Cheapest return flights from Dallas-Fort Worth to Chicago in May from $143

AirHint found the following cheapest return flights from Dallas-Fort Worth (DFW) to Chicago (MDW) in May 2026 (see full year).

Return flights

11 May - 13 May Southwest Airlines direct
07 May - 11 May Southwest Airlines
06 May - 09 May Southwest Airlines direct
13 May - 16 May Southwest Airlines direct
09 May - 19 May Southwest Airlines direct
15 May - 19 May Southwest Airlines direct
01 May - 03 May Southwest Airlines direct
15 May - 18 May Southwest Airlines direct
15 May - 17 May Southwest Airlines direct
14 May - 17 May Southwest Airlines direct

Also check the deals for one-way flights from Dallas-Fort Worth to Chicago in May.

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