United flights from Boston to Chicago from $ 99* or from $/mo

More United deals on Boston (BOS) to Chicago (ORD) flights

$
More United deals on Boston (BOS) to Chicago (ORD) flights
From
To
Fare Type
Dates
Price
Boston (BOS)Chicago (ORD)Roundtrip
|
Economy
08/16/25 - 08/20/25

from

$ 99
or from $/mo

Viewed: 22 hours ago

Boston (BOS)Chicago (ORD)Roundtrip
|
Economy
09/22/25 - 09/25/25

from

$ 99
or from $/mo

Viewed: 17 hours ago

Boston (BOS)Chicago (ORD)Roundtrip
|
Economy
09/04/25 - 09/07/25

from

$ 108
or from $/mo

Viewed: 20 hours ago

Boston (BOS)Chicago (ORD)Roundtrip
|
Economy
09/19/25 - 09/21/25

from

$ 112
or from $/mo

Viewed: 23 hours ago

Boston (BOS)Chicago (ORD)Roundtrip
|
Economy
08/22/25 - 08/24/25

from

$ 112
or from $/mo

Viewed: 20 hours ago

Boston (BOS)Chicago (ORD)Roundtrip
|
Economy
10/31/25 - 11/03/25

from

$ 117
or from $/mo

Viewed: 10 hours ago

Boston (BOS)Chicago (ORD)Roundtrip
|
Economy
09/25/25 - 09/28/25

from

$ 117
or from $/mo

Viewed: 6 hours ago

Boston (BOS)Chicago (ORD)Roundtrip
|
Economy
08/14/25 - 08/18/25

from

$ 117
or from $/mo

Viewed: 4 hours ago

Boston (BOS)Chicago (ORD)Roundtrip
|
Economy
07/11/25 - 08/06/25

from

$ 117
or from $/mo

Viewed: 40 minutes ago

Boston (BOS)Chicago (ORD)Roundtrip
|
Economy
06/13/25 - 06/15/25

from

$ 117
or from $/mo

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.