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Flight Deals from Massachusetts to Illinois from $116

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Top Deals on flights from Boston to Chicago

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)

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)

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 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 22

BOS
3h 57m
DTW

Aug 22

ORD
Delta Air Lines Logo
Delta Air Lines

Aug 27

ORD
3h 42m
Direct

Aug 27

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)

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)

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
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
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 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 Boston to Peoria

Boston, US (BOS) - Peoria, US (PIA)

American Airlines Logo
American Airlines

May 30

BOS
9h 46m
DFW

May 30

PIA
American Airlines Logo
American Airlines

Jun 6

PIA
4h 33m
ORD

Jun 6

BOS

as low as

$462

Boston, US (BOS) - Peoria, US (PIA)

American Airlines Logo
American Airlines

May 30

BOS
9h 46m
DFW

May 30

PIA
American Airlines Logo
American Airlines

Jun 6

PIA
7h 32m
ORD

Jun 6

BOS

as low as

$462

Boston, US (BOS) - Peoria, US (PIA)

American Airlines Logo
American Airlines

May 30

BOS
9h 46m
DFW

May 30

PIA
American Airlines Logo
American Airlines

Jun 6

PIA
4h 54m
ORD

Jun 7

BOS

as low as

$462

Boston, US (BOS) - Peoria, US (PIA)

American Airlines Logo
American Airlines

May 30

BOS
9h 46m
DFW

May 30

PIA
American Airlines Logo
American Airlines

Jun 6

PIA
5h 41m
CLT

Jun 6

BOS

as low as

$462

Boston, US (BOS) - Peoria, US (PIA)

American Airlines Logo
American Airlines

May 30

BOS
9h 46m
DFW

May 30

PIA
American Airlines Logo
American Airlines

Jun 6

PIA
6h 18m
ORD

Jun 6

BOS

as low as

$462

Boston, US (BOS) - Peoria, US (PIA)

American Airlines Logo
American Airlines

May 30

BOS
9h 46m
DFW

May 30

PIA
American Airlines Logo
American Airlines

Jun 6

PIA
5h 9m
CLT

Jun 6

BOS

as low as

$505

Boston, US (BOS) - Peoria, US (PIA)

United Airlines Logo
United Airlines

May 30

BOS
5h 21m
ORD

May 30

PIA
United Airlines Logo
United Airlines

Jun 6

PIA
4h 55m
ORD

Jun 6

BOS

as low as

$540

Boston, US (BOS) - Peoria, US (PIA)

United Airlines Logo
United Airlines

May 30

BOS
5h 35m
ORD

May 30

PIA
United Airlines Logo
United Airlines

Jun 6

PIA
4h 55m
ORD

Jun 6

BOS

as low as

$540

Boston, US (BOS) - Peoria, US (PIA)

United Airlines Logo
United Airlines

May 30

BOS
7h 4m
ORD

May 30

PIA
United Airlines Logo
United Airlines

Jun 6

PIA
4h 55m
ORD

Jun 6

BOS

as low as

$540

Boston, US (BOS) - Peoria, US (PIA)

American Airlines Logo
American Airlines

May 30

BOS
6h 20m
CLT

May 30

PIA
American Airlines Logo
American Airlines

Jun 6

PIA
5h 41m
CLT

Jun 6

BOS

as low as

$545

Boston, US (BOS) - Peoria, US (PIA)

United Airlines Logo
United Airlines

May 30

BOS
12h 21m
DEN

May 30

PIA
United Airlines Logo
United Airlines

Jun 6

PIA
4h 55m
ORD

Jun 6

BOS

as low as

$563

Boston, US (BOS) - Peoria, US (PIA)

United Airlines Logo
United Airlines

May 30

BOS
24h 52m
DEN

May 31

PIA
United Airlines Logo
United Airlines

Jun 6

PIA
4h 55m
ORD

Jun 6

BOS

as low as

$578

Top Deals on flights from Worcester to Peoria

Worcester, US (ORH) - Peoria, US (PIA)

American Airlines Logo
American Airlines

May 30

ORH
26h 18m
JFK
DFW

May 31

PIA
American Airlines Logo
American Airlines

Jun 6

PIA
25h 47m
ORD
JFK

Jun 7

ORH

as low as

$490

Worcester, US (ORH) - Peoria, US (PIA)

American Airlines Logo
American Airlines

May 30

ORH
22h 2m
JFK
DFW

May 31

PIA
American Airlines Logo
American Airlines

Jun 6

PIA
25h 47m
ORD
JFK

Jun 7

ORH

as low as

$490

Worcester, US (ORH) - Peoria, US (PIA)

