$105+ Cheap flights from Reagan-National (DCA) 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 12/8. Fares are subject to change and may not be available on all flights or dates of travel.
DCA — CHI
Nov 13 — Nov 201
Round-trip
1 adult, Economy
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Find cheap flights from Reagan-National 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. Reagan-National to Chicago are usually found in February or January, booked 62 days in advance, depart on a Saturday or Thursday and return on a Saturday
Cheap flight deals from Reagan-National to Chicago
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Cheapest flights from Reagan-National to ChicagoExplore the most affordable flight options available from Reagan-National to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 14, 2026.
Explore the most affordable flight options available from Reagan-National to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 14, 2026.
This JetBlue deal was found by Cheapflights users on 10/9. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/271:09 pm -
1 stop7h 20m
Wed 10/281:00 pm -
1 stop6h 09m
Deal found 10/9![JetBlue logo]()
$209
This Super.com deal was found by Cheapflights users on 10/9. 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 11/176:00 pm -
1 stop7h 21m
Sat 11/216:40 am -
1 stop29h 19m
Deal found 10/9![Frontier logo]()
$213
This Kiwi.com deal was found by Cheapflights users on 10/9. 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 11/51:00 pm -
1 stop12h 21m
Mon 11/96:30 am -
1 stop9h 17m
Deal found 10/9![Frontier logo]()
$225
This Cheapflightsfares deal was found by Cheapflights users on 10/13. 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.
Mon 11/91:00 pm -
1 stop12h 21m
Thu 11/126:30 am -
1 stop14h 20m
Deal found 10/13![Frontier logo]()
$232
This Kiwi.com deal was found by Cheapflights users on 10/9. 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 11/36:00 pm -
1 stop7h 21m
Wed 11/46:30 am -
1 stop14h 20m
Deal found 10/9![Frontier logo]()
$234
This Cheapflightsfares deal was found by Cheapflights users on 10/13. 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 11/36:00 pm -
1 stop7h 21m
Sat 11/76:30 am -
1 stop14h 20m
Deal found 10/13![Frontier logo]()
$237
This Orbitz deal was found by Cheapflights users on 10/13. 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.
Mon 11/91:00 pm -
1 stop12h 21m
Thu 11/196:30 am -
1 stop14h 20m
Deal found 10/13![Frontier logo]()
$239
This Cheapflightsfares deal was found by Cheapflights users on 10/10. 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 11/51:00 pm -
1 stop12h 21m
Wed 11/116:30 am -
1 stop14h 20m
Deal found 10/10![Frontier logo]()
$242
This Super.com deal was found by Cheapflights users on 10/12. 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 11/66:00 pm -
1 stop7h 21m
Mon 11/96:30 am -
1 stop9h 17m
Deal found 10/12![Frontier logo]()
$243
This Frontier deal was found by Cheapflights users on 10/9. 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 11/56:00 pm -
1 stop7h 21m
Tue 11/106:30 am -
1 stop9h 17m
Deal found 10/9![Frontier logo]()
$244
This Kiwi.com deal was found by Cheapflights users on 10/10. 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 11/36:00 pm -
1 stop7h 21m
Tue 11/106:30 am -
1 stop9h 17m
Deal found 10/10![Frontier logo]()
$247
This Southwest deal was found by Cheapflights users on 10/13. 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 11/512:40 pm -
Nonstop2h 05m
Mon 11/912:25 pm -
Nonstop1h 50m
Deal found 10/13![Southwest logo]()
$297
Best flights from Reagan-National to ChicagoDiscover carefully curated flight deals from Reagan-National to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 14, 2026.
Discover carefully curated flight deals from Reagan-National to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 14, 2026.
