Cheap Flights from Chicago to Windsor Locks
Cheap Flights from Chicago to Windsor Locks
Looking for cheap flights from Chicago to Windsor Locks? 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 Windsor Locks 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 Chicago to Windsor Locks for specific travel dates.
2026-11-05
ORD - BDL
Economy | Non stop | 9+ left
From 7,500 Pts + $25.6
2026-11-06
ORD - BDL
Economy | Non stop | 9+ left
From 7,500 Pts + $25.6
2026-11-07
ORD - BDL
Economy | Non stop | 9+ left
From 7,500 Pts + $25.6
2026-11-08
ORD - BDL
Economy | Non stop | 9+ left
From 7,500 Pts + $25.6
2026-11-09
ORD - BDL
Economy | Non stop | 9+ left
From 7,500 Pts + $25.6
2026-11-10
ORD - BDL
Economy | Non stop | 9+ left
From 7,500 Pts + $25.6
Chicago to Windsor Locks flight facts
Distance
785 mi
1,263 km in a straight line
Estimated flight time
about 2h
In the air, for the straight-line distance
Time difference
+1h
Windsor Locks is 1 hour ahead of Chicago.
Airports in Chicago
DPA · Dupage
MDW · Chicago Midway Intl
ORD · Chicago O'Hare Intl
Airports in Windsor Locks
BDL · Bradley Intl
Nearby airport alternatives
Flights Chicago - Worcester · Worcester is 47 mi from Windsor Locks
Flights Chicago - Providence · Providence is 67 mi from Windsor Locks
Flights Milwaukee - Windsor Locks · Milwaukee is 73 mi from Chicago
Flights Chicago - Albany · Albany is 80 mi from Windsor Locks
Flights Chicago - White Plains · White Plains is 80 mi from Windsor Locks
Flights Chicago - Boston · Boston is 91 mi from Windsor Locks
Premium cabin flights from Chicago to Windsor Locks
Premium cabin
2026-11-11
ORD - BDL
First | Non stop | 8 left
From 15,000 Pts + $25.6
Premium cabin
2026-11-12
ORD - BDL
First | Non stop | 2 left
From 15,000 Pts + $25.6
Premium cabin
2026-11-13
ORD - BDL
First | Non stop | 3 left
From 15,000 Pts + $25.6
Premium cabin
2026-11-14
ORD - BDL
First | Non stop | 9+ left
From 15,000 Pts + $25.6
Premium cabin
2026-11-15
ORD - BDL
First | Non stop | 7 left
From 15,000 Pts + $25.6
Premium cabin
2026-11-16
ORD - BDL
First | Non stop | 7 left
From 15,000 Pts + $25.6
Selected hotels for your next stay
Lenox (United States)
Miraval Berkshires Resort and Spa
From 40,000 Pts or $967
Frequently Asked Questions
The cheapest route from Chicago to Windsor Locks 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 Windsor Locks.
Yes. Searching metro codes when available helps compare nearby airport combinations for flights from Chicago to Windsor Locks.
Chicago and Windsor Locks are about 785 miles (1,263 km) apart in a straight line.
Flying the 785-mile straight-line distance takes about 2h in the air, estimated from typical cruising speed. Actual travel time depends on the routing; itineraries with connections take longer.
Windsor Locks is 1 hour ahead of Chicago.
Departures from Chicago: Dupage (DPA), Chicago Midway Intl (MDW), Chicago O'Hare Intl (ORD). Arrivals in Windsor Locks: Bradley Intl (BDL).
Travelers searching this route also look at other popular routes into Windsor Locks, plus the return trip when we track it. Fares and award space change daily.
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