Cheap Flights from Washington, D.C. to Chicago
Browse current best options from Washington, D.C.. Become a member to unlock all deals and get alerts when new deals appear.
Deals from
Washington, D.C.
RatePunk searches hundreds of travel sites at once for deals on flights to Chicago
Prices updated 5 days ago
402 airlines compared
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Fares are subject to change and may not be available for all dates. (Data last updated Jul 12, 2026.)
Today’s best flight deals from Washington, D.C. to Chicago
Explore current cheapest deals departing from Washington, D.C. to Chicago
Round trip
Sort by: Cheapest
September 10 - September 17
BWI - Chicago
$104
$62
Round trip
October 15 - October 28
BWI - Chicago
$106
$65
Round trip
August 24 - August 27
BWI - Chicago
$139
$66
Round trip
August 20 - August 24
BWI - Chicago
$140
$66
Round trip
October 10 - October 14
BWI - Chicago
$123
$66
Round trip
September 24 - October 1
BWI - Chicago
$105
$66
Round trip
September 10 - October 1
BWI - Chicago
$89
$66
Round trip
October 10 - November 5
BWI - Chicago
$100
$67
Round trip
October 15 - October 29
BWI - Chicago
$106
$67
Round trip
October 17 - November 5
BWI - Chicago
$106
$67
Round trip
Unlock all 500+ flight deals to Chicago and get alerts when great deals appear
Washington, D.C. to Chicago: Overview
Insights for flights from Washington, D.C. to Chicago
How much is a round trip from Washington, D.C. to Chicago
Regular price: $83 - $209
Prices for flights from Washington, D.C. to Chicago are currently below the regular range.
The regular price range for this route is $83 to $209. The current lowest deal is $65 with Frontier Airlines for travel from Sep 10-Sep 17.
now $65
Low $83
High $209
The cheapest time to fly from Washington, D.C. to Chicago
The cheapest month to fly from WAS to CHI is January, with a median price of $147. The most expensive month is June, with a median price of $596. Prices are generally lower from January to December.
January
Flights from $147
June
Flights from $596
Direct flights from Washington, D.C. to Chicago
Frontier Airlines
Southwest Airlines
Last-minute flights going from Washington, D.C. to Chicago
Wed, Jul 22
IAD - Chicago
Washington, D.C. (IAD) - Chicago (RFD)
Frontier Airlines
$366
$227
One-way
Wed, Aug 5
IAD - Chicago
Washington, D.C. (IAD) - Chicago (RFD)
Frontier Airlines
$316
$159
One-way
Wed, Aug 5
IAD - Chicago
Washington, D.C. (IAD) - Chicago (RFD)
Frontier Airlines
$305
$175
One-way
Thu, Aug 6
IAD - Chicago
Washington, D.C. (IAD) - Chicago (MDW)
Frontier Airlines
$321
$175
One-way
Tue, Aug 11
BWI - Chicago
Washington, D.C. (BWI) - Chicago (ORD)
Frontier Airlines
$226
$124
One-way
Wed, Aug 12
IAD - Chicago
Washington, D.C. (IAD) - Chicago (RFD)
Frontier Airlines
$303
$162
One-way
Biggest price drops on these dates for flights from Washington, D.C. to Chicago
Aug 1 - Aug 4
$325 → $177
46%
Aug 1 - Aug 5
$325 → $177
46%
Aug 5 - Aug 8
$325 → $177
46%
Oct 25 - Oct 28
$316 → $169
47%
Popular Airports to fly from Washington, D.C. to Chicago
Washington, D.C. - Chicago route insights
💸 Price insights
Recent fares are below the typical level
Recent fares from Washington, D.C. to Chicago are below the typical level at $65.
📅 Best time to fly
October is historically the cheapest month to fly
Historically, October is the cheapest month to fly from Washington, D.C. to Chicago, with a median price of $132.
⏱️ Flight duration
Direct flights take 2h 19m
Direct flights from Washington, D.C. to Chicago typically take 2h 19m.
✈️ Airlines & availability
40% of recent fares are direct
40% of recent fares for this route are direct, with connecting flights having 2 stopovers.
🏆 Airline highlight
Frontier Airlines offers direct flights
Frontier Airlines is one of the airlines offering direct flights from Washington, D.C. to Chicago.
🎯 Booking tip
Deals appear frequently
Deals for flights from Washington, D.C. to Chicago appear frequently.
Washington, D.C. main airports to depart from
Baltimore–Washington International (BWI)
Baltimore–Washington International is a great option for flights from Washington, D.C. to Chicago.
