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Business Class Flight Deals from Massachusetts to Chicago from $413

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Top Deals on Business Class Flights from Boston to Chicago

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

American Airlines Logo
American Airlines

May 30

BOS
6h 30m
IND

May 30

ORD
American Airlines Logo
American Airlines

Jun 6

ORD
2h 40m
Direct

Jun 7

BOS

as low as

$413

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

American Airlines Logo
American Airlines

May 30

BOS
6h 30m
IND

May 30

ORD
American Airlines Logo
American Airlines

Jun 6

ORD
2h 23m
Direct

Jun 6

BOS

as low as

$431

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

American Airlines Logo
American Airlines

May 30

BOS
5h 41m
CLT

May 30

ORD
American Airlines Logo
American Airlines

Jun 6

ORD
2h 40m
Direct

Jun 7

BOS

as low as

$436

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

American Airlines Logo
American Airlines

May 30

BOS
6h 13m
PHL

May 30

ORD
American Airlines Logo
American Airlines

Jun 6

ORD
2h 40m
Direct

Jun 7

BOS

as low as

$436

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

American Airlines Logo
American Airlines

May 30

BOS
5h 41m
CLT

May 30

ORD
American Airlines Logo
American Airlines

Jun 6

ORD
2h 23m
Direct

Jun 6

BOS

as low as

$453

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

American Airlines Logo
American Airlines

May 30

BOS
6h 30m
IND

May 30

ORD
American Airlines Logo
American Airlines

Jun 6

ORD
2h 26m
Direct

Jun 6

BOS

as low as

$453

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

American Airlines Logo
American Airlines

May 30

BOS
6h 13m
PHL

May 30

ORD
American Airlines Logo
American Airlines

Jun 6

ORD
2h 23m
Direct

Jun 6

BOS

as low as

$453

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

American Airlines Logo
American Airlines

May 30

BOS
3h
Direct

May 30

ORD
American Airlines Logo
American Airlines

Jun 6

ORD
2h 40m
Direct

Jun 7

BOS

as low as

$463

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

American Airlines Logo
American Airlines

May 30

BOS
5h 14m
PHL

May 30

ORD
American Airlines Logo
American Airlines

Jun 6

ORD
2h 40m
Direct

Jun 7

BOS

as low as

$471

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

American Airlines Logo
American Airlines

May 30

BOS
5h 41m
CLT

May 30

ORD
American Airlines Logo
American Airlines

Jun 6

ORD
2h 26m
Direct

Jun 6

BOS

as low as

$476

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

American Airlines Logo
American Airlines

May 30

BOS
3h
Direct

May 30

ORD
American Airlines Logo
American Airlines

Jun 6

ORD
2h 23m
Direct

Jun 6

BOS

as low as

$480

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

American Airlines Logo
American Airlines

May 30

BOS
3h
Direct

May 30

ORD
American Airlines Logo
American Airlines

Jun 6

ORD
2h 26m
Direct

Jun 6

BOS

as low as

$503

Top Deals on Business Class Flights from Worcester to Chicago

Worcester, US (ORH) - Chicago, US (CHI)

American Airlines Logo
American Airlines

May 30

ORH
4h 48m
JFK

May 30

ORD
American Airlines Logo
American Airlines

Jun 6

ORD
15h 7m
PIT
JFK

Jun 7

ORH

as low as

$648

Worcester, US (ORH) - Chicago, US (CHI)

American Airlines Logo
American Airlines

May 30

ORH
4h 48m
JFK

May 30

ORD
American Airlines Logo
American Airlines

Jun 6

ORD
14h 59m
RDU
JFK

Jun 7

ORH

as low as

$716

Worcester, US (ORH) - Chicago, US (CHI)

American Airlines Logo
American Airlines

May 30

ORH
4h 48m
JFK

May 30

ORD
American Airlines Logo
American Airlines

Jun 6

ORD
16h 57m
RDU
JFK

Jun 7

ORH

as low as

$716

Worcester, US (ORH) - Chicago, US (CHI)

American Airlines Logo
American Airlines

May 30

ORH
4h 48m
JFK

May 30

ORD
American Airlines Logo
American Airlines

Jun 6

ORD
28h 47m
CLT
JFK

Jun 7

ORH

as low as

$768

Worcester, US (ORH) - Chicago, US (CHI)

American Airlines Logo
American Airlines

May 30

ORH
4h 48m
JFK

May 30

ORD
American Airlines Logo
American Airlines

Jun 6

ORD
30h 23m
CLT
JFK

Jun 7

ORH

as low as

$768

Worcester, US (ORH) - Chicago, US (CHI)

American Airlines Logo
American Airlines

May 30

ORH
4h 48m
JFK

May 30

ORD
American Airlines Logo
American Airlines

Jun 6

ORD
15h 2m
CLT
JFK

Jun 7

ORH

as low as

$840

Worcester, US (ORH) - Chicago, US (CHI)

American Airlines Logo
American Airlines

May 30

ORH
4h 48m
JFK

May 30

ORD
American Airlines Logo
American Airlines

Jun 6

ORD
17h 27m
CLT
JFK

Jun 7

ORH

as low as

$840

Worcester, US (ORH) - Chicago, US (CHI)

American Airlines Logo
American Airlines

May 30

ORH
4h 48m
JFK

May 30

ORD
American Airlines Logo
American Airlines

Jun 6

ORD
27h 17m
CLT
JFK

Jun 7

ORH

as low as

$855

Worcester, US (ORH) - Chicago, US (CHI)

American Airlines Logo
American Airlines

May 30

ORH
4h 48m
JFK

May 30

ORD
American Airlines Logo
American Airlines

Jun 6

ORD
15h 12m
BOS
JFK

Jun 7

ORH

as low as

$1018

Worcester, US (ORH) - Chicago, US (CHI)

American Airlines Logo
American Airlines

May 30

ORH
4h 48m
JFK

May 30

ORD
American Airlines Logo
American Airlines

Jun 6

ORD
18h 53m
JFK

Jun 7

ORH

as low as

$1038

Worcester, US (ORH) - Chicago, US (CHI)

American Airlines Logo
American Airlines

May 30

ORH
4h 48m
JFK

May 30

ORD
American Airlines Logo
American Airlines

Jun 6

ORD
25h 49m
JFK

Jun 7

ORH

as low as

$1141