$145+ Cheap flights from Anaheim, CA 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 8/27. Fares are subject to change and may not be available on all flights or dates of travel.
SNA — CHI
Sep 5 — Sep 121
Round-trip
1 adult, Economy
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Find cheap flights from Anaheim 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 Anaheim to Chicago are usually found in October or September, booked 79 days in advance, depart on a Saturday or Wednesday and return on a Tuesday
Cheap flight deals from Anaheim to Chicago
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Cheapest flights from Anaheim to ChicagoExplore the most affordable flight options available from Anaheim to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 6, 2026.
Explore the most affordable flight options available from Anaheim to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 6, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/97:30 am -
1 stop20h 08m
Wed 9/161:21 pm -
1 stop29h 54m
Deal found 8/3![Multiple Airlines logo]()
$327
This Kiwi.com deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” 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 9/2411:50 am -
1 stop10h 33m
Sat 9/264:35 pm -
2 stops25h 13m
Deal found 8/1![Frontier logo]()
$328
This Frontier deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/210:45 am -
1 stop12h 00m
Sun 10/181:02 pm -
1 stop6h 33m
Deal found 8/3![Frontier logo]()
$329
This Super.com deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/177:53 pm -
1 stop7h 44m
Wed 8/192:41 pm -
1 stop20h 13m
Deal found 8/4![Frontier logo]()
$330
This Kiwi.com deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” 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 9/87:30 am -
1 stop8h 51m
Sat 9/126:30 am -
2 stops28h 15m
Deal found 8/1![Multiple Airlines logo]()
$331
This Kiwi.com deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” 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 9/39:39 am -
2 stops37h 10m
Thu 9/108:55 pm -
1 stop21h 20m
Deal found 8/5![Multiple Airlines logo]()
$332
This Southwest deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” 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 9/28:45 am -
1 stop6h 50m
Sat 9/510:05 am -
1 stop7h 40m
Deal found 8/5![Southwest logo]()
$333
This Kiwi.com deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” 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 8/223:53 pm -
1 stop26h 52m
Wed 8/262:13 pm -
1 stop25h 29m
Deal found 8/5![Multiple Airlines logo]()
$333
This United Airlines deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” 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 9/112:17 pm -
Nonstop4h 14m
Mon 9/147:55 pm -
Nonstop4h 30m
Deal found 8/5![United Airlines logo]()
$333
This Delta deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” 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 11/261:55 pm -
1 stop7h 01m
Wed 12/21:00 pm -
1 stop7h 42m
Deal found 8/3![Delta logo]()
$334
This Delta deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” 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 9/612:15 pm -
1 stop9h 42m
Mon 9/147:00 am -
1 stop8h 11m
Deal found 8/3![Delta logo]()
$334
This Kiwi.com deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” 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 10/163:07 pm -
1 stop7h 26m
Mon 10/196:05 am -
2 stops10h 07m
Deal found 8/3![Frontier logo]()
$335
Best flights from Anaheim to ChicagoDiscover carefully curated flight deals from Anaheim to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 6, 2026.
Discover carefully curated flight deals from Anaheim to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 6, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” 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.
Sun 8/166:03 pm -
1 stop24h 31m
Wed 8/262:13 pm -
1 stop25h 29m
Deal found 8/3![Multiple Airlines logo]()
$342
This United Airlines deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” 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 9/162:17 pm -
Nonstop4h 14m
Sun 9/205:00 am -
1 stop6h 07m
Deal found 8/2![United Airlines logo]()
$345
This Southwest deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” 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 9/188:30 pm -
1 stop7h 15m
Tue 9/2210:30 am -
2 stops8h 15m
Deal found 8/4![Southwest logo]()
$363
This Delta deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” 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 9/182:00 pm -
1 stop7h 59m
Tue 9/2211:17 am -
2 stops12h 47m
Deal found 8/5![Delta logo]()
$364
This Kiwi.com deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” 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 8/2210:39 am -
2 stops26h 30m
Wed 8/262:13 pm -
1 stop21h 38m
Deal found 8/5![Allegiant Air logo]()
$402
This United Airlines deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/162:26 pm -
Nonstop4h 14m
Sun 10/185:00 am -
1 stop6h 29m
Deal found 8/4![United Airlines logo]()
$345
This Delta deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” 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 9/16:45 am -
2 stops11h 45m
Tue 9/152:05 pm -
2 stops10h 25m
Deal found 8/2![Delta logo]()
$369
This Kiwi.com deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” 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.
