Cheap Flights from Worcester to Chicago
Cheap Flights from Worcester to Chicago
Looking for cheap flights from Worcester 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 Worcester to Chicago vary by season, cabin, and date, but available award flights can start around 10,000–20,500 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 Worcester to Chicago for specific travel dates.
2026-12-23
ORH - ORD
Economy | 1 Stop
From 10,000 Pts + $5.6
2026-12-23
ORH - ORD
First | 1 Stop
From 20,500 Pts + $5.6
Worcester to Chicago flight facts
Distance
824 mi
1,327 km in a straight line
Estimated flight time
about 2h 15m
In the air, for the straight-line distance
Time difference
−1h
Chicago is 1 hour behind Worcester.
Airports in Worcester
ORH · Worcester Regional
Airports in Chicago
DPA · Dupage
MDW · Chicago Midway Intl
ORD · Chicago O'Hare Intl
Nearby airport alternatives
Flights Providence - Chicago · Providence is 44 mi from Worcester
Flights Boston - Chicago · Boston is 45 mi from Worcester
Flights Windsor Locks - Chicago · Windsor Locks is 47 mi from Worcester
Flights Manchester NH - Chicago · Manchester NH is 51 mi from Worcester
Flights Worcester - Milwaukee · Milwaukee is 73 mi from Chicago
Flights Albany - Chicago · Albany is 104 mi from Worcester
Premium cabin flights from Worcester to Chicago
Premium cabin
2026-12-23
ORH - ORD
First | 1 Stop
From 20,500 Pts + $5.6
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 Worcester 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 Worcester to Chicago.
Yes. Searching metro codes when available helps compare nearby airport combinations for flights from Worcester to Chicago.
Worcester and Chicago are about 824 miles (1,327 km) apart in a straight line.
Flying the 824-mile straight-line distance takes about 2h 15m 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 Worcester.
Departures from Worcester: Worcester Regional (ORH). 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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