Book United Chicago to Boston flight deals from $89

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Search flights from Chicago to Boston (ORD - BOS)

October

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Wednesday 10th

Return Thursday 25th
from$ 89*Viewed: 2 hours ago

Saturday 20th

Return Tuesday 23rd
from$ 89*Viewed: 21 minutes ago

Tuesday 23rd

Return Wednesday 7th
from$ 89*Viewed: 2 hours ago

November

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Saturday 3rd

Return Sunday 18th
from$ 151*Viewed: 2 hours ago

Sunday 4th

Return Monday 19th
from$ 151*Viewed: 2 hours ago

Wednesday 7th

Return Thursday 22nd
from$ 151*Viewed: 2 hours ago

December

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Saturday 1st

Return Sunday 16th
from$ 175*Viewed: 2 hours ago

Tuesday 4th

Return Wednesday 19th
from$ 175*Viewed: 2 hours ago

Wednesday 12th

Return Thursday 27th
from$ 175*Viewed: 2 hours 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..
Downtown Boston viewed from the harbor

Plan ahead for flights from Chicago to Boston

from
to
Type
Dates
Price*
Chicago (ORD)
to Boston (BOS)
Roundtrip
Depart Wed 10 Oct 2018
Return Thu 25 Oct 2018
from$ 89*Viewed: 2 hours ago
Chicago (ORD)
to Boston (BOS)
Roundtrip
Depart Tue 23 Oct 2018
Return Wed 7 Nov 2018
from$ 89*Viewed: 2 hours ago
Chicago (ORD)
to Boston (BOS)
Roundtrip
Depart Sat 20 Oct 2018
Return Tue 23 Oct 2018
from$ 89*Viewed: 21 minutes ago
Chicago (ORD)
to Boston (BOS)
Roundtrip
Depart Tue 30 Oct 2018
Return Wed 14 Nov 2018
from$ 113*Viewed: 2 hours ago
Chicago (ORD)
to Boston (BOS)
Roundtrip
Depart Tue 16 Oct 2018
Return Tue 23 Oct 2018
from$ 113*Viewed: 1 hour ago
Chicago (ORD)
to Boston (BOS)
Roundtrip
Depart Sun 7 Oct 2018
Return Mon 22 Oct 2018
from$ 122*Viewed: 2 hours ago
Chicago (ORD)
to Boston (BOS)
Roundtrip
Depart Wed 3 Oct 2018
Return Thu 18 Oct 2018
from$ 151*Viewed: 2 hours ago
Chicago (ORD)
to Boston (BOS)
Roundtrip
Depart Sat 13 Oct 2018
Return Sun 28 Oct 2018
from$ 151*Viewed: 2 hours ago
Chicago (ORD)
to Boston (BOS)
Roundtrip
Depart Sat 27 Oct 2018
Return Sun 11 Nov 2018
from$ 151*Viewed: 2 hours ago
Chicago (ORD)
to Boston (BOS)
Roundtrip
Depart Sun 28 Oct 2018
Return Mon 12 Nov 2018
from$ 151*Viewed: 2 hours 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.