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Flight Deals from Massachusetts to Chicago from $116

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Top Deals on flights from Boston to Chicago

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

Delta Air Lines Logo
Delta Air Lines

Aug 23

BOS
1h 53m
Direct

Aug 23

ORD
Delta Air Lines Logo
Delta Air Lines

Aug 26

ORD
3h 42m
Direct

Aug 26

BOS

as low as

$116

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

American Airlines Logo
American Airlines

Aug 13

BOS
1h 56m
Direct

Aug 13

ORD
American Airlines Logo
American Airlines

Aug 20

ORD
3h 21m
Direct

Aug 20

BOS

as low as

$116

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

JetBlue Logo
JetBlue

Aug 13

BOS
1h 55m
Direct

Aug 13

ORD
JetBlue Logo
JetBlue

Aug 20

ORD
3h 35m
Direct

Aug 20

BOS

as low as

$148

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

United Airlines Logo
United Airlines

Aug 13

BOS
1h 58m
Direct

Aug 13

ORD
United Airlines Logo
United Airlines

Aug 20

ORD
3h 31m
Direct

Aug 20

BOS

as low as

$182

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

American Airlines Logo
American Airlines

Aug 13

BOS
4h 40m
CLT

Aug 13

ORD
American Airlines Logo
American Airlines

Aug 20

ORD
3h 27m
Direct

Aug 20

BOS

as low as

$183

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

JetBlue Logo
JetBlue

Aug 13

BOS
1h 55m
Direct

Aug 13

ORD
JetBlue Logo
JetBlue

Aug 20

ORD
5h 51m
JFK

Aug 20

BOS

as low as

$193

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

Delta Air Lines Logo
Delta Air Lines

Aug 9

BOS
5h 51m
MSP

Aug 9

MDW
Delta Air Lines Logo
Delta Air Lines

Aug 12

MDW
3h 42m
Direct

Aug 12

BOS

as low as

$216

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

Delta Air Lines Logo
Delta Air Lines

Aug 8

BOS
1h 58m
Direct

Aug 8

ORD
Delta Air Lines Logo
Delta Air Lines

Aug 12

ORD
5h 27m
LGA

Aug 12

BOS

as low as

$216

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

Delta Air Lines Logo
Delta Air Lines

Aug 21

BOS
1h 59m
Direct

Aug 21

ORD
Delta Air Lines Logo
Delta Air Lines

Aug 25

ORD
5h 48m
DTW

Aug 25

BOS

as low as

$216

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

Spirit Airlines Logo
Spirit Airlines

Aug 13

BOS
8h 44m
FLL

Aug 13

ORD
Spirit Airlines Logo
Spirit Airlines

Aug 20

ORD
11h 34m
ATL

Aug 20

BOS

as low as

$216

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

Delta Air Lines Logo
Delta Air Lines

Aug 16

BOS
3h 15m
DTW

Aug 16

MDW
Delta Air Lines Logo
Delta Air Lines

Aug 20

MDW
3h 30m
Direct

Aug 20

BOS

as low as

$216

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

United Airlines Logo
United Airlines

Aug 5

BOS
4h 13m
IAD

Aug 5

ORD
United Airlines Logo
United Airlines

Aug 5

ORD
3h 37m
Direct

Aug 5

BOS

as low as

$221

Top Deals on flights from Worcester to Chicago

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

American Airlines Logo
American Airlines

May 14

ORH
3h 48m
JFK

May 14

ORD
American Airlines Logo
American Airlines

May 15

ORD
20h 32m
