$116+ Cheap flights from Washington, D.C. (WAS) to Chicago (CHI)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/23. Fares are subject to change and may not be available on all flights or dates of travel.
WAS — CHI
Dec 4 — Dec 111
Round-trip
1 adult, Economy
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Find cheap flights from Washington, D.C. to Chicago with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheapflights Tip: The best prices from Washington, D.C. to Chicago are usually found in January or February, booked 60 days in advance, depart on a Saturday or Thursday and return on a Friday
Cheap flight deals from Washington, D.C. to Chicago
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Cheapest flights from Washington, D.C. to ChicagoExplore the most affordable flight options available from Washington, D.C. to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 4, 2026.
Explore the most affordable flight options available from Washington, D.C. to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 4, 2026.
This Frontier deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/219:56 pm -
1 stop10h 51m
Tue 11/247:49 am -
1 stop6h 14m
Deal found 11/2![Frontier logo]()
$220
This Frontier deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/2110:47 pm -
1 stop10h 27m
Tue 11/249:09 am -
1 stop4h 54m
Deal found 11/2![Frontier logo]()
$220
This Orbitz deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/136:07 pm -
1 stop22h 30m
Mon 11/167:55 am -
1 stop11h 16m
Deal found 11/3![Frontier logo]()
$223
This CheapOair deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/112:06 pm -
1 stop24h 27m
Mon 12/75:02 pm -
1 stop20h 47m
Deal found 11/3![Frontier logo]()
$223
This Cheapflightsfares deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/181:55 pm -
1 stop10h 36m
Wed 12/234:59 pm -
1 stop6h 52m
Deal found 11/2![Frontier logo]()
$224
This Kiwi.com deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/310:22 pm -
1 stop9h 53m
Sun 12/68:30 am -
1 stop5h 19m
Deal found 11/3![Frontier logo]()
$225
This Trip.com deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/126:00 pm -
1 stop7h 54m
Mon 12/147:25 am -
1 stop8h 30m
Deal found 11/3![Frontier logo]()
$226
This CheapOair deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/197:32 am -
1 stop12h 13m
Thu 11/266:20 am -
1 stop6h 05m
Deal found 10/30![Frontier logo]()
$226
This Kiwi.com deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/1410:35 pm -
1 stop13h 58m
Mon 12/211:11 pm -
1 stop10h 40m
Deal found 10/30![Frontier logo]()
$226
This CheapOair deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/27:00 am -
1 stop18h 53m
Fri 12/47:00 am -
1 stop13h 55m
Deal found 11/2![Frontier logo]()
$227
This CheapOair deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/310:22 pm -
1 stop9h 53m
Sat 12/58:30 am -
1 stop5h 19m
Deal found 11/1![Frontier logo]()
$227
This Kiwi.com deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/187:48 am -
1 stop10h 59m
Thu 11/196:08 am -
1 stop16h 35m
Deal found 11/2![Frontier logo]()
$227
Best flights from Washington, D.C. to ChicagoDiscover carefully curated flight deals from Washington, D.C. to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated November 4, 2026.
Discover carefully curated flight deals from Washington, D.C. to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated November 4, 2026.
This United Airlines deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/37:42 am -
Nonstop2h 18m
Mon 12/75:00 pm -
Nonstop2h 11m
Deal found 11/4![United Airlines logo]()
$277
This Southwest deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/159:35 pm -
Nonstop2h 05m
Tue 1/196:00 am -
Nonstop1h 55m
Deal found 10/30![Southwest logo]()
$277
This Delta deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/119:55 am -
1 stop4h 01m
Mon 1/115:18 pm -
1 stop4h 48m
Deal found 10/30![Delta logo]()
$297
This United Airlines deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/1610:10 am -
Nonstop2h 23m
Sat 12/197:04 am -
Nonstop1h 58m
Deal found 11/3![United Airlines logo]()
$277
This Southwest deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/258:25 am -
1 stop4h 40m
Wed 12/308:55 pm -
Nonstop1h 45m
Deal found 10/31![Southwest logo]()
$287
This Delta deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/112:30 pm -
1 stop4h 47m
Fri 12/411:39 am -
1 stop6h 00m
Deal found 11/1![Delta logo]()
