Cheap Flights from MDW to BOS

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The Cheapest Round-trip Tickets from to Boston

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11 October 202318 October 2023DirectFrontier AirlinesRT from 124

The Cheapest Flights for this Month from to Boston

Departure atReturn atStopsAirlineFind tickets
4 October 20235 October 20231 StopDelta Air LinesRT from 486
7 October 202313 October 20231 StopDelta Air LinesRT from 640
8 October 20239 October 20231 StopDelta Air LinesRT from 825
9 October 202314 October 20231 StopDelta Air LinesRT from 841
10 October 202317 October 20231 StopFrontier AirlinesRT from 137
11 October 202318 October 20231 StopFrontier AirlinesRT from 124
12 October 202318 October 20231 StopFrontier AirlinesRT from 247
13 October 202318 October 20231 StopDelta Air LinesRT from 597
14 October 202320 October 20231 StopDelta Air LinesRT from 307
15 October 202319 October 20231 StopFrontier AirlinesRT from 277
17 October 202324 October 20231 StopFrontier AirlinesRT from 87
19 October 202324 October 20231 StopFrontier AirlinesRT from 167
20 October 202322 October 20231 StopDelta Air LinesRT from 667
21 October 202324 October 20231 StopFrontier AirlinesRT from 87
22 October 202326 October 20231 StopFrontier AirlinesRT from 197
24 October 202311 November 20231 StopFrontier AirlinesRT from 127
26 October 20232 November 20231 StopDelta Air LinesRT from 476
27 October 202330 October 20231 StopFrontier AirlinesRT from 197
28 October 20232 November 20231 StopFrontier AirlinesRT from 147
29 October 20232 November 20231 StopFrontier AirlinesRT from 197
30 October 202331 October 20231 StopDelta Air LinesRT from 316
1 November 20232 November 20231 StopDelta Air LinesRT from 316
2 November 20233 November 20231 StopDelta Air LinesRT from 456
3 November 20236 November 20231 StopFrontier AirlinesRT from 117
4 November 20236 November 20231 StopFrontier AirlinesRT from 97
5 November 20239 November 20231 StopFrontier AirlinesRT from 201
7 November 202312 November 20231 StopDelta Air LinesRT from 346
10 November 202313 November 20231 StopFrontier AirlinesRT from 157
11 November 202318 November 20231 StopFrontier AirlinesRT from 207
12 November 202315 November 20231 StopFrontier AirlinesRT from 277
13 November 202318 November 20231 StopDelta Air LinesRT from 391
14 November 202317 November 20231 StopDelta Air LinesRT from 287
15 November 20233 December 20231 StopDelta Air LinesRT from 336
16 November 20234 December 20231 StopFrontier AirlinesRT from 111
18 November 202322 November 20231 StopDelta Air LinesRT from 317
19 November 202327 November 20231 StopFrontier AirlinesRT from 297
20 November 202313 December 20231 StopDelta Air LinesRT from 267
22 November 202327 November 20231 StopDelta Air LinesRT from 507
23 November 202330 November 20231 StopDelta Air LinesRT from 316
24 November 202326 November 2023DirectSouthwest AirlinesRT from 469
25 November 202329 November 20231 StopDelta Air LinesRT from 356
26 November 202329 November 20231 StopDelta Air LinesRT from 861
27 November 20232 December 20231 StopDelta Air LinesRT from 496
28 November 20231 December 20231 StopFrontier AirlinesRT from 146
29 November 20234 December 20231 StopFrontier AirlinesRT from 127
30 November 20234 December 20231 StopFrontier AirlinesRT from 127
2 December 20233 December 20231 StopDelta Air LinesRT from 316
3 December 20236 December 20231 StopDelta Air LinesRT from 346
4 December 202313 December 20231 StopDelta Air LinesRT from 336
5 December 202313 December 20231 StopFrontier AirlinesRT from 127
6 December 202313 December 20231 StopFrontier AirlinesRT from 127
7 December 202313 December 20231 StopFrontier AirlinesRT from 127
8 December 202315 December 20231 StopDelta Air LinesRT from 336