JFK

May 16

ORH

as low as

$191

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

Delta Air Lines Logo
Delta Air Lines

May 14

ORH
6h 31m
LGA

May 14

ORD
Delta Air Lines Logo
Delta Air Lines

May 15

ORD
8h 5m
LGA

May 15

ORH

as low as

$207

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

Delta Air Lines Logo
Delta Air Lines

May 14

ORH
7h 48m
LGA
ATL

May 14

ORD
Delta Air Lines Logo
Delta Air Lines

May 15

ORD
8h 5m
LGA

May 15

ORH

as low as

$221

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

American Airlines Logo
American Airlines

May 14

ORH
3h 48m
JFK

May 14

ORD
American Airlines Logo
American Airlines

May 15

ORD
22h 56m
RDU
JFK

May 16

ORH

as low as

$308

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

Delta Air Lines Logo
Delta Air Lines

May 14

ORH
7h 48m
LGA
ATL

May 14

ORD
Delta Air Lines Logo
Delta Air Lines

May 15

ORD
9h 35m
ATL
LGA

May 15

ORH

as low as

$357

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

American Airlines Logo
American Airlines

May 14

ORH
17h 39m
JFK
BNA

May 15

ORD
American Airlines Logo
American Airlines

May 15

ORD
22h 56m
RDU
JFK

May 16

ORH

as low as

$467

Top Deals on flights from West Tisbury to Chicago

West Tisbury, US (MVY) - Chicago, US (CHI)

JetBlue Logo
JetBlue

May 29

MVY
16h 5m
BOS

May 30

ORD
JetBlue Logo
JetBlue

Jun 5

ORD
5h 29m
BOS

Jun 5

MVY

as low as

$849

West Tisbury, US (MVY) - Chicago, US (CHI)

JetBlue Logo
JetBlue

May 29

MVY
16h 35m
BOS

May 30

ORD
JetBlue Logo
JetBlue

Jun 5

ORD
5h 29m
BOS

Jun 5

MVY

as low as

$849

West Tisbury, US (MVY) - Chicago, US (CHI)

JetBlue Logo
JetBlue

May 29

MVY
15h 40m
BOS

May 30

ORD
JetBlue Logo
JetBlue

Jun 5

ORD
5h 29m
BOS

Jun 5

MVY

as low as

$849

West Tisbury, US (MVY) - Chicago, US (CHI)

JetBlue Logo
JetBlue

May 29

MVY
15h 40m
BOS

May 30

ORD
JetBlue Logo
JetBlue

Jun 5

ORD
5h 5m
BOS

Jun 5

MVY

as low as

$879

West Tisbury, US (MVY) - Chicago, US (CHI)

JetBlue Logo
JetBlue

May 29

MVY
16h 35m
BOS

May 30

ORD
JetBlue Logo
JetBlue

Jun 5

ORD
5h 5m
BOS

Jun 5

MVY

as low as

$879

West Tisbury, US (MVY) - Chicago, US (CHI)

JetBlue Logo
JetBlue

May 29

MVY
29h 34m
BOS
JFK

May 30

ORD
JetBlue Logo
JetBlue

Jun 5

ORD
5h 29m
BOS

Jun 5

MVY

as low as

$888

West Tisbury, US (MVY) - Chicago, US (CHI)

JetBlue Logo
JetBlue

May 29

MVY
29h 34m
BOS
JFK

May 30

ORD
JetBlue Logo
JetBlue

Jun 5

ORD
5h 5m
BOS

Jun 5

MVY

as low as

$918

West Tisbury, US (MVY) - Chicago, US (CHI)

JetBlue Logo
JetBlue

May 29

MVY
29h 34m
BOS
JFK

May 30

ORD
JetBlue Logo
JetBlue

Jun 5

ORD
9h 20m
BOS

Jun 5

MVY

as low as

$918

West Tisbury, US (MVY) - Chicago, US (CHI)

Cape Air Logo
Cape Air

May 29

MVY
10h 5m
BOS

May 29

ORD
United Airlines Logo
United Airlines

Jun 5

ORD
5h 50m
BOS

Jun 5

MVY

as low as

$998

West Tisbury, US (MVY) - Chicago, US (CHI)

Cape Air Logo
Cape Air

May 29

MVY
10h 5m
BOS

May 29

ORD
United Airlines Logo
United Airlines

Jun 5

ORD
5h 15m
BOS

Jun 5

MVY

as low as

$998

West Tisbury, US (MVY) - Chicago, US (CHI)

