$114+ Cheap flights from Dulles Intl (IAD) 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 11/11. Fares are subject to change and may not be available on all flights or dates of travel.
IAD — CHI
Nov 25 — Dec 21
Round-trip
1 adult, Economy
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Find cheap flights from Dulles Intl 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. Dulles Intl to Chicago are usually found in February or December, booked 60 days in advance, depart on a Thursday or Friday and return on a Friday
Cheap flight deals from Dulles Intl to Chicago
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Cheapest flights from Dulles Intl to ChicagoExplore the most affordable flight options available from Dulles Intl to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 26, 2026.
Explore the most affordable flight options available from Dulles Intl to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 26, 2026.
This Mytrip deal was found by Cheapflights users on 10/21. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/99:06 pm -
2 stops19h 25m
Wed 11/118:59 am -
2 stops13h 44m
Deal found 10/21![Frontier logo]()
$213
This Delta deal was found by Cheapflights users on 10/22. 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.
Sun 12/66:00 am -
1 stop4h 37m
Sun 12/136:41 pm -
1 stop3h 42m
Deal found 10/22![Delta logo]()
$213
This Mytrip deal was found by Cheapflights users on 10/21. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/710:35 pm -
2 stops27h 33m
Thu 12/1010:37 pm -
2 stops14h 45m
Deal found 10/21![Frontier logo]()
$214
This Expedia deal was found by Cheapflights users on 10/22. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/66:07 pm -
1 stop22h 30m
Mon 11/97:55 am -
1 stop11h 16m
Deal found 10/22![Frontier logo]()
$215
This Mytrip deal was found by Cheapflights users on 10/24. 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.
Tue 11/36:07 pm -
1 stop6h 40m
Tue 11/106:08 am -
1 stop10h 04m
Deal found 10/24![Frontier logo]()
$215
This Kiwi.com deal was found by Cheapflights users on 10/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/147:48 am -
1 stop6h 03m
Sat 11/217:49 am -
1 stop6h 14m
Deal found 10/21![Frontier logo]()
$216
This Mytrip deal was found by Cheapflights users on 10/25. 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 11/46:07 pm -
1 stop6h 40m
Wed 11/116:08 am -
1 stop10h 04m
Deal found 10/25![Frontier logo]()
$216
This Mytrip deal was found by Cheapflights users on 10/25. 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.
Thu 12/36:42 pm -
1 stop13h 33m
Sun 12/68:15 am -
1 stop8h 23m
Deal found 10/25![Frontier logo]()
$217
This Cheapflightsfares deal was found by Cheapflights users on 10/23. 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.
Thu 11/127:32 am -
1 stop11h 15m
Sun 11/156:08 am -
1 stop10h 04m
Deal found 10/23![Frontier logo]()
$217
This Orbitz deal was found by Cheapflights users on 10/21. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/219:56 pm -
1 stop10h 51m
Sun 11/228:52 am -
1 stop11h 09m
Deal found 10/21![Frontier logo]()
$218
This CheapOair deal was found by Cheapflights users on 10/21. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/2110:47 pm -
1 stop10h 27m
Mon 11/238:42 pm -
1 stop22h 58m
Deal found 10/21![Frontier logo]()
$218
This Mytrip deal was found by Cheapflights users on 10/25. 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 12/48:57 pm -
2 stops18h 33m
Sun 12/68:53 pm -
2 stops19h 45m
Deal found 10/25![Frontier logo]()
$219
Best flights from Dulles Intl to ChicagoDiscover carefully curated flight deals from Dulles Intl to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 26, 2026.
Discover carefully curated flight deals from Dulles Intl to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 26, 2026.
This Delta deal was found by Cheapflights users on 10/23. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/1211:11 am -
1 stop6h 55m
Sun 12/135:05 pm -
1 stop5h 18m
Deal found 10/23![Delta logo]()
$237
This United Airlines deal was found by Cheapflights users on 10/22. 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.
