Cheap Flights from Chicago to Charlottesville VA
Cheap Flights from Chicago to Charlottesville VA
Looking for cheap flights from Chicago to Charlottesville VA? 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 Charlottesville VA vary by season, cabin, and date, but available award flights can start around 8,500–10,000 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 Charlottesville VA for specific travel dates.
2026-12-13
ORD - CHO
Economy | Non stop | 9+ left
From 8,500 Pts + $10.1
2027-01-01
ORD - CHO
Economy | Non stop | 9+ left
From 8,500 Pts + $10.1
2027-01-04
ORD - CHO
Economy | Non stop | 6 left
From 8,500 Pts + $10.1
2026-12-13
ORD - CHO
First | Non stop | 7 left
From 9,000 Pts + $25.6
2026-12-28
ORD - CHO
First | Non stop | 6 left
From 9,000 Pts + $25.6
2026-12-13
ORD - CHO
Economy | 1 Stop
From 10,000 Pts + $5.6
Chicago to Charlottesville VA 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
Charlottesville VA is 1 hour ahead of Chicago.
Airports in Chicago
DPA · Dupage
MDW · Chicago Midway Intl
ORD · Chicago O'Hare Intl
Airports in Charlottesville VA
CHO · Charlottesville Albemarle
Nearby airport alternatives
Flights Chicago - Richmond · Richmond is 76 mi from Charlottesville VA
Flights Chicago - Washington · Washington is 84 mi from Charlottesville VA
Flights Chicago - Roanoke VA · Roanoke VA is 100 mi from Charlottesville VA
Flights Chicago - Baltimore · Baltimore is 120 mi from Charlottesville VA
Flights Chicago - Morgantown · Morgantown is 130 mi from Charlottesville VA
Flights Chicago - Norfolk · Norfolk is 150 mi from Charlottesville VA
Premium cabin flights from Chicago to Charlottesville VA
Premium cabin
2026-12-28
ORD - CHO
First | Non stop
From 20,500 Pts + $5.6
Premium cabin
2026-12-13
ORD - CHO
First | Non stop | 7 left
From 39,700 Pts + $5.6
Premium cabin
2026-12-13
ORD - CHO
First | 1 Stop | 3 left
From 40,000 Pts + $5.6
Premium cabin
2026-12-28
ORD - CHO
First | Non stop | 7 left
From 44,700 Pts + $5.6
Premium cabin
2026-12-28
ORD - CHO
First | 1 Stop | 4 left
From 49,600 Pts + $5.6
Premium cabin
2026-12-13
ORD - CHO
Business | Non stop
From 19,300 Pts + $5.6
Selected hotels for your next stay
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Frequently Asked Questions
The cheapest route from Chicago to Charlottesville VA 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 Charlottesville VA.
Yes. Searching metro codes when available helps compare nearby airport combinations for flights from Chicago to Charlottesville VA.
Chicago and Charlottesville VA 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.
Charlottesville VA is 1 hour ahead of Chicago.
Departures from Chicago: Dupage (DPA), Chicago Midway Intl (MDW), Chicago O'Hare Intl (ORD). Arrivals in Charlottesville VA: Charlottesville Albemarle (CHO).
Travelers searching this route also look at other popular routes into Charlottesville VA, plus the return trip when we track it. Fares and award space change daily.
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