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Business Class Flight Deals from Chicago to Massachusetts from $454

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Top Deals on Business Class Flights from Chicago to Boston

Chicago, US (CHI) - Boston, US (BOS)

American Airlines Logo
American Airlines

May 29

ORD
4h 54m
IND

May 29

BOS
American Airlines Logo
American Airlines

Jun 5

BOS
2h 54m
Direct

Jun 5

ORD

as low as

$454

Chicago, US (CHI) - Boston, US (BOS)

American Airlines Logo
American Airlines

May 29

ORD
4h 11m
PHL

May 29

BOS
American Airlines Logo
American Airlines

Jun 5

BOS
2h 54m
Direct

Jun 5

ORD

as low as

$477

Chicago, US (CHI) - Boston, US (BOS)

American Airlines Logo
American Airlines

May 29

ORD
2h 24m
Direct

May 29

BOS
American Airlines Logo
American Airlines

Jun 5

BOS
2h 54m
Direct

Jun 5

ORD

as low as

$501

Chicago, US (CHI) - Boston, US (BOS)

American Airlines Logo
American Airlines

May 29

ORD
2h 22m
Direct

May 29

BOS
American Airlines Logo
American Airlines

Jun 5

BOS
2h 54m
Direct

Jun 5

ORD

as low as

$547

Chicago, US (CHI) - Boston, US (BOS)

American Airlines Logo
American Airlines

May 29

ORD
2h 26m
Direct

May 29

BOS
American Airlines Logo
American Airlines

Jun 5

BOS
2h 54m
Direct

Jun 5

ORD

as low as

$547

Chicago, US (CHI) - Boston, US (BOS)

American Airlines Logo
American Airlines

May 29

ORD
2h 24m
Direct

May 29

BOS
American Airlines Logo
American Airlines

Jun 5

BOS
3h 5m
Direct

Jun 5

ORD

as low as

$556

Chicago, US (CHI) - Boston, US (BOS)

American Airlines Logo
American Airlines

May 29

ORD
2h 35m
Direct

May 29

BOS
American Airlines Logo
American Airlines

Jun 5

BOS
2h 54m
Direct

Jun 5

ORD

as low as

$593

Chicago, US (CHI) - Boston, US (BOS)

American Airlines Logo
American Airlines

May 29

ORD
2h 22m
Direct

May 29

BOS
American Airlines Logo
American Airlines

Jun 5

BOS
3h 5m
Direct

Jun 5

ORD

as low as

$602

Chicago, US (CHI) - Boston, US (BOS)

American Airlines Logo
American Airlines

May 29

ORD
2h 24m
Direct

May 29

BOS
American Airlines Logo
American Airlines

Jun 5

BOS
2h 56m
Direct

Jun 5

ORD

as low as

$602

Chicago, US (CHI) - Boston, US (BOS)

American Airlines Logo
American Airlines

May 29

ORD
2h 24m
Direct

May 29

BOS
American Airlines Logo
American Airlines

Jun 5

BOS
2h 55m
Direct

Jun 5

ORD

as low as

$602

Chicago, US (CHI) - Boston, US (BOS)

American Airlines Logo
American Airlines

May 29

ORD
2h 24m
Direct

May 29

BOS
American Airlines Logo
American Airlines

Jun 5

BOS
3h 1m
Direct

Jun 5

ORD

as low as

$602

Chicago, US (CHI) - Boston, US (BOS)

American Airlines Logo
American Airlines

May 29

ORD
2h 26m
Direct

May 29

BOS
American Airlines Logo
American Airlines

Jun 5

BOS
3h 5m
Direct

Jun 5

ORD

as low as

$602