Cape Air Logo
Cape Air

May 29

MVY
10h 5m
BOS

May 29

ORD
United Airlines Logo
United Airlines

Jun 5

ORD
4h 40m
BOS

Jun 5

MVY

as low as

$1028

West Tisbury, US (MVY) - Chicago, US (CHI)

Cape Air Logo
Cape Air

May 29

MVY
7h 50m
BOS

May 29

ORD
United Airlines Logo
United Airlines

Jun 5

ORD
5h 50m
BOS

Jun 5

MVY

as low as

$1028

Top Deals on flights from Hyannis to Chicago

Hyannis, US (HYA) - Chicago, US (CHI)

JetBlue Logo
JetBlue

May 30

HYA
19h 18m
BOS

May 31

ORD
JetBlue Logo
JetBlue

Jun 6

ORD
19h 9m
BOS

Jun 7

HYA

as low as

$665

Hyannis, US (HYA) - Chicago, US (CHI)

JetBlue Logo
JetBlue

May 30

HYA
19h 18m
BOS

May 31

ORD
JetBlue Logo
JetBlue

Jun 6

ORD
6h 50m
BOS

Jun 6

HYA

as low as

$685

Hyannis, US (HYA) - Chicago, US (CHI)

JetBlue Logo
JetBlue

May 30

HYA
19h 18m
BOS

May 31

ORD
JetBlue Logo
JetBlue

Jun 6

ORD
9h 49m
BOS

Jun 6

HYA

as low as

$685

Hyannis, US (HYA) - Chicago, US (CHI)

JetBlue Logo
JetBlue

May 30

HYA
19h 18m
BOS

May 31

ORD
JetBlue Logo
JetBlue

Jun 6

ORD
13h 39m
BOS

Jun 7

HYA

as low as

$695

Hyannis, US (HYA) - Chicago, US (CHI)

JetBlue Logo
JetBlue

May 30

HYA
19h 18m
BOS

May 31

ORD
JetBlue Logo
JetBlue

Jun 6

ORD
4h 55m
BOS

Jun 6

HYA

as low as

$715

Hyannis, US (HYA) - Chicago, US (CHI)

Cape Air Logo
Cape Air

May 30

HYA
21h 58m
BOS

May 31

ORD
United Airlines Logo
United Airlines

Jun 6

ORD
4h 9m
BOS

Jun 6

HYA

as low as

$779

Hyannis, US (HYA) - Chicago, US (CHI)

Cape Air Logo
Cape Air

May 30

HYA
22h 38m
BOS

May 31

ORD
United Airlines Logo
United Airlines

Jun 6

ORD
4h 9m
BOS

Jun 6

HYA

as low as

$779

Hyannis, US (HYA) - Chicago, US (CHI)

Cape Air Logo
Cape Air

May 30

HYA
21h 58m
BOS

May 31

ORD
United Airlines Logo
United Airlines

Jun 6

ORD
10h 45m
BOS

Jun 6

HYA

as low as

$779

Hyannis, US (HYA) - Chicago, US (CHI)

Cape Air Logo
Cape Air

May 30

HYA
19h 3m
BOS

May 31

ORD
United Airlines Logo
United Airlines

Jun 6

ORD
10h 45m
BOS

Jun 6

HYA

as low as

$779

Hyannis, US (HYA) - Chicago, US (CHI)

Cape Air Logo
Cape Air

May 30

HYA
22h 38m
BOS

May 31

ORD
United Airlines Logo
United Airlines

Jun 6

ORD
10h 45m
BOS

Jun 6

HYA

as low as

$779

Hyannis, US (HYA) - Chicago, US (CHI)

JetBlue Logo
JetBlue

May 30

HYA
13h 19m
JFK

May 30

ORD
JetBlue Logo
JetBlue

Jun 6

ORD
19h 9m
BOS

Jun 7

HYA

as low as

$901

Hyannis, US (HYA) - Chicago, US (CHI)