Tue 12/293:30 pm -
Nonstop2h 24m
Sat 1/28:52 am -
Nonstop2h 02m
Deal found 10/22![United Airlines logo]()
$271
This Expedia deal was found by Cheapflights users on 10/21. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/57:32 am -
1 stop11h 15m
Mon 11/96:08 am -
1 stop10h 04m
Deal found 10/21![Frontier logo]()
$282
This Delta deal was found by Cheapflights users on 10/22. 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 11/215:18 pm -
1 stop6h 36m
Wed 12/21:02 pm -
1 stop6h 09m
Deal found 10/22![Delta logo]()
$237
This Delta deal was found by Cheapflights users on 10/22. 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 11/215:18 pm -
1 stop6h 36m
Tue 12/16:00 am -
1 stop4h 39m
Deal found 10/22![Delta logo]()
$237
This United Airlines deal was found by Cheapflights users on 10/21. 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.
Thu 11/126:11 am -
Nonstop2h 19m
Mon 11/162:21 pm -
Nonstop2h 03m
Deal found 10/21![United Airlines logo]()
$276
This Delta deal was found by Cheapflights users on 10/23. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/1012:34 pm -
1 stop4h 42m
Tue 12/296:15 pm -
1 stop3h 55m
Deal found 10/23![Delta logo]()
$237
This United Airlines deal was found by Cheapflights users on 10/23. 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 11/286:11 am -
Nonstop2h 18m
Wed 12/210:35 am -
Nonstop2h 03m
Deal found 10/23![United Airlines logo]()
$280
This Delta deal was found by Cheapflights users on 10/23. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/136:00 am -
1 stop5h 39m
Fri 11/135:05 pm -
1 stop5h 16m
Deal found 10/23![Delta logo]()
$243
This KAYAK deal was found by Cheapflights users on 10/21. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/95:00 pm -
1 stop4h 49m
Wed 11/116:15 pm -
1 stop5h 26m
Deal found 10/21![Delta logo]()
$247
This United Airlines deal was found by Cheapflights users on 10/22. 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 11/1812:55 pm -
1 stop3h 54m
Sat 11/219:41 pm -
Nonstop1h 49m
Deal found 10/22![United Airlines logo]()
$316
This United Airlines deal was found by Cheapflights users on 10/25. 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 12/118:15 am -
Nonstop2h 22m
Mon 12/149:35 pm -
Nonstop1h 49m
Deal found 10/25![United Airlines logo]()
$317
This Delta deal was found by Cheapflights users on 10/23. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/166:00 am -
1 stop4h 46m
Mon 11/166:44 pm -
1 stop3h 37m
Deal found 10/23![Delta logo]()
$271
This United Airlines deal was found by Cheapflights users on 10/24. 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 12/31:00 pm -
Nonstop2h 24m
Mon 12/78:45 am -
Nonstop2h 01m
Deal found 10/24![United Airlines logo]()
$317
This Delta deal was found by Cheapflights users on 10/23. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/136:00 am -
1 stop5h 25m
Mon 12/1411:39 am -
1 stop3h 44m
Deal found 10/23![Delta logo]()
$282
This United Airlines deal was found by Cheapflights users on 10/25. 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 12/103:37 pm -
Nonstop2h 23m
Wed 12/169:35 pm -
Nonstop1h 49m
Deal found 10/25![United Airlines logo]()
$317
This Delta deal was found by Cheapflights users on 10/21. 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.
Fri 1/16:00 am -
1 stop3h 50m
Mon 1/45:59 pm -
1 stop4h 03m
Deal found 10/21![Delta logo]()
$291
This United Airlines deal was found by Cheapflights users on 10/22. 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.
Tue 11/1010:47 pm -
Nonstop2h 14m
Thu 11/121:30 pm -
Nonstop2h 03m
Deal found 10/22![United Airlines logo]()
$325
This Delta deal was found by Cheapflights users on 10/22. 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.
Tue 11/246:00 am -
1 stop4h 46m
Tue 12/19:37 am -
1 stop5h 46m
Deal found 10/22![Delta logo]()
$297
This Delta deal was found by Cheapflights users on 10/21. 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.