This JetBlue deal was found by Cheapflights users on 10/9. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/271:09 pm -
1 stop7h 20m
Wed 10/281:00 pm -
1 stop6h 09m
Deal found 10/9![JetBlue logo]()
$209
This United Airlines deal was found by Cheapflights users on 10/9. 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 11/109:30 am -
Nonstop2h 20m
Tue 11/107:45 pm -
Nonstop1h 58m
Deal found 10/9![United Airlines logo]()
$297
This Southwest deal was found by Cheapflights users on 10/11. 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 11/69:15 pm -
Nonstop2h 05m
Sat 11/711:05 am -
Nonstop1h 50m
Deal found 10/11![Southwest logo]()
$297
This Delta deal was found by Cheapflights users on 10/12. 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 11/239:45 am -
1 stop5h 14m
Thu 11/266:23 am -
1 stop14h 37m
Deal found 10/12![Delta logo]()
$309
This JetBlue deal was found by Cheapflights users on 10/9. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/122:06 pm -
1 stop6h 11m
Mon 11/161:00 pm -
1 stop6h 09m
Deal found 10/9![JetBlue logo]()
$295
This Southwest deal was found by Cheapflights users on 10/10. 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 12/38:55 pm -
Nonstop2h 15m
Sat 12/511:05 am -
Nonstop1h 50m
Deal found 10/10![Southwest logo]()
$297
This Delta deal was found by Cheapflights users on 10/10. 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 12/146:00 am -
1 stop5h 35m
Mon 12/145:05 pm -
1 stop5h 29m
Deal found 10/10![Delta logo]()
$317
This JetBlue deal was found by Cheapflights users on 10/11. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/121:09 pm -
1 stop7h 08m
Sat 11/141:00 pm -
1 stop6h 09m
Deal found 10/11![JetBlue logo]()
$297
This Southwest deal was found by Cheapflights users on 10/11. 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 11/112:40 pm -
1 stop4h 10m
Tue 11/179:15 am -
Nonstop1h 45m
Deal found 10/11![Southwest logo]()
$303
This United Airlines deal was found by Cheapflights users on 10/10. 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 1/298:40 am -
Nonstop2h 24m
Sun 1/316:00 pm -
Nonstop2h 05m
Deal found 10/10![United Airlines logo]()
$334
This Delta deal was found by Cheapflights users on 10/10. 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 11/196:05 am -
1 stop5h 25m
Sat 11/213:00 pm -
1 stop6h 01m
Deal found 10/10![Delta logo]()
$317
This Southwest deal was found by Cheapflights users on 10/13. 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 11/278:25 am -
1 stop6h 45m
Fri 12/49:15 am -
Nonstop1h 45m
Deal found 10/13![Southwest logo]()
$307
This United Airlines deal was found by Cheapflights users on 10/9. 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 2/196:00 pm -
Nonstop2h 14m
Sun 2/217:30 am -
Nonstop1h 47m
Deal found 10/9![United Airlines logo]()
$346
This Delta deal was found by Cheapflights users on 10/13. 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 11/131:20 pm -
1 stop6h 02m
Mon 11/168:45 am -
1 stop6h 12m
Deal found 10/13![Delta logo]()
$317
This Southwest deal was found by Cheapflights users on 10/12. 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 11/128:25 am -
1 stop4h 15m
Mon 11/168:15 am -
1 stop4h 50m
Deal found 10/12![Southwest logo]()
$312
This Delta deal was found by Cheapflights users on 10/12. 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 11/59:40 am -
1 stop4h 19m
Sat 11/77:00 am -
1 stop4h 39m
Deal found 10/12![Delta logo]()
$317
This Delta deal was found by Cheapflights users on 10/11. 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 11/176:10 am -
1 stop5h 29m
Tue 11/175:05 pm -
1 stop5h 21m
Deal found 10/11![Delta logo]()
$317
This Southwest deal was found by Cheapflights users on 10/9. 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 11/216:00 pm -
1 stop6h 05m
Mon 11/2310:20 am -
1 stop5h 35m
Deal found 10/9![Southwest logo]()
