Cheap Flights from Vail to Chicago
Cheap Flights from Vail to Chicago
Looking for cheap flights from Vail 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 Vail 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 Vail to Chicago for specific travel dates.
2026-12-17
EGE - ORD
Economy | Non stop | 9+ left
From 7,500 Pts + $25.6
2026-12-18
EGE - ORD
Economy | Non stop | 9+ left
From 7,500 Pts + $25.6
2026-12-19
EGE - ORD
Economy | Non stop | 9+ left
From 7,500 Pts + $25.6
2026-12-20
EGE - ORD
Economy | Non stop | 9+ left
From 7,500 Pts + $25.6
2026-12-21
EGE - ORD
Economy | Non stop | 9+ left
From 7,500 Pts + $25.6
2026-12-22
EGE - ORD
Economy | Non stop | 9+ left
From 7,500 Pts + $25.6
Vail to Chicago 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
Chicago is 1 hour ahead of Vail.
Airports in Vail
EGE · Eagle County Regional
Airports in Chicago
DPA · Dupage
MDW · Chicago Midway Intl
ORD · Chicago O'Hare Intl
Nearby airport alternatives
Flights Aspen - Chicago · Aspen is 29 mi from Vail
Flights Hayden - Chicago · Hayden is 60 mi from Vail
Flights Gunnison - Chicago · Gunnison is 77 mi from Vail
Flights Grand Junction - Chicago · Grand Junction is 93 mi from Vail
Flights Montrose CO - Chicago · Montrose CO is 94 mi from Vail
Flights Denver - Chicago · Denver is 120 mi from Vail
Premium cabin flights from Vail to Chicago
Premium cabin
2026-11-05
EGE - ORD
First | 2 Stops | 1 left
From 45,000 Pts + $25.6
Premium cabin
2026-11-06
EGE - ORD
First | 2 Stops | 3 left
From 45,000 Pts + $25.6
Premium cabin
2026-11-07
EGE - ORD
First | 2 Stops | 1 left
From 45,000 Pts + $25.6
Premium cabin
2026-11-08
EGE - ORD
First | 2 Stops | 2 left
From 45,000 Pts + $25.6
Premium cabin
2026-11-09
EGE - ORD
First | 2 Stops | 3 left
From 45,000 Pts + $25.6
Premium cabin
2026-11-10
EGE - ORD
First | 2 Stops | 5 left
From 45,000 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 Vail 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 Vail to Chicago.
Yes. Searching metro codes when available helps compare nearby airport combinations for flights from Vail to Chicago.
Vail and Chicago 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.
Chicago is 1 hour ahead of Vail.
Departures from Vail: Eagle County Regional (EGE). 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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