Cheap Flights from Asheville to Chicago
Cheap Flights from Asheville to Chicago
Looking for cheap flights from Asheville 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 Asheville to Chicago vary by season, cabin, and date, but available award flights can start around 4,500 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 Asheville to Chicago for specific travel dates.
2026-11-05
AVL - ORD
Economy | Non stop | 3 left
From 4,500 Pts + $25.6
2026-11-06
AVL - ORD
Economy | Non stop | 1 left
From 4,500 Pts + $25.6
2026-11-07
AVL - ORD
Economy | Non stop | 9+ left
From 4,500 Pts + $25.6
2026-11-10
AVL - ORD
Economy | Non stop | 9+ left
From 4,500 Pts + $25.6
2026-11-11
AVL - ORD
Economy | Non stop | 9+ left
From 4,500 Pts + $25.6
2026-11-12
AVL - ORD
Economy | Non stop | 5 left
From 4,500 Pts + $25.6
Asheville to Chicago flight facts
Distance
533 mi
858 km in a straight line
Estimated flight time
about 1h 30m
In the air, for the straight-line distance
Time difference
−1h
Chicago is 1 hour behind Asheville.
Airports in Asheville
AVL · Asheville Regional
Airports in Chicago
DPA · Dupage
MDW · Chicago Midway Intl
ORD · Chicago O'Hare Intl
Nearby airport alternatives
Flights Greenville - Chicago · Greenville is 42 mi from Asheville
Flights BRISTOL - Chicago · BRISTOL is 72 mi from Asheville
Flights Asheville - Milwaukee · Milwaukee is 73 mi from Chicago
Flights Knoxville - Chicago · Knoxville is 86 mi from Asheville
Flights Asheville - South Bend · South Bend is 86 mi from Chicago
Flights Charlotte - Chicago · Charlotte is 91 mi from Asheville
Premium cabin flights from Asheville to Chicago
Premium cabin
2026-11-09
AVL - ORD
First | Non stop | 9+ left
From 9,000 Pts + $25.6
Premium cabin
2026-11-13
AVL - ORD
First | Non stop | 2 left
From 9,000 Pts + $25.6
Premium cabin
2026-11-14
AVL - ORD
First | Non stop | 8 left
From 9,000 Pts + $25.6
Premium cabin
2026-11-16
AVL - ORD
First | Non stop | 7 left
From 9,000 Pts + $25.6
Premium cabin
2026-11-17
AVL - ORD
First | Non stop | 4 left
From 9,000 Pts + $25.6
Premium cabin
2026-11-18
AVL - ORD
First | Non stop | 8 left
From 9,000 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 Asheville 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 Asheville to Chicago.
Yes. Searching metro codes when available helps compare nearby airport combinations for flights from Asheville to Chicago.
Asheville and Chicago are about 533 miles (858 km) apart in a straight line.
Flying the 533-mile straight-line distance takes about 1h 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 behind Asheville.
Departures from Asheville: Asheville Regional (AVL). 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!
