$116+ Cheap flights from Raleigh (RDU) 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 11/17. Fares are subject to change and may not be available on all flights or dates of travel.
RDU — CHI
Nov 29 — Dec 61
Round-trip
1 adult, Economy
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Find cheap flights from Raleigh 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 Raleigh-Durham to Chicago are usually found in December or April, booked 76 days in advance, depart on a Thursday or Friday and return on a Friday
Cheap flight deals from Raleigh to Chicago
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Cheapest flights from Raleigh to ChicagoExplore the most affordable flight options available from Raleigh to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 30, 2026.
Explore the most affordable flight options available from Raleigh to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 30, 2026.
This American Airlines deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” 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.
Fri 12/185:28 am -
Nonstop2h 31m
Mon 12/217:29 pm -
Nonstop2h 07m
Deal found 10/28![American Airlines logo]()
$257
This Southwest deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” 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 12/197:50 pm -
Nonstop2h 05m
Tue 12/227:05 pm -
Nonstop2h 00m
Deal found 10/28![Southwest logo]()
$257
This Frontier deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” 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 12/263:34 pm -
1 stop8h 19m
Fri 1/15:58 am -
1 stop7h 23m
Deal found 10/29![Frontier logo]()
$258
This Frontier deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” 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 12/241:38 pm -
1 stop6h 52m
Sat 1/21:11 pm -
1 stop9h 55m
Deal found 10/29![Frontier logo]()
$258
This Kiwi.com deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 11/121:39 pm -
2 stops26h 58m
Sat 11/147:05 am -
1 stop6h 51m
Deal found 10/26![Frontier logo]()
$259
This Southwest deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” 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 11/211:15 pm -
2 stops5h 20m
Mon 11/235:05 am -
1 stop6h 15m
Deal found 10/28![Southwest logo]()
$259
This United Airlines deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” 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 12/38:05 am -
Nonstop2h 25m
Sun 12/68:52 am -
1 stop4h 08m
Deal found 10/29![United Airlines logo]()
$260
This Frontier deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” 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 12/283:20 pm -
1 stop9h 41m
Wed 1/65:21 pm -
1 stop5h 57m
Deal found 10/29![Frontier logo]()
$260
This American Airlines deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” 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.
Tue 11/246:00 am -
1 stop5h 15m
Fri 11/2711:50 am -
Nonstop2h 07m
Deal found 10/28![American Airlines logo]()
$261
This Southwest deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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 11/207:15 pm -
Nonstop2h 05m
Tue 11/244:20 pm -
1 stop5h 30m
Deal found 10/27![Southwest logo]()
$261
This Mytrip deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” 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 11/1911:10 am -
2 stops10h 23m
Fri 11/207:49 am -
1 stop5h 48m
Deal found 10/28![Frontier logo]()
$262
This Trip.com deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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.
Sun 11/152:02 pm -
1 stop10h 45m
Tue 11/176:08 am -
1 stop8h 15m
Deal found 10/26![Frontier logo]()
$262
Best flights from Raleigh to ChicagoDiscover carefully curated flight deals from Raleigh to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 30, 2026.
Discover carefully curated flight deals from Raleigh to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 30, 2026.
This United Airlines deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” 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 12/138:05 am -
Nonstop2h 25m
Mon 12/148:45 am -
1 stop4h 15m
Deal found 10/29![United Airlines logo]()
$260
This Delta deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” 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 12/115:30 am -
1 stop5h 07m
Fri 12/115:12 pm -
1 stop5h 05m
Deal found 10/28![Delta logo]()
$271
This Southwest deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” 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 12/1011:30 am -
2 stops9h 00m
Tue 12/151:15 pm -
2 stops7h 45m
Deal found 10/29![Southwest logo]()
$272
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.
