Cheap Flights from CHI to BOS

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The Cheapest Round-trip Tickets from Chicago to Boston

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4 January 20246 January 2024DirectSouthwest AirlinesRT from 92

The Cheapest Flights for this Month from Chicago to Boston

Departure atReturn atStopsAirlineFind tickets
28 November 202329 November 20231 StopSpirit AirlinesRT from 216
29 November 20236 December 20231 StopFrontier AirlinesRT from 113
30 November 202312 December 2023DirectJetBlue AirwaysRT from 202
1 December 20236 December 20231 StopFrontier AirlinesRT from 117
2 December 20234 December 20231 StopFrontier AirlinesRT from 127
3 December 20236 December 20231 StopFrontier AirlinesRT from 127
4 December 20237 December 2023DirectJetBlue AirwaysRT from 149
5 December 202313 December 20231 StopFrontier AirlinesRT from 87
6 December 202313 December 20231 StopFrontier AirlinesRT from 127
7 December 202318 December 20231 StopFrontier AirlinesRT from 97
8 December 202310 December 20231 StopSpirit AirlinesRT from 130
9 December 202317 December 2023DirectJetBlue AirwaysRT from 148
10 December 202317 December 2023DirectJetBlue AirwaysRT from 163
11 December 202313 December 20231 StopSpirit AirlinesRT from 133
12 December 202318 December 20231 StopFrontier AirlinesRT from 111
13 December 202318 December 2023DirectJetBlue AirwaysRT from 133
14 December 202319 December 20231 StopSpirit AirlinesRT from 132
15 December 202315 December 2023DirectJetBlue AirwaysRT from 84
16 December 202313 January 20241 StopFrontier AirlinesRT from 121
17 December 202320 December 20231 StopFrontier AirlinesRT from 146
18 December 202320 December 2023DirectJetBlue AirwaysRT from 123
19 December 202322 December 2023DirectUnited AirlinesRT from 219
20 December 202331 December 2023DirectJetBlue AirwaysRT from 123
21 December 202326 December 2023DirectSouthwest AirlinesRT from 307
22 December 202325 December 2023DirectSouthwest AirlinesRT from 235
23 December 202325 December 2023DirectJetBlue AirwaysRT from 128
24 December 202330 December 2023DirectJetBlue AirwaysRT from 128
25 December 202328 December 2023DirectJetBlue AirwaysRT from 128
26 December 202331 December 2023DirectSouthwest AirlinesRT from 242
27 December 20233 January 2024DirectJetBlue AirwaysRT from 128
28 December 20231 January 2024DirectSouthwest AirlinesRT from 253
29 December 202331 December 2023DirectJetBlue AirwaysRT from 128
30 December 20234 January 2024DirectJetBlue AirwaysRT from 128
31 December 20234 January 2024DirectJetBlue AirwaysRT from 89
1 January 20245 January 2024DirectJetBlue AirwaysRT from 128
2 January 20244 January 2024DirectJetBlue AirwaysRT from 128
3 January 20249 January 2024DirectJetBlue AirwaysRT from 113
4 January 20246 January 2024DirectSouthwest AirlinesRT from 92
5 January 20247 January 20241 StopAmerican AirlinesRT from 117
6 January 20242 February 2024DirectJetBlue AirwaysRT from 107
7 January 202410 January 20241 StopFrontier AirlinesRT from 107
8 January 202410 January 20241 StopFrontier AirlinesRT from 96
9 January 202412 January 2024DirectDelta Air LinesRT from 125
10 January 202414 January 2024DirectJetBlue AirwaysRT from 125
11 January 202414 January 2024DirectDelta Air LinesRT from 125
12 January 202416 January 20241 StopSpirit AirlinesRT from 147