Tue 11/246:00 am -
1 stop4h 46m
Sat 11/286:44 pm -
1 stop3h 37m
Deal found 10/21![Delta logo]()
$341
This Delta deal was found by Cheapflights users on 10/23. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/125:27 pm -
1 stop6h 27m
Sat 1/29:30 am -
1 stop5h 08m
Deal found 10/23![Delta logo]()
$361
This Delta deal was found by Cheapflights users on 10/25. 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 11/196:00 am -
1 stop4h 46m
Mon 11/236:44 pm -
1 stop3h 37m
Deal found 10/25![Delta logo]()
$368
This Delta deal was found by Cheapflights users on 10/25. 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 11/2010:11 am -
1 stop7h 07m
Mon 11/239:30 am -
1 stop5h 56m
Deal found 10/25![Delta logo]()
$368
This Delta deal was found by Cheapflights users on 10/25. 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 11/196:00 am -
1 stop6h 59m
Sun 11/226:44 pm -
1 stop3h 37m
Deal found 10/25![Delta logo]()
$374
Last-minute flights from Dulles Intl to ChicagoDiscover last-minute flight deals from Dulles Intl to Chicago. Data last updated October 26, 2026 and is based on user searches.
Discover last-minute flight deals from Dulles Intl to Chicago. Data last updated October 26, 2026 and is based on user searches.
This Mytrip deal was found by Cheapflights users on 10/24. 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.
Tue 11/36:07 pm -
1 stop6h 40m
Tue 11/106:08 am -
1 stop10h 04m
Deal found 10/24![Frontier logo]()
$215
This Mytrip deal was found by Cheapflights users on 10/25. 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 11/46:07 pm -
1 stop6h 40m
Wed 11/116:08 am -
1 stop10h 04m
Deal found 10/25![Frontier logo]()
$216
This Expedia deal was found by Cheapflights users on 10/23. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/48:05 am -
1 stop11h 25m
Mon 11/97:55 am -
1 stop11h 16m
Deal found 10/23![Frontier logo]()
$217
This Expedia deal was found by Cheapflights users on 10/22. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/66:07 pm -
1 stop22h 30m
Mon 11/97:55 am -
1 stop11h 16m
Deal found 10/22![Frontier logo]()
$215
This Frontier deal was found by Cheapflights users on 10/23. 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 11/77:48 am -
1 stop10h 59m
Sat 11/147:15 am -
1 stop8h 57m
Deal found 10/23![Frontier logo]()
$220
This Mytrip deal was found by Cheapflights users on 10/21. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/99:06 pm -
2 stops19h 25m
Wed 11/118:59 am -
2 stops13h 44m
Deal found 10/21![Frontier logo]()
$213
This Cheapflightsfares deal was found by Cheapflights users on 10/23. 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.
Thu 11/127:32 am -
1 stop11h 15m
Sun 11/156:08 am -
1 stop10h 04m
Deal found 10/23![Frontier logo]()
$217
This Kissandfly.com deal was found by Cheapflights users on 10/21. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1211:16 am -
1 stop22h 30m
Mon 11/167:50 pm -
2 stops14h 46m
Deal found 10/21![Frontier logo]()
$219
This Kiwi.com deal was found by Cheapflights users on 10/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/147:48 am -
1 stop6h 03m
Sat 11/217:49 am -
1 stop6h 14m
Deal found 10/21![Frontier logo]()
$216
This Orbitz deal was found by Cheapflights users on 10/21. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/219:56 pm -
1 stop10h 51m
Sun 11/228:52 am -
1 stop11h 09m
Deal found 10/21![Frontier logo]()
$218
This CheapOair deal was found by Cheapflights users on 10/21. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/2110:47 pm -
1 stop10h 27m
Mon 11/238:42 pm -
1 stop22h 58m
Deal found 10/21![Frontier logo]()
$218
This Cheapflightsfares deal was found by Cheapflights users on 10/23. 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.
Wed 11/256:50 am -
1 stop6h 31m
Thu 11/269:09 am -
1 stop4h 54m
Deal found 10/23![Frontier logo]()
$219
One-way flights from Dulles Intl to ChicagoSearch for one-way flight options from Dulles Intl to Chicago. Find affordable one-way fares based on user searches. Data last updated October 26, 2026.
Search for one-way flight options from Dulles Intl to Chicago. Find affordable one-way fares based on user searches. Data last updated October 26, 2026.
