$89+ Cheap flights from Reagan-National (DCA) to Chicago (CHI)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/14. Fares are subject to change and may not be available on all flights or dates of travel.
DCA — CHI
Sep 20 — Sep 271
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
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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 October, booked 84 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 August 21, 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 August 21, 2026.
This Southwest deal was found by Cheapflights users on 8/17. 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 11/182:40 pm -
1 stop4h 05m
Thu 11/197:25 am -
Nonstop1h 50m
Deal found 8/17![Southwest logo]()
$183
This Frontier deal was found by Cheapflights users on 8/20. 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 Frontier 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 8/20![Frontier logo]()
$187
This Southwest deal was found by Cheapflights users on 8/17. 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 9/126:00 am -
1 stop6h 20m
Sat 9/121:20 pm -
Nonstop1h 55m
Deal found 8/17![Southwest logo]()
$187
This Southwest deal was found by Cheapflights users on 8/20. 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.
Mon 10/268:40 pm -
Nonstop2h 00m
Wed 10/283:30 pm -
2 stops7h 25m
Deal found 8/20![Southwest logo]()
$188
This Frontier deal was found by Cheapflights users on 8/16. 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.
Mon 10/51:06 pm -
1 stop12h 17m
Tue 10/136:30 am -
1 stop9h 26m
Deal found 8/16![Frontier logo]()
$189
This Kissandfly.com deal was found by Cheapflights users on 8/19. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/107:00 am -
1 stop18h 23m
Mon 9/147:47 pm -
Nonstop2h 07m
Deal found 8/19![Frontier logo]()
$192
This Southwest deal was found by Cheapflights users on 8/18. 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 10/310:15 am -
2 stops8h 40m
Mon 10/56:00 am -
Nonstop1h 50m
Deal found 8/18![Southwest logo]()
$192
This Expedia deal was found by Cheapflights users on 8/17. 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 9/181:06 pm -
1 stop12h 17m
Sat 9/196:30 am -
1 stop14h 29m
Deal found 8/17![Frontier logo]()
$193
This Southwest deal was found by Cheapflights users on 8/17. 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 10/106:05 am -
1 stop9h 50m
Thu 10/155:00 pm -
Nonstop1h 50m
Deal found 8/17![Southwest logo]()
$193
This Delta deal was found by Cheapflights users on 8/17. 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 9/2611:00 am -
1 stop6h 30m
Wed 9/305:10 pm -
1 stop4h 52m
Deal found 8/17![Delta logo]()
$197
This Delta deal was found by Cheapflights users on 8/18. 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.
Thu 10/16:10 am -
1 stop3h 57m
Mon 10/59:29 am -
1 stop6h 09m
Deal found 8/18![Delta logo]()
$197
This American Airlines deal was found by Cheapflights users on 8/18. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/13:58 pm -
Nonstop2h 30m
Mon 10/56:55 pm -
Nonstop2h 05m
Deal found 8/18![American Airlines logo]()
$198
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 August 21, 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 August 21, 2026.
This Southwest deal was found by Cheapflights users on 8/20. 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.
Sat 11/79:25 am -
Nonstop2h 05m
Mon 11/98:45 am -
1 stop6h 30m
Deal found 8/20![Southwest logo]()
$187
This Delta deal was found by Cheapflights users on 8/15. 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 10/171:25 pm -
1 stop6h 55m
Mon 10/191:25 pm -
1 stop4h 12m
Deal found 8/15![Delta logo]()
$197
This United Airlines deal was found by Cheapflights users on 8/18. 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.
Tue 10/69:30 am -
Nonstop2h 17m
Fri 10/92:00 pm -
Nonstop2h 08m
Deal found 8/18![United Airlines logo]()
$216
This Southwest deal was found by Cheapflights users on 8/16. 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 10/176:00 am -
1 stop7h 05m
Mon 10/198:45 pm -
Nonstop1h 45m
Deal found 8/16![Southwest logo]()
$187
This Delta deal was found by Cheapflights users on 8/17. 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 10/2812:27 pm -
1 stop5h 05m
Sat 10/317:00 am -
1 stop3h 32m
Deal found 8/17![Delta logo]()
$197
This Delta deal was found by Cheapflights users on 8/17. 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 9/95:35 pm -
1 stop3h 55m
Tue 9/1511:30 am -
1 stop6h 01m
Deal found 8/17![Delta logo]()
$197
This Southwest deal was found by Cheapflights users on 8/18. 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 9/93:00 pm -
1 stop5h 20m
Mon 9/148:15 am -
1 stop5h 40m
Deal found 8/18![Southwest logo]()
$197
This United Airlines deal was found by Cheapflights users on 8/20. 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.
