$174+ 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 6/6. Fares are subject to change and may not be available on all flights or dates of travel.
SNA — CHI
Jun 12 — Jun 191
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 August or September, booked 65 days in advance, depart on a Wednesday or Saturday and return on a Saturday
Cheap flight deals from Anaheim to Chicago
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Best
Last-minute
One-way
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 May 13, 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 May 13, 2026.
This Kiwi.com deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” 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 6/88:10 pm
SNA
- ORD
2 stops21h 43m
Frontier
Thu 6/117:20 am
ORD
- SNA
1 stop7h 14m
Frontier
Deal found 5/8![Frontier logo]()
$327
This Kiwi.com deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/77:54 pm
SNA
- ORD
1 stop7h 34m
Frontier
Wed 8/127:15 am
ORD
- SNA
2 stops32h 27m
Frontier
Deal found 5/9![Frontier logo]()
$328
This Kiwi.com deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” 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 7/302:27 pm
SNA
- MDW
2 stops22h 00m
Multiple Airlines
Sun 8/28:11 pm
MDW
- SNA
1 stop14h 42m
Multiple Airlines
Deal found 5/8![Multiple Airlines logo]()
$329
This United Airlines deal was found by Cheapflights users on 5/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/236:45 am
SNA
- ORD
Nonstop4h 20m
United Airlines
Sat 9/267:45 pm
ORD
- SNA
Nonstop4h 20m
United Airlines
Deal found 5/10![United Airlines logo]()
$329
This American Airlines deal was found by Cheapflights users on 5/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/283:08 pm
SNA
- ORD
Nonstop4h 31m
American Airlines
Sun 5/3111:54 am
ORD
- SNA
Nonstop4h 24m
American Airlines
Deal found 5/10![American Airlines logo]()
$330
This Expedia deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/13:31 pm
SNA
- ORD
1 stop12h 49m
Multiple Airlines
Thu 6/49:37 pm
ORD
- SNA
1 stop13h 32m
Multiple Airlines
Deal found 5/9![Multiple Airlines logo]()
$331
This Southwest deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” 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 6/27:25 am
SNA
- MDW
1 stop6h 30m
Southwest
Thu 6/45:20 am
MDW
- SNA
1 stop7h 55m
Southwest
Deal found 5/8![Southwest logo]()
$333
This United Airlines deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/304:00 pm
SNA
- ORD
1 stop6h 44m
United Airlines
Tue 6/25:00 am
ORD
- SNA
1 stop6h 07m
United Airlines
Deal found 5/9![United Airlines logo]()
$334
This Frontier deal was found by Cheapflights users on 5/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/208:55 am
SNA
- ORD
1 stop9h 58m
Frontier
Mon 8/249:33 am
ORD
- SNA
1 stop10h 20m
Frontier
Deal found 5/10![Frontier logo]()
$335
This United Airlines deal was found by Cheapflights users on 5/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/242:10 pm
SNA
- ORD
Nonstop4h 16m
United Airlines
Mon 6/15:00 am
ORD
- SNA
1 stop6h 07m
United Airlines
Deal found 5/10![United Airlines logo]()
$336
This Southwest deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” 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 8/2710:05 am
SNA
- MDW
1 stop6h 20m
Southwest
Mon 8/317:10 am
MDW
- SNA
1 stop7h 20m
Southwest
Deal found 5/8![Southwest logo]()
$337
This Southwest deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” 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 5/304:20 pm
SNA
- MDW
1 stop10h 40m
Southwest
Tue 6/212:35 pm
MDW
- SNA
1 stop8h 30m
Southwest
Deal found 5/8![Southwest logo]()
$338
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 May 13, 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 May 13, 2026.
