Cheap Flights from Charlottesville VA to Chicago
Cheap Flights from Charlottesville VA to Chicago
Looking for cheap flights from Charlottesville VA 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 Charlottesville VA to Chicago vary by season, cabin, and date, but available award flights can start around 7,500–13,800 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 Charlottesville VA to Chicago for specific travel dates.
2026-12-12
CHO - ORD
Economy | 1 Stop | 9+ left
From 7,500 Pts + $25.6
2027-01-01
CHO - ORD
Economy | Non stop | 5 left
From 8,500 Pts + $10.1
2026-12-12
CHO - ORD
First | Non stop | 9+ left
From 9,000 Pts + $25.6
2026-12-12
CHO - ORD
Economy | Non stop
From 10,000 Pts + $5.6
2027-01-04
CHO - ORD
Economy | 1 Stop | 7 left
From 12,500 Pts + $14.6
2026-12-12
CHO - ORD
Economy | 1 Stop
From 13,800 Pts + $5.6
Charlottesville VA to Chicago flight facts
Distance
566 mi
911 km in a straight line
Estimated flight time
about 1h 45m
In the air, for the straight-line distance
Time difference
−1h
Chicago is 1 hour behind Charlottesville VA.
Airports in Charlottesville VA
CHO · Charlottesville Albemarle
Airports in Chicago
DPA · Dupage
MDW · Chicago Midway Intl
ORD · Chicago O'Hare Intl
Nearby airport alternatives
Flights Lynchburg - Chicago · Lynchburg is 69 mi from Charlottesville VA
Flights Richmond - Chicago · Richmond is 76 mi from Charlottesville VA
Flights Washington - Chicago · Washington is 84 mi from Charlottesville VA
Flights Roanoke VA - Chicago · Roanoke VA is 100 mi from Charlottesville VA
Flights Charlottesville VA - Madison · Madison is 111 mi from Chicago
Flights Baltimore - Chicago · Baltimore is 120 mi from Charlottesville VA
Premium cabin flights from Charlottesville VA to Chicago
Premium cabin
2026-12-12
CHO - ORD
First | 1 Stop | 6 left
From 40,000 Pts + $5.6
Premium cabin
2026-12-12
CHO - ORD
First | 1 Stop | 9+ left
From 41,400 Pts + $5.6
Premium cabin
2026-12-12
CHO - ORD
First | Non stop | 9+ 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 Charlottesville VA 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 Charlottesville VA to Chicago.
Yes. Searching metro codes when available helps compare nearby airport combinations for flights from Charlottesville VA to Chicago.
Charlottesville VA and Chicago are about 566 miles (911 km) apart in a straight line.
Flying the 566-mile straight-line distance takes about 1h 45m 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 Charlottesville VA.
Departures from Charlottesville VA: Charlottesville Albemarle (CHO). 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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