Cheap Flights from Washington, D.C. to Chicago
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Deals from
Washington, D.C.
RatePunk searches hundreds of travel sites at once for deals on flights to Chicago
Prices updated 24 days ago
486,190 searches this week
171 airlines compared
80%+ AI score for best value
Fares are subject to change and may not be available for all dates. (Data last updated May 29, 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
October 21 - October 28
BWI - Chicago
$144
$92
Round trip
October 21 - November 18
BWI - Chicago
$124
$92
Round trip
October 21 - October 27
BWI - Chicago
$144
$92
Round trip
October 14 - October 27
BWI - Chicago
$128
$92
Round trip
October 14 - October 28
BWI - Chicago
$128
$92
Round trip
October 27 - October 28
BWI - Chicago
$153
$92
Round trip
October 28 - November 18
BWI - Chicago
$128
$92
Round trip
October 27 - November 18
BWI - Chicago
$128
$92
Round trip
October 20 - October 27
BWI - Chicago
$144
$102
Round trip
October 14 - October 17
BWI - Chicago
$150
$111
Round trip
Unlock all 500+ flight deals to Chicago and get alerts when great deals appear
Route Intelligence — 486,190 Searches this Week
Insights for flights from Washington, D.C. to Chicago
How much is a round trip from Washington, D.C. to Chicago
Regular price: $112 - $251
Prices are currently below the regular range.
The regular price range for flights from Washington, D.C. to Chicago is $112-$251. The current lowest deal is $92 with Frontier Airlines for travel from Oct 21-Oct 28.
now $92
Low $112
High $251
The cheapest time to fly from Washington, D.C. to Chicago
The cheapest month to fly from Washington to Chicago is October, with a median price of $132. The most expensive month is June, with a median price of $588. Prices are generally lower from January to December.
October
Flights from $132
June
Flights from $588
Direct flights from Washington, D.C. to Chicago
Frontier Airlines
Southwest Airlines
Last-minute flights going from Washington, D.C. to Chicago
Wed, Jun 17
DCA - Chicago
Washington, D.C. (DCA) - Chicago (ORD)
JetBlue Airways
$448
$277
One-way
Wed, Jun 17
BWI - Chicago
Washington, D.C. (BWI) - Chicago (MDW)
Frontier Airlines
$567
$308
One-way
Wed, Jun 17
BWI - Chicago
Washington, D.C. (BWI) - Chicago (MDW)
Frontier Airlines
$565
$319
One-way
Sat, Jun 20
BWI - Chicago
Washington, D.C. (BWI) - Chicago (MDW)
Frontier Airlines
$552
$273
One-way
Sat, Jun 20
BWI - Chicago
Washington, D.C. (BWI) - Chicago (MDW)
Frontier Airlines
$478
$273
One-way
Tue, Jun 23
BWI - Chicago
Washington, D.C. (BWI) - Chicago (MDW)
Frontier Airlines
$483
$268
One-way
Biggest price drops on these dates for flights from Washington, D.C. to Chicago
Jun 20 - Jun 24
$552 → $273
50%
Jun 17 - Jun 18
$567 → $308
46%
Jun 17 - Jun 19
$565 → $319
44%
Jun 23 - Jun 24
$483 → $268
44%
Popular Airports to fly from Washington, D.C. to Chicago
Washington, D.C. - Chicago route insights
💸 Price insights
Recent fares are above the typical level
Recent fares for Washington, D.C. to Chicago are above the typical level at $348.
📅 Best time to fly
Fly in October for the best prices
Historically, October is the cheapest month to fly from Washington, D.C. to Chicago, at $132.
⏱️ Flight duration
Average flight time is 7h 19m
The typical flight duration from Washington, D.C. to Chicago is 7 hours and 19 minutes.
✈️ Airlines & availability
Mixed availability of direct flights
About 47.6% of recent deals for this route are direct, with connecting flights having 2 stopovers.
🏆 Airline highlight
Frontier Airlines offers direct flights
Frontier Airlines has recently offered direct flights from Washington, D.C. to Chicago.
🎯 Booking tip
Deals are frequent for this route
Deals for flights from Washington, D.C. to Chicago are frequent, appearing daily.