This Alaska Airlines deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/910:34 am
SNA
- ORD
1 stop11h 25m
Alaska Airlines
Mon 9/148:42 pm
ORD
- SNA
1 stop15h 33m
Alaska Airlines
Deal found 5/9![Alaska Airlines logo]()
$329
This United Airlines deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/86:45 am
SNA
- ORD
Nonstop4h 24m
United Airlines
Sat 7/115:00 am
ORD
- SNA
1 stop6h 07m
United Airlines
Deal found 5/9![United Airlines logo]()
$335
This Southwest deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” 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 5/304:20 pm
SNA
- MDW
1 stop10h 40m
Southwest
Tue 6/212:35 pm
MDW
- SNA
1 stop8h 30m
Southwest
Deal found 5/8![Southwest logo]()
$338
This Delta deal was found by Cheapflights users on 5/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/252:00 pm
SNA
- ORD
1 stop7h 59m
Delta
Tue 6/306:55 am
ORD
- SNA
1 stop8h 15m
Delta
Deal found 5/10![Delta logo]()
$339
This Kiwi.com deal was found by Cheapflights users on 5/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/119:20 pm
SNA
- RFD
1 stop21h 00m
Allegiant Air
Wed 6/178:50 pm
RFD
- SNA
1 stop19h 25m
Allegiant Air
Deal found 5/10![Allegiant Air logo]()
$343
This Kiwi.com deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/219:20 pm
SNA
- RFD
1 stop21h 00m
Multiple Airlines
Fri 6/2610:05 pm
RFD
- SNA
2 stops23h 20m
Multiple Airlines
Deal found 5/9![Multiple Airlines logo]()
$346
This Southwest deal was found by Cheapflights users on 5/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/168:15 pm
SNA
- MDW
1 stop6h 55m
Southwest
Fri 6/196:40 pm
MDW
- SNA
1 stop5h 45m
Southwest
Deal found 5/10![Southwest logo]()
$339
This Delta deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/277:05 pm
SNA
- ORD
2 stops12h 59m
Delta
Wed 10/77:00 am
ORD
- SNA
1 stop9h 40m
Delta
Deal found 5/12![Delta logo]()
$344
This Kiwi.com deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” 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 7/312:27 pm
SNA
- RFD
1 stop19h 41m
Multiple Airlines
Mon 8/37:50 pm
RFD
- SNA
1 stop18h 25m
Multiple Airlines
Deal found 5/8![Multiple Airlines logo]()
$352
This Southwest deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” 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 8/77:55 pm
SNA
- MDW
1 stop7h 05m
Southwest
Sun 8/95:40 am
MDW
- SNA
1 stop7h 55m
Southwest
Deal found 5/8![Southwest logo]()
$349
This Delta deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/2512:18 pm
SNA
- MDW
1 stop7h 59m
Delta
Thu 7/21:49 pm
MDW
- SNA
1 stop8h 35m
Delta
Deal found 5/11![Delta logo]()
$349
This United Airlines deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/124:00 pm
SNA
- ORD
1 stop6h 44m
United Airlines
Tue 6/168:50 am
ORD
- SNA
Nonstop4h 41m
United Airlines
Deal found 5/11![United Airlines logo]()
$399
This Delta deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/268:00 am
SNA
- MDW
1 stop8h 18m
Delta
Sun 6/286:00 am
MDW
- SNA
1 stop8h 40m
Delta
Deal found 5/12![Delta logo]()
$349
This Kiwi.com deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/259:20 pm
SNA
- RFD
1 stop21h 55m
Multiple Airlines
Mon 6/297:48 pm
RFD
- SNA
1 stop18h 27m
Multiple Airlines
Deal found 5/12![Multiple Airlines logo]()
$386
This Alaska Airlines deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/157:45 am
SNA
- ORD
Nonstop4h 20m
Alaska Airlines
Mon 8/1712:12 pm
ORD
- SNA
Nonstop4h 22m
Alaska Airlines
Deal found 5/8![Alaska Airlines logo]()
$429
This United Airlines deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/132:25 pm
SNA
- ORD
Nonstop4h 14m
United Airlines
Sun 8/164:10 pm
ORD
- SNA
Nonstop4h 41m
United Airlines
Deal found 5/12![United Airlines logo]()
$408
This Southwest deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/1310:05 am
SNA
- MDW
1 stop8h 10m
Southwest
Sun 8/167:10 am
MDW
- SNA
1 stop7h 40m
Southwest
Deal found 5/12![Southwest logo]()
$383
This Delta deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/308:00 am
SNA
- ORD
1 stop7h 02m
Delta
Fri 7/38:36 am
ORD
- SNA
1 stop6h 20m
Delta
Deal found 5/9![Delta logo]()
$349
This Alaska Airlines deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/53:27 pm
SNA
- ORD
Nonstop4h 33m
Alaska Airlines
Sat 8/85:55 pm
ORD
- SNA
Nonstop4h 20m
Alaska Airlines
Deal found 5/9![Alaska Airlines logo]()