Sun 9/137:45 am -
1 stop10h 54m
Fri 9/187:01 pm -
2 stops42h 04m
Deal found 8/2![Multiple Airlines logo]()
$377
This United Airlines deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” 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 9/262:26 pm -
Nonstop4h 14m
Wed 9/305:00 am -
1 stop6h 29m
Deal found 8/4![United Airlines logo]()
$345
This Southwest deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” 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 9/278:55 pm -
1 stop6h 05m
Wed 9/302:15 pm -
1 stop8h 40m
Deal found 8/2![Southwest logo]()
$392
This Delta deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” 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 10/136:02 pm -
2 stops11h 39m
Tue 10/2011:19 am -
2 stops13h 11m
Deal found 8/1![Delta logo]()
$369
This Kiwi.com deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” 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 8/205:07 pm -
1 stop17h 16m
Sun 8/239:35 pm -
2 stops12h 49m
Deal found 8/6![Multiple Airlines logo]()
$385
This Southwest deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” 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 9/188:45 pm -
1 stop6h 55m
Sun 9/205:40 am -
1 stop7h 55m
Deal found 8/1![Southwest logo]()
$393
This Kiwi.com deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” 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.
Sun 11/224:23 pm -
1 stop18h 03m
Fri 11/271:16 pm -
1 stop26h 45m
Deal found 8/3![Allegiant Air logo]()
$444
This Delta deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” 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 9/269:55 am -
2 stops9h 43m
Wed 9/302:05 pm -
2 stops10h 25m
Deal found 8/4![Delta logo]()
$369
This Southwest deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” 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 8/2111:45 am -
1 stop5h 15m
Sat 8/2910:05 am -
1 stop6h 30m
Deal found 8/2![Southwest logo]()
$393
This United Airlines deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” 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 9/32:10 pm -
Nonstop4h 14m
Sun 9/67:55 pm -
Nonstop4h 30m
Deal found 8/3![United Airlines logo]()
$414
This Kiwi.com deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” 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 8/226:30 pm -
2 stops18h 39m
Wed 8/262:13 pm -
1 stop25h 29m
Deal found 8/4![Multiple Airlines logo]()
$427
This Southwest deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” 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 8/2211:55 am -
1 stop5h 35m
Wed 8/2610:30 am -
2 stops8h 15m
Deal found 8/4![Southwest logo]()
$398
This United Airlines deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” 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 9/56:45 am -
Nonstop4h 22m
Thu 9/107:55 pm -
Nonstop4h 30m
Deal found 8/6![United Airlines logo]()
$414
This Delta deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” 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 9/1611:38 am -
1 stop9h 06m
Wed 9/231:00 pm -
1 stop7h 29m
Deal found 8/5![Delta logo]()
$419
This Kiwi.com deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” 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.
Sun 10/47:45 am -
1 stop11h 01m
Thu 10/89:03 pm -
1 stop21h 12m
Deal found 8/1![Multiple Airlines logo]()
$432
This Southwest deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” 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 9/510:40 am -
2 stops8h 10m
Fri 9/115:00 pm -
2 stops6h 55m
Deal found 8/2![Southwest logo]()
$402
This Delta deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” 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 8/2811:45 am -
1 stop8h 51m
Thu 9/39:59 am -
2 stops10h 23m
Deal found 8/6![Delta logo]()
$424
This United Airlines deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” 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 9/32:10 pm -
Nonstop4h 14m
Tue 9/85:00 am -
1 stop6h 07m
Deal found 8/2![United Airlines logo]()
$445
This Delta deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” 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 9/2711:59 am -
1 stop9h 58m
Wed 10/79:59 am -
2 stops8h 11m
Deal found 8/5![Delta logo]()
$424
This Southwest deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” 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 8/218:20 pm -
1 stop7h 35m
Sun 8/237:10 am -
1 stop6h 25m
Deal found 8/3![Southwest logo]()
$429
This Kiwi.com deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” 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 8/223:53 pm -
1 stop26h 52m
Fri 8/2812:13 pm -
2 stops23h 36m
Deal found 8/5![Multiple Airlines logo]()
$483
This United Airlines deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” 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 9/22:10 pm -
Nonstop4h 14m
Mon 9/77:55 pm -
Nonstop4h 30m
Deal found 8/5![United Airlines logo]()
$453
This Southwest deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” 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 8/191:00 pm -
1 stop8h 20m
Sun 8/236:30 am -
1 stop5h 35m
Deal found 8/4![Southwest logo]()
$429
Last-minute flights from Anaheim to ChicagoDiscover last-minute flight deals from Anaheim to Chicago. Data last updated August 6, 2026 and is based on user searches.