Thu 10/87:46 am -
Nonstop2h 14m
Mon 10/125:59 am -
Nonstop1h 55m
Deal found 8/20![United Airlines logo]()
$236
This Delta deal was found by Cheapflights users on 8/17. 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 9/85:35 pm -
1 stop3h 55m
Tue 9/1511:30 am -
1 stop6h 01m
Deal found 8/17![Delta logo]()
$197
This Southwest deal was found by Cheapflights users on 8/17. 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 9/191:20 pm -
1 stop4h 20m
Sat 9/268:05 am -
1 stop5h 55m
Deal found 8/17![Southwest logo]()
$197
This Delta deal was found by Cheapflights users on 8/16. 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 10/156:10 am -
1 stop4h 07m
Mon 10/196:44 pm -
1 stop3h 23m
Deal found 8/16![Delta logo]()
$197
This United Airlines deal was found by Cheapflights users on 8/20. 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 9/197:10 pm -
Nonstop2h 20m
Sun 9/207:59 am -
Nonstop2h 01m
Deal found 8/20![United Airlines logo]()
$273
This Southwest deal was found by Cheapflights users on 8/18. 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.
Tue 10/63:40 pm -
1 stop4h 45m
Fri 10/97:55 am -
1 stop4h 50m
Deal found 8/18![Southwest logo]()
$236
This United Airlines deal was found by Cheapflights users on 8/18. 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.
Sun 10/181:15 pm -
Nonstop2h 17m
Mon 11/97:00 am -
Nonstop1h 56m
Deal found 8/18![United Airlines logo]()
$273
This Delta deal was found by Cheapflights users on 8/16. 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 10/167:40 pm -
1 stop5h 17m
Mon 10/195:29 pm -
1 stop4h 38m
Deal found 8/16![Delta logo]()
$236
This Delta deal was found by Cheapflights users on 8/15. 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 10/159:32 am -
1 stop4h 27m
Sat 10/1710:05 am -
1 stop5h 15m
Deal found 8/15![Delta logo]()
$236
This Southwest deal was found by Cheapflights users on 8/15. 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 10/86:50 pm -
1 stop5h 15m
Thu 10/153:50 pm -
1 stop5h 00m
Deal found 8/15![Southwest logo]()
$268
This Southwest deal was found by Cheapflights users on 8/19. 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.
Sun 10/46:10 am -
Nonstop1h 55m
Wed 10/71:15 pm -
Nonstop1h 50m
Deal found 8/19![Southwest logo]()
$273
This Delta deal was found by Cheapflights users on 8/15. 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 10/178:25 am -
1 stop6h 14m
Tue 10/207:00 am -
1 stop4h 39m
Deal found 8/15![Delta logo]()
$268
This Southwest deal was found by Cheapflights users on 8/19. 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.
Sun 9/206:55 am -
2 stops6h 50m
Thu 9/2412:00 pm -
Nonstop1h 50m
Deal found 8/19![Southwest logo]()
$288
This Delta deal was found by Cheapflights users on 8/16. 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 10/16:10 am -
1 stop5h 27m
Mon 10/58:55 am -
1 stop6h 43m
Deal found 8/16![Delta logo]()
$268
This Southwest deal was found by Cheapflights users on 8/19. 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.
Sun 9/69:00 pm -
Nonstop2h 05m
Fri 9/113:20 pm -
1 stop6h 10m
Deal found 8/19![Southwest logo]()
$320
This Southwest deal was found by Cheapflights users on 8/18. 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.
Fri 10/98:05 pm -
1 stop6h 00m
Sun 10/119:25 am -
Nonstop1h 50m
Deal found 8/18![Southwest logo]()
$322
Last-minute flights from Reagan-National to ChicagoDiscover last-minute flight deals from Reagan-National to Chicago. Data last updated August 21, 2026 and is based on user searches.
Discover last-minute flight deals from Reagan-National to Chicago. Data last updated August 21, 2026 and is based on user searches.
This Kissandfly.com deal was found by Cheapflights users on 8/19. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/107:00 am -
1 stop18h 23m
Mon 9/147:47 pm -
Nonstop2h 07m
Deal found 8/19![Frontier logo]()
$192
This Expedia deal was found by Cheapflights users on 8/20. 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.
Fri 9/117:00 am -
1 stop18h 23m
Sat 9/126:30 am -
1 stop14h 29m
Deal found 8/20![Frontier logo]()
$187
This Southwest deal was found by Cheapflights users on 8/17. 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 9/126:00 am -
1 stop6h 20m
Sat 9/121:20 pm -
Nonstop1h 55m
Deal found 8/17![Southwest logo]()
$187
This Delta deal was found by Cheapflights users on 8/18. 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.
