Cheap Flights from Chicago to Vail
Cheap Flights from Chicago to Vail
Looking for cheap flights from Chicago to Vail? 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 Chicago to Vail 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 Chicago to Vail for specific travel dates.
2026-12-18
ORD - EGE
Economy | Non stop | 9+ left
From 7,500 Pts + $25.6
2026-12-21
ORD - EGE
Economy | Non stop | 9+ left
From 7,500 Pts + $25.6
2026-12-22
ORD - EGE
Economy | Non stop | 9+ left
From 7,500 Pts + $25.6
2026-12-24
ORD - EGE
Economy | Non stop | 9+ left
From 7,500 Pts + $25.6
2026-12-25
ORD - EGE
Economy | Non stop | 9+ left
From 7,500 Pts + $25.6
2026-12-30
ORD - EGE
Economy | Non stop | 9+ left
From 7,500 Pts + $25.6
Chicago to Vail flight facts
Distance
1,002 mi
1,612 km in a straight line
Estimated flight time
about 2h 30m
In the air, for the straight-line distance
Time difference
−1h
Vail is 1 hour behind Chicago.
Airports in Chicago
DPA · Dupage
MDW · Chicago Midway Intl
ORD · Chicago O'Hare Intl
Airports in Vail
EGE · Eagle County Regional
Nearby airport alternatives
Flights Chicago - Aspen · Aspen is 29 mi from Vail
Flights Chicago - Hayden · Hayden is 60 mi from Vail
Flights Chicago - Gunnison · Gunnison is 77 mi from Vail
Flights Chicago - Montrose CO · Montrose CO is 94 mi from Vail
Flights Chicago - Denver · Denver is 120 mi from Vail
Flights Chicago - Colorado Springs · Colorado Springs is 132 mi from Vail
Premium cabin flights from Chicago to Vail
Premium cabin
2026-11-14
ORD - EGE
First | 1 Stop | 4 left
From 35,000 Pts + $25.6
Premium cabin
2026-11-05
ORD - EGE
First | 1 Stop | 3 left
From 35,000 Pts + $31.2
Premium cabin
2026-11-06
ORD - EGE
First | 1 Stop | 2 left
From 35,000 Pts + $31.2
Premium cabin
2026-11-07
ORD - EGE
First | 1 Stop | 1 left
From 35,000 Pts + $31.2
Premium cabin
2026-11-10
ORD - EGE
First | 1 Stop | 5 left
From 35,000 Pts + $31.2
Premium cabin
2026-11-11
ORD - EGE
First | 1 Stop | 4 left
From 35,000 Pts + $31.2
Selected hotels for your next stay
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Frequently Asked Questions
The cheapest route from Chicago to Vail 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 Chicago to Vail.
Yes. Searching metro codes when available helps compare nearby airport combinations for flights from Chicago to Vail.
Chicago and Vail are about 1,002 miles (1,612 km) apart in a straight line.
Flying the 1,002-mile straight-line distance takes about 2h 30m in the air, estimated from typical cruising speed. Actual travel time depends on the routing; itineraries with connections take longer.
Vail is 1 hour behind Chicago.
Departures from Chicago: Dupage (DPA), Chicago Midway Intl (MDW), Chicago O'Hare Intl (ORD). Arrivals in Vail: Eagle County Regional (EGE).
Travelers searching this route also look at other popular routes into Vail, plus the return trip when we track it. Fares and award space change daily.
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