13 January 202419 January 2024DirectJetBlue AirwaysRT from 125
14 January 202417 January 20241 StopJetBlue AirwaysRT from 135
15 January 202422 January 2024DirectDelta Air LinesRT from 125
16 January 202419 January 2024DirectJetBlue AirwaysRT from 125
17 January 202423 January 2024DirectJetBlue AirwaysRT from 125
18 January 202420 January 2024DirectJetBlue AirwaysRT from 125
19 January 202422 January 20241 StopSpirit AirlinesRT from 109
20 January 202420 January 2024DirectJetBlue AirwaysRT from 120
21 January 202428 January 2024DirectDelta Air LinesRT from 125
22 January 202425 January 2024DirectJetBlue AirwaysRT from 125
23 January 202425 January 2024DirectDelta Air LinesRT from 125
24 January 202420 February 2024DirectJetBlue AirwaysRT from 125
25 January 202428 January 2024DirectJetBlue AirwaysRT from 125
26 January 202428 January 2024DirectJetBlue AirwaysRT from 125
27 January 202429 January 2024DirectJetBlue AirwaysRT from 125
28 January 20244 February 2024DirectDelta Air LinesRT from 125
29 January 20245 February 2024DirectJetBlue AirwaysRT from 125
30 January 20241 February 2024DirectJetBlue AirwaysRT from 125
31 January 20245 February 2024DirectJetBlue AirwaysRT from 125
1 February 20244 February 2024DirectJetBlue AirwaysRT from 125
2 February 20244 February 2024DirectDelta Air LinesRT from 125
3 February 20245 February 2024DirectDelta Air LinesRT from 125
4 February 202411 February 2024DirectDelta Air LinesRT from 125
5 February 202412 February 2024DirectDelta Air LinesRT from 125
6 February 202413 February 2024DirectJetBlue AirwaysRT from 125
7 February 202411 February 2024DirectJetBlue AirwaysRT from 125
8 February 202411 February 2024DirectDelta Air LinesRT from 125
9 February 202412 February 2024DirectJetBlue AirwaysRT from 125
10 February 202413 February 2024DirectJetBlue AirwaysRT from 125
11 February 202413 February 2024DirectDelta Air LinesRT from 125
12 February 202414 February 2024DirectJetBlue AirwaysRT from 125
13 February 202414 February 2024DirectJetBlue AirwaysRT from 137
14 February 202421 February 2024DirectJetBlue AirwaysRT from 137
15 February 202420 February 2024DirectJetBlue AirwaysRT from 125
16 February 202420 February 2024DirectJetBlue AirwaysRT from 125
17 February 202424 February 2024DirectJetBlue AirwaysRT from 125
18 February 202422 February 2024DirectDelta Air LinesRT from 125
19 February 202423 February 2024DirectUnited AirlinesRT from 178
20 February 202427 February 2024DirectJetBlue AirwaysRT from 125
21 February 202429 February 2024DirectJetBlue AirwaysRT from 125
22 February 202426 February 2024DirectJetBlue AirwaysRT from 125
23 February 202423 February 2024DirectJetBlue AirwaysRT from 172
24 February 202426 February 20241 StopDelta Air LinesRT from 192
25 February 202428 February 20241 StopJetBlue AirwaysRT from 232
26 February 20244 March 2024DirectJetBlue AirwaysRT from 181
27 February 202428 February 2024DirectJetBlue AirwaysRT from 137
28 February 20243 March 20241 StopFrontier AirlinesRT from 117
29 February 20244 March 2024DirectJetBlue AirwaysRT from 125
1 March 20243 March 2024DirectJetBlue AirwaysRT from 166
2 March 20244 March 2024DirectJetBlue AirwaysRT from 125
3 March 20246 March 20241 StopFrontier AirlinesRT from 147
4 March 20245 March 2024DirectJetBlue AirwaysRT from 172