$333
This Southwest deal was found by Cheapflights users on 10/13. 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
Sat 11/285:30 am -
Nonstop1h 50m
Deal found 10/13![Southwest logo]()
$338
This Delta deal was found by Cheapflights users on 10/13. 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 12/46:00 am -
1 stop4h 37m
Sun 12/66:41 pm -
1 stop3h 53m
Deal found 10/13![Delta logo]()
$354
This Southwest deal was found by Cheapflights users on 10/13. 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 11/137:35 pm -
1 stop5h 35m
Sun 11/1511:00 am -
Nonstop1h 50m
Deal found 10/13![Southwest logo]()
$344
This Southwest deal was found by Cheapflights users on 10/9. 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 10/311:00 pm -
Nonstop2h 00m
Sun 11/17:20 am -
Nonstop1h 50m
Deal found 10/9![Southwest logo]()
$351
This Southwest deal was found by Cheapflights users on 10/10. 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 12/57:25 am -
2 stops9h 05m
Sun 12/65:30 am -
1 stop6h 00m
Deal found 10/10![Southwest logo]()
$359
Last-minute flights from Reagan-National to ChicagoDiscover last-minute flight deals from Reagan-National to Chicago. Data last updated October 14, 2026 and is based on user searches.
Discover last-minute flight deals from Reagan-National to Chicago. Data last updated October 14, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 10/9. 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 11/36:00 pm -
1 stop7h 21m
Wed 11/46:30 am -
1 stop14h 20m
Deal found 10/9![Frontier logo]()
$234
This Kiwi.com deal was found by Cheapflights users on 10/10. 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 11/36:00 pm -
1 stop7h 21m
Tue 11/106:30 am -
1 stop9h 17m
Deal found 10/10![Frontier logo]()
$247
This Cheapflightsfares deal was found by Cheapflights users on 10/10. 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 11/51:00 pm -
1 stop12h 21m
Wed 11/116:30 am -
1 stop14h 20m
Deal found 10/10![Frontier logo]()
$242
This Frontier deal was found by Cheapflights users on 10/9. 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 11/56:00 pm -
1 stop7h 21m
Tue 11/106:30 am -
1 stop9h 17m
Deal found 10/9![Frontier logo]()
$244
This Kiwi.com deal was found by Cheapflights users on 10/10. 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 11/56:00 pm -
1 stop7h 21m
Mon 11/96:30 am -
1 stop9h 17m
Deal found 10/10![Frontier logo]()
$245
This Southwest deal was found by Cheapflights users on 10/13. 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 11/512:40 pm -
Nonstop2h 05m
Mon 11/912:25 pm -
Nonstop1h 50m
Deal found 10/13![Southwest logo]()
$297
This Super.com deal was found by Cheapflights users on 10/12. 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 11/66:00 pm -
1 stop7h 21m
Mon 11/96:30 am -
1 stop9h 17m
Deal found 10/12![Frontier logo]()
$243
This Cheapflightsfares deal was found by Cheapflights users on 10/13. 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.
Mon 11/91:00 pm -
1 stop12h 21m
Thu 11/126:30 am -
1 stop14h 20m
Deal found 10/13![Frontier logo]()
$232
This Cheapflightsfares deal was found by Cheapflights users on 10/13. 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 11/126:00 pm -
1 stop7h 21m
Thu 11/196:30 am -
1 stop14h 20m
Deal found 10/13![Frontier logo]()
$237
This CheapOair deal was found by Cheapflights users on 10/14. 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.
Fri 11/136:00 pm -
1 stop7h 21m
Sat 11/146:30 am -
1 stop9h 17m
Deal found 10/14![Frontier logo]()
$239
This Cheapflightsfares deal was found by Cheapflights users on 10/13. 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 11/137:00 am -
1 stop18h 21m
Sun 11/156:30 am -
1 stop28h 39m
Deal found 10/13![Frontier logo]()
$249
This CheapOair deal was found by Cheapflights users on 10/13. 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.