9 December 202312 December 20231 StopDelta Air LinesRT from 316
10 December 202311 December 20231 StopDelta Air LinesRT from 316
12 December 202313 December 20231 StopDelta Air LinesRT from 316
13 December 202314 December 20231 StopDelta Air LinesRT from 316
14 December 202319 December 20231 StopDelta Air LinesRT from 316
15 December 202320 December 20231 StopFrontier AirlinesRT from 160
16 December 202319 December 20231 StopDelta Air LinesRT from 316
17 December 202320 December 20231 StopFrontier AirlinesRT from 160
18 December 202321 December 20231 StopDelta Air LinesRT from 316
19 December 202320 December 20231 StopDelta Air LinesRT from 316
20 December 202325 December 20231 StopDelta Air LinesRT from 316
21 December 202326 December 20231 StopDelta Air LinesRT from 570
24 December 202325 December 20231 StopDelta Air LinesRT from 316
25 December 202326 December 20231 StopDelta Air LinesRT from 396
26 December 202327 December 20231 StopDelta Air LinesRT from 426
27 December 20233 January 20241 StopDelta Air LinesRT from 476
29 December 20231 January 20241 StopDelta Air LinesRT from 456
30 December 20234 January 20241 StopDelta Air LinesRT from 316
1 January 20248 January 20241 StopDelta Air LinesRT from 506
2 January 20249 January 20241 StopDelta Air LinesRT from 396
3 January 20248 January 20241 StopDelta Air LinesRT from 316
5 January 20246 January 20241 StopDelta Air LinesRT from 316
6 January 20247 January 20241 StopDelta Air LinesRT from 316
7 January 20248 January 20241 StopDelta Air LinesRT from 316
8 January 202411 January 20241 StopDelta Air LinesRT from 316
9 January 202410 January 20241 StopDelta Air LinesRT from 316
10 January 202413 January 20241 StopDelta Air LinesRT from 316
11 January 202414 January 20241 StopDelta Air LinesRT from 316
12 January 202413 January 20241 StopDelta Air LinesRT from 316
13 January 202414 January 20241 StopDelta Air LinesRT from 316
14 January 202415 January 20241 StopDelta Air LinesRT from 316
15 January 202418 January 20241 StopDelta Air LinesRT from 316
16 January 202417 January 20241 StopDelta Air LinesRT from 316
17 January 202420 January 20241 StopDelta Air LinesRT from 316
18 January 202421 January 20241 StopDelta Air LinesRT from 316
19 January 202420 January 20241 StopDelta Air LinesRT from 316
20 January 202421 January 20241 StopDelta Air LinesRT from 316
21 January 202422 January 20241 StopDelta Air LinesRT from 316
22 January 202423 January 20241 StopDelta Air LinesRT from 316
23 January 202424 January 20241 StopDelta Air LinesRT from 316
24 January 202425 January 20241 StopDelta Air LinesRT from 316
29 January 20241 February 20241 StopDelta Air LinesRT from 316
30 January 202431 January 20241 StopDelta Air LinesRT from 316
31 January 20245 February 20241 StopDelta Air LinesRT from 336
1 February 20244 February 20241 StopFrontier AirlinesRT from 197
14 April 202416 April 20241 StopDelta Air LinesRT from 357
15 April 202420 April 20241 StopDelta Air LinesRT from 582
20 July 202422 July 20241 StopDelta Air LinesRT from 675
28 July 202430 July 20241 StopDelta Air LinesRT from 566
11 August 202417 August 20241 StopDelta Air LinesRT from 540

The Cheapest Flights from to Boston for the Year Ahead

Departure atReturn atStopsAirlineFind tickets
11 October 202318 October 20231 StopFrontier AirlinesRT from 124
24 November 202326 November 2023DirectSouthwest AirlinesRT from 469
5 December 202313 December 20231 StopFrontier AirlinesRT from 127
3 January 20248 January 20241 StopDelta Air LinesRT from 316
1 February 20244 February 20241 StopFrontier AirlinesRT from 197
14 April 202416 April 20241 StopDelta Air LinesRT from 357
28 July 202430 July 20241 StopDelta Air LinesRT from 566
11 August 202417 August 20241 StopDelta Air LinesRT from 540
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