Wed 11/188:50 am -
1 stop6h 04m
Sat 11/212:30 pm -
Nonstop2h 11m
Deal found 10/25![United Airlines logo]()
$263
This Southwest deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/189:00 pm -
1 stop4h 20m
Sun 12/207:35 am -
Nonstop1h 55m
Deal found 10/29![Southwest logo]()
$278
This United Airlines deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” 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 12/36:00 am -
1 stop4h 37m
Sun 12/68:52 am -
1 stop4h 08m
Deal found 10/29![United Airlines logo]()
$269
This Southwest deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” 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 11/208:00 am -
Nonstop2h 05m
Sun 11/227:45 am -
Nonstop1h 55m
Deal found 10/29![Southwest logo]()
$279
This Delta deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” 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 12/68:35 am -
1 stop4h 49m
Sun 12/137:05 am -
1 stop3h 56m
Deal found 10/28![Delta logo]()
$317
This United Airlines deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/2011:25 am -
Nonstop2h 34m
Sun 11/222:30 pm -
Nonstop2h 11m
Deal found 10/28![United Airlines logo]()
$274
This Southwest deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/45:25 pm -
1 stop6h 45m
Sun 12/67:45 am -
Nonstop1h 55m
Deal found 10/27![Southwest logo]()
$284
This Southwest deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” 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 12/1011:30 am -
2 stops9h 00m
Sun 12/1312:50 pm -
2 stops7h 40m
Deal found 10/28![Southwest logo]()
$284
This United Airlines deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/168:05 am -
Nonstop2h 25m
Sun 12/206:44 am -
Nonstop2h 12m
Deal found 10/26![United Airlines logo]()
$299
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/213:25 pm -
2 stops6h 10m
Thu 11/267:10 am -
2 stops8h 50m
Deal found 10/25![Southwest logo]()
$295
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.
Wed 12/99:55 am -
Nonstop2h 29m
Sun 12/132:25 pm -
Nonstop2h 14m
Deal found 10/25![United Airlines logo]()
$299
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/111:55 pm -
2 stops7h 10m
Wed 12/1610:20 am -
2 stops6h 25m
Deal found 10/25![Southwest logo]()
$295
This United Airlines deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” 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 12/1510:29 am -
1 stop4h 54m
Sat 12/266:25 pm -
Nonstop2h 09m
Deal found 10/29![United Airlines logo]()
$319
This Southwest deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” 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 1/318:05 am -
Nonstop2h 00m
Wed 2/38:15 am -
Nonstop2h 00m
Deal found 10/28![Southwest logo]()
$299
This United Airlines deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” 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 12/1510:29 am -
1 stop4h 54m
Sun 12/276:44 am -
Nonstop2h 12m
Deal found 10/29![United Airlines logo]()
$326
This Southwest deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” 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 12/311:30 am -
2 stops9h 00m
Sun 12/66:30 am -
1 stop5h 35m
Deal found 10/29![Southwest logo]()
$310
This United Airlines deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/208:05 am -
Nonstop2h 27m
Mon 11/239:05 am -
Nonstop2h 19m
Deal found 10/28![United Airlines logo]()
$331
This United Airlines deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 1/16:12 am -
Nonstop2h 34m
Sun 1/36:44 am -
Nonstop2h 12m
Deal found 10/26![United Airlines logo]()
$332
Last-minute flights from Raleigh to ChicagoDiscover last-minute flight deals from Raleigh to Chicago. Data last updated October 30, 2026 and is based on user searches.
Discover last-minute flight deals from Raleigh to Chicago. Data last updated October 30, 2026 and is based on user searches.
This Cheapflightsfares deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” 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 11/49:30 pm -
1 stop12h 16m
Wed 11/116:30 am -
1 stop10h 08m
Deal found 10/28![Frontier logo]()
$258
This Kiwi.com deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 11/710:06 am -
1 stop6h 31m
Wed 11/116:30 am -
1 stop10h 08m
Deal found 10/26![Frontier logo]()
$257
This Frontier deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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 11/73:05 pm -
1 stop9h 26m
Tue 11/109:51 am -
1 stop5h 40m
Deal found 10/27![Frontier logo]()
$260
This Frontier deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” 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 11/104:18 pm -
1 stop8h 29m
Wed 11/116:08 am -
1 stop8h 15m
Deal found 10/28![Frontier logo]()
$260
This Kiwi.com deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 11/121:39 pm -
2 stops26h 58m
Sat 11/147:05 am -
1 stop6h 51m
Deal found 10/26![Frontier logo]()
$259
This Trip.com deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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.
Sun 11/152:02 pm -
1 stop10h 45m
Tue 11/176:08 am -
1 stop8h 15m
Deal found 10/26![Frontier logo]()
$262
This Cheapflightsfares deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” 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 11/174:18 pm -
1 stop8h 29m
Fri 11/208:16 am -
1 stop5h 21m
Deal found 10/28![Frontier logo]()
$258
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.