Sat 9/129:40 am -
1 stop4h 18m
Sat 9/126:00 pm -
1 stop4h 02m
Deal found 8/18![Delta logo]()
$197
This Southwest deal was found by Cheapflights users on 8/18. 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 9/121:20 pm -
1 stop4h 20m
Mon 9/148:15 am -
1 stop5h 40m
Deal found 8/18![Southwest logo]()
$197
This CheapOair deal was found by Cheapflights users on 8/17. 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 9/126:00 pm -
1 stop7h 23m
Fri 9/183:00 pm -
1 stop7h 27m
Deal found 8/17![Multiple Airlines logo]()
$205
This Expedia deal was found by Cheapflights users on 8/17. 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.
Mon 9/146:00 pm -
1 stop7h 23m
Mon 9/216:30 am -
1 stop14h 29m
Deal found 8/17![Frontier logo]()
$203
This Expedia deal was found by Cheapflights users on 8/17. 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.
Mon 9/146:00 pm -
1 stop7h 23m
Thu 9/176:00 am -
1 stop7h 58m
Deal found 8/17![Multiple Airlines logo]()
$206
This Southwest deal was found by Cheapflights users on 8/18. 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.
Tue 9/156:00 am -
2 stops7h 05m
Thu 9/172:05 pm -
Nonstop1h 50m
Deal found 8/18![Southwest logo]()
$192
This American Airlines deal was found by Cheapflights users on 8/20. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/176:30 am -
Nonstop2h 28m
Thu 9/246:55 pm -
Nonstop2h 05m
Deal found 8/20![American Airlines logo]()
$182
This Expedia deal was found by Cheapflights users on 8/17. 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 9/181:06 pm -
1 stop12h 17m
Sat 9/196:30 am -
1 stop14h 29m
Deal found 8/17![Frontier logo]()
$193
This Expedia deal was found by Cheapflights users on 8/17. 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.
Sat 9/197:00 am -
1 stop18h 23m
Sun 9/206:30 am -
1 stop28h 41m
Deal found 8/17![Frontier logo]()
$204
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 August 21, 2026.
Search for one-way flight options from Reagan-National to Chicago. Find affordable one-way fares based on user searches. Data last updated August 21, 2026.
This United Airlines deal was found by Cheapflights users on 8/18. 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.
Mon 9/145:10 pm -
Nonstop2h 23m
Deal found 8/18![United Airlines logo]()
$89
This Southwest deal was found by Cheapflights users on 8/17. 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 9/94:35 pm -
Nonstop2h 00m
Deal found 8/17![Southwest logo]()
$89
This Super.com deal was found by Cheapflights users on 8/17. 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 9/82:25 pm -
1 stop6h 00m
Deal found 8/17![JetBlue logo]()
$90
This Booking.com deal was found by Cheapflights users on 8/18. 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.
Mon 9/287:00 am -
1 stop18h 23m
Deal found 8/18![Frontier logo]()
$91
This Mytrip deal was found by Cheapflights users on 8/16. 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 10/27:00 am -
1 stop18h 23m
Deal found 8/16![Frontier logo]()
$94
This Southwest deal was found by Cheapflights users on 8/16. 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 11/162:40 pm -
1 stop4h 05m
Deal found 8/16![Southwest logo]()
$94
This Delta deal was found by Cheapflights users on 8/17. 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 9/85:35 pm -
1 stop3h 55m
Deal found 8/17![Delta logo]()
$99
This Southwest deal was found by Cheapflights users on 8/16. 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 9/141:00 pm -
2 stops5h 50m
Deal found 8/16![Southwest logo]()
$104
This Expedia deal was found by Cheapflights users on 8/20. 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.
Fri 10/306:00 pm -
1 stop7h 21m
Deal found 8/20![Frontier logo]()
$108
This Delta deal was found by Cheapflights users on 8/18. 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.
Wed 9/1611:10 am -
1 stop6h 49m
Deal found 8/18![Delta logo]()
$109
This Delta deal was found by Cheapflights users on 8/19. 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.