5 March 20246 March 2024DirectJetBlue AirwaysRT from 125
6 March 202411 March 2024DirectJetBlue AirwaysRT from 151
7 March 202412 March 2024DirectJetBlue AirwaysRT from 157
8 March 202413 March 2024DirectJetBlue AirwaysRT from 187
9 March 202412 March 2024DirectJetBlue AirwaysRT from 187
10 March 202413 March 2024DirectJetBlue AirwaysRT from 247
11 March 202412 March 2024DirectJetBlue AirwaysRT from 157
12 March 202413 March 2024DirectJetBlue AirwaysRT from 137
13 March 202414 March 2024DirectJetBlue AirwaysRT from 187
14 March 202419 March 2024DirectJetBlue AirwaysRT from 177
15 March 202417 March 2024DirectUnited AirlinesRT from 195
16 March 202419 March 2024DirectJetBlue AirwaysRT from 177
17 March 202420 March 2024DirectJetBlue AirwaysRT from 247
18 March 202419 March 2024DirectJetBlue AirwaysRT from 172
19 March 202420 March 2024DirectJetBlue AirwaysRT from 137
20 March 202420 March 2024DirectJetBlue AirwaysRT from 132
21 March 202426 March 2024DirectJetBlue AirwaysRT from 202
22 March 202426 March 2024DirectJetBlue AirwaysRT from 247
23 March 202426 March 2024DirectJetBlue AirwaysRT from 202
24 March 202425 March 20241 StopJetBlue AirwaysRT from 292
25 March 202426 March 2024DirectJetBlue AirwaysRT from 202
26 March 202427 March 2024DirectDelta Air LinesRT from 177
27 March 20247 April 20241 StopJetBlue AirwaysRT from 226
28 March 20244 April 20241 StopJetBlue AirwaysRT from 241
29 March 20242 April 20241 StopJetBlue AirwaysRT from 222
30 March 20242 April 20241 StopJetBlue AirwaysRT from 202
31 March 20247 April 20241 StopJetBlue AirwaysRT from 307
1 April 20247 April 20241 StopJetBlue AirwaysRT from 256
2 April 20244 April 20241 StopJetBlue AirwaysRT from 232
3 April 20247 April 20241 StopJetBlue AirwaysRT from 226
4 April 20247 April 20241 StopJetBlue AirwaysRT from 226
5 April 20247 April 20241 StopJetBlue AirwaysRT from 231
6 April 202411 April 20241 StopUnited AirlinesRT from 353
7 April 20249 April 20241 StopJetBlue AirwaysRT from 307
8 April 202412 April 20241 StopJetBlue AirwaysRT from 312
9 April 202414 April 20241 StopJetBlue AirwaysRT from 273
10 April 202417 April 20241 StopAmerican AirlinesRT from 188
11 April 202417 April 20241 StopUnited AirlinesRT from 266
12 April 202417 April 20241 StopJetBlue AirwaysRT from 241
13 April 202419 April 20241 StopJetBlue AirwaysRT from 281
14 April 202417 April 20241 StopJetBlue AirwaysRT from 291
15 April 202422 April 2024DirectUnited AirlinesRT from 247
16 April 202419 April 20241 StopDelta Air LinesRT from 267
17 April 202421 April 20241 StopJetBlue AirwaysRT from 226
18 April 202421 April 20241 StopJetBlue AirwaysRT from 246
19 April 202421 April 20241 StopJetBlue AirwaysRT from 292
20 April 202423 April 20241 StopJetBlue AirwaysRT from 292
21 April 202430 April 20241 StopUnited AirlinesRT from 550
22 April 202425 April 20241 StopJetBlue AirwaysRT from 316
23 April 202430 April 2024DirectDelta Air LinesRT from 177
24 April 202427 April 20241 StopJetBlue AirwaysRT from 236
25 April 20242 May 2024DirectDelta Air LinesRT from 200
26 April 202429 April 20241 StopJetBlue AirwaysRT from 252
27 April 202430 April 2024DirectDelta Air LinesRT from 177
30 April 20247 May 2024DirectUnited AirlinesRT from 247
1 May 20244 May 2024DirectDelta Air LinesRT from 177