This United Airlines deal was found by Cheapflights users on 10/21. 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.
Wed 11/111:15 pm -
Nonstop2h 23m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![United Airlines logo]()
$114
This Mytrip deal was found by Cheapflights users on 10/21. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/1910:42 pm -
2 stops21h 48m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![Frontier logo]()
$114
This Kiwi.com deal was found by Cheapflights users on 10/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/1810:59 pm -
2 stops24h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![Frontier logo]()
$115
This Booking.com deal was found by Cheapflights users on 10/23. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/137:32 am -
2 stops26h 14m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![Frontier logo]()
$116
This Mytrip deal was found by Cheapflights users on 10/24. 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.
Mon 12/2110:59 pm -
1 stop14h 11m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/24![Frontier logo]()
$116
This Super.com deal was found by Cheapflights users on 10/25. 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 11/147:48 am -
1 stop6h 03m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/25![Frontier logo]()
$117
This Super.com deal was found by Cheapflights users on 10/21. 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.
Sat 11/77:48 am -
1 stop6h 03m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![Frontier logo]()
$118
This Mytrip deal was found by Cheapflights users on 10/22. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/2110:47 pm -
1 stop14h 34m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![Frontier logo]()
$118
This Mytrip deal was found by Cheapflights users on 10/24. 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 11/116:07 pm -
2 stops22h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/24![Frontier logo]()
$119
This Cheapflightsfares deal was found by Cheapflights users on 10/23. 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.
Thu 11/266:50 am -
1 stop6h 31m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![Frontier logo]()
$119
This Frontier deal was found by Cheapflights users on 10/25. 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 11/246:50 am -
1 stop7h 54m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/25![Frontier logo]()
$120
This Frontier deal was found by Cheapflights users on 10/25. 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 11/246:50 am -
1 stop6h 31m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/25![Frontier logo]()
$120
Find flight deals from Dulles Intl to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from Dulles Intl (IAD) 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 October 26, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $213 (Mytrip) |
One-way from | $114 (United Airlines) |
Popular in | January |
Cheapest in | February |
Average price | $410 |
Good round-trip deal | $408 or less |
Good one-way deal | $248 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Dulles Intl 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 October 26, 2026.
Use the filters below to find and compare flights from Washington, D.C. Dulles Intl Airport to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Washington, D.C.Chicago
IAD Washington, D.C. Dulles Intl - ORD Chicago O'Hare Intl
IADORD
Washington, D.C. Dulles Intl
Sat 11/21
8:23 am-9:45 am
Nonstop2h 22m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$114
Washington, D.C.Chicago
IAD Washington, D.C. Dulles Intl - ORD Chicago O'Hare Intl
IADORD
Washington, D.C. Dulles Intl
Fri 11/13
12:32 pm-7:05 pm
1 stop7h 33m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$122
Washington, D.C.Chicago
IAD Washington, D.C. Dulles Intl - MDW Chicago Midway
IADMDW
Washington, D.C. Dulles Intl
Tue 11/24
6:00 am-9:46 am
1 stop4h 46m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$122
Washington, D.C.Chicago
IAD Washington, D.C. Dulles Intl - MDW Chicago Midway
IADMDW
Washington, D.C. Dulles Intl
Thu 1/21
6:10 am-8:45 am
1 stop3h 35m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$122
Washington, D.C.Chicago
IAD Washington, D.C. Dulles Intl - MDW Chicago Midway
IADMDW
Washington, D.C. Dulles Intl
Tue 12/22
6:00 am-8:50 am
1 stop3h 50m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$122
Washington, D.C.Chicago
IAD Washington, D.C. Dulles Intl - MDW Chicago Midway
IADMDW
Washington, D.C. Dulles Intl
Wed 11/25
6:00 am-9:46 am
1 stop4h 46m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$122
Washington, D.C.Chicago
IAD Washington, D.C. Dulles Intl - ORD Chicago O'Hare Intl
IADORD
Washington, D.C. Dulles Intl
Tue 11/10
8:05 am-12:20 pm
1 stop5h 15m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$124
Washington, D.C.Chicago
IAD Washington, D.C. Dulles Intl - MDW Chicago Midway
IADMDW
Washington, D.C. Dulles Intl
Mon 11/9
12:32 pm-4:18 pm
1 stop4h 46m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$124
Washington, D.C.Chicago
IAD Washington, D.C. Dulles Intl - ORD Chicago O'Hare Intl
IADORD
Washington, D.C. Dulles Intl
Fri 12/25
8:15 am-9:40 am
Nonstop2h 25m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$136
Washington, D.C.Chicago
IAD Washington, D.C. Dulles Intl - MDW Chicago Midway
IADMDW
Washington, D.C. Dulles Intl
Wed 12/23
12:36 pm-5:44 pm
1 stop6h 08m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$146
Showing 1-10 of 45 resultsSorted by cheapest first
Compare providers for flights from Dulles Intl 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 Dulles Intl to Chicago in October.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Washington, D.C. Dulles Intl Airport-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. Dulles Intl Airport-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Washington, D.C. Dulles Intl Airport-Chicago flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Washington, D.C. Dulles Intl Airport-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. Dulles Intl Airport-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 Dulles Intl to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Dulles Intl with our price prediction graph.