Mon 10/126:10 am -
1 stop4h 07m
Deal found 8/19![Delta logo]()
$109
This Booking.com deal was found by Cheapflights users on 8/20. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/106:00 pm -
1 stop7h 23m
Deal found 8/20![Frontier logo]()
$110
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 August 21, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $183 (Southwest) |
One-way from | $89 (United Airlines) |
Popular in | June |
Cheapest in | February |
Average price | $348 |
Good round-trip deal | $263 or less |
Good one-way deal | $186 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 August 21, 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 - MDW Chicago Midway
DCAMDW
Washington, D.C. Reagan-National
Sat 11/7
9:25 am-10:30 am
Nonstop2h 05m
Chicago Midway
Mon 11/9
8:45 am-4:15 pm
1 stop6h 30m
$187
Washington, D.C.Chicago
DCA Washington, D.C. Reagan-National - MDW Chicago Midway
DCAMDW
Washington, D.C. Reagan-National
Sat 10/17
6:00 am-12:05 pm
1 stop7h 05m
Chicago Midway
Mon 10/19
8:45 pm-11:30 pm
Nonstop1h 45m
$187
Washington, D.C.Chicago
DCA Washington, D.C. Reagan-National - ORD Chicago O'Hare Intl
DCAORD
Washington, D.C. Reagan-National
Sat 10/17
1:25 pm-7:20 pm
1 stop6h 55m
Chicago O'Hare Intl
Mon 10/19
1:25 pm-6:37 pm
1 stop4h 12m
$197
Washington, D.C.Chicago
DCA Washington, D.C. Reagan-National - ORD Chicago O'Hare Intl
DCAORD
Washington, D.C. Reagan-National
Wed 10/28
12:27 pm-4:32 pm
1 stop5h 05m
Chicago O'Hare Intl
Sat 10/31
7:00 am-11:32 am
1 stop3h 32m
$197
Washington, D.C.Chicago
DCA Washington, D.C. Reagan-National - ORD Chicago O'Hare Intl
DCAORD
Washington, D.C. Reagan-National
Wed 9/9
5:35 pm-8:30 pm
1 stop3h 55m
Chicago O'Hare Intl
Tue 9/15
11:30 am-6:31 pm
1 stop6h 01m
$197
Washington, D.C.Chicago
DCA Washington, D.C. Reagan-National - MDW Chicago Midway
DCAMDW
Washington, D.C. Reagan-National
Wed 9/9
3:00 pm-7:20 pm
1 stop5h 20m
Chicago Midway
Mon 9/14
8:15 am-2:55 pm
1 stop5h 40m
$197
Washington, D.C.Chicago
DCA Washington, D.C. Reagan-National - ORD Chicago O'Hare Intl
DCAORD
Washington, D.C. Reagan-National
Tue 9/8
5:35 pm-8:30 pm
1 stop3h 55m
Chicago O'Hare Intl
Tue 9/15
11:30 am-6:31 pm
1 stop6h 01m
$197
Washington, D.C.Chicago
DCA Washington, D.C. Reagan-National - MDW Chicago Midway
DCAMDW
Washington, D.C. Reagan-National
Sat 9/19
1:20 pm-4:40 pm
1 stop4h 20m
Chicago Midway
Sat 9/26
8:05 am-3:00 pm
1 stop5h 55m
$197
Washington, D.C.Chicago
DCA Washington, D.C. Reagan-National - MDW Chicago Midway
DCAMDW
Washington, D.C. Reagan-National
Thu 10/15
6:10 am-9:17 am
1 stop4h 07m
Chicago Midway
Mon 10/19
6:44 pm-11:07 pm
1 stop3h 23m
$197
Washington, D.C.Chicago
DCA Washington, D.C. Reagan-National - ORD Chicago O'Hare Intl
DCAORD
Washington, D.C. Reagan-National
Tue 10/6
9:30 am-10:47 am
Nonstop2h 17m
Chicago O'Hare Intl
Fri 10/9
2:00 pm-5:08 pm
Nonstop2h 08m
$216
Showing 1-10 of 53 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 August.
| 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
DCA-RFD
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
DCA-RFD
What is the cheapest month to book a flight from Washington, D.C. Reagan-National Airport to Chicago?
Currently, September is the cheapest month in which you can book a flight from Washington, D.C. Reagan-National Airport to Chicago (average of $317). Flying from Washington, D.C. Reagan-National Airport to Chicago in March is currently the most expensive (average of $402). 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 August 21, 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 9% 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 August 21, 2026.
The most flights from DCA to CHI are scheduled on a Wednesday (62 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (24 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 $272 and $444 in September.The cheapest round-trip price found within the last 5 days was $182 on American Airlines (Sep 17-Sep 24).
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 August 15, 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 August 21, 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.
Comfort
8.0
Food
7.0
Entertainment
7.5
Crew
8.6
Boarding
8.1
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Food
7.0
Entertainment
7.5
Crew
8.6
Boarding
8.1
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Food
7.0
Entertainment
7.5
Crew
8.6
Boarding
8.1
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Food
7.0
Entertainment
7.5
Crew
8.6
Boarding
8.1
Overall
8.0
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 August 21, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$29 | Average$169 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$198 | Average$351 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$227 | Average$370 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$229 | Average$386 | FlexibilityNo cancel fee | On-time69% |