ left
From 7,500 Pts + $25.6
2026-11-10
DEN - ORD
Economy | Non stop | 9+ left
From 7,500 Pts + $25.6
Denver to Chicago flight facts
Distance
882 mi
1,420 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 Denver.
Airports in Denver
DEN · Denver Intl
Airports in Chicago
DPA · Dupage
MDW · Chicago Midway Intl
ORD · Chicago O'Hare Intl
Nearby airport alternatives
Flights Colorado Springs - Chicago · Colorado Springs is 73 mi from Denver
Flights Denver - Milwaukee · Milwaukee is 73 mi from Chicago
Flights Denver - Madison · Madison is 111 mi from Chicago
Flights Vail - Chicago · Vail is 120 mi from Denver
Flights Denver - Peoria · Peoria is 123 mi from Chicago
Flights Aspen - Chicago · Aspen is 125 mi from Denver
Premium cabin flights from Denver to Chicago
Premium cabin
2026-11-11
DEN - ORD
First | Non stop | 2 left
From 15,000 Pts + $25.6
Premium cabin
2026-11-12
DEN - ORD
First | Non stop | 9+ left
From 15,000 Pts + $25.6
Premium cabin
2026-11-13
DEN - ORD
First | Non stop | 9+ left
From 15,000 Pts + $25.6
Premium cabin
2026-11-14
DEN - ORD
First | Non stop | 9+ left
From 15,000 Pts + $25.6
Premium cabin
2026-11-15
DEN - ORD
First | Non stop | 5 left
From 15,000 Pts + $25.6
Premium cabin
2026-11-09
DEN - ORD
First | 1 Stop | 3 left
From 25,000 Pts + $5.6
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 Denver 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 Denver to Chicago.
Yes. Searching metro codes when available helps compare nearby airport combinations for flights from Denver to Chicago.
Denver and Chicago are about 882 miles (1,420 km) apart in a straight line.
Flying the 882-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 Denver.
Departures from Denver: Denver Intl (DEN). 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.
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