Cheap Flights from LGA to MDW

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The Cheapest Round-trip Tickets from to

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11 June 202614 June 2026DirectSouthwest AirlinesRT from 138

The Cheapest Flights for this Month from to

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25 May 202629 May 2026DirectSouthwest AirlinesRT from 299
26 May 202626 May 2026DirectSouthwest AirlinesRT from 472
28 May 202630 May 2026DirectSouthwest AirlinesRT from 383
29 May 20261 June 2026DirectSouthwest AirlinesRT from 398
30 May 20262 June 2026DirectSouthwest AirlinesRT from 327
31 May 20262 June 2026DirectSouthwest AirlinesRT from 326
1 June 20262 June 20261 StopSouthwest AirlinesRT from 244
2 June 20263 June 2026DirectSouthwest AirlinesRT from 165
3 June 20268 June 20261 StopSouthwest AirlinesRT from 386
4 June 202612 June 2026DirectSouthwest AirlinesRT from 271
5 June 20267 June 2026DirectSouthwest AirlinesRT from 444
6 June 20268 June 20261 StopSouthwest AirlinesRT from 245
7 June 202612 June 2026DirectSouthwest AirlinesRT from 218
10 June 202612 June 2026DirectSouthwest AirlinesRT from 190
11 June 202614 June 2026DirectSouthwest AirlinesRT from 138
12 June 202614 June 20261 StopSouthwest AirlinesRT from 337
13 June 202614 June 20261 StopSouthwest AirlinesRT from 287
17 June 202621 June 2026DirectSouthwest AirlinesRT from 305
19 June 202626 June 2026DirectSouthwest AirlinesRT from 229
20 June 202622 June 20261 StopSouthwest AirlinesRT from 223
25 June 20263 July 20261 StopFrontier AirlinesRT from 230
26 June 202626 June 2026DirectSouthwest AirlinesRT from 269
3 July 20268 July 2026DirectSouthwest AirlinesRT from 167
6 July 202625 July 2026DirectSouthwest AirlinesRT from 191
9 July 202610 July 20261 StopSouthwest AirlinesRT from 215
3 August 20266 August 2026DirectSouthwest AirlinesRT from 205
7 August 202615 August 2026DirectSouthwest AirlinesRT from 263
10 August 202617 August 2026DirectSouthwest AirlinesRT from 206
14 August 202617 August 2026DirectSouthwest AirlinesRT from 209
19 August 202622 August 2026DirectSouthwest AirlinesRT from 213
27 August 20262 September 2026DirectSouthwest AirlinesRT from 162
10 September 202613 September 2026DirectSouthwest AirlinesRT from 209
30 September 20264 October 2026DirectSouthwest AirlinesRT from 274
13 October 202614 October 20261 StopSouthwest AirlinesRT from 246
1 November 20268 November 2026DirectSouthwest AirlinesRT from 343
23 November 202627 November 20261 StopSouthwest AirlinesRT from 315

The Cheapest Flights from to for the Year Ahead

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25 May 202629 May 2026DirectSouthwest AirlinesRT from 299
11 June 202614 June 2026DirectSouthwest AirlinesRT from 138
3 July 20268 July 2026DirectSouthwest AirlinesRT from 167
27 August 20262 September 2026DirectSouthwest AirlinesRT from 162
10 September 202613 September 2026DirectSouthwest AirlinesRT from 209
13 October 202614 October 20261 StopSouthwest AirlinesRT from 246
23 November 202627 November 20261 StopSouthwest AirlinesRT from 315
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