United flights from Boston to Chicago from $ 99* or from $/mo
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today
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More United deals on Boston (BOS) to Chicago (ORD) flights
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From | To | Fare Type | Dates | Price |
|---|---|---|---|---|
| Boston (BOS) | Chicago (ORD) | Roundtrip | Economy | 08/16/25 - 08/20/25 | from $ 99 Viewed: 22 hours ago |
| Boston (BOS) | Chicago (ORD) | Roundtrip | Economy | 09/22/25 - 09/25/25 | from $ 99 Viewed: 17 hours ago |
| Boston (BOS) | Chicago (ORD) | Roundtrip | Economy | 09/04/25 - 09/07/25 | from $ 108 Viewed: 20 hours ago |
| Boston (BOS) | Chicago (ORD) | Roundtrip | Economy | 09/19/25 - 09/21/25 | from $ 112 Viewed: 23 hours ago |
| Boston (BOS) | Chicago (ORD) | Roundtrip | Economy | 08/22/25 - 08/24/25 | from $ 112 Viewed: 20 hours ago |
| Boston (BOS) | Chicago (ORD) | Roundtrip | Economy | 10/31/25 - 11/03/25 | from $ 117 Viewed: 10 hours ago |
| Boston (BOS) | Chicago (ORD) | Roundtrip | Economy | 09/25/25 - 09/28/25 | from $ 117 Viewed: 6 hours ago |
| Boston (BOS) | Chicago (ORD) | Roundtrip | Economy | 08/14/25 - 08/18/25 | from $ 117 Viewed: 4 hours ago |
| Boston (BOS) | Chicago (ORD) | Roundtrip | Economy | 07/11/25 - 08/06/25 | from $ 117 Viewed: 40 minutes ago |
| Boston (BOS) | Chicago (ORD) | Roundtrip | Economy | 06/13/25 - 06/15/25 | from $ 117 Viewed: 5 hours ago |
*Prices have been available for round trips within the last 48 hours and may not be currently available. For Economy class, fares listed may be Basic Economy, which is our most restrictive fare option and subject to additional restrictions. Additional baggage charges and fees for other optional service may apply. Other terms and conditions may apply.