Washington, D.C. main airports to depart from
Baltimore–Washington International (BWI)
Consider BWI for flights from the Washington, D.C. area to Chicago, often with competitive pricing.
📍 ~45 km from Washington, D.C. (reachable by car or train)
💸 Flights from ~$92
Ronald Reagan Washington National (DCA)
DCA is a convenient option for flights from Washington, D.C. to Chicago.
📍 ~5 km from Washington, D.C. (reachable by car or train)
💸 Flights from ~$177
Washington Dulles International (IAD)
IAD offers another choice for flights from the Washington, D.C. region to Chicago.
📍 ~40 km from Washington, D.C. (reachable by car)
💸 Flights from ~$174
Chicago main airports to arrive at
O Hare International (ORD)
O'Hare International Airport is a good option for flights to Chicago, offering a wide range of connections.
📍 ~25 km from Chicago city center (reachable by car or public transport)
💸 Flights from ~$92
Chicago Midway International (MDW)
Chicago Midway International Airport provides a convenient arrival point for travelers heading to Chicago.
📍 ~15 km from Chicago city center (reachable by car or public transport)
💸 Flights from ~$177
Chicago Rockford International (RFD)
Chicago Rockford International Airport serves as an alternative arrival option for the Chicago area.
📍 ~120 km from Chicago city center (reachable by car)
💸 Flights from ~$171
Airports nearby Chicago used as alternative
General Mitchell International (MKE)
General Mitchell International offers excellent proximity to Chicago with high-frequency flight options.
📍 ~135 km from Chicago (reachable by rail)
💸 Flights from ~$223
South Bend International (SBN)
South Bend International is the geographically closest alternative to the Chicago area, with easier security and parking.
📍 ~125 km from Chicago (reachable by rail)
💸 Flights from ~$138
Gerald R. Ford International (GRR)
Gerald R. Ford International is a major regional hub, offering a wide range of cabin classes.
📍 ~200 km from Chicago (reachable by car)
💸 Flights from ~$196
Dane County Regional (MSN)
Dane County Regional is a reliable regional airport with consistent service levels and less congestion.
📍 ~205 km from Chicago (reachable by car)
💸 Flights from ~$257
Fort Wayne International (FWA)
Fort Wayne International provides stable regional service with multiple cabin class options.
📍 ~240 km from Chicago (reachable by car)
💸 Flights from ~$200
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
Jul 14
Chicago, United States
78% AI deal score
$1,249
$477
Save $772
From DCA
Elite
Jun 29
Chicago, United States
78% AI deal score
$1,307
$504
Save $803
From DCA
Elite
Jul 28
Chicago, United States
77% AI deal score
$1,065
$516
Save $549
From DCA
Elite
Jun 23
Chicago, United States
77% AI deal score
$1,556
$847
Save $709
From DCA
Elite
Aug 19
Chicago, United States
77% AI deal score
$779
$459
Save $320
From DCA
Elite
Aug 11
Chicago, United States
77% AI deal score
$779
$459
Save $320
From DCA
Elite
Jul 13
Chicago, United States
77% AI deal score
$1,251
$700
Save $551
From DCA
Elite
Jun 17
Chicago, United States
76% AI deal score
$1,877
$772
Save $1,105
From DCA
Elite
Jul 14
Chicago, United States
76% AI deal score
$616
$459
Save $157
From DCA
Elite
Sep 09
Chicago, United States
76% AI deal score
$718
$459
Save $259
From DCA
Elite
Jul 07
Chicago, United States
76% AI deal score
$615
$459
Save $156
From DCA
Elite
Aug 09
Chicago, United States
75% AI deal score
$1,562
$698
Save $864
From DCA
Elite
Aug 14
Chicago, United States
