$89+ 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 12/21. Fares are subject to change and may not be available on all flights or dates of travel.
WAS — CHI
Oct 23 — Oct 301
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 58 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 September 23, 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 September 23, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 9/18. 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 10/229:58 am -
Nonstop2h 23m
Mon 10/268:04 am -
1 stop27h 57m
Deal found 9/18![Frontier logo]()
$177
This Kiwi.com deal was found by Cheapflights users on 9/18. 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 12/216:12 pm -
Nonstop2h 24m
Fri 12/2510:53 am -
Nonstop2h 07m
Deal found 9/18![Frontier logo]()
$179
This Kiwi.com deal was found by Cheapflights users on 9/18. 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 10/299:53 am -
Nonstop2h 30m
Fri 11/66:00 am -
Nonstop1h 57m
Deal found 9/18![Frontier logo]()
$180
This Cheapflightsfares deal was found by Cheapflights users on 9/19. 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.
Wed 10/217:50 am -
1 stop11h 41m
Sat 10/246:00 am -
1 stop10h 13m
Deal found 9/19![Frontier logo]()
$181
This Kiwi.com deal was found by Cheapflights users on 9/18. 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 10/299:53 am -
Nonstop2h 30m
Wed 11/47:15 am -
1 stop7h 59m
Deal found 9/18![Frontier logo]()
$181
This Mytrip deal was found by Cheapflights users on 9/18. 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.
Wed 10/288:05 am -
2 stops14h 05m
Sat 10/317:15 am -
1 stop15h 28m
Deal found 9/18![Frontier logo]()
$182
This Kiwi.com deal was found by Cheapflights users on 9/18. 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 11/199:53 am -
Nonstop2h 30m
Fri 11/272:52 pm -
Nonstop2h 10m
Deal found 9/18![Frontier logo]()
$182
This Expedia deal was found by Cheapflights users on 9/20. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/217:50 am -
1 stop11h 41m
Tue 10/277:15 am -
1 stop8h 57m
Deal found 9/20![Frontier logo]()
$183
This Frontier deal was found by Cheapflights users on 9/23. 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 10/1710:22 am -
1 stop9h 09m
Sun 10/186:00 am -
Nonstop2h 03m
Deal found 9/23![Frontier logo]()
$183
This Expedia deal was found by Cheapflights users on 9/18. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/136:08 pm -
1 stop22h 22m
Fri 10/168:11 pm -
1 stop13h 06m
Deal found 9/18![Frontier logo]()
$184
This Super.com deal was found by Cheapflights users on 9/21. 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 10/269:58 am -
Nonstop2h 23m
Thu 10/296:00 am -
Nonstop1h 57m
Deal found 9/21![Frontier logo]()
$185
This Expedia deal was found by Cheapflights users on 9/18. 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 Expedia 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 11/1610:26 am -
1 stop5h 46m
Deal found 9/18![Frontier logo]()
$186
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 September 23, 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 September 23, 2026.
This United Airlines deal was found by Cheapflights users on 9/23. 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 11/76:11 am -
Nonstop2h 19m
Wed 11/111:30 pm -
Nonstop2h 03m
Deal found 9/23![United Airlines logo]()
$297
This Southwest deal was found by Cheapflights users on 9/22. 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 10/216:25 pm -
Nonstop2h 00m
Sat 10/242:40 pm -
Nonstop1h 45m
Deal found 9/22![Southwest logo]()
$297
This Delta deal was found by Cheapflights users on 9/20. 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.
Wed 10/2112:27 pm -
1 stop4h 47m
Sat 10/2412:27 pm -
1 stop9h 59m
Deal found 9/20![Delta logo]()
$309
This United Airlines deal was found by Cheapflights users on 9/18. 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 10/248:20 am -
Nonstop2h 17m
Wed 10/289:41 pm -
Nonstop1h 49m
Deal found 9/18![United Airlines logo]()
$297
This Southwest deal was found by Cheapflights users on 9/22. 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.
