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Flight Deals from Washington, D.C. to Chicago from $189

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Top Deals on flights from Washington to Chicago

Washington, US (WAS) - Chicago, US (CHI)

Frontier Airlines Logo
Frontier Airlines

May 16

IAD
6h 6m
MCO

May 16

ORD
Frontier Airlines Logo
Frontier Airlines

May 18

ORD
16h 24m
TPA

May 19

IAD

as low as

$189

Washington, US (WAS) - Chicago, US (CHI)

Delta Air Lines Logo
Delta Air Lines

May 24

IAD
5h 36m
ATL

May 24

MDW
Delta Air Lines Logo
Delta Air Lines

May 31

MDW
4h 45m
DTW

May 31

IAD

as low as

$197

Washington, US (WAS) - Chicago, US (CHI)

Delta Air Lines Logo
Delta Air Lines

May 25

DCA
3h 18m
DTW

May 25

ORD
Delta Air Lines Logo
Delta Air Lines

May 29

ORD
5h 38m
ATL

May 29

DCA

as low as

$197

Washington, US (WAS) - Chicago, US (CHI)

Delta Air Lines Logo
Delta Air Lines

May 21

IAD
4h 49m
MSP

May 21

ORD
Delta Air Lines Logo
Delta Air Lines

May 25

ORD
7h 17m
ATL

May 25

IAD

as low as

$213

Washington, US (WAS) - Chicago, US (CHI)

Frontier Airlines Logo
Frontier Airlines

May 24

DCA
10h 52m
DEN

May 24

ORD
Frontier Airlines Logo
Frontier Airlines

May 26

ORD
20h 1m
MCO

May 27

DCA

as low as

$219

Washington, US (WAS) - Chicago, US (CHI)

JetBlue Logo
JetBlue

May 21

DCA
6h 51m
BOS

May 21

ORD
JetBlue Logo
JetBlue

May 28

ORD
6h 55m
JFK

May 28

DCA

as low as

$219

Washington, US (WAS) - Chicago, US (CHI)

United Airlines Logo
United Airlines

May 25

DCA
1h 15m
Direct

May 25

ORD
United Airlines Logo
United Airlines

May 29

ORD
3h 3m
Direct

May 29

DCA

as low as

$229

Washington, US (WAS) - Chicago, US (CHI)

American Airlines Logo
American Airlines

May 25

DCA
1h 13m
Direct

May 25

ORD
American Airlines Logo
American Airlines

May 29

ORD
3h 1m
Direct

May 29

DCA

as low as

$229

Washington, US (WAS) - Chicago, US (CHI)

United Airlines Logo
United Airlines

Jun 12

IAD
4h 37m
EWR

Jun 12

ORD
United Airlines Logo
United Airlines

Jun 14

ORD
3h 3m
Direct

Jun 14

IAD

as low as

$269

Washington, US (WAS) - Chicago, US (CHI)

American Airlines Logo
American Airlines

Jun 3

DCA
3h 49m
LGA

Jun 3

ORD
American Airlines Logo
American Airlines

Jun 4

ORD
3h 1m
Direct

Jun 4

DCA

as low as

$270

Washington, US (WAS) - Chicago, US (CHI)

American Airlines Logo
American Airlines

May 25

DCA
1h 14m
Direct

May 25

ORD
American Airlines Logo
American Airlines

May 27

ORD
5h 57m
CMH

May 27

DCA

as low as

$275

Washington, US (WAS) - Chicago, US (CHI)

American Airlines Logo
American Airlines

May 24

DCA
4h 20m
CLT

May 24

ORD
American Airlines Logo
American Airlines

May 25

ORD
2h 47m
Direct

May 25

DCA

as low as

$275