Wed 11/188:50 am -
1 stop6h 04m
Sat 11/212:30 pm -
Nonstop2h 11m
Deal found 10/25![United Airlines logo]()
$263
This Mytrip deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” 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 11/1911:10 am -
2 stops10h 23m
Fri 11/207:49 am -
1 stop5h 48m
Deal found 10/28![Frontier logo]()
$262
This Southwest deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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 11/207:15 pm -
Nonstop2h 05m
Tue 11/244:20 pm -
1 stop5h 30m
Deal found 10/27![Southwest logo]()
$261
This Southwest deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” 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 11/211:15 pm -
2 stops5h 20m
Mon 11/235:05 am -
1 stop6h 15m
Deal found 10/28![Southwest logo]()
$259
This American Airlines deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” 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.
Tue 11/246:00 am -
1 stop5h 15m
Fri 11/2711:50 am -
Nonstop2h 07m
Deal found 10/28![American Airlines logo]()
$261
One-way flights from Raleigh to ChicagoSearch for one-way flight options from Raleigh to Chicago. Find affordable one-way fares based on user searches. Data last updated October 30, 2026.
Search for one-way flight options from Raleigh to Chicago. Find affordable one-way fares based on user searches. Data last updated October 30, 2026.
This Delta deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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 11/1712:56 pm -
1 stop4h 22m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![Delta logo]()
$116
This CheapOair deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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.
Mon 12/219:52 pm -
1 stop22h 38m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![Frontier logo]()
$117
This Cheapflightsfares deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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 11/1010:12 am -
1 stop7h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![Frontier logo]()
$118
This Kiwi.com deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” 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 11/2712:35 pm -
1 stop11h 43m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![Frontier logo]()
$120
This Frontier deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” 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 11/2512:28 pm -
1 stop8h 19m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![Frontier logo]()
$120
This Southwest deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” 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 11/1811:30 am -
2 stops9h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![Southwest logo]()
$121
This Kiwi.com deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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 11/610:06 am -
1 stop30h 31m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![Frontier logo]()
$122
This CheapOair deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/243:07 pm -
1 stop5h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![Frontier logo]()
$122
This Super.com deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” 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 11/175:26 pm -
1 stop24h 41m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![Frontier logo]()
$124
This Super.com deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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 11/104:18 pm -
1 stop8h 29m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![Frontier logo]()
$124
This Kiwi.com deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/236:41 pm -
2 stops20h 03m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/29![Frontier logo]()
$125
This United Airlines deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/278:05 am -
Nonstop2h 27m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![United Airlines logo]()
$126
Find flight deals from Raleigh to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from Raleigh (RDU) 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 30, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $257 (United Airlines) |
One-way from | $116 (Delta) |
Popular in | July |
Cheapest in | December |
Average price | $333 |
Good round-trip deal | $330 or less |
Good one-way deal | $195 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Raleigh 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 30, 2026.
Use the filters below to find and compare flights from Raleigh to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
RaleighChicago
RDU Raleigh-Durham - MDW Chicago Midway
RDUMDW
Raleigh-Durham
Tue 11/17
12:56 pm-4:18 pm
1 stop4h 22m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$116
RaleighChicago
RDU Raleigh-Durham - MDW Chicago Midway
RDUMDW
Raleigh-Durham
Thu 12/10
11:30 am-7:30 pm
2 stops9h 00m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$121
RaleighChicago
RDU Raleigh-Durham - MDW Chicago Midway
RDUMDW
Raleigh-Durham
Tue 12/15
11:30 am-7:30 pm
2 stops9h 00m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$121
RaleighChicago
RDU Raleigh-Durham - MDW Chicago Midway
RDUMDW
Raleigh-Durham
Mon 3/1
5:35 am-1:00 pm
2 stops8h 25m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$124
RaleighChicago
RDU Raleigh-Durham - ORD Chicago O'Hare Intl
RDUORD
Raleigh-Durham
Fri 11/27
8:05 am-9:32 am
Nonstop2h 27m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$126
Quickest round-trip
RaleighChicago
RDU Raleigh-Durham - MDW Chicago Midway
RDUMDW
Raleigh-Durham
Fri 12/4
1:50 pm-2:50 pm
Nonstop2h 00m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$126
RaleighChicago
RDU Raleigh-Durham - ORD Chicago O'Hare Intl
RDUORD
Raleigh-Durham
Wed 12/23
8:00 am-9:34 am
Nonstop2h 34m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$129
RaleighChicago
RDU Raleigh-Durham - MDW Chicago Midway
RDUMDW
Raleigh-Durham
Tue 12/22
7:35 pm-8:35 pm
Nonstop2h 00m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$129
RaleighChicago
RDU Raleigh-Durham - MDW Chicago Midway
RDUMDW
Raleigh-Durham
Fri 12/25
8:05 am-9:10 am
Nonstop2h 05m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$129
RaleighChicago
RDU Raleigh-Durham - MDW Chicago Midway
RDUMDW
Raleigh-Durham
Mon 12/7
12:56 pm-6:01 pm
1 stop6h 05m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$139
Showing 1-10 of 44 resultsSorted by cheapest first
Compare providers for flights from Raleigh 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 Raleigh to Chicago in October.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Raleigh-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Raleigh-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Raleigh-Chicago flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Raleigh-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 Raleigh-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 Raleigh to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Raleigh with our price prediction graph.