Discover last-minute flight deals from Anaheim to Chicago. Data last updated August 6, 2026 and is based on user searches.
This Super.com deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/177:53 pm -
1 stop7h 44m
Wed 8/192:41 pm -
1 stop20h 13m
Deal found 8/4![Frontier logo]()
$330
This Kiwi.com deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” 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 8/223:53 pm -
1 stop26h 52m
Wed 8/262:13 pm -
1 stop25h 29m
Deal found 8/5![Multiple Airlines logo]()
$333
This Kiwi.com deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” 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 8/247:53 pm -
2 stops32h 24m
Thu 8/272:41 pm -
1 stop19h 43m
Deal found 8/4![Frontier logo]()
$336
This Expedia deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” 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 8/288:59 pm -
1 stop13h 08m
Sun 8/308:11 pm -
1 stop18h 20m
Deal found 8/6![Multiple Airlines logo]()
$335
This Southwest deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” 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 9/28:45 am -
1 stop6h 50m
Sat 9/510:05 am -
1 stop7h 40m
Deal found 8/5![Southwest logo]()
$333
This Kiwi.com deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” 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 9/39:39 am -
2 stops37h 10m
Thu 9/108:55 pm -
1 stop21h 20m
Deal found 8/5![Multiple Airlines logo]()
$332
This United Airlines deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” 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 9/44:14 pm -
1 stop5h 45m
Sat 9/55:00 am -
1 stop6h 07m
Deal found 8/5![United Airlines logo]()
$329
This Delta deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” 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 9/612:15 pm -
1 stop9h 42m
Mon 9/147:00 am -
1 stop8h 11m
Deal found 8/3![Delta logo]()
$334
This Kiwi.com deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” 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 9/87:30 am -
1 stop8h 51m
Sat 9/126:30 am -
2 stops28h 15m
Deal found 8/1![Multiple Airlines logo]()
$331
This Kiwi.com deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/97:30 am -
1 stop20h 08m
Wed 9/161:21 pm -
1 stop29h 54m
Deal found 8/3![Multiple Airlines logo]()
$327
This United Airlines deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” 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 9/112:17 pm -
Nonstop4h 14m
Mon 9/147:55 pm -
Nonstop4h 30m
Deal found 8/5![United Airlines logo]()
$333
This Kiwi.com deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” 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 9/2411:50 am -
1 stop10h 33m
Sat 9/264:35 pm -
2 stops25h 13m
Deal found 8/1![Frontier logo]()
$328
One-way flights from Anaheim to ChicagoSearch for one-way flight options from Anaheim to Chicago. Find affordable one-way fares based on user searches. Data last updated August 6, 2026.
Search for one-way flight options from Anaheim to Chicago. Find affordable one-way fares based on user searches. Data last updated August 6, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” 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 8/272:27 pm -
2 stops26h 35m
Deal found 8/4![Frontier logo]()
$145
This Kiwi.com deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” 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 9/53:53 pm -
2 stops12h 06m
Deal found 8/4![Frontier logo]()
$146
This Kiwi.com deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” 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 8/319:09 am -
1 stop26h 27m
Deal found 8/4![Frontier logo]()
$147
This Kiwi.com deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/14:35 pm -
2 stops29h 48m
Deal found 8/3![Frontier logo]()
$148
This Kiwi.com deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” 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 9/297:30 am -
1 stop20h 08m
Deal found 8/1![Multiple Airlines logo]()
$149
This CheapOair deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” 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.