Tue 11/171:35 pm -
Nonstop2h 05m
Tue 11/176:15 pm -
Nonstop1h 55m
Deal found 9/22![Southwest logo]()
$297
This Delta deal was found by Cheapflights users on 9/22. 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.
Wed 11/46:10 am -
1 stop5h 18m
Mon 11/98:45 am -
1 stop6h 12m
Deal found 9/22![Delta logo]()
$317
This Southwest deal was found by Cheapflights users on 9/19. 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.
Tue 12/2210:05 pm -
Nonstop2h 05m
Tue 12/299:05 pm -
Nonstop1h 45m
Deal found 9/19![Southwest logo]()
$297
This United Airlines deal was found by Cheapflights users on 9/22. 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 10/217:10 pm -
Nonstop2h 19m
Sat 10/247:30 am -
Nonstop2h 00m
Deal found 9/22![United Airlines logo]()
$297
This Delta deal was found by Cheapflights users on 9/22. 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 10/155:35 pm -
1 stop3h 55m
Mon 10/196:00 am -
1 stop5h 39m
Deal found 9/22![Delta logo]()
$317
This Southwest deal was found by Cheapflights users on 9/21. 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 10/159:00 am -
Nonstop2h 00m
Mon 10/196:25 pm -
Nonstop1h 50m
Deal found 9/21![Southwest logo]()
$297
This United Airlines deal was found by Cheapflights users on 9/22. 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.
Fri 11/136:25 am -
Nonstop2h 17m
Mon 11/165:59 am -
Nonstop1h 56m
Deal found 9/22![United Airlines logo]()
$308
This Delta deal was found by Cheapflights users on 9/22. 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 10/2412:20 pm -
1 stop5h 06m
Mon 10/266:10 am -
1 stop4h 40m
Deal found 9/22![Delta logo]()
$317
This Southwest deal was found by Cheapflights users on 9/23. 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 10/199:00 pm -
Nonstop2h 00m
Wed 10/286:30 pm -
Nonstop1h 55m
Deal found 9/23![Southwest logo]()
$297
This United Airlines deal was found by Cheapflights users on 9/18. 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.
Fri 10/237:46 am -
Nonstop2h 14m
Mon 10/269:00 am -
Nonstop2h 05m
Deal found 9/18![United Airlines logo]()
$308
This Delta deal was found by Cheapflights users on 9/22. 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 10/156:05 am -
1 stop4h 27m
Mon 10/196:44 pm -
1 stop3h 32m
Deal found 9/22![Delta logo]()
$317
This Southwest deal was found by Cheapflights users on 9/20. 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 10/151:05 pm -
Nonstop2h 00m
Mon 10/1911:10 am -
Nonstop1h 50m
Deal found 9/20![Southwest logo]()
$297
This United Airlines deal was found by Cheapflights users on 9/20. 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 10/286:10 am -
Nonstop2h 19m
Fri 10/306:29 pm -
Nonstop2h 13m
Deal found 9/20![United Airlines logo]()
$310
This Delta deal was found by Cheapflights users on 9/19. 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 11/76:00 am -
1 stop5h 37m
Tue 11/106:44 pm -
1 stop3h 37m
Deal found 9/19![Delta logo]()
$317
This Southwest deal was found by Cheapflights users on 9/21. 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 10/243:10 pm -
Nonstop2h 00m
Tue 10/271:15 pm -
1 stop3h 30m
Deal found 9/21![Southwest logo]()
$303
This Delta deal was found by Cheapflights users on 9/21. 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 11/512:37 pm -
1 stop4h 55m
Mon 11/96:15 pm -
1 stop5h 43m
Deal found 9/21![Delta logo]()
$317
This United Airlines deal was found by Cheapflights users on 9/19. 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 12/2211:51 am -
Nonstop2h 24m
Sat 12/267:45 pm -