📍 ~44 km from Washington, D.C. (reachable by car or train)
💸 Flights from ~$65
Ronald Reagan Washington National (DCA)
Ronald Reagan Washington National is a convenient choice for flights from Washington, D.C. to Chicago.
📍 ~6 km from Washington, D.C. (reachable by car or train)
💸 Flights from ~$176
Washington Dulles International (IAD)
Washington Dulles International is a good alternative for flights from Washington, D.C. to Chicago.
📍 ~36 km from Washington, D.C. (reachable by car or train)
💸 Flights from ~$159
Chicago main airports to arrive at
O Hare International (ORD)
O'Hare International Airport is a major hub for flights to Chicago from Washington, D.C.
📍 ~25 km from Chicago city center (reachable by car)
💸 Flights from ~$65
Chicago Midway International (MDW)
Chicago Midway International Airport offers another convenient option for arriving in Chicago.
📍 ~14 km from Chicago city center (reachable by car)
💸 Flights from ~$166
Chicago Rockford International (RFD)
Chicago Rockford International Airport is an alternative for reaching the wider Chicago area.
📍 ~126 km from Chicago city center (reachable by car)
💸 Flights from ~$185
Airports nearby Chicago used as alternative
General Mitchell International (MKE)
General Mitchell International offers significant carrier presence and direct flight options for Chicago travelers.
📍 ~135 km from Chicago (reachable by rail or car)
💸 Flights from ~$196
Gerald R. Ford International (GRR)
Gerald R. Ford International provides a robust domestic network with both legacy and low-cost airlines.
📍 ~245 km from Chicago (reachable by car)
💸 Flights from ~$209
Dane County Regional (MSN)
Dane County Regional is a reliable regional hub with efficient operations and good amenities for travelers.
📍 ~200 km from Chicago (reachable by car)
💸 Flights from ~$258
South Bend International (SBN)
South Bend International is the geographically closest alternative, offering convenient access to the Chicago metro area.
📍 ~130 km from Chicago (reachable by rail)
💸 Flights from ~$158
Fort Wayne International (FWA)
Fort Wayne International offers multiple cabin classes and solid connectivity for eastern domestic destinations.
📍 ~230 km from Chicago (reachable by car)
💸 Flights from ~$240
Business & First Class Flight Deals to Chicago
Discover luxury on the budget with premium cabin class on flights from Washington, D.C. to Chicago.
Elite
Best Elite deals to Chicago
Exclusive daily First Class, Business Class, and Premium Economy flight deals, refreshed every 24 hours.
From DCA
Elite
Aug 31
Chicago, United States
80% AI deal score
$4,672
$1,962
Save $2,710
From DCA
Elite
Dec 03
Chicago, United States
80% AI deal score
$1,237
$423
Save $814
From DCA
Elite
Aug 31
Chicago, United States
79% AI deal score
$4,268
$1,957
Save $2,311
From DCA
Elite
Aug 31
Chicago, United States
79% AI deal score
$4,271
$1,962
Save $2,309
From DCA
Elite
Aug 31
Chicago, United States
79% AI deal score
$4,703
$2,111
Save $2,592
From DCA
Elite
Aug 31
Chicago, United States
78% AI deal score
$4,013
$1,962
Save $2,051
From DCA
Elite
Aug 31
Chicago, United States
78% AI deal score
$4,014
$1,962
Save $2,052
From DCA
Elite
Aug 31
Chicago, United States
78% AI deal score
$4,013
$1,962
Save $2,051
From DCA
Elite
Aug 31
Chicago, United States
78% AI deal score
$4,013
$1,962
Save $2,051
From DCA
Elite
Aug 13
Chicago, United States
78% AI deal score
$1,194
$602
Save $592
From DCA
Elite
Dec 03
Chicago, United States
78% AI deal score
$1,230
$464
Save $766
From DCA
Elite
Dec 04
Chicago, United States
78% AI deal score
$1,237
$464
Save $773
From DCA
Elite
Jul 11
Chicago, United States
77% AI deal score
$1,627
$847
Save $780
From DCA
Elite
Jul 14
Chicago, United States