RDU-CHI
RDU-MDW
RDU-ORD
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 Raleigh to Chicago
RDU-CHI
RDU-MDW
RDU-ORD
What is the cheapest month to book a flight from Raleigh to Chicago?
Currently, December is the cheapest month in which you can book a flight from Raleigh to Chicago (average of $267). Flying from Raleigh to Chicago in July is currently the most expensive (average of $393). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from RDU to CHI?
Find hourly flight availability from Raleigh 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 30, 2026.
One of the essential ways to save on airfare from Raleigh to Chicago is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the evening could potentially save you up to 20% on airfare.
How much does it cost to fly round-trip from Raleigh to Chicago?
Airfare is typical for this route at the moment.
Raleigh to Chicago flights typically cost between $247 and $382 in January.The cheapest round-trip price found within the last 5 days was $257 on United Airlines (Jan 22-Jan 26).
How often are flights from Raleigh to Chicago delayed?
About 10% of weekly flights between Raleigh and Chicago have experienced delays in the past year, with the average delay time being 147 minutes.
What is the most punctual flight time for Raleigh to Chicago flights?
Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving at night tend to experience delays more often.
What day of the week experiences the fewest flight delays on this route?
Tuesday tends to have the lowest number of delays on this route, whereas Sunday has historically faced a higher average of delays compared to other days of the week.
Which airline has the best punctuality record on Raleigh to Chicago flights?
Over the last year, United Airlines have had the lowest number of delays on this route, with just 8% of flights being delayed.
How far ahead should I book a flight from Raleigh to Chicago?
Booking 75 days in advance of your planned departure date is, on average, the best time to get cheap flights from Raleigh 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 Raleigh to Chicago?
Use this chart to determine the cheapest time to fly round-trip from Raleigh to Chicago. Price data was last updated on October 24, 2026.
Travelers seeking maximum savings on their Raleigh to Chicago flight should consider departing on Monday evenings 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 Raleigh 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 Raleigh 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 30, 2026.
Get a feel of what it's like to fly with Southwest,United Airlines, andJetBlue from Raleigh 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
7.4
Crew
8.6
Comfort
8.0
Boarding
8.1
Food
7.0
Overall
7.9
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.4
Crew
8.6
Comfort
8.0
Boarding
8.1
Food
7.0
Overall
7.9
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.4
Crew
8.6
Comfort
8.0
Boarding
8.1
Food
7.0
Overall
7.9
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.4
Crew
8.6
Comfort
8.0
Boarding
8.1
Food
7.0
Overall
7.9
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.4
Crew
8.6
Comfort
8.0
Boarding
8.1
Food
7.0
Overall
7.9
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.4
Crew
8.6
Comfort
8.0
Boarding
8.1
Food
7.0
Overall
7.9
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Related info for your journey
Find useful and relevant information for your journey from Raleigh to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Merrillville
Lansing
Valparaiso
Hammond
Saint Joseph
Porter
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Other flights to Chicago
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Raleigh and Chicago flights
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Other flights from Raleigh
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Top 6 airlines flying from Raleigh to Chicago
Discover the top 6 airlines that operate flights from Raleigh 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 30, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$55 | Average$231 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$88 | Average$392 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$160 | Average$327 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$206 | Average$361 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$214 | Average$339 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$243 | Average$374 | FlexibilityNo cancel fee | On-time63% |