Cheap Flights from CHI to BOS

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The Cheapest Round-trip Tickets from Chicago to Boston

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19 August 202225 August 2022DirectRT from 116
26 August 202230 August 20221 StopRT from 130

The Cheapest Flights for this Month from Chicago to Boston

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13 August 202220 August 2022DirectRT from 151
14 August 202220 August 20221 StopRT from 179
15 August 202231 August 2022DirectRT from 166
17 August 202224 August 2022DirectRT from 116
19 August 202225 August 2022DirectRT from 116
20 August 202222 August 20221 StopRT from 144
21 August 202222 August 20221 StopRT from 221
22 August 202225 August 2022DirectRT from 135
24 August 202226 August 20221 StopRT from 144
25 August 202227 August 20221 StopRT from 150
26 August 202230 August 20221 StopRT from 130
31 August 20224 September 20221 StopRT from 138
1 September 20224 September 20221 StopRT from 145
2 September 20224 September 20221 StopRT from 144
16 September 202219 September 20221 StopRT from 159
21 September 202230 September 20221 StopRT from 166
29 September 20223 October 20221 StopRT from 162
6 October 20229 October 20221 StopRT from 176
11 October 202214 October 20221 StopRT from 158
14 October 202217 October 20221 StopRT from 156
21 October 202223 October 20221 StopRT from 173
27 October 202231 October 2022DirectRT from 154
28 October 202231 October 2022DirectRT from 146
11 November 202214 November 2022DirectRT from 139
15 November 202217 November 2022DirectRT from 150
18 November 202227 November 20221 StopRT from 276
19 November 202220 November 20221 StopRT from 237

The Cheapest Flights from Chicago to Boston for the Year Ahead

Departure atReturn atStopsAirlineFind tickets
19 August 202225 August 2022DirectRT from 116
2 September 20224 September 20221 StopRT from 144
28 October 202231 October 2022DirectRT from 146
11 November 202214 November 2022DirectRT from 139
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