75% AI deal score
$1,537
$912
Save $625
From DCA
Elite
Jun 17
Chicago, United States
75% AI deal score
$1,859
$1,118
Save $741
From DCA
Elite
Jun 18
Chicago, United States
75% AI deal score
$1,879
$1,118
Save $761
From DCA
Elite
Jul 28
Chicago, United States
75% AI deal score
$616
$459
Save $157
From DCA
Elite
Jul 14
Chicago, United States
75% AI deal score
$607
$459
Save $148
From IAD
Elite
Jul 28
Chicago, United States
74% AI deal score
$571
$477
Save $94
From IAD
Elite
Jul 08
Chicago, United States
74% AI deal score
$591
$477
Save $114
From IAD
Elite
Jul 21
Chicago, United States
74% AI deal score
$575
$477
Save $98
From IAD
Elite
Aug 11
Chicago, United States
74% AI deal score
$611
$477
Save $134
From IAD
Elite
Aug 26
Chicago, United States
74% AI deal score
$605
$477
Save $128
From BWI
Elite
Jul 07
Chicago, United States
74% AI deal score
$584
$477
Save $107
From BWI
Elite
Oct 21
Chicago, United States
74% AI deal score
$642
$477
Save $165
From DCA
Elite
Jul 28
Chicago, United States
74% AI deal score
$1,016
$631
Save $385
From DCA
Elite
Jul 04
Chicago, United States
74% AI deal score
$1,080
$673
Save $407
From DCA
Elite
Nov 03
Chicago, United States
74% AI deal score
$1,206
$748
Save $458
From BWI
Elite
Jul 14
Chicago, United States
74% AI deal score
$575
$459
Save $116
From BWI
Elite
Jul 08
Chicago, United States
74% AI deal score
$573
$459
Save $114
From BWI
Elite
Jul 15
Chicago, United States
74% AI deal score
$575
$459
Save $116
From DCA
Elite
Jun 30
Chicago, United States
74% AI deal score
$689
$479
Save $210
From DCA
Elite
Aug 18
Chicago, United States
73% AI deal score
$582
$477
Save $105
From DCA
Elite
Oct 13
Chicago, United States
73% AI deal score
$591
$477
Save $114
From DCA
Elite
Jun 25
Chicago, United States
73% AI deal score
$1,611
$1,073
Save $538
From DCA
Elite
Jul 15
Chicago, United States
72% AI deal score
$607
$459
Save $148
From DCA
Elite
Jul 22
Chicago, United States
71% AI deal score
$1,020
$747
Save $273
From DCA
Elite
Jul 07
Chicago, United States
71% AI deal score
$1,142
$868
Save $274
From DCA
Elite
Jul 04
Chicago, United States
70% AI deal score
$1,054
$769
Save $285
From DCA
Elite
Oct 29
Chicago, United States
69% AI deal score
$718
$527
Save $191
From DCA
Elite
Sep 09
Chicago, United States
68% AI deal score
$545
$477
Save $68
From DCA
Elite
Sep 02
Chicago, United States
68% AI deal score
$544
$477
Save $67
From IAD
Elite
Sep 23
Chicago, United States
68% AI deal score
$566
$477
Save $89
From IAD
Elite
Jul 14
Chicago, United States
68% AI deal score
$516
$459
Save $57
From IAD
Elite
Jul 28
Chicago, United States
68% AI deal score
$518
$459
Save $59
From IAD
Elite
Aug 12
Chicago, United States
68% AI deal score
$615
$459
Save $156
From IAD
Elite
Aug 19
Chicago, United States
68% AI deal score
$615
$459
Save $156
From IAD
Elite
Aug 11
Chicago, United States
68% AI deal score
$615
$459
Save $156
From DCA
Elite
Nov 11
Chicago, United States
68% AI deal score
$699
$550
Save $149
From IAD
Elite
Jul 14
Chicago, United States
67% AI deal score
$511
$459
Save $52
From IAD
Elite
Jul 15
Chicago, United States
67% AI deal score
$511
$459
Save $52
From IAD
Elite
Jul 07
Chicago, United States
67% AI deal score
$508
$459
Save $49
From DCA
Elite
Nov 07
Chicago, United States
66% AI deal score
$602
$545
Save $57
From DCA
Elite
Sep 03
Chicago, United States
66% AI deal score
$696
$493
Save $203
From DCA
Elite
Jul 14
Chicago, United States
65% AI deal score
$1,102
$918
Save $184
From DCA
Elite
Jul 02
Chicago, United States
65% AI deal score