Nonstop2h 00m
Deal found 9/19![United Airlines logo]()
$336
This Southwest deal was found by Cheapflights users on 9/18. 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 10/246:00 am -
1 stop5h 45m
Wed 10/284:50 pm -
Nonstop1h 50m
Deal found 9/18![Southwest logo]()
$307
This Delta deal was found by Cheapflights users on 9/20. 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 10/265:05 pm -
1 stop5h 38m
Thu 10/296:00 am -
1 stop5h 39m
Deal found 9/20![Delta logo]()
$328
This Southwest deal was found by Cheapflights users on 9/18. 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 10/298:40 pm -
Nonstop2h 00m
Mon 11/210:15 am -
1 stop4h 30m
Deal found 9/18![Southwest logo]()
$307
This United Airlines deal was found by Cheapflights users on 9/21. 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 10/3110:09 am -
Nonstop2h 20m
Sun 11/811:00 am -
Nonstop2h 06m
Deal found 9/21![United Airlines logo]()
$348
This Delta deal was found by Cheapflights users on 9/18. 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 11/66:12 pm -
1 stop6h 45m
Tue 11/105:30 am -
1 stop7h 24m
Deal found 9/18![Delta logo]()
$328
This Southwest deal was found by Cheapflights users on 9/18. 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 10/1410:20 am -
Nonstop2h 00m
Sat 10/172:20 pm -
2 stops7h 30m
Deal found 9/18![Southwest logo]()
$308
This United Airlines deal was found by Cheapflights users on 9/20. 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 10/245:10 pm -
Nonstop2h 23m
Sun 10/258:00 am -
Nonstop2h 08m
Deal found 9/20![United Airlines logo]()
$353
This Delta deal was found by Cheapflights users on 9/20. 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 10/306:12 pm -
1 stop5h 21m
Mon 11/26:04 am -
1 stop7h 05m
Deal found 9/20![Delta logo]()
$328
This Southwest deal was found by Cheapflights users on 9/18. 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 10/176:30 am -
Nonstop2h 00m
Sat 10/242:20 pm -
2 stops7h 30m
Deal found 9/18![Southwest logo]()
$308
Last-minute flights from Washington, D.C. to ChicagoDiscover last-minute flight deals from Washington, D.C. to Chicago. Data last updated September 23, 2026 and is based on user searches.
Discover last-minute flight deals from Washington, D.C. to Chicago. Data last updated September 23, 2026 and is based on user searches.
This Frontier deal was found by Cheapflights users on 9/18. 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.
Fri 10/99:58 am -
Nonstop2h 23m
Sat 10/106:00 am -
1 stop11h 30m
Deal found 9/18![Frontier logo]()
$177
This Kiwi.com deal was found by Cheapflights users on 9/18. 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 10/129:58 am -
Nonstop2h 23m
Thu 10/156:00 am -
Nonstop2h 03m
Deal found 9/18![Frontier logo]()
$179
This Kiwi.com deal was found by Cheapflights users on 9/18. 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.
Tue 10/131:56 pm -
1 stop26h 34m
Thu 10/156:00 am -
Nonstop2h 03m
Deal found 9/18![Frontier logo]()
$178
This Expedia deal was found by Cheapflights users on 9/18. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/136:08 pm -
1 stop22h 22m
Fri 10/168:11 pm -
1 stop13h 06m
Deal found 9/18![Frontier logo]()
$184
This Super.com deal was found by Cheapflights users on 9/18. 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.
Fri 10/169:58 am -
Nonstop2h 23m
Mon 10/196:00 am -
Nonstop2h 03m
Deal found 9/18![Frontier logo]()
$183
This Cheapflightsfares deal was found by Cheapflights users on 9/19. 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.