2 May 20245 May 2024DirectDelta Air LinesRT from 177
3 May 20244 May 20241 StopJetBlue AirwaysRT from 217
4 May 202411 May 2024DirectJetBlue AirwaysRT from 212
5 May 20249 May 20241 StopJetBlue AirwaysRT from 241
6 May 202412 May 20241 StopJetBlue AirwaysRT from 222
7 May 202411 May 2024DirectDelta Air LinesRT from 177
9 May 202412 May 2024DirectJetBlue AirwaysRT from 217
10 May 202415 May 2024DirectJetBlue AirwaysRT from 227
11 May 202413 May 20241 StopJetBlue AirwaysRT from 227
12 May 202418 May 20241 StopJetBlue AirwaysRT from 246
13 May 202416 May 20241 StopJetBlue AirwaysRT from 231
14 May 202420 May 20241 StopJetBlue AirwaysRT from 222
15 May 202425 May 20241 StopJetBlue AirwaysRT from 227
16 May 202420 May 20241 StopJetBlue AirwaysRT from 236
17 May 202420 May 20241 StopJetBlue AirwaysRT from 236
18 May 202425 May 20241 StopJetBlue AirwaysRT from 222
20 May 202425 May 20241 StopJetBlue AirwaysRT from 222
21 May 202426 May 20241 StopJetBlue AirwaysRT from 222
22 May 202425 May 20241 StopJetBlue AirwaysRT from 222
23 May 202426 May 20241 StopJetBlue AirwaysRT from 232
24 May 202426 May 20241 StopJetBlue AirwaysRT from 232
25 May 202429 May 20241 StopJetBlue AirwaysRT from 241
26 May 202428 May 2024DirectUnited AirlinesRT from 247
27 May 20242 June 20241 StopJetBlue AirwaysRT from 282
28 May 20242 June 20241 StopJetBlue AirwaysRT from 262
29 May 20241 June 20241 StopJetBlue AirwaysRT from 226
30 May 20244 June 20241 StopJetBlue AirwaysRT from 222
31 May 20244 June 20241 StopJetBlue AirwaysRT from 231
1 June 20244 June 20241 StopJetBlue AirwaysRT from 231
2 June 202412 June 20241 StopJetBlue AirwaysRT from 261
3 June 202415 June 20241 StopJetBlue AirwaysRT from 232
4 June 20249 June 20241 StopJetBlue AirwaysRT from 241
5 June 20248 June 20241 StopJetBlue AirwaysRT from 241
6 June 202410 June 20241 StopJetBlue AirwaysRT from 256
7 June 202411 June 20241 StopJetBlue AirwaysRT from 237
8 June 202412 June 2024DirectUnited AirlinesRT from 247
9 June 202415 June 20241 StopJetBlue AirwaysRT from 262
10 June 202415 June 20241 StopJetBlue AirwaysRT from 247
11 June 202413 June 20241 StopJetBlue AirwaysRT from 237
12 June 202419 June 20241 StopJetBlue AirwaysRT from 262
13 June 202416 June 2024DirectJetBlue AirwaysRT from 287
14 June 202419 June 20241 StopJetBlue AirwaysRT from 277
15 June 202413 July 2024DirectDelta Air LinesRT from 272
16 June 202423 June 20241 StopJetBlue AirwaysRT from 317
17 June 202427 June 20241 StopJetBlue AirwaysRT from 262
18 June 202421 June 2024DirectJetBlue AirwaysRT from 297
19 June 202424 June 20241 StopDelta Air LinesRT from 240
20 June 202425 June 2024DirectJetBlue AirwaysRT from 287
21 June 202430 June 20241 StopJetBlue AirwaysRT from 262
22 June 202430 June 20241 StopJetBlue AirwaysRT from 262
23 June 202426 June 20241 StopJetBlue AirwaysRT from 277
24 June 202429 June 2024DirectUnited AirlinesRT from 492
25 June 202430 June 2024DirectJetBlue AirwaysRT from 227
26 June 20242 July 20241 StopDelta Air LinesRT from 272
27 June 202430 June 2024DirectJetBlue AirwaysRT from 252
28 June 202430 June 20241 StopJetBlue AirwaysRT from 262
29 June 20246 July 2024DirectJetBlue AirwaysRT from 307
30 June 20246 July 20241 StopJetBlue AirwaysRT from 317
1 July 202411 July 20241 StopJetBlue AirwaysRT from 262
