Cheap Flights from Chicago to Hailey
Cheap Flights from Chicago to Hailey
Looking for cheap flights from Chicago to Hailey? 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 Hailey vary by season, cabin, and date, but available award flights can start around 19,000 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 Hailey for specific travel dates.
2027-01-01
ORD - SUN
Economy | Non stop | 9+ left
From 19,000 Pts + $10.1
2027-01-02
ORD - SUN
Economy | Non stop | 9+ left
From 19,000 Pts + $10.1
2027-01-03
ORD - SUN
Economy | Non stop | 9+ left
From 19,000 Pts + $10.1
Chicago to Hailey flight facts
Distance
1,336 mi
2,150 km in a straight line
Estimated flight time
about 3h 15m
In the air, for the straight-line distance
Time difference
−1h
Hailey is 1 hour behind Chicago.
Airports in Chicago
DPA · Dupage
MDW · Chicago Midway Intl
ORD · Chicago O'Hare Intl
Airports in Hailey
SUN · Friedman Memorial
Nearby airport alternatives
Flights Chicago - Boise · Boise is 97 mi from Hailey
Flights Chicago - Jacksn Hole · Jacksn Hole is 178 mi from Hailey
Premium cabin flights from Chicago to Hailey
Selected hotels for your next stay
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Frequently Asked Questions
The cheapest route from Chicago to Hailey 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 Hailey.
Yes. Searching metro codes when available helps compare nearby airport combinations for flights from Chicago to Hailey.
Chicago and Hailey are about 1,336 miles (2,150 km) apart in a straight line.
Flying the 1,336-mile straight-line distance takes about 3h 15m in the air, estimated from typical cruising speed. Actual travel time depends on the routing; itineraries with connections take longer.
Hailey is 1 hour behind Chicago.
Departures from Chicago: Dupage (DPA), Chicago Midway Intl (MDW), Chicago O'Hare Intl (ORD). Arrivals in Hailey: Friedman Memorial (SUN).
Travelers searching this route also look at other popular routes into Hailey, plus the return trip when we track it. Fares and award space change daily.
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points travel planning experience. Yeah!