Fri 11/136:00 pm -
1 stop7h 21m
Mon 11/166:30 am -
1 stop9h 17m
Deal found 10/13![Frontier logo]()
$250
One-way flights from Reagan-National to ChicagoSearch for one-way flight options from Reagan-National to Chicago. Find affordable one-way fares based on user searches. Data last updated October 14, 2026.
Search for one-way flight options from Reagan-National to Chicago. Find affordable one-way fares based on user searches. Data last updated October 14, 2026.
This JetBlue deal was found by Cheapflights users on 10/10. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/811:20 am -
1 stop6h 22m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/10![JetBlue logo]()
$105
This JetBlue deal was found by Cheapflights users on 10/9. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/92:06 pm -
1 stop6h 11m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/9![JetBlue logo]()
$106
This Super.com deal was found by Cheapflights users on 10/13. 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 11/36:00 pm -
1 stop7h 21m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/13![Frontier logo]()
$115
This Super.com deal was found by Cheapflights users on 10/14. 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 11/146:00 pm -
1 stop7h 21m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/14![Frontier logo]()
$116
This Priceline deal was found by Cheapflights users on 10/14. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/96:00 pm -
1 stop7h 21m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/14![Frontier logo]()
$117
This Flightnetwork deal was found by Cheapflights users on 10/14. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/106:00 pm -
1 stop7h 21m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/14![Frontier logo]()
$118
This Super.com deal was found by Cheapflights users on 10/12. 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 11/66:00 pm -
1 stop7h 21m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/12![Frontier logo]()
$119
This Super.com deal was found by Cheapflights users on 10/10. 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 11/56:00 pm -
1 stop7h 21m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/10![Frontier logo]()
$120
This Frontier deal was found by Cheapflights users on 10/9. 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 11/126:00 pm -
1 stop7h 21m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/9![Frontier logo]()
$122
This Frontier deal was found by Cheapflights users on 10/14. 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 11/111:00 pm -
1 stop12h 21m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/14![Frontier logo]()
$123
This Trip.com deal was found by Cheapflights users on 10/13. 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 11/76:00 pm -
1 stop7h 21m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/13![Frontier logo]()
$124
This Kiwi.com deal was found by Cheapflights users on 10/13. 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 11/121:00 pm -
2 stops29h 47m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/13![Frontier logo]()
$148
Find flight deals from Reagan-National to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from Reagan-National (DCA) 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 14, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $232 (Cheapflightsfares) |
One-way from | $105 (JetBlue) |
Popular in | June |
Cheapest in | February |
Average price | $363 |
Good round-trip deal | $342 or less |
Good one-way deal | $209 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Reagan-National 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 14, 2026.
Use the filters below to find and compare flights from Washington, D.C. Reagan-National Airport 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
Sat 12/12
9:59 am-4:47 pm
1 stop7h 48m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$105
Washington, D.C.Chicago
DCA Washington, D.C. Reagan-National - ORD Chicago O'Hare Intl
DCAORD
Washington, D.C. Reagan-National
Wed 12/9
11:20 am-4:42 pm
1 stop6h 22m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$105
Washington, D.C.Chicago
DCA Washington, D.C. Reagan-National - ORD Chicago O'Hare Intl
DCAORD
Washington, D.C. Reagan-National
Mon 11/9
2:06 pm-7:17 pm
1 stop6h 11m
Chicago O'Hare Intl
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
Thu 12/10
9:59 am-4:42 pm
1 stop7h 43m
Chicago O'Hare Intl
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 12/14
11:20 am-4:42 pm
1 stop6h 22m
Chicago O'Hare Intl
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
Wed 12/2
7:41 am-8:59 am
Nonstop2h 18m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$149
Quickest round-trip
Washington, D.C.Chicago
DCA Washington, D.C. Reagan-National - MDW Chicago Midway
DCAMDW
Washington, D.C. Reagan-National
Mon 11/23
10:45 am-11:50 am
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
Tue 12/22
9:30 am-10:54 am
Nonstop2h 24m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$149
Washington, D.C.Chicago
DCA Washington, D.C. Reagan-National - MDW Chicago Midway
DCAMDW
Washington, D.C. Reagan-National
Thu 12/10
8:55 pm-10:05 pm
Nonstop2h 10m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$149
Washington, D.C.Chicago
DCA Washington, D.C. Reagan-National - MDW Chicago Midway
DCAMDW
Washington, D.C. Reagan-National
Tue 12/29
9:10 am-10:20 am
Nonstop2h 10m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$149
Showing 1-10 of 45 resultsSorted by cheapest first
Compare providers for flights from Reagan-National 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 Reagan-National to Chicago in October.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Washington, D.C. Reagan-National 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. Reagan-National Airport-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Washington, D.C. Reagan-National Airport-Chicago flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Washington, D.C. Reagan-National 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. Reagan-National 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 Reagan-National to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Reagan-National with our price prediction graph.