2 July 202423 July 20241 StopUnited AirlinesRT from 257
3 July 20247 July 20241 StopJetBlue AirwaysRT from 282
4 July 202411 July 2024DirectJetBlue AirwaysRT from 252
5 July 202412 July 20241 StopJetBlue AirwaysRT from 322
6 July 20248 July 20241 StopJetBlue AirwaysRT from 337
7 July 202414 July 20241 StopJetBlue AirwaysRT from 317
8 July 202422 July 20241 StopJetBlue AirwaysRT from 337
10 July 202416 July 2024DirectUnited AirlinesRT from 247
11 July 202414 July 2024DirectJetBlue AirwaysRT from 287
12 July 202414 July 20241 StopJetBlue AirwaysRT from 297
13 July 202417 July 2024DirectUnited AirlinesRT from 247
14 July 202420 July 20241 StopJetBlue AirwaysRT from 317
15 July 202420 July 20241 StopJetBlue AirwaysRT from 297
16 July 202419 July 2024DirectJetBlue AirwaysRT from 297
17 July 202420 July 20241 StopJetBlue AirwaysRT from 282
18 July 202421 July 2024DirectJetBlue AirwaysRT from 287
19 July 202424 July 20241 StopJetBlue AirwaysRT from 277
20 July 202424 July 2024DirectUnited AirlinesRT from 277
21 July 202428 July 20241 StopJetBlue AirwaysRT from 317
22 July 202431 July 2024DirectUnited AirlinesRT from 277
23 July 202430 July 2024DirectDelta Air LinesRT from 197
24 July 202430 July 2024DirectUnited AirlinesRT from 247
25 July 202428 July 20241 StopSun Country AirlinesRT from 296
26 July 202430 July 2024DirectUnited AirlinesRT from 277
27 July 20243 August 20241 StopJetBlue AirwaysRT from 297
28 July 20244 August 20241 StopJetBlue AirwaysRT from 297
30 July 20246 August 2024DirectUnited AirlinesRT from 247
31 July 20247 August 2024DirectDelta Air LinesRT from 202
1 August 20244 August 20241 StopJetBlue AirwaysRT from 277
2 August 20244 August 20241 StopJetBlue AirwaysRT from 277
4 August 202411 August 2024DirectUnited AirlinesRT from 549
6 August 202413 August 2024DirectDelta Air LinesRT from 187
7 August 202414 August 2024DirectUnited AirlinesRT from 247
8 August 202414 August 20241 StopJetBlue AirwaysRT from 262
9 August 202411 August 2024DirectDelta Air LinesRT from 257
11 August 202415 August 20241 StopJetBlue AirwaysRT from 282
12 August 202415 August 2024DirectUnited AirlinesRT from 277
13 August 202419 August 2024DirectJetBlue AirwaysRT from 272
15 August 202418 August 20241 StopJetBlue AirwaysRT from 297
16 August 202420 August 2024DirectUnited AirlinesRT from 247
18 August 202424 August 20241 StopJetBlue AirwaysRT from 262
20 August 20241 September 2024DirectUnited AirlinesRT from 247
21 August 20241 September 20241 StopUnited AirlinesRT from 257
22 August 202425 August 20241 StopJetBlue AirwaysRT from 262
23 August 202428 August 20241 StopJetBlue AirwaysRT from 252
24 August 202425 August 20241 StopJetBlue AirwaysRT from 262
25 August 20248 September 20241 StopJetBlue AirwaysRT from 262
26 August 20248 September 2024DirectDelta Air LinesRT from 177
27 August 20245 September 2024DirectDelta Air LinesRT from 187
28 August 20245 September 2024DirectUnited AirlinesRT from 247
29 August 20242 September 20241 StopSun Country AirlinesRT from 296
30 August 20242 September 2024DirectUnited AirlinesRT from 406
31 August 20247 September 2024DirectUnited AirlinesRT from 247
1 September 20248 September 20241 StopJetBlue AirwaysRT from 262
4 September 20247 September 2024DirectUnited AirlinesRT from 247
5 September 20248 September 2024DirectJetBlue AirwaysRT from 237
