Cheap Flights from Dallas to Chicago
Cheap Flights from Dallas to Chicago
Looking for cheap flights from Dallas 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 Dallas to Chicago vary by season, cabin, and date, but available award flights can start around 16,000–18,000 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 Dallas to Chicago for specific travel dates.
2026-12-01
DAL - ORD
Economy | 1 Stop | 9+ left
From 16,000 Pts + $5.6
2026-12-10
DAL - ORD
Economy | 1 Stop | 3 left
From 16,000 Pts + $5.6
2026-12-11
DAL - ORD
Economy | 1 Stop | 9+ left
From 16,000 Pts + $5.6
2026-12-19
DAL - ORD
Economy | 1 Stop | 9+ left
From 16,000 Pts + $5.6
2026-12-19
DAL - ORD
Economy | 1 Stop | 9+ left
From 16,000 Pts + $5.6
2026-12-01
DAL - ORD
Economy | 1 Stop | 9+ left
From 18,000 Pts + $17.6
Dallas to Chicago flight facts
Distance
792 mi
1,274 km in a straight line
Estimated flight time
about 2h
In the air, for the straight-line distance
Time difference
Same time zone
Chicago is in the same time zone as Dallas.
Airports in Dallas
DAL · Dallas Love Field
Airports in Chicago
DPA · Dupage
MDW · Chicago Midway Intl
ORD · Chicago O'Hare Intl
Nearby airport alternatives
Flights Dallas-Fort Worth - Chicago · Dallas-Fort Worth is 11 mi from Dallas
Flights Dallas - Milwaukee · Milwaukee is 73 mi from Chicago
Flights Tyler - Chicago · Tyler is 91 mi from Dallas
Flights Longview - Chicago · Longview is 129 mi from Dallas
Flights Killeen - Chicago · Killeen is 136 mi from Dallas
Flights College Station - Chicago · College Station is 159 mi from Dallas
Premium cabin flights from Dallas to Chicago
Premium cabin
2026-12-23
DAL - ORD
First | 1 Stop | 3 left
From 26,300 Pts + $5.6
Premium cabin
2026-11-07
DAL - ORD
First | 1 Stop | 4 left
From 34,300 Pts + $5.6
Premium cabin
2026-11-07
DAL - ORD
First | 1 Stop | 4 left
From 34,300 Pts + $5.6
Premium cabin
2026-11-07
DAL - ORD
First | 1 Stop | 4 left
From 34,300 Pts + $5.6
Premium cabin
2026-11-08
DAL - ORD
First | 1 Stop | 4 left
From 34,300 Pts + $5.6
Premium cabin
2026-11-08
DAL - ORD
First | 1 Stop | 4 left
From 34,300 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 Dallas 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 Dallas to Chicago.
Yes. Searching metro codes when available helps compare nearby airport combinations for flights from Dallas to Chicago.
Dallas and Chicago are about 792 miles (1,274 km) apart in a straight line.
Flying the 792-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.
Chicago is in the same time zone as Dallas.
Departures from Dallas: Dallas Love Field (DAL). 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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points travel planning experience. Yeah!