JetBlue Logo
JetBlue

May 30

HYA
19h 18m
BOS

May 31

ORD
JetBlue Logo
JetBlue

Jun 6

ORD
21h 4m
JFK

Jun 7

HYA

as low as

$915

Top Deals on flights from Provincetown to Chicago

Provincetown, US (PVC) - Chicago, US (CHI)

Cape Air Logo
Cape Air

May 29

PVC
12h 12m
BOS

May 29

ORD
American Airlines Logo
American Airlines

Jun 5

ORD
5h 20m
BOS

Jun 5

PVC

as low as

$574

Provincetown, US (PVC) - Chicago, US (CHI)

Cape Air Logo
Cape Air

May 29

PVC
9h 37m
BOS

May 29

ORD
American Airlines Logo
American Airlines

Jun 5

ORD
4h 35m
BOS

Jun 5

PVC

as low as

$574

Provincetown, US (PVC) - Chicago, US (CHI)

Cape Air Logo
Cape Air

May 29

PVC
7h 32m
BOS

May 29

ORD
American Airlines Logo
American Airlines

Jun 5

ORD
4h 35m
BOS

Jun 5

PVC

as low as

$574

Provincetown, US (PVC) - Chicago, US (CHI)

Cape Air Logo
Cape Air

May 29

PVC
7h 32m
BOS

May 29

ORD
American Airlines Logo
American Airlines

Jun 5

ORD
5h 20m
BOS

Jun 5

PVC

as low as

$574

Provincetown, US (PVC) - Chicago, US (CHI)

JetBlue Logo
JetBlue

May 29

PVC
30h 34m
BOS
JFK

May 30

ORD
JetBlue Logo
JetBlue

Jun 5

ORD
6h 5m
BOS

Jun 5

PVC

as low as

$582

Provincetown, US (PVC) - Chicago, US (CHI)

JetBlue Logo
JetBlue

May 29

PVC
30h 34m
BOS
JFK

May 30

ORD
JetBlue Logo
JetBlue

Jun 5

ORD
8h
BOS

Jun 5

PVC

as low as

$582

Provincetown, US (PVC) - Chicago, US (CHI)

JetBlue Logo
JetBlue

May 29

PVC
16h 40m
BOS

May 30

ORD
JetBlue Logo
JetBlue

Jun 5

ORD
8h
BOS

Jun 5

PVC

as low as

$630

Provincetown, US (PVC) - Chicago, US (CHI)

JetBlue Logo
JetBlue

May 29

PVC
25h 30m
BOS

May 30

ORD
JetBlue Logo
JetBlue

Jun 5

ORD
6h 5m
BOS

Jun 5

PVC

as low as

$630

Provincetown, US (PVC) - Chicago, US (CHI)

JetBlue Logo
JetBlue

May 29

PVC
8h 34m
BOS
JFK

May 29

ORD
JetBlue Logo
JetBlue

Jun 5

ORD
6h 5m
BOS

Jun 5

PVC

as low as

$649

Provincetown, US (PVC) - Chicago, US (CHI)

JetBlue Logo
JetBlue

May 29

PVC
8h 34m
BOS
JFK

May 29

ORD
JetBlue Logo
JetBlue

Jun 5

ORD
8h
BOS

Jun 5

PVC

as low as

$649

Provincetown, US (PVC) - Chicago, US (CHI)

Cape Air Logo
Cape Air

May 29

PVC
4h 56m
BOS

May 29

ORD
United Airlines Logo
United Airlines

Jun 5

ORD
5h 35m
BOS

Jun 5

PVC

as low as

$709

Provincetown, US (PVC) - Chicago, US (CHI)

Cape Air Logo
Cape Air

May 29

PVC
4h 56m
BOS

May 29

ORD
United Airlines Logo
United Airlines

Jun 5

ORD
10h 15m
BOS

Jun 5

PVC

as low as

$709