Sun 8/307:53 pm -
1 stop21h 09m
Deal found 8/1![Frontier logo]()
$150
This Kiwi.com deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” 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 11/37:30 am -
2 stops24h 31m
Deal found 8/5![Multiple Airlines logo]()
$151
This Kiwi.com deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” 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 8/272:27 pm -
2 stops30h 20m
Deal found 8/4![Frontier logo]()
$152
This Kiwi.com deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” 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 11/27:28 pm -
2 stops36h 33m
Deal found 8/5![Frontier logo]()
$152
This Kiwi.com deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” 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 9/286:00 pm -
2 stops28h 23m
Deal found 8/1![Frontier logo]()
$153
This Kiwi.com deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” 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 9/32:27 pm -
2 stops30h 20m
Deal found 8/5![Frontier logo]()
$154
This Kiwi.com deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” 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 10/29:30 am -
2 stops12h 53m
Deal found 8/1![Frontier logo]()
$154
Find flight deals from Anaheim to Chicago
Keep the following information in mind while searching for Anaheim to Chicago flight deals. Data was last updated August 6, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $327 (Kiwi.com) |
One-way from | $145 (Kiwi.com) |
Popular in | April |
Cheapest in | October |
Average price | $397 |
Cheapflights Fare Finder
Customize your flight search to find flights from Anaheim 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 2,558,603 searches. Data last updated August 6, 2026.
Use the filters below to find and compare flights from Anaheim to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Santa AnaChicago
SNA Santa Ana J. Wayne/Orange Cnty - RFD Chicago Greater Rockford
SNARFD
Santa Ana J. Wayne/Orange Cnty
Sun 8/16
6:03 pm-8:34 pm
1 stop24h 31m
Chicago Greater Rockford
Wed 8/26
2:13 pm-1:42 pm
1 stop25h 29m
$342
Santa AnaChicago
SNA Santa Ana J. Wayne/Orange Cnty - ORD Chicago O'Hare Intl
SNAORD
Santa Ana J. Wayne/Orange Cnty
Wed 9/16
2:17 pm-8:31 pm
Nonstop4h 14m
Chicago O'Hare Intl
Sun 9/20
5:00 am-9:07 am
1 stop6h 07m
$345
Santa AnaChicago
SNA Santa Ana J. Wayne/Orange Cnty - ORD Chicago O'Hare Intl
SNAORD
Santa Ana J. Wayne/Orange Cnty
Fri 10/16
2:26 pm-8:40 pm
Nonstop4h 14m
Chicago O'Hare Intl
Sun 10/18
5:00 am-9:29 am
1 stop6h 29m
$345
Santa AnaChicago
SNA Santa Ana J. Wayne/Orange Cnty - ORD Chicago O'Hare Intl
SNAORD
Santa Ana J. Wayne/Orange Cnty
Sat 9/26
2:26 pm-8:40 pm
Nonstop4h 14m
Chicago O'Hare Intl
Wed 9/30
5:00 am-9:29 am
1 stop6h 29m
$345
Santa AnaChicago
SNA Santa Ana J. Wayne/Orange Cnty - MDW Chicago Midway
SNAMDW
Santa Ana J. Wayne/Orange Cnty
Fri 9/18
8:30 pm-5:45 am
1 stop7h 15m
Chicago Midway
Tue 9/22
10:30 am-4:45 pm
2 stops8h 15m
$363
Santa AnaChicago
SNA Santa Ana J. Wayne/Orange Cnty - ORD Chicago O'Hare Intl
SNAORD
Santa Ana J. Wayne/Orange Cnty
Fri 9/18
2:00 pm-11:59 pm
1 stop7h 59m
Chicago O'Hare Intl
Tue 9/22
11:17 am-10:04 pm
2 stops12h 47m
$364
Santa AnaChicago
SNA Santa Ana J. Wayne/Orange Cnty - ORD Chicago O'Hare Intl
SNAORD
Santa Ana J. Wayne/Orange Cnty
Tue 9/1
6:45 am-8:30 pm
2 stops11h 45m
Chicago O'Hare Intl
Tue 9/15
2:05 pm-10:30 pm
2 stops10h 25m
$369
Santa AnaChicago
SNA Santa Ana J. Wayne/Orange Cnty - ORD Chicago O'Hare Intl
SNAORD
Santa Ana J. Wayne/Orange Cnty
Tue 10/13
6:02 pm-7:41 am
2 stops11h 39m
Chicago O'Hare Intl
Tue 10/20
11:19 am-10:30 pm
2 stops13h 11m
$369
Santa AnaChicago
SNA Santa Ana J. Wayne/Orange Cnty - ORD Chicago O'Hare Intl
SNAORD
Santa Ana J. Wayne/Orange Cnty
Sat 9/26
9:55 am-9:38 pm
2 stops9h 43m
Chicago O'Hare Intl
Wed 9/30
2:05 pm-10:30 pm
2 stops10h 25m
$369
Santa AnaChicago
SNA Santa Ana J. Wayne/Orange Cnty - RFD Chicago Greater Rockford
SNARFD
Santa Ana J. Wayne/Orange Cnty
Sun 9/13
7:45 am-8:39 pm
1 stop10h 54m