American Airlines Logo
American Airlines

May 30

ORH
22h 2m
JFK
DFW

May 31

PIA
American Airlines Logo
American Airlines

Jun 6

PIA
30h 52m
CLT
JFK

Jun 7

ORH

as low as

$502

Worcester, US (ORH) - Peoria, US (PIA)

American Airlines Logo
American Airlines

May 30

ORH
26h 18m
JFK
DFW

May 31

PIA
American Airlines Logo
American Airlines

Jun 6

PIA
30h 52m
CLT
JFK

Jun 7

ORH

as low as

$502

Worcester, US (ORH) - Peoria, US (PIA)

American Airlines Logo
American Airlines

May 30

ORH
22h 2m
JFK
DFW

May 31

PIA
American Airlines Logo
American Airlines

Jun 6

PIA
29h 52m
ORD
JFK

Jun 7

ORH

as low as

$530

Worcester, US (ORH) - Peoria, US (PIA)

American Airlines Logo
American Airlines

May 30

ORH
26h 18m
JFK
DFW

May 31

PIA
American Airlines Logo
American Airlines

Jun 6

PIA
29h 52m
ORD
JFK

Jun 7

ORH

as low as

$530

Worcester, US (ORH) - Peoria, US (PIA)

American Airlines Logo
American Airlines

May 30

ORH
22h 2m
JFK
DFW

May 31

PIA
American Airlines Logo
American Airlines

Jun 6

PIA
19h 46m
CLT
JFK

Jun 7

ORH

as low as

$557

Worcester, US (ORH) - Peoria, US (PIA)

American Airlines Logo
American Airlines

May 30

ORH
26h 18m
JFK
DFW

May 31

PIA
American Airlines Logo
American Airlines

Jun 6

PIA
19h 46m
CLT
JFK

Jun 7

ORH

as low as

$557

Worcester, US (ORH) - Peoria, US (PIA)

American Airlines Logo
American Airlines

May 30

ORH
32h 33m
JFK
DFW

May 31

PIA
American Airlines Logo
American Airlines

Jun 6

PIA
25h 47m
ORD
JFK

Jun 7

ORH

as low as

$628

Worcester, US (ORH) - Peoria, US (PIA)

American Airlines Logo
American Airlines

May 30

ORH
9h 10m
JFK
ORD

May 30

PIA
American Airlines Logo
American Airlines

Jun 6

PIA
25h 47m
ORD
JFK

Jun 7

ORH

as low as

$688

Worcester, US (ORH) - Peoria, US (PIA)

American Airlines Logo
American Airlines

May 30

ORH
32h 33m
JFK
DFW

May 31

PIA
American Airlines Logo
American Airlines

Jun 6

PIA
19h 46m
CLT
JFK

Jun 7

ORH

as low as

$695

Top Deals on flights from Boston to Moline

Boston, US (BOS) - Moline, US (MLI)

United Airlines Logo
United Airlines

May 30

BOS
25h 2m
DEN

May 31

MLI
United Airlines Logo
United Airlines

Jun 6

MLI
9h 15m
ORD

Jun 6

BOS

as low as

$509

Boston, US (BOS) - Moline, US (MLI)

American Airlines Logo
American Airlines

May 30

BOS
9h 51m
DFW

May 30

MLI
American Airlines Logo
American Airlines

Jun 6

MLI
5h 27m
CLT

Jun 6

BOS

as low as

$511

Boston, US (BOS) - Moline, US (MLI)

American Airlines Logo
American Airlines

May 30

BOS
10h 19m
DFW

May 30

MLI
American Airlines Logo
American Airlines

Jun 6

MLI
6h 13m
ORD

Jun 6

BOS

as low as

$511

Boston, US (BOS) - Moline, US (MLI)

American Airlines Logo
American Airlines

May 30

BOS
9h 51m
DFW

May 30

MLI
American Airlines Logo
American Airlines

Jun 6

MLI
4h 18m
ORD

Jun 6

BOS

as low as

$511

Boston, US (BOS) - Moline, US (MLI)

American Airlines Logo
American Airlines

May 30

BOS
10h 19m
DFW

May 30

MLI
American Airlines Logo
American Airlines

Jun 6

MLI
5h 27m
CLT

Jun 6

BOS

as low as

$511

Boston, US (BOS) - Moline, US (MLI)

American Airlines Logo
American Airlines

May 30

BOS
9h 51m
DFW

May 30

MLI
American Airlines Logo
American Airlines

Jun 6

MLI
6h 13m
ORD

Jun 6

BOS

as low as

$511

Boston, US (BOS) - Moline, US (MLI)

American Airlines Logo
American Airlines

May 30

BOS
10h 19m
DFW

May 30

MLI
American Airlines Logo
American Airlines

Jun 6

MLI
4h 18m
ORD

Jun 6

BOS

as low as

$511

Boston, US (BOS) - Moline, US (MLI)

