Book United Boston to Chicago flight deals from $161

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Search flights from Boston to Chicago (BOS - ORD)

July

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Thursday 5th

Return Friday 20th
from$ 161*Viewed: 1 hour ago

Wednesday 18th

Return Thursday 2nd
from$ 171*Viewed: 1 hour ago

Monday 23rd

Return Tuesday 7th
from$ 171*Viewed: 1 hour ago

August

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Wednesday 22nd

Return Thursday 6th
from$ 171*Viewed: 1 hour ago

Tuesday 28th

Return Wednesday 12th
from$ 171*Viewed: 1 hour ago

Wednesday 29th

Return Thursday 13th
from$ 171*Viewed: 1 hour ago

September

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Tuesday 11th

Return Wednesday 26th
from$ 171*Viewed: 1 hour ago

Wednesday 12th

Return Thursday 27th
from$ 171*Viewed: 1 hour ago

Tuesday 18th

Return Wednesday 3rd
from$ 171*Viewed: 1 hour ago
**Prices have been available for round trips within the last 48 hours and may not be currently available. 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..
Cruise ships and tour boats docked by a ferris wheel and urban buildings at Navy Pier in Chicago

Plan ahead for flights from Boston to Chicago

from
to
Type
Dates
Price*
Boston (BOS)
to Chicago (ORD)
Roundtrip
Depart Thu 5 Jul 2018
Return Fri 20 Jul 2018
from$ 161*Viewed: 1 hour ago
Boston (BOS)
to Chicago (ORD)
Roundtrip
Depart Wed 18 Jul 2018
Return Thu 2 Aug 2018
from$ 171*Viewed: 1 hour ago
Boston (BOS)
to Chicago (ORD)
Roundtrip
Depart Mon 23 Jul 2018
Return Tue 7 Aug 2018
from$ 171*Viewed: 1 hour ago
Boston (BOS)
to Chicago (ORD)
Roundtrip
Depart Mon 13 Aug 2018
Return Tue 28 Aug 2018
from$ 171*Viewed: 1 hour ago
Boston (BOS)
to Chicago (ORD)
Roundtrip
Depart Tue 21 Aug 2018
Return Wed 5 Sep 2018
from$ 171*Viewed: 1 hour ago
Boston (BOS)
to Chicago (ORD)
Roundtrip
Depart Wed 22 Aug 2018
Return Thu 6 Sep 2018
from$ 171*Viewed: 1 hour ago
Boston (BOS)
to Chicago (ORD)
Roundtrip
Depart Tue 28 Aug 2018
Return Wed 12 Sep 2018
from$ 171*Viewed: 1 hour ago
Boston (BOS)
to Chicago (ORD)
Roundtrip
Depart Wed 29 Aug 2018
Return Thu 13 Sep 2018
from$ 171*Viewed: 1 hour ago
Boston (BOS)
to Chicago (ORD)
Roundtrip
Depart Tue 4 Sep 2018
Return Wed 19 Sep 2018
from$ 171*Viewed: 1 hour ago
Boston (BOS)
to Chicago (ORD)
Roundtrip
Depart Wed 5 Sep 2018
Return Thu 20 Sep 2018
from$ 171*Viewed: 1 hour ago
*Prices have been available for round trips within the last 48 hours and may not be currently available. 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.

Weather in Chicago

75 °FSunday06/24/2018
64 °FMonday06/25/2018
70 °FTuesday06/26/2018
85 °FWednesday06/27/2018
87 °FThursday06/28/2018
90 °FFriday06/29/2018
86 °FSaturday06/30/2018
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