$429
This Kiwi.com deal was found by Cheapflights users on 5/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/297:30 am
SNA
- RFD
1 stop26h 54m
Multiple Airlines
Mon 8/37:50 pm
RFD
- SNA
1 stop18h 25m
Multiple Airlines
Deal found 5/10![Multiple Airlines logo]()
$393
This Southwest deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/226:00 pm
SNA
- MDW
1 stop5h 25m
Southwest
Mon 6/297:30 am
MDW
- SNA
1 stop6h 15m
Southwest
Deal found 5/12![Southwest logo]()
$383
This Delta deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1810:15 am
SNA
- ORD
2 stops11h 42m
Delta
Mon 9/211:55 pm
ORD
- SNA
2 stops10h 34m
Delta
Deal found 5/12![Delta logo]()
$359
This Kiwi.com deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/208:10 pm
SNA
- RFD
1 stop14h 13m
Multiple Airlines
Sat 7/111:03 pm
RFD
- SNA
1 stop23h 40m
Multiple Airlines
Deal found 5/12![Multiple Airlines logo]()
$416
This Kiwi.com deal was found by Cheapflights users on 5/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/262:24 pm
SNA
- RFD
1 stop19h 50m
Multiple Airlines
Mon 6/297:48 pm
RFD
- SNA
1 stop18h 27m
Multiple Airlines
Deal found 5/10![Multiple Airlines logo]()
$417
This Southwest deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” 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 7/315:15 pm
SNA
- MDW
1 stop5h 20m
Southwest
Mon 8/37:30 am
MDW
- SNA
1 stop6h 10m
Southwest
Deal found 5/8![Southwest logo]()
$418
This Delta deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/306:45 am
SNA
- MDW
1 stop7h 27m
Delta
Sat 6/61:59 pm
MDW
- SNA
1 stop8h 35m
Delta
Deal found 5/12![Delta logo]()
$384
This Delta deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/52:00 pm
SNA
- ORD
1 stop7h 59m
Delta
Wed 6/106:55 am
ORD
- SNA
1 stop11h 36m
Delta
Deal found 5/12![Delta logo]()
$384
This Southwest deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/67:45 pm
SNA
- MDW
1 stop7h 25m
Southwest
Mon 6/85:20 am
MDW
- SNA
1 stop6h 10m
Southwest
Deal found 5/12![Southwest logo]()
$425
This Kiwi.com deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/149:20 pm
SNA
- RFD
1 stop21h 00m
Multiple Airlines
Wed 6/178:50 pm
RFD
- SNA
2 stops17h 44m
Multiple Airlines
Deal found 5/12![Multiple Airlines logo]()
$427
This Delta deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/197:10 pm
SNA
- MDW
2 stops12h 04m
Delta
Tue 6/239:17 am
MDW
- SNA
2 stops8h 56m
Delta
Deal found 5/12![Delta logo]()
$385
Last-minute flights from Anaheim to ChicagoDiscover last-minute flight deals from Anaheim to Chicago. Data last updated May 13, 2026 and is based on user searches.
Discover last-minute flight deals from Anaheim to Chicago. Data last updated May 13, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 5/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/242:10 pm
SNA
- ORD
Nonstop4h 16m
United Airlines
Mon 6/15:00 am
ORD
- SNA
1 stop6h 07m
United Airlines
Deal found 5/10![United Airlines logo]()
$336
This American Airlines deal was found by Cheapflights users on 5/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/283:08 pm
SNA
- ORD
Nonstop4h 31m
American Airlines
Sun 5/3111:54 am
ORD
- SNA
Nonstop4h 24m
American Airlines
Deal found 5/10![American Airlines logo]()
$330
This United Airlines deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/304:00 pm
SNA
- ORD
1 stop6h 44m
United Airlines
Tue 6/25:00 am
ORD
- SNA
1 stop6h 07m
United Airlines
Deal found 5/9![United Airlines logo]()
$334
This Southwest deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” 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 5/304:20 pm
SNA
- MDW
1 stop10h 40m
Southwest
Tue 6/212:35 pm
MDW
- SNA
1 stop8h 30m
Southwest
Deal found 5/8![Southwest logo]()
$338
This Expedia deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/13:31 pm
SNA
- ORD
1 stop12h 49m
Multiple Airlines
Thu 6/49:37 pm
ORD
- SNA
1 stop13h 32m
Multiple Airlines
Deal found 5/9![Multiple Airlines logo]()
$331
This Southwest deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” 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 6/27:25 am
SNA
- MDW
1 stop6h 30m
Southwest
Thu 6/45:20 am
MDW
- SNA
1 stop7h 55m
Southwest
Deal found 5/8![Southwest logo]()
$333
This Delta deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/311:53 am
SNA
- ORD
1 stop6h 21m