$297
This United Airlines deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/226:10 am -
Nonstop2h 22m
Tue 12/298:52 am -
Nonstop2h 02m
Deal found 11/1![United Airlines logo]()
$277
This Southwest deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/256:10 am -
Nonstop2h 05m
Thu 12/318:15 am -
1 stop4h 50m
Deal found 10/31![Southwest logo]()
$287
This Delta deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/251:50 pm -
1 stop7h 13m
Thu 12/317:00 am -
1 stop3h 56m
Deal found 10/30![Delta logo]()
$297
This United Airlines deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/58:15 am -
Nonstop2h 22m
Mon 12/79:35 pm -
Nonstop1h 49m
Deal found 10/31![United Airlines logo]()
$277
This Southwest deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/101:00 pm -
Nonstop2h 15m
Mon 12/148:15 am -
1 stop4h 50m
Deal found 11/3![Southwest logo]()
$287
This Delta deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/76:00 am -
1 stop7h 04m
Fri 12/116:00 am -
1 stop4h 43m
Deal found 11/2![Delta logo]()
$297
This Southwest deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/279:35 am -
Nonstop2h 10m
Mon 2/18:40 am -
1 stop4h 55m
Deal found 11/3![Southwest logo]()
$287
This Delta deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/108:07 am -
1 stop4h 57m
Thu 12/106:41 pm -
1 stop3h 42m
Deal found 11/2![Delta logo]()
$297
This United Airlines deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/1010:15 pm -
Nonstop2h 14m
Sun 12/138:52 am -
Nonstop2h 01m
Deal found 11/2![United Airlines logo]()
$318
This Delta deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/256:00 am -
1 stop3h 49m
Mon 1/46:40 pm -
1 stop3h 37m
Deal found 11/3![Delta logo]()
$297
This Southwest deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/216:45 pm -
Nonstop2h 15m
Sun 1/248:25 am -
Nonstop2h 00m
Deal found 11/2![Southwest logo]()
$318
This Delta deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/38:07 am -
1 stop4h 57m
Tue 12/81:02 pm -
1 stop6h 09m
Deal found 11/3![Delta logo]()
$297
This Southwest deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/142:40 pm -
1 stop4h 10m
Mon 12/215:10 pm -
Nonstop1h 45m
Deal found 10/30![Southwest logo]()
$319
This United Airlines deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/286:25 am -
Nonstop2h 18m
Thu 12/33:00 pm -
Nonstop2h 15m
Deal found 11/3![United Airlines logo]()
$358
This Delta deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/227:43 pm -
1 stop5h 12m
Mon 1/251:41 pm -
1 stop3h 53m
Deal found 11/1![Delta logo]()
$297
This United Airlines deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/25:05 pm -
Nonstop2h 25m
Sun 1/107:45 am -
Nonstop2h 10m
Deal found 11/3![United Airlines logo]()
$363
This Southwest deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/207:40 pm -
1 stop5h 40m
Fri 12/253:50 pm -
1 stop5h 20m
Deal found 11/2![Southwest logo]()
$338
This Delta deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/236:01 am -
1 stop4h 15m
Sun 1/246:00 am -
1 stop5h 03m
Deal found 10/31![Delta logo]()
$338
This United Airlines deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/266:25 am -
Nonstop2h 18m
Mon 11/307:45 pm -
Nonstop1h 58m
Deal found 11/2![United Airlines logo]()
$374
This Southwest deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/216:55 pm -
1 stop5h 05m
Tue 11/2412:50 pm -
2 stops7h 55m
Deal found 10/30![Southwest logo]()
$353
This Delta deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/36:00 am -
1 stop4h 37m
Sun 12/66:41 pm -
1 stop3h 42m
Deal found 10/31![Delta logo]()
$338
This United Airlines deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/215:05 pm -
Nonstop2h 25m
Wed 12/307:00 am -
Nonstop1h 59m
Deal found 11/3![United Airlines logo]()
$377
This Delta deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 1/1912:53 pm -
1 stop6h 07m
Sun 1/246:00 am -
1 stop5h 03m
Deal found 11/1![Delta logo]()
$338
This Southwest deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/191:55 pm -
2 stops7h 15m
Sat 12/265:30 am -
Nonstop1h 50m
Deal found 11/3![Southwest logo]()
$374
Last-minute flights from Washington, D.C. to ChicagoDiscover last-minute flight deals from Washington, D.C. to Chicago. Data last updated November 4, 2026 and is based on user searches.
Discover last-minute flight deals from Washington, D.C. to Chicago. Data last updated November 4, 2026 and is based on user searches.