77% AI deal score
$1,617
$847
Save $770
From DCA
Elite
Jul 14
Chicago, United States
77% AI deal score
$1,619
$872
Save $747
From DCA
Elite
Aug 04
Chicago, United States
77% AI deal score
$1,371
$545
Save $826
From DCA
Elite
Nov 08
Chicago, United States
76% AI deal score
$1,205
$668
Save $537
From DCA
Elite
Jul 08
Chicago, United States
76% AI deal score
$1,463
$850
Save $613
From DCA
Elite
Jul 12
Chicago, United States
76% AI deal score
$1,405
$874
Save $531
From DCA
Elite
Aug 03
Chicago, United States
76% AI deal score
$1,629
$882
Save $747
From DCA
Elite
Aug 04
Chicago, United States
76% AI deal score
$1,629
$904
Save $725
From IAD
Elite
Aug 10
Chicago, United States
75% AI deal score
$689
$511
Save $178
From DCA
Elite
Aug 25
Chicago, United States
75% AI deal score
$1,580
$693
Save $887
From DCA
Elite
Oct 03
Chicago, United States
75% AI deal score
$1,146
$693
Save $453
From DCA
Elite
Aug 14
Chicago, United States
75% AI deal score
$1,599
$939
Save $660
From DCA
Elite
Jul 05
Chicago, United States
75% AI deal score
$1,887
$1,083
Save $804
From DCA
Elite
Jul 05
Chicago, United States
75% AI deal score
$1,865
$1,083
Save $782
From DCA
Elite
Dec 03
Chicago, United States
75% AI deal score
$1,223
$564
Save $659
From DCA
Elite
Dec 04
Chicago, United States
75% AI deal score
$1,230
$564
Save $666
From DCA
Elite
Jul 14
Chicago, United States
75% AI deal score
$1,265
$611
Save $654
From DCA
Elite
Aug 10
Chicago, United States
74% AI deal score
$663
$511
Save $152
From DCA
Elite
Sep 12
Chicago, United States
74% AI deal score
$1,020
$611
Save $409
From DCA
Elite
Oct 26
Chicago, United States
74% AI deal score
$1,145
$718
Save $427
From DCA
Elite
Aug 23
Chicago, United States
74% AI deal score
$1,572
$724
Save $848
From DCA
Elite
Jul 14
Chicago, United States
74% AI deal score
$1,564
$745
Save $819
From DCA
Elite
Aug 09
Chicago, United States
74% AI deal score
$1,645
$762
Save $883
From DCA
Elite
Jul 09
Chicago, United States
74% AI deal score
$1,325
$797
Save $528
From DCA
Elite
Jul 29
Chicago, United States
74% AI deal score
$1,328
$833
Save $495
From DCA
Elite
Jul 15
Chicago, United States
74% AI deal score
$1,266
$632
Save $634
From DCA
Elite
Dec 04
Chicago, United States
73% AI deal score
$1,226
$782
Save $444
From DCA
Elite
Jul 08
Chicago, United States
73% AI deal score
$1,470
$993
Save $477
From DCA
Elite
Jul 06
Chicago, United States
73% AI deal score
$1,885
$1,183
Save $702
From DCA
Elite
Aug 05
Chicago, United States
72% AI deal score
$1,592
$1,076
Save $516
From DCA
Elite
Jul 11
Chicago, United States
72% AI deal score
$1,644
$1,083
Save $561
From DCA
Elite
Jul 06
Chicago, United States
72% AI deal score
$1,823
$1,208
Save $615
From DCA
Elite
Jul 04
Chicago, United States
72% AI deal score
$1,885
$1,229
Save $656
From IAD
Elite
Aug 19
Chicago, United States
72% AI deal score
$1,654
$1,133
Save $521
From DCA
Elite
Aug 26
Chicago, United States
71% AI deal score
$930
$689
Save $241
From DCA
Elite
Oct 03
Chicago, United States
71% AI deal score
$1,186
$838
Save $348
From DCA
Elite
Jul 29
Chicago, United States
71% AI deal score
$1,108
$872
Save $236
From DCA
Elite
Jul 21
Chicago, United States
71% AI deal score
$1,392
$996
Save $396
From DCA
Elite
Aug 04
Chicago, United States
71% AI deal score
$1,537
$1,076
Save $461
From DCA
Elite
Aug 27
Chicago, United States
71% AI deal score
$1,523
$1,081
Save $442
From DCA
Elite
Aug 14
Chicago, United States
71% AI deal score
$1,619
$1,119
Save $500
From DCA
Elite
Oct 02
Chicago, United States
70% AI deal score
$1,178
$872
Save $306
From DCA
Elite
Aug 27
Chicago, United States
70% AI deal score
$1,557
$1,099
Save $458
From IAD
Elite
Aug 25
Chicago, United States
68% AI deal score
$1,591
$1,133
Save $458