Wed 10/217:50 am -
1 stop11h 41m
Tue 10/277:15 am -
1 stop8h 57m
Deal found 9/19![Frontier logo]()
$181
This Expedia deal was found by Cheapflights users on 9/20. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/217:50 am -
1 stop11h 41m
Sat 10/246:00 am -
1 stop10h 13m
Deal found 9/20![Frontier logo]()
$183
This Mytrip deal was found by Cheapflights users on 9/18. 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 10/239:12 pm -
1 stop15h 20m
Thu 10/296:00 am -
Nonstop1h 57m
Deal found 9/18![Frontier logo]()
$182
This Super.com deal was found by Cheapflights users on 9/21. 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 10/269:58 am -
Nonstop2h 23m
Thu 10/296:00 am -
Nonstop1h 57m
Deal found 9/21![Frontier logo]()
$185
This Mytrip deal was found by Cheapflights users on 9/18. 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.
Wed 10/288:05 am -
2 stops14h 05m
Sat 10/317:15 am -
1 stop15h 28m
Deal found 9/18![Frontier logo]()
$182
This Kiwi.com deal was found by Cheapflights users on 9/18. 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 10/299:53 am -
Nonstop2h 30m
Sat 10/317:15 am -
1 stop7h 59m
Deal found 9/18![Frontier logo]()
$180
This Kiwi.com deal was found by Cheapflights users on 9/18. 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 10/299:53 am -
Nonstop2h 30m
Wed 11/47:15 am -
1 stop7h 59m
Deal found 9/18![Frontier logo]()
$181
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 September 23, 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 September 23, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/20. 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 12/216:12 pm -
Nonstop2h 24m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/20![Frontier logo]()
$89
This Super.com deal was found by Cheapflights users on 9/21. 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.
Tue 10/206:08 pm -
1 stop22h 22m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Frontier logo]()
$90
This Kiwi.com deal was found by Cheapflights users on 9/19. 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 12/169:35 am -
1 stop28h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/19![Frontier logo]()
$90
This Super.com deal was found by Cheapflights users on 9/18. 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.
Tue 11/177:05 pm -
1 stop22h 58m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Frontier logo]()
$91
This Super.com deal was found by Cheapflights users on 9/18. 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 10/247:50 am -
1 stop11h 41m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Frontier logo]()
$92
This Booking.com deal was found by Cheapflights users on 9/18. 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 10/99:58 am -
Nonstop2h 23m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Frontier logo]()
$92
This CheapOair deal was found by Cheapflights users on 9/19. 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 11/118:05 am -
1 stop5h 46m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/19![Frontier logo]()
$93
This Super.com deal was found by Cheapflights users on 9/23. 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.
Thu 11/262:42 pm -
Nonstop2h 28m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/23![Frontier logo]()
$93
This Jetabroad deal was found by Cheapflights users on 9/21. 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 Jetabroad is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/1512:06 pm -
1 stop7h 31m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Frontier logo]()
$94
This Cheapflightsfares deal was found by Cheapflights users on 9/19. 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 10/159:58 am -
Nonstop2h 23m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/19![Frontier logo]()
$94
This Super.com deal was found by Cheapflights users on 9/22. 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.
Tue 10/66:13 pm -
1 stop22h 07m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/22![Frontier logo]()
$95
This Cheapflightsfares deal was found by Cheapflights users on 9/23. 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.