American Airlines Logo
American Airlines

May 30

BOS
10h 19m
DFW

May 30

MLI
American Airlines Logo
American Airlines

Jun 6

MLI
6h 54m
DFW

Jun 6

BOS

as low as

$511

Boston, US (BOS) - Moline, US (MLI)

United Airlines Logo
United Airlines

May 30

BOS
25h 2m
DEN

May 31

MLI
United Airlines Logo
United Airlines

Jun 6

MLI
5h 5m
ORD

Jun 6

BOS

as low as

$555

Boston, US (BOS) - Moline, US (MLI)

United Airlines Logo
United Airlines

May 30

BOS
25h 2m
DEN

May 31

MLI
United Airlines Logo
United Airlines

Jun 6

MLI
6h 33m
ORD

Jun 6

BOS

as low as

$555

Boston, US (BOS) - Moline, US (MLI)

United Airlines Logo
United Airlines

May 30

BOS
25h 2m
DEN

May 31

MLI
United Airlines Logo
United Airlines

Jun 6

MLI
5h 2m
ORD

Jun 6

BOS

as low as

$555

Boston, US (BOS) - Moline, US (MLI)

United Airlines Logo
United Airlines

May 30

BOS
25h 2m
DEN

May 31

MLI
United Airlines Logo
United Airlines

Jun 6

MLI
4h 45m
ORD

Jun 6

BOS

as low as

$555

Top Deals on flights from Worcester to Moline

Worcester, US (ORH) - Moline, US (MLI)

American Airlines Logo
American Airlines

May 30

ORH
32h 38m
JFK
DFW

May 31

MLI
American Airlines Logo
American Airlines

Jun 6

MLI
30h 7m
DFW
JFK

Jun 7

ORH

as low as

$348

Worcester, US (ORH) - Moline, US (MLI)

American Airlines Logo
American Airlines

May 30

ORH
26h 8m
JFK
DFW

May 31

MLI
American Airlines Logo
American Airlines

Jun 6

MLI
30h 7m
DFW
JFK

Jun 7

ORH

as low as

$348

Worcester, US (ORH) - Moline, US (MLI)

American Airlines Logo
American Airlines

May 30

ORH
32h 38m
JFK
DFW

May 31

MLI
American Airlines Logo
American Airlines

Jun 6

MLI
24h 28m
ORD
JFK

Jun 7

ORH

as low as

$490

Worcester, US (ORH) - Moline, US (MLI)

American Airlines Logo
American Airlines

May 30

ORH
26h 8m
JFK
DFW

May 31

MLI
American Airlines Logo
American Airlines

Jun 6

MLI
29h 37m
ORD
JFK

Jun 7

ORH

as low as

$490

Worcester, US (ORH) - Moline, US (MLI)

American Airlines Logo
American Airlines

May 30

ORH
32h 38m
JFK
DFW

May 31

MLI
American Airlines Logo
American Airlines

Jun 6

MLI
29h 37m
ORD
JFK

Jun 7

ORH

as low as

$490

Worcester, US (ORH) - Moline, US (MLI)

American Airlines Logo
American Airlines

May 30

ORH
26h 8m
JFK
DFW

May 31

MLI
American Airlines Logo
American Airlines

Jun 6

MLI
24h 28m
ORD
JFK

Jun 7

ORH

as low as

$490

Worcester, US (ORH) - Moline, US (MLI)

American Airlines Logo
American Airlines

May 30

ORH
21h 56m
JFK
ORD

May 31

MLI
American Airlines Logo
American Airlines

Jun 6

MLI
24h 28m
ORD
JFK

Jun 7

ORH

as low as

$506

Worcester, US (ORH) - Moline, US (MLI)

American Airlines Logo
American Airlines

May 30

ORH
27h 9m
JFK
CLT

May 31

MLI
American Airlines Logo
American Airlines

Jun 6

MLI
30h 7m
DFW
JFK

Jun 7

ORH

as low as

$545

Worcester, US (ORH) - Moline, US (MLI)

American Airlines Logo
American Airlines

May 30

ORH
27h 9m
JFK
CLT

May 31

MLI
American Airlines Logo
American Airlines

Jun 6

MLI
24h 28m
ORD
JFK

Jun 7

ORH

as low as

$793

Worcester, US (ORH) - Moline, US (MLI)

American Airlines Logo
American Airlines

May 30

ORH
27h 9m
JFK
CLT

May 31

MLI
American Airlines Logo
American Airlines

Jun 6

MLI
29h 37m
ORD
JFK

Jun 7

ORH

as low as

$793