Cheap Flights from Chicago to Cleveland
Cheap Flights from Chicago to Cleveland
Looking for cheap flights from Chicago to Cleveland? 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 Cleveland vary by season, cabin, and date, but available award flights can start around 4,500 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 Cleveland for specific travel dates.
2026-11-05
ORD - CLE
Economy | Non stop | 7 left
From 4,500 Pts + $25.6
2026-11-06
ORD - CLE
Economy | Non stop | 9+ left
From 4,500 Pts + $25.6
2026-11-07
ORD - CLE
Economy | Non stop | 9+ left
From 4,500 Pts + $25.6
2026-11-09
ORD - CLE
Economy | Non stop | 9+ left
From 4,500 Pts + $25.6
2026-11-10
ORD - CLE
Economy | Non stop | 9+ left
From 4,500 Pts + $25.6
2026-11-11
ORD - CLE
Economy | Non stop | 9+ left
From 4,500 Pts + $25.6
Chicago to Cleveland flight facts
Distance
318 mi
511 km in a straight line
Estimated flight time
about 1h 15m
In the air, for the straight-line distance
Time difference
+1h
Cleveland is 1 hour ahead of Chicago.
Airports in Chicago
DPA · Dupage
MDW · Chicago Midway Intl
ORD · Chicago O'Hare Intl
Airports in Cleveland
CLE · Cleveland Hopkins Intl
Nearby airport alternatives
Flights Chicago - Akron · Akron is 40 mi from Cleveland
Flights Milwaukee - Cleveland · Milwaukee is 73 mi from Chicago
Flights Chicago - Detroit · Detroit is 95 mi from Cleveland
Flights Chicago - Pittsburgh · Pittsburgh is 106 mi from Cleveland
Flights Madison - Cleveland · Madison is 111 mi from Chicago
Flights Chicago - Columbus · Columbus is 112 mi from Cleveland
Premium cabin flights from Chicago to Cleveland
Premium cabin
2026-11-06
ORD - CLE
First | Non stop
From 18,000 Pts + $5.6
Premium cabin
2026-11-09
ORD - CLE
First | Non stop
From 20,000 Pts + $5.6
Premium cabin
2026-11-08
ORD - CLE
First | Non stop
From 21,500 Pts + $5.6
Premium cabin
2026-11-08
ORD - CLE
First | 1 Stop | 4 left
From 25,000 Pts + $25.6
Premium cabin
2026-11-06
ORD - CLE
First | 1 Stop | 4 left
From 31,300 Pts + $5.6
Premium cabin
2026-11-08
ORD - CLE
First | 1 Stop | 5 left
From 31,300 Pts + $5.6
Selected hotels for your next stay
Cleveland, OH (USA)
Metropolitan at The 9, Autograph Collection
From Pts or $168
Cleveland, OH (USA)
The Ritz-Carlton, Cleveland
From Pts or $482
Frequently Asked Questions
The cheapest route from Chicago to Cleveland 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 Cleveland.
Yes. Searching metro codes when available helps compare nearby airport combinations for flights from Chicago to Cleveland.
Chicago and Cleveland are about 318 miles (511 km) apart in a straight line.
Flying the 318-mile straight-line distance takes about 1h 15m in the air, estimated from typical cruising speed. Actual travel time depends on the routing; itineraries with connections take longer.
Cleveland is 1 hour ahead of Chicago.
Departures from Chicago: Dupage (DPA), Chicago Midway Intl (MDW), Chicago O'Hare Intl (ORD). Arrivals in Cleveland: Cleveland Hopkins Intl (CLE).
Travelers searching this route also look at other popular routes into Cleveland, plus the return trip when we track it. Fares and award space change daily.
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