Tue 10/136:08 pm -
1 stop22h 22m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/23![Frontier logo]()
$96
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 September 23, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $177 (Cheapflightsfares) |
One-way from | $89 (Kiwi.com) |
Popular in | June |
Cheapest in | January |
Average price | $294 |
Good round-trip deal | $291 or less |
Good one-way deal | $167 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 September 23, 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
BaltimoreChicago
BWI Baltimore/Washington - ORD Chicago O'Hare Intl
BWIORD
Baltimore/Washington
Thu 10/15
9:58 am-11:21 am
Nonstop2h 23m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$94
Washington, D.C.Chicago
IAD Washington, D.C. Dulles Intl - MDW Chicago Midway
IADMDW
Washington, D.C. Dulles Intl
Sat 10/24
7:50 am-11:43 pm
1 stop16h 53m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$106
Washington, D.C.Chicago
DCA Washington, D.C. Reagan-National - ORD Chicago O'Hare Intl
DCAORD
Washington, D.C. Reagan-National
Mon 11/9
7:40 am-9:00 am
Nonstop2h 20m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$149
BaltimoreChicago
BWI Baltimore/Washington - MDW Chicago Midway
BWIMDW
Baltimore/Washington
Wed 10/28
8:20 pm-9:25 pm
Nonstop2h 05m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$149
Washington, D.C.Chicago
DCA Washington, D.C. Reagan-National - ORD Chicago O'Hare Intl
DCAORD
Washington, D.C. Reagan-National
Thu 10/22
10:30 am-11:46 am
Nonstop2h 16m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$149
BaltimoreChicago
BWI Baltimore/Washington - MDW Chicago Midway
BWIMDW
Baltimore/Washington
Sat 11/21
9:55 pm-11:05 pm
Nonstop2h 10m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$149
Washington, D.C.Chicago
IAD Washington, D.C. Dulles Intl - ORD Chicago O'Hare Intl
IADORD
Washington, D.C. Dulles Intl
Sat 10/24
10:18 pm-11:31 pm
Nonstop2h 13m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$149
BaltimoreChicago
BWI Baltimore/Washington - MDW Chicago Midway
BWIMDW
Baltimore/Washington
Mon 11/23
12:35 pm-1:40 pm
Nonstop2h 05m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$149
Washington, D.C.Chicago
IAD Washington, D.C. Dulles Intl - ORD Chicago O'Hare Intl
IADORD
Washington, D.C. Dulles Intl
Thu 10/22
3:47 pm-5:05 pm
Nonstop2h 18m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$149
BaltimoreChicago
BWI Baltimore/Washington - MDW Chicago Midway
BWIMDW
Baltimore/Washington
Wed 10/14
8:20 pm-9:25 pm
Nonstop2h 05m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$149
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 September.
| 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 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
BWI-ORD
DCA-ORD
BWI-MDW
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
BWI-ORD
DCA-ORD
BWI-MDW
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 $293). Flying from Washington, D.C. to Chicago in June is currently the most expensive (average of $393). 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 September 23, 2026.
Unlike in the morning, when flights are generally more expensive, you can save up to 9% on flights from Washington, D.C. to Chicago by exploring options for tickets in the evening.
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 September 23, 2026.
The most flights from WAS to CHI are scheduled on a Tuesday (103 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (36 on average).
How much does it cost to fly round-trip from Washington, D.C. to Chicago?
Airfare is below average for this route at the moment.
Washington, D.C. to Chicago flights typically cost between $205 and $362 in October.The cheapest round-trip price found within the last 5 days was $177 on Frontier (Oct 22-Oct 26).
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 47 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 September 19, 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 September 23, 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.
Boarding
8.1
Comfort
8.0
Overall
8.0
Food
7.0
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Comfort
8.0
Overall
8.0
Food
7.0
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Comfort
8.0
Overall
8.0
Food
7.0
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Comfort
8.0
Overall
8.0
Food
7.0
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Comfort
8.0
Overall
8.0
Food
7.0
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Comfort
8.0
Overall
8.0
Food
7.0
Entertainment
7.5
Crew
8.6
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
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter
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Washington, D.C. and Chicago flights
Browse other Washington, D.C. and Chicago flight options. Last updated on September 23, 2026.
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Top 5 airlines flying from Washington, D.C. to Chicago
Discover the top 5 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 September 23, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$29 | Average$209 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$149 | Average$441 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$176 | Average$379 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$179 | Average$373 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$186 | Average$342 | FlexibilityNo cancel fee | On-time71% |