Delta
Mon 6/82:09 pm
ORD
- SNA
1 stop6h 21m
Delta
Deal found 5/12![Delta logo]()
$339
This Kiwi.com deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” 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 6/88:10 pm
SNA
- ORD
2 stops21h 43m
Frontier
Thu 6/117:20 am
ORD
- SNA
1 stop7h 14m
Frontier
Deal found 5/8![Frontier logo]()
$327
This Delta deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/92:05 pm
SNA
- ORD
1 stop7h 34m
Delta
Tue 6/166:55 am
ORD
- SNA
1 stop8h 15m
Delta
Deal found 5/11![Delta logo]()
$329
This Frontier deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/198:55 am
SNA
- ORD
1 stop9h 48m
Frontier
Mon 6/227:20 am
ORD
- SNA
1 stop7h 14m
Frontier
Deal found 5/9![Frontier logo]()
$335
This American Airlines deal was found by Cheapflights users on 5/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/277:43 pm
SNA
- ORD
1 stop8h 36m
American Airlines
Sun 6/288:15 am
ORD
- SNA
Nonstop4h 32m
American Airlines
Deal found 5/10![American Airlines logo]()
$338
This Delta deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/308:00 am
SNA
- MDW
1 stop8h 18m
Delta
Fri 7/34:25 pm
MDW
- SNA
1 stop8h 03m
Delta
Deal found 5/11![Delta logo]()
$339
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 May 13, 2026.
Search for one-way flight options from Anaheim to Chicago. Find affordable one-way fares based on user searches. Data last updated May 13, 2026.
This Southwest deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” 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 6/65:50 pm
SNA
- MDW
2 stops9h 30m
Southwest
Deal found 5/8![Southwest logo]()
$174
This Kiwi.com deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” 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 6/44:20 pm
SNA
- ORD
2 stops26h 12m
Frontier
Deal found 5/8![Frontier logo]()
$174
This Southwest deal was found by Cheapflights users on 5/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/155:15 pm
SNA
- MDW
1 stop5h 20m
Southwest
Deal found 5/10![Southwest logo]()
$175
This Alaska Airlines deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/175:33 pm
SNA
- ORD
1 stop10h 49m
Alaska Airlines
Deal found 5/11![Alaska Airlines logo]()
$175
This Southwest deal was found by Cheapflights users on 5/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/2410:30 am
SNA
- MDW
1 stop8h 15m
Southwest
Deal found 5/10![Southwest logo]()
$176
This Southwest deal was found by Cheapflights users on 5/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/241:55 pm
SNA
- ORD
1 stop7h 00m
Southwest
Deal found 5/10![Southwest logo]()
$176
This Kiwi.com deal was found by Cheapflights users on 5/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/67:54 pm
SNA
- ORD
1 stop7h 34m
Frontier
Deal found 5/10![Frontier logo]()
$177
This CheapOair deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” 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 6/13:31 pm
SNA
- ORD
1 stop12h 49m
Alaska Airlines
Deal found 5/8![Alaska Airlines logo]()
$180
This Kiwi.com deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/149:20 pm
SNA
- ORD
2 stops25h 28m
Multiple Airlines
Deal found 5/12![Multiple Airlines logo]()
$183
This Kiwi.com deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/73:34 pm
SNA
- MDW
2 stops41h 38m
Multiple Airlines
Deal found 5/9![Multiple Airlines logo]()
$184
This Kiwi.com deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/73:34 pm
SNA
- ORD
2 stops38h 29m
Multiple Airlines
Deal found 5/11![Multiple Airlines logo]()
$184
This Frontier deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/239:54 am
SNA
- ORD
1 stop8h 38m
Frontier
Deal found 5/11![Frontier logo]()
$185
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 May 13, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $327 (Kiwi.com) |
One-way from | $174 (Southwest) |
Popular in | April |
Cheapest in | August |
Average price | $443 |
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 May 13, 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 - ORD
SNAORD
Santa Ana J. Wayne/Orange Cnty
Wed 9/9
10:34 am-11:59 pm
1 stop11h 25m
Chicago O'Hare Intl
Mon 9/14
8:42 pm-10:15 am
1 stop15h 33m
$329
Santa AnaChicago
SNA - ORD
SNAORD
Santa Ana J. Wayne/Orange Cnty
Wed 7/8
6:45 am-1:09 pm
Nonstop4h 24m
Chicago O'Hare Intl
Sat 7/11