IAD-CHI
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. Dulles Intl Airport to Chicago
IAD-CHI
IAD-ORD
IAD-MDW
What is the cheapest month to book a flight from Washington, D.C. Dulles Intl Airport to Chicago?
Currently, September is the cheapest month in which you can book a flight from Washington, D.C. Dulles Intl Airport to Chicago (average of $345). Flying from Washington, D.C. Dulles Intl Airport to Chicago in March is currently the most expensive (average of $461). 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 IAD to CHI?
Find hourly flight availability from Dulles Intl 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 October 26, 2026.
Unlike in the afternoon, when flights are generally more expensive, you can save up to 14% on flights from Washington, D.C. Dulles Intl Airport to Chicago by exploring options for tickets in the evening.
Weekly flight availability from Washington, D.C. Dulles Intl Airport to Chicago
Explore weekly flight availability from Dulles Intl 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 October 26, 2026.
The most flights from IAD to CHI are scheduled on a Sunday (36 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (7 on average).
How much does it cost to fly round-trip from Washington, D.C. Dulles Intl Airport to Chicago?
Airfare is below average for this route at the moment.
Washington, D.C. Dulles Intl Airport to Chicago flights typically cost between $298 and $577 in November.The cheapest round-trip price found within the last 5 days was $213 on Frontier (Nov 9-Nov 11).
How far ahead should I book a flight from Washington, D.C. Dulles Intl Airport to Chicago?
Booking 85 days in advance of your planned departure date is, on average, the best time to get cheap flights from Washington, D.C. Dulles Intl Airport to Chicago. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
What is the cheapest day to fly from Washington, D.C. Dulles Intl Airport to Chicago?
Use this chart to determine the cheapest time to fly round-trip from Dulles Intl to Chicago. Price data was last updated on October 24, 2026.
Travelers seeking maximum savings on their Washington, D.C. Dulles Intl Airport to Chicago flight should consider departing on Wednesday evenings when fares are most often at their lowest. Sunday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.
The best insider tips for Washington, D.C. Dulles Intl Airport 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. Dulles Intl Airport 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 October 26, 2026.
See what other customers who have flown with United Airlines and Frontier from Washington, D.C. Dulles Intl Airport to Chicago have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.1
Food
6.7
Comfort
7.3
Overall
7.3
Boarding
7.7
Entertainment
7.1
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Crew
8.1
Food
6.7
Comfort
7.3
Overall
7.3
Boarding
7.7
Entertainment
7.1
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Crew
8.1
Food
6.7
Comfort
7.3
Overall
7.3
Boarding
7.7
Entertainment
7.1
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Related info for your journey
Find useful and relevant information for your journey from Dulles Intl to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Dulles Intl and Chicago flights
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Top 2 airlines flying from Dulles Intl to Chicago
Discover the top 2 airlines that operate flights from Dulles Intl 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 October 26, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$70 | Average$260 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$210 | Average$417 | FlexibilityNo cancel fee | On-time69% |