Chicago Greater Rockford
Fri 9/18
7:01 pm-11:05 am
2 stops42h 04m
$377
Showing 1-10 of 57 resultsSorted by cheapest first
Best time to book a flight from Anaheim to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Anaheim with our price prediction graph.
SNA-RFD
SNA-MDW
SNA-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 Anaheim to Chicago
AN4-CHI
SNA-RFD
SNA-MDW
SNA-ORD
What is the cheapest time of day to fly from AN4 to CHI?
Find hourly flight availability from Anaheim 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 6, 2026.
Unlike at noon, when flights are generally more expensive, you can save up to 16% on flights from Anaheim to Chicago by exploring options for tickets in the afternoon.
Weekly flight availability from Anaheim to Chicago
Explore weekly flight availability from Anaheim 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 6, 2026.
The most flights from AN4 to CHI are scheduled on a Wednesday (24 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (13 on average).
How much does it cost to fly round-trip from Anaheim to Chicago?
Airfare is below average for this route at the moment.
Anaheim to Chicago flights typically cost between $348 and $474 in September.The cheapest round-trip price found within the last 5 days was $327 on Multiple Airlines (Sep 9-Sep 16).
What is the cheapest day to fly from Anaheim to Chicago?
Use this chart to determine the cheapest time to fly round-trip from Anaheim to Chicago. Price data was last updated on August 1, 2026.
Travelers seeking maximum savings on their Anaheim to Chicago flight should consider departing on Wednesday mornings when fares are most often at their lowest. Sunday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.
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 6, 2026.
Peruse reviews from past customers who have flown with Southwest,Alaska Airlines, andUnited Airlines from Anaheim to Chicago to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Comfort
8.0
Entertainment
7.5
Overall
8.0
Boarding
8.1
Food
7.0
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Entertainment
7.5
Overall
8.0
Boarding
8.1
Food
7.0
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Entertainment
7.5
Overall
8.0
Boarding
8.1
Food
7.0
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Entertainment
7.5
Overall
8.0
Boarding
8.1
Food
7.0
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Entertainment
7.5
Overall
8.0
Boarding
8.1
Food
7.0
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Entertainment
7.5
Overall
8.0
Boarding
8.1
Food
7.0
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 Anaheim to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter
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Alternative routes for Anaheim to Chicago
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Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on August 6, 2026.
Complete your trip
Complete your trip to Chicago by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Anaheim to Chicago by cabin class
Find flights from Anaheim to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Anaheim and Chicago flights
Browse other Anaheim and Chicago flight options. Last updated on August 6, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 7 airlines flying from Anaheim to Chicago
Discover the top 7 airlines that operate flights from Anaheim 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 2,558,603 searches. Data last updated August 6, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$97 | Average$268 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$166 | Average$356 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$195 | Average$373 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$197 | Average$428 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$198 | Average$454 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$223 | Average$459 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$253 | Average$504 | FlexibilityNo cancel fee | On-time75% |