6 September 202410 September 20241 StopJetBlue AirwaysRT from 236
11 September 202416 September 20241 StopJetBlue AirwaysRT from 236
12 September 202415 September 20241 StopJetBlue AirwaysRT from 237
13 September 202416 September 20241 StopJetBlue AirwaysRT from 236
14 September 202421 September 2024DirectUnited AirlinesRT from 277
15 September 202421 September 20241 StopJetBlue AirwaysRT from 246
17 September 202417 September 20241 StopJetBlue AirwaysRT from 221
18 September 202430 September 20241 StopDelta Air LinesRT from 247
19 September 202423 September 20241 StopJetBlue AirwaysRT from 237
20 September 202420 September 20241 StopJetBlue AirwaysRT from 231
22 September 202426 September 20241 StopJetBlue AirwaysRT from 246
23 September 202425 September 2024DirectUnited AirlinesRT from 277
24 September 20241 October 2024DirectJetBlue AirwaysRT from 227
25 September 20244 October 2024DirectUnited AirlinesRT from 341
26 September 202430 September 2024DirectUnited AirlinesRT from 388
27 September 202429 September 20241 StopJetBlue AirwaysRT from 236
28 September 202428 September 20241 StopJetBlue AirwaysRT from 231
29 September 202411 October 20241 StopJetBlue AirwaysRT from 256
30 September 202411 October 20241 StopJetBlue AirwaysRT from 246
1 October 20245 October 20241 StopJetBlue AirwaysRT from 237
2 October 20249 October 20241 StopUnited AirlinesRT from 266
3 October 20248 October 20241 StopUnited AirlinesRT from 323
4 October 20247 October 20241 StopJetBlue AirwaysRT from 236
5 October 20248 October 20241 StopJetBlue AirwaysRT from 236
6 October 202412 October 20241 StopJetBlue AirwaysRT from 246
7 October 202411 October 20241 StopJetBlue AirwaysRT from 246
9 October 202414 October 20241 StopJetBlue AirwaysRT from 236
10 October 202414 October 20241 StopJetBlue AirwaysRT from 246
11 October 202415 October 20241 StopDelta Air LinesRT from 235
12 October 202419 October 20241 StopJetBlue AirwaysRT from 236
13 October 202418 October 20241 StopJetBlue AirwaysRT from 271
14 October 202422 October 2024DirectJetBlue AirwaysRT from 227
15 October 202418 October 20241 StopUnited AirlinesRT from 445
16 October 202419 October 20241 StopUnited AirlinesRT from 381
17 October 202420 October 20241 StopJetBlue AirwaysRT from 277
18 October 202421 October 20241 StopUnited AirlinesRT from 429
19 October 202422 October 20241 StopUnited AirlinesRT from 266

The Cheapest Flights from Chicago to Boston for the Year Ahead

Departure atReturn atStopsAirlineFind tickets
29 November 20236 December 20231 StopFrontier AirlinesRT from 113
1 December 20236 December 20231 StopFrontier AirlinesRT from 117
4 January 20246 January 2024DirectSouthwest AirlinesRT from 92
19 February 202423 February 2024DirectUnited AirlinesRT from 178
15 March 202417 March 2024DirectUnited AirlinesRT from 195
10 April 202417 April 20241 StopAmerican AirlinesRT from 188
2 May 20245 May 2024DirectDelta Air LinesRT from 177
25 June 202430 June 2024DirectJetBlue AirwaysRT from 227
23 July 202430 July 2024DirectDelta Air LinesRT from 197
26 August 20248 September 2024DirectDelta Air LinesRT from 177
17 September 202417 September 20241 StopJetBlue AirwaysRT from 221
14 October 202422 October 2024DirectJetBlue AirwaysRT from 227
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