$1,361
$1,038
Save $323
From DCA
Elite
Jun 19
Chicago, United States
65% AI deal score
$934
$779
Save $155
From DCA
Elite
Aug 14
Chicago, United States
50% AI deal score
$1,553
$1,179
Save $374
From DCA
Elite
Jun 28
Chicago, United States
50% AI deal score
$707
$602
Save $105
From DCA
Elite
Jul 23
Chicago, United States
49% AI deal score
$1,333
$1,078
Save $255
From DCA
Elite
Jun 18
Chicago, United States
49% AI deal score
$1,859
$1,509
Save $350
From DCA
Elite
Jul 15
Chicago, United States
49% AI deal score
$613
$519
Save $94
From BWI
Elite
Sep 25
Chicago, United States
48% AI deal score
$2,200
$2,116
Save $84
From BWI
Elite
Sep 04
Chicago, United States
48% AI deal score
$2,170
$2,151
Save $19
From DCA
Elite
Aug 02
Chicago, United States
48% AI deal score
$1,211
$969
Save $242
From DCA
Elite
Jun 18
Chicago, United States
48% AI deal score
$1,816
$1,509
Save $307
From DCA
Elite
Aug 02
Chicago, United States
48% AI deal score
$829
$663
Save $166
From DCA
Elite
Nov 13
Chicago, United States
47% AI deal score
$1,085
$938
Save $147
From DCA
Elite
Jul 15
Chicago, United States
47% AI deal score
$609
$550
Save $59
From DCA
Elite
Jun 18
Chicago, United States
47% AI deal score
$924
$825
Save $99
From BWI
Elite
Sep 04
Chicago, United States
46% AI deal score
$2,116
From DCA
Elite
Nov 06
Chicago, United States
46% AI deal score
$609
From DCA
Elite
Jul 01
Chicago, United States
46% AI deal score
$1,231
$1,116
Save $115
From DCA
Elite
Jun 29
Chicago, United States
46% AI deal score
$1,426
$1,274
Save $152
From DCA
Elite
Jul 31
Chicago, United States
45% AI deal score
$1,317
$1,219
Save $98
From DCA
Elite
Jul 18
Chicago, United States
45% AI deal score
$1,342
$1,238
Save $104
From DCA
Elite
Sep 15
Chicago, United States
44% AI deal score
$561
$543
Save $18
From DCA
Elite
Oct 16
Chicago, United States
44% AI deal score
$1,233
$1,159
Save $74
From BWI
Elite
Sep 25
Chicago, United States
43% AI deal score
$2,172
From BWI
Elite
Sep 04
Chicago, United States
43% AI deal score
$2,207
From DCA
Elite
Jun 20
Chicago, United States
43% AI deal score
$1,284
$1,277
Save $7
From DCA
Elite
Jul 31
Chicago, United States
43% AI deal score
$1,332
$1,319
Save $13
From DCA
Elite
Jul 30
Chicago, United States
43% AI deal score
$619
$610
Save $9
From DCA
Elite
Jul 11
Chicago, United States
42% AI deal score
$643
From DCA
Elite
Jul 10
Chicago, United States
42% AI deal score
$651
From DCA
Elite
Jul 09
Chicago, United States
42% AI deal score
$668
From DCA
Elite
Jul 02
Chicago, United States
42% AI deal score
$705
From DCA
Elite
Dec 23
Chicago, United States
42% AI deal score
$1,512
From BWI
Elite
Sep 25
Chicago, United States
41% AI deal score
$2,202
From DCA
Elite
Nov 21
Chicago, United States
41% AI deal score
$827
From DCA
Elite
Jul 03
Chicago, United States
41% AI deal score
$1,116
From BWI
Elite
Sep 25
Chicago, United States
40% AI deal score
$2,334
From BWI
Elite
Sep 04
Chicago, United States
40% AI deal score
$2,452
From BWI
Elite
Sep 25
Chicago, United States
40% AI deal score
$2,497
From DCA
Elite
Dec 02
Chicago, United States
40% AI deal score
$797
From DCA
Elite
Aug 01
Chicago, United States
40% AI deal score
$1,664
From BWI
Elite
Sep 04
Chicago, United States
39% AI deal score
$2,497
From DCA
Elite
Jun 27
Chicago, United States
39% AI deal score
$1,571
From IAD
Elite
Jul 08
Chicago, United States
37% AI deal score
$2,349
From IAD
Elite
Jun 16
Chicago, United States
36% AI deal score
$4,284
From DCA
Elite
Aug 12
Chicago, United States
36% AI deal score
$1,131