DCA-CHI
DCA-ORD
DCA-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. Reagan-National Airport to Chicago
DCA-CHI
DCA-ORD
DCA-MDW
What is the cheapest month to book a flight from Washington, D.C. Reagan-National Airport to Chicago?
Currently, February is the cheapest month in which you can book a flight from Washington, D.C. Reagan-National Airport to Chicago (average of $319). Flying from Washington, D.C. Reagan-National Airport to Chicago in March 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 DCA to CHI?
Find hourly flight availability from Reagan-National 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 14, 2026.
It’s typically best to fly out from Washington, D.C. Reagan-National Airport to Chicago at noon. Doing so could potentially save you 6% on the flight price compared to flying in the afternoon, which is usually more expensive.
Weekly flight availability from Washington, D.C. Reagan-National Airport to Chicago
Explore weekly flight availability from Reagan-National 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 14, 2026.
The most flights from DCA to CHI are scheduled on a Monday (65 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (33 on average).
How much does it cost to fly round-trip from Washington, D.C. Reagan-National Airport to Chicago?
Airfare is below average for this route at the moment.
Washington, D.C. Reagan-National Airport to Chicago flights typically cost between $285 and $481 in November.The cheapest round-trip price found within the last 5 days was $232 on Frontier (Nov 9-Nov 12).
How far ahead should I book a flight from Washington, D.C. Reagan-National Airport to Chicago?
The best time to book flights from Washington, D.C. Reagan-National Airport to Chicago is 67 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
What is the cheapest day to fly from Washington, D.C. Reagan-National Airport to Chicago?
Use this chart to determine the cheapest time to fly round-trip from Reagan-National to Chicago. Price data was last updated on October 10, 2026.
Travelers seeking maximum savings on their Washington, D.C. Reagan-National Airport to Chicago flight should consider departing on Wednesday 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. Reagan-National 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. Reagan-National 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 14, 2026.
Get a feel of what it's like to fly with Southwest,United Airlines, andAmerican Airlines from Washington, D.C. Reagan-National Airport to Chicago by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.5
Boarding
8.1
Food
7.0
Overall
7.9
Comfort
8.0
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Boarding
8.1
Food
7.0
Overall
7.9
Comfort
8.0
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Boarding
8.1
Food
7.0
Overall
7.9
Comfort
8.0
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Boarding
8.1
Food
7.0
Overall
7.9
Comfort
8.0
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 Reagan-National 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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Reagan-National and Chicago flights
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Other flights from Reagan-National
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Top 4 airlines flying from Reagan-National to Chicago
Discover the top 4 airlines that operate flights from Reagan-National 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 14, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$29 | Average$187 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$204 | Average$365 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$233 | Average$399 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$236 | Average$381 | FlexibilityNo cancel fee | On-time63% |