This Orbitz deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/136:07 pm -
1 stop22h 30m
Mon 11/167:55 am -
1 stop11h 16m
Deal found 11/3![Frontier logo]()
$223
This Kiwi.com deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/187:48 am -
1 stop10h 59m
Thu 11/196:08 am -
1 stop16h 35m
Deal found 11/2![Frontier logo]()
$227
This CheapOair deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/197:32 am -
1 stop12h 13m
Thu 11/266:20 am -
1 stop6h 05m
Deal found 10/30![Frontier logo]()
$226
This Frontier deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/219:56 pm -
1 stop10h 51m
Tue 11/247:49 am -
1 stop6h 14m
Deal found 11/2![Frontier logo]()
$220
This Frontier deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/2110:47 pm -
1 stop10h 27m
Tue 11/249:09 am -
1 stop4h 54m
Deal found 11/2![Frontier logo]()
$220
This CheapOair deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/112:06 pm -
1 stop24h 27m
Mon 12/75:02 pm -
1 stop20h 47m
Deal found 11/3![Frontier logo]()
$223
This CheapOair deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/27:00 am -
1 stop18h 53m
Fri 12/47:00 am -
1 stop13h 55m
Deal found 11/2![Frontier logo]()
$227
This Kiwi.com deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/310:22 pm -
1 stop9h 53m
Sun 12/68:30 am -
1 stop5h 19m
Deal found 11/3![Frontier logo]()
$225
This CheapOair deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/310:22 pm -
1 stop9h 53m
Sat 12/58:30 am -
1 stop5h 19m
Deal found 11/1![Frontier logo]()
$227
This Mytrip deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/510:35 pm -
2 stops25h 31m
Fri 12/1110:29 pm -
1 stop15h 20m
Deal found 11/3![Frontier logo]()
$228
This Trip.com deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/126:00 pm -
1 stop7h 54m
Mon 12/147:25 am -
1 stop8h 30m
Deal found 11/3![Frontier logo]()
$226
This Cheapflightsfares deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/181:55 pm -
1 stop10h 36m
Thu 12/245:58 am -
1 stop8h 15m
Deal found 11/2![Frontier logo]()
$224
One-way flights from Washington, D.C. to ChicagoSearch for one-way flight options from Washington, D.C. to Chicago. Find affordable one-way fares based on user searches. Data last updated November 4, 2026.
Search for one-way flight options from Washington, D.C. to Chicago. Find affordable one-way fares based on user searches. Data last updated November 4, 2026.
This Super.com deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/236:00 pm -
1 stop7h 53m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/1![Frontier logo]()
$116
This Booking.com deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/46:00 pm -
1 stop7h 53m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/1![Frontier logo]()
$117
This Frontier deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/263:58 pm -
1 stop8h 36m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Frontier logo]()
$117
This Super.com deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/216:00 pm -
1 stop7h 53m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Frontier logo]()
$118
This Kiwi.com deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/216:50 am -
1 stop17h 28m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![Frontier logo]()
$118
This Super.com deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/216:50 am -
1 stop7h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![Frontier logo]()
$118
This CheapOair deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/36:00 pm -
1 stop7h 53m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Frontier logo]()
$119
This Mytrip deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/2010:47 pm -
1 stop15h 57m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/31![Frontier logo]()
$119
This Trip.com deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/76:00 pm -
1 stop7h 54m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/31![Frontier logo]()
$120
This Frontier deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/225:30 am -
1 stop7h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/30![Frontier logo]()
$120
This Frontier deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/186:07 pm -
1 stop6h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![Frontier logo]()
$120
This Cheapflightsfares deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/261:54 pm -
1 stop11h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![Frontier logo]()
$121
Find flight deals from Washington, D.C. to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from Washington, D.C. (WAS) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated November 4, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $220 (Frontier) |
One-way from | $116 (Super.com) |
Popular in | October |
Cheapest in | January |
Average price | $318 |
Good round-trip deal | $323 or less |
Good one-way deal | $166 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Washington, D.C. to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated November 4, 2026.
