Cheap Flights from Chicago to Midland
Cheap Flights from Chicago to Midland
Looking for cheap flights from Chicago to Midland? 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 Midland vary by season, cabin, and date, but available award flights can start around 7,500–13,800 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 Midland for specific travel dates.
2026-11-22
ORD - MAF
Economy | 1 Stop | 9+ left
From 7,500 Pts + $30.6
2026-11-21
ORD - MAF
Economy | 1 Stop
From 9,000 Pts + $11.2
2026-11-22
ORD - MAF
Economy | 1 Stop
From 10,500 Pts + $11.2
2026-11-21
ORD - MAF
Economy | 1 Stop | 9+ left
From 12,500 Pts + $25.6
2026-11-21
ORD - MAF
Economy | 1 Stop
From 13,800 Pts + $5.6
2026-11-22
ORD - MAF
Economy | 1 Stop
From 13,800 Pts + $11.2
Chicago to Midland flight facts
Distance
1,042 mi
1,677 km in a straight line
Estimated flight time
about 2h 30m
In the air, for the straight-line distance
Time difference
Same time zone
Midland is in the same time zone as Chicago.
Airports in Chicago
DPA · Dupage
MDW · Chicago Midway Intl
ORD · Chicago O'Hare Intl
Airports in Midland
MAF · Midland Intl
Nearby airport alternatives
Flights Chicago - Abilene · Abilene is 151 mi from Midland
Premium cabin flights from Chicago to Midland
Premium cabin
2026-11-22
ORD - MAF
First | 2 Stops | 1 left
From 45,000 Pts + $25.6
Premium cabin
2026-11-21
ORD - MAF
First | 1 Stop | 6 left
From 25,000 Pts + $25.6
Premium cabin
2026-11-22
ORD - MAF
First | 2 Stops
From 28,000 Pts + $5.6
Premium cabin
2026-11-21
ORD - MAF
First | 1 Stop
From 28,000 Pts + $11.2
Premium cabin
2026-11-21
ORD - MAF
Business | 1 Stop
From 29,000 Pts + $5.6
Premium cabin
2026-11-22
ORD - MAF
Business | 1 Stop
From 29,000 Pts + $11.2
Selected hotels for your next stay
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Frequently Asked Questions
The cheapest route from Chicago to Midland 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 Midland.
Yes. Searching metro codes when available helps compare nearby airport combinations for flights from Chicago to Midland.
Chicago and Midland are about 1,042 miles (1,677 km) apart in a straight line.
Flying the 1,042-mile straight-line distance takes about 2h 30m in the air, estimated from typical cruising speed. Actual travel time depends on the routing; itineraries with connections take longer.
Midland is in the same time zone as Chicago.
Departures from Chicago: Dupage (DPA), Chicago Midway Intl (MDW), Chicago O'Hare Intl (ORD). Arrivals in Midland: Midland Intl (MAF).
Travelers searching this route also look at other popular routes into Midland, plus the return trip when we track it. Fares and award space change daily.
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