Cheap Flights from LGA to MDW

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The Cheapest Round-trip Tickets from to

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26 August 202631 August 2026DirectSouthwest AirlinesRT from 120

The Cheapest Flights for this Month from to

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16 July 202616 July 2026DirectSouthwest AirlinesRT from 615
17 July 202619 July 20261 StopSouthwest AirlinesRT from 422
18 July 202621 July 2026DirectSouthwest AirlinesRT from 364
19 July 202613 August 2026DirectSouthwest AirlinesRT from 271
20 July 202623 July 2026DirectSouthwest AirlinesRT from 450
21 July 202623 July 2026DirectSouthwest AirlinesRT from 384
22 July 202629 July 2026DirectSouthwest AirlinesRT from 260
24 July 202629 July 2026DirectSouthwest AirlinesRT from 344
25 July 20267 August 2026DirectSouthwest AirlinesRT from 291
27 July 202630 July 2026DirectSouthwest AirlinesRT from 278
28 July 20261 August 2026DirectSouthwest AirlinesRT from 318
29 July 20263 August 20262 StopsAir CanadaRT from 409
30 July 20267 August 2026DirectSouthwest AirlinesRT from 417
31 July 20266 August 20261 StopSouthwest AirlinesRT from 294
1 August 202625 August 2026DirectSouthwest AirlinesRT from 262
4 August 202614 August 2026DirectSouthwest AirlinesRT from 217
5 August 202615 August 2026DirectSouthwest AirlinesRT from 217
6 August 202613 August 2026DirectSouthwest AirlinesRT from 198
7 August 202615 August 20261 StopSouthwest AirlinesRT from 246
11 August 202618 August 2026DirectSouthwest AirlinesRT from 190
12 August 202619 August 2026DirectSouthwest AirlinesRT from 192
13 August 202616 August 20261 StopSouthwest AirlinesRT from 206
14 August 202616 August 20261 StopSouthwest AirlinesRT from 236
15 August 202616 August 2026DirectSouthwest AirlinesRT from 262
24 August 202628 August 2026DirectSouthwest AirlinesRT from 158
26 August 202631 August 2026DirectSouthwest AirlinesRT from 120
27 August 202630 August 2026DirectSouthwest AirlinesRT from 217
30 August 20262 September 2026DirectSouthwest AirlinesRT from 216
4 September 20267 September 2026DirectSouthwest AirlinesRT from 280
10 September 202614 September 2026DirectSouthwest AirlinesRT from 217
12 September 202616 September 2026DirectSouthwest AirlinesRT from 189
17 September 202621 September 2026DirectSouthwest AirlinesRT from 207
3 October 202610 October 20261 StopSouthwest AirlinesRT from 237
6 October 202613 October 2026DirectSouthwest AirlinesRT from 216
8 October 202610 October 20261 StopSouthwest AirlinesRT from 210
9 October 202612 October 20261 StopSouthwest AirlinesRT from 356
4 November 202611 November 2026DirectSouthwest AirlinesRT from 129
5 November 20265 November 2026DirectSouthwest AirlinesRT from 222
29 December 20266 January 2027DirectSouthwest AirlinesRT from 315

The Cheapest Flights from to for the Year Ahead

Departure atReturn atStopsAirlineFind tickets
22 July 202629 July 2026DirectSouthwest AirlinesRT from 260
26 August 202631 August 2026DirectSouthwest AirlinesRT from 120
12 September 202616 September 2026DirectSouthwest AirlinesRT from 189
8 October 202610 October 20261 StopSouthwest AirlinesRT from 210
4 November 202611 November 2026DirectSouthwest AirlinesRT from 129
29 December 20266 January 2027DirectSouthwest AirlinesRT from 315
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