5:00 am-9:07 am
1 stop6h 07m
$335
Santa AnaChicago
SNA - MDW
SNAMDW
Santa Ana J. Wayne/Orange Cnty
Sat 5/30
4:20 pm-5:00 am
1 stop10h 40m
Chicago Midway
Tue 6/2
12:35 pm-7:05 pm
1 stop8h 30m
$338
Santa AnaChicago
SNA - ORD
SNAORD
Santa Ana J. Wayne/Orange Cnty
Thu 6/25
2:00 pm-11:59 pm
1 stop7h 59m
Chicago O'Hare Intl
Tue 6/30
6:55 am-1:10 pm
1 stop8h 15m
$339
Santa AnaChicago
SNA - MDW
SNAMDW
Santa Ana J. Wayne/Orange Cnty
Tue 6/16
8:15 pm-5:10 am
1 stop6h 55m
Chicago Midway
Fri 6/19
6:40 pm-10:25 pm
1 stop5h 45m
$339
Santa AnaChicago
SNA - RFD
SNARFD
Santa Ana J. Wayne/Orange Cnty
Thu 6/11
9:20 pm-8:20 pm
1 stop21h 00m
Chicago Greater Rockford
Wed 6/17
8:50 pm-2:15 pm
1 stop19h 25m
$343
Santa AnaChicago
SNA - ORD
SNAORD
Santa Ana J. Wayne/Orange Cnty
Sun 9/27
7:05 pm-10:04 am
2 stops12h 59m
Chicago O'Hare Intl
Wed 10/7
7:00 am-2:40 pm
1 stop9h 40m
$344
Santa AnaChicago
SNA - RFD
SNARFD
Santa Ana J. Wayne/Orange Cnty
Sun 6/21
9:20 pm-8:20 pm
1 stop21h 00m
Chicago Greater Rockford
Fri 6/26
10:05 pm-7:25 pm
2 stops23h 20m
$346
Santa AnaChicago
SNA - MDW
SNAMDW
Santa Ana J. Wayne/Orange Cnty
Fri 8/7
7:55 pm-5:00 am
1 stop7h 05m
Chicago Midway
Sun 8/9
5:40 am-11:35 am
1 stop7h 55m
$349
Santa AnaChicago
SNA - MDW
SNAMDW
Santa Ana J. Wayne/Orange Cnty
Thu 6/25
12:18 pm-10:17 pm
1 stop7h 59m
Chicago Midway
Thu 7/2
1:49 pm-8:24 pm
1 stop8h 35m
$349
Showing 1-10 of 60 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-MDW
SNA-ORD
SNA-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 Anaheim to Chicago
AN4-CHI
SNA-MDW
SNA-ORD
SNA-RFD
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 May 13, 2026.
Unlike at noon, when flights are generally more expensive, you can save up to 25% on flights from Anaheim to Chicago by exploring options for tickets in the afternoon.
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 May 9, 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 evenings flights should be avoided if possible as fares are typically the most expensive at this time.
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 May 13, 2026.
The most flights from AN4 to CHI are scheduled on a Monday (25 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?
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 May 13, 2026.
Peruse reviews from past customers who have flown with Alaska Airlines,Southwest, 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.
Boarding
8.1
Entertainment
7.0
Crew
8.5
Food
7.0
Overall
7.9
Comfort
7.8
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
Boarding
8.1
Entertainment
7.0
Crew
8.5
Food
7.0
Overall
7.9
Comfort
7.8
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
Boarding
8.1
Entertainment
7.0
Crew
8.5
Food
7.0
Overall
7.9
Comfort
7.8
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
Boarding
8.1
Entertainment
7.0
Crew
8.5
Food
7.0
Overall
7.9
Comfort
7.8
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
Boarding
8.1
Entertainment
7.0
Crew
8.5
Food
7.0
Overall
7.9
Comfort
7.8
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
Boarding
8.1
Entertainment
7.0
Crew
8.5
Food
7.0
Overall
7.9
Comfort
7.8
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
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
Hammond
Porter
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See prices for flight routes from nearby airports that may be better suited for you.
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 May 13, 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 May 13, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 8 airlines flying from Anaheim to Chicago
Discover the top 8 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 May 13, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$92 | Average$253 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$103 | Average$197 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$166 | Average$344 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$179 | Average$418 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$182 | Average$430 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$190 | Average$437 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$202 | Average$409 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$226 | Average$375 | FlexibilityNo cancel fee | On-timeN/A |