From DCA
Elite
Sep 08
Chicago, United States
67% AI deal score
$2,743
$1,957
Save $786
From DCA
Elite
Sep 24
Chicago, United States
67% AI deal score
$2,826
$1,960
Save $866
From DCA
Elite
Sep 27
Chicago, United States
67% AI deal score
$2,845
$1,962
Save $883
From DCA
Elite
Sep 25
Chicago, United States
67% AI deal score
$2,826
$1,962
Save $864
From DCA
Elite
Sep 03
Chicago, United States
66% AI deal score
$2,521
$1,957
Save $564
From DCA
Elite
Sep 07
Chicago, United States
66% AI deal score
$2,648
$1,957
Save $691
From DCA
Elite
Sep 04
Chicago, United States
66% AI deal score
$2,513
$1,957
Save $556
From DCA
Elite
Sep 01
Chicago, United States
66% AI deal score
$2,518
$1,957
Save $561
From DCA
Elite
Sep 05
Chicago, United States
66% AI deal score
$2,541
$1,957
Save $584
From DCA
Elite
Sep 17
Chicago, United States
66% AI deal score
$2,513
$1,959
Save $554
From DCA
Elite
Sep 18
Chicago, United States
66% AI deal score
$2,529
$1,959
Save $570
From DCA
Elite
Sep 24
Chicago, United States
66% AI deal score
$2,728
$1,959
Save $769
From DCA
Elite
Sep 18
Chicago, United States
66% AI deal score
$2,556
$1,960
Save $596
From DCA
Elite
Sep 18
Chicago, United States
66% AI deal score
$2,525
$1,960
Save $565
From DCA
Elite
Sep 24
Chicago, United States
66% AI deal score
$2,622
$1,960
Save $662
From DCA
Elite
Sep 17
Chicago, United States
66% AI deal score
$2,519
$1,960
Save $559
From DCA
Elite
Sep 18
Chicago, United States
66% AI deal score
$2,530
$1,960
Save $570
From DCA
Elite
Sep 17
Chicago, United States
66% AI deal score
$2,510
$1,960
Save $550
From DCA
Elite
Sep 20
Chicago, United States
66% AI deal score
$2,599
$1,962
Save $637
From DCA
Elite
Sep 22
Chicago, United States
66% AI deal score
$2,666
$1,962
Save $704
From DCA
Elite
Sep 20
Chicago, United States
66% AI deal score
$2,728
$1,962
Save $766
From DCA
Elite
Sep 22
Chicago, United States
66% AI deal score
$2,622
$1,962
Save $660
From DCA
Elite
Sep 20
Chicago, United States
66% AI deal score
$2,603
$1,962
Save $641
From DCA
Elite
Sep 25
Chicago, United States
66% AI deal score
$2,666
$1,962
Save $704
From DCA
Elite
Sep 26
Chicago, United States
66% AI deal score
$2,747
$1,962
Save $785
From DCA
Elite
Sep 20
Chicago, United States
66% AI deal score
$2,591
$1,962
Save $629
From DCA
Elite
Sep 22
Chicago, United States
66% AI deal score
$2,607
$1,962
Save $645
From DCA
Elite
Sep 04
Chicago, United States
66% AI deal score
$2,584
$1,962
Save $622
From DCA
Elite
Sep 03
Chicago, United States
66% AI deal score
$2,542
$1,962
Save $580
From DCA
Elite
Sep 19
Chicago, United States
66% AI deal score
$2,599
$1,994
Save $605
From DCA
Elite
Sep 22
Chicago, United States
66% AI deal score
$2,844
$2,111
Save $733
From BWI
Elite
Aug 30
Chicago, United States
66% AI deal score
$2,673
$2,129
Save $544
From DCA
Elite
Nov 03
Chicago, United States
66% AI deal score
$597
$545
Save $52
From DCA
Elite
Nov 02
Chicago, United States
66% AI deal score
$597
$545
Save $52
From IAD
Elite
Dec 05
Chicago, United States
66% AI deal score
$605
$545
Save $60
From DCA
Elite
Oct 29
Chicago, United States
66% AI deal score
$605
$545
Save $60
From IAD
Elite
Aug 26
Chicago, United States
66% AI deal score
$615
$545
Save $70
From DCA
Elite
Sep 17
Chicago, United States
65% AI deal score
$2,500
$1,960
Save $540
From DCA
Elite
Sep 04
Chicago, United States
65% AI deal score
$2,420
$1,962
Save $458
From DCA
Elite
Sep 03
Chicago, United States
65% AI deal score
$2,424
$1,962
Save $462
From DCA
Elite
Sep 07
Chicago, United States
65% AI deal score
$2,415
$1,962
Save $453
From DCA
Elite
Sep 08
Chicago, United States
65% AI deal score
$2,449
$1,962
Save $487
From DCA
Elite
Sep 03
Chicago, United States
65% AI deal score
$2,424
$1,962
Save $462