Use the filters below to find and compare flights from Washington, D.C. to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Washington, D.C.Chicago
DCA Washington, D.C. Reagan-National - ORD Chicago O'Hare Intl
DCAORD
Washington, D.C. Reagan-National
Wed 11/25
6:06 pm-7:30 pm
Nonstop2h 24m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$139
Washington, D.C.Chicago
DCA Washington, D.C. Reagan-National - MDW Chicago Midway
DCAMDW
Washington, D.C. Reagan-National
Tue 12/15
8:55 pm-10:10 pm
Nonstop2h 15m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$139
Washington, D.C.Chicago
DCA Washington, D.C. Reagan-National - ORD Chicago O'Hare Intl
DCAORD
Washington, D.C. Reagan-National
Fri 11/27
6:06 pm-7:30 pm
Nonstop2h 24m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$139
Quickest round-trip
Washington, D.C.Chicago
DCA Washington, D.C. Reagan-National - MDW Chicago Midway
DCAMDW
Washington, D.C. Reagan-National
Thu 12/17
10:45 am-11:50 am
Nonstop2h 05m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$139
Washington, D.C.Chicago
DCA Washington, D.C. Reagan-National - ORD Chicago O'Hare Intl
DCAORD
Washington, D.C. Reagan-National
Fri 1/8
2:25 pm-3:49 pm
Nonstop2h 24m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$139
Washington, D.C.Chicago
DCA Washington, D.C. Reagan-National - MDW Chicago Midway
DCAMDW
Washington, D.C. Reagan-National
Wed 12/23
9:00 pm-10:05 pm
Nonstop2h 05m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$139
Washington, D.C.Chicago
DCA Washington, D.C. Reagan-National - ORD Chicago O'Hare Intl
DCAORD
Washington, D.C. Reagan-National
Sat 12/12
6:25 am-7:43 am
Nonstop2h 18m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$139
Washington, D.C.Chicago
DCA Washington, D.C. Reagan-National - MDW Chicago Midway
DCAMDW
Washington, D.C. Reagan-National
Fri 11/27
6:30 pm-7:40 pm
Nonstop2h 10m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$139
Washington, D.C.Chicago
IAD Washington, D.C. Dulles Intl - ORD Chicago O'Hare Intl
IADORD
Washington, D.C. Dulles Intl
Sat 1/9
8:15 am-9:40 am
Nonstop2h 25m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$139
Washington, D.C.Chicago
IAD Washington, D.C. Dulles Intl - ORD Chicago O'Hare Intl
IADORD
Washington, D.C. Dulles Intl
Sat 12/19
10:45 pm-12:01 am
Nonstop2h 16m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$139
Showing 1-10 of 60 resultsSorted by cheapest first
Compare providers for flights from Washington, D.C. to Chicago
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Washington, D.C. to Chicago in November.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star | |
| Price Accuracy1 star | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Washington, D.C.-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Washington, D.C.-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Washington, D.C.-Chicago flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Washington, D.C.-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Washington, D.C.-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Washington, D.C. to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Washington, D.C. with our price prediction graph.
WAS-CHI
DCA-ORD
DCA-MDW
IAD-ORD
IAD-MDW
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Washington, D.C. to Chicago
WAS-CHI
DCA-ORD
DCA-MDW
IAD-ORD
IAD-MDW
What is the cheapest month to book a flight from Washington, D.C. to Chicago?
Currently, January is the cheapest month in which you can book a flight from Washington, D.C. to Chicago (average of $299). Flying from Washington, D.C. to Chicago in October is currently the most expensive (average of $401). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from WAS to CHI?
Find hourly flight availability from Washington, D.C. to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated November 4, 2026.
Unlike in the morning, when flights are generally more expensive, you can save up to 10% on flights from Washington, D.C. to Chicago by exploring options for tickets at noon.
Weekly flight availability from Washington, D.C. to Chicago
Explore weekly flight availability from Washington, D.C. to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated November 4, 2026.
The most flights from WAS to CHI are scheduled on a Monday (97 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (38 on average).
How much does it cost to fly round-trip from Washington, D.C. to Chicago?
Airfare is typical for this route at the moment.
Washington, D.C. to Chicago flights typically cost between $218 and $399 in November.The cheapest round-trip price found within the last 5 days was $220 on Frontier (Nov 21-Nov 24).
How far ahead should I book a flight from Washington, D.C. to Chicago?
To ensure you get the cheapest price possible for a flight from Washington, D.C. to Chicago, you should look to book at least 59 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
What is the cheapest day to fly from Washington, D.C. to Chicago?
Use this chart to determine the cheapest time to fly round-trip from Washington, D.C. to Chicago. Price data was last updated on October 31, 2026.
Travelers seeking maximum savings on their Washington, D.C. to Chicago flight should consider departing on Friday at noon when fares are most often at their lowest. Sunday evenings flights should be avoided if possible as fares are typically the most expensive at this time.
The best insider tips for Washington, D.C. to Chicago flights
AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Washington, D.C. to Chicago trip
Our travel experts
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated November 4, 2026.
Read reviews from past customers who have flown Southwest,Delta, andUnited Airlines from Washington, D.C. to Chicago. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Overall
8.0
Food
7.0
Crew
8.6
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
8.0
Food
7.0
Crew
8.6
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
8.0
Food
7.0
Crew
8.6
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
8.0
Food
7.0
Crew
8.6
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
8.0
Food
7.0
Crew
8.6
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
8.0
Food
7.0
Crew
8.6
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Related info for your journey
Find useful and relevant information for your journey from Washington, D.C. to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
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Hammond
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Porter
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Washington, D.C. and Chicago flights
Browse other Washington, D.C. and Chicago flight options. Last updated on November 4, 2026.
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Top 4 airlines flying from Washington, D.C. to Chicago
Discover the top 4 airlines that operate flights from Washington, D.C. to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated November 4, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$29 | Average$234 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$177 | Average$393 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$197 | Average$347 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$198 | Average$378 | FlexibilityNo cancel fee | On-time63% |