Book United Boston to Chicago flight deals from $89

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Search flights from Boston to Chicago (BOS - ORD)

September

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Sunday 2nd

Return Monday 17th
from$ 89*Viewed: 57 minutes ago

Monday 3rd

Return Tuesday 18th
from$ 89*Viewed: 57 minutes ago

Monday 10th

Return Tuesday 25th
from$ 89*Viewed: 57 minutes ago

October

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Tuesday 9th

Return Wednesday 24th
from$ 151*Viewed: 57 minutes ago

Friday 12th

Return Saturday 27th
from$ 151*Viewed: 57 minutes ago

Tuesday 16th

Return Wednesday 31st
from$ 151*Viewed: 57 minutes ago

November

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Wednesday 7th

Return Thursday 22nd
from$ 151*Viewed: 56 minutes ago

Tuesday 13th

Return Wednesday 28th
from$ 137*Viewed: 56 minutes ago

Friday 16th

Return Saturday 1st
from$ 175*Viewed: 56 minutes 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 Sun 2 Sep 2018
Return Mon 17 Sep 2018
from$ 89*Viewed: 57 minutes ago
Boston (BOS)
to Chicago (ORD)
Roundtrip
Depart Mon 3 Sep 2018
Return Tue 18 Sep 2018
from$ 89*Viewed: 57 minutes ago
Boston (BOS)
to Chicago (ORD)
Roundtrip
Depart Mon 10 Sep 2018
Return Tue 25 Sep 2018
from$ 89*Viewed: 57 minutes ago
Boston (BOS)
to Chicago (ORD)
Roundtrip
Depart Tue 11 Sep 2018
Return Wed 26 Sep 2018
from$ 89*Viewed: 57 minutes ago
Boston (BOS)
to Chicago (ORD)
Roundtrip
Depart Sat 8 Sep 2018
Return Sun 23 Sep 2018
from$ 122*Viewed: 57 minutes ago
Boston (BOS)
to Chicago (ORD)
Roundtrip
Depart Sat 15 Sep 2018
Return Sun 30 Sep 2018
from$ 122*Viewed: 57 minutes ago
Boston (BOS)
to Chicago (ORD)
Roundtrip
Depart Mon 17 Sep 2018
Return Tue 2 Oct 2018
from$ 122*Viewed: 57 minutes ago
Boston (BOS)
to Chicago (ORD)
Roundtrip
Depart Tue 18 Sep 2018
Return Wed 3 Oct 2018
from$ 122*Viewed: 57 minutes ago
Boston (BOS)
to Chicago (ORD)
Roundtrip
Depart Tue 13 Nov 2018
Return Wed 28 Nov 2018
from$ 137*Viewed: 56 minutes ago
Boston (BOS)
to Chicago (ORD)
Roundtrip
Depart Thu 6 Dec 2018
Return Wed 12 Dec 2018
from$ 137*Viewed: 4 days 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

71 °FTuesday08/21/2018
71 °FWednesday08/22/2018
75 °FThursday08/23/2018
67 °FFriday08/24/2018
81 °FSaturday08/25/2018
84 °FSunday08/26/2018
74 °FMonday08/27/2018
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