Cheap Flights from WAS to MDW

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The Cheapest Round-trip Tickets from Washington to

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15 May 202617 May 2026DirectSouthwest AirlinesRT from 184

The Cheapest Flights for this Month from Washington to

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20 March 202629 March 2026DirectSouthwest AirlinesRT from 521
22 March 202629 March 2026DirectSouthwest AirlinesRT from 651
23 March 202630 March 20261 StopFrontier AirlinesRT from 443
24 March 202631 March 2026DirectSouthwest AirlinesRT from 517
25 March 202626 March 20262 StopsFrontier AirlinesRT from 330
4 April 20267 April 2026DirectSouthwest AirlinesRT from 255
14 April 202615 April 2026DirectSouthwest AirlinesRT from 211
15 April 202616 April 2026DirectSouthwest AirlinesRT from 227
16 April 202617 April 20261 StopFrontier AirlinesRT from 258
20 April 20261 May 20261 StopSouthwest AirlinesRT from 270
15 May 202617 May 2026DirectSouthwest AirlinesRT from 184
9 July 202612 July 2026DirectSouthwest AirlinesRT from 324
21 July 202625 July 2026DirectSouthwest AirlinesRT from 295
3 September 20268 September 2026DirectSouthwest AirlinesRT from 324
10 September 202614 September 2026DirectSouthwest AirlinesRT from 315
9 October 202613 October 2026DirectSouthwest AirlinesRT from 328

The Cheapest Flights from Washington to for the Year Ahead

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25 March 202626 March 20262 StopsFrontier AirlinesRT from 330
14 April 202615 April 2026DirectSouthwest AirlinesRT from 211
15 May 202617 May 2026DirectSouthwest AirlinesRT from 184
21 July 202625 July 2026DirectSouthwest AirlinesRT from 295
10 September 202614 September 2026DirectSouthwest AirlinesRT from 315
9 October 202613 October 2026DirectSouthwest AirlinesRT from 328
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