$145+ Cheap flights from Chicago (CHI) to Anaheim, CA
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 6/20. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SNA
Jun 7 — Jun 141
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Anaheim 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 Chicago to Anaheim are usually found in September or May, booked 83 days in advance, depart on a Saturday or Thursday and return on a Wednesday
Cheap flight deals from Chicago to Anaheim
Cheapest
Best
Last-minute
One-way
Cheapest flights from Chicago to AnaheimExplore the most affordable flight options available from Chicago to Anaheim. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 8, 2026.
Explore the most affordable flight options available from Chicago to Anaheim. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 8, 2026.
This Kiwi.com deal was found by Cheapflights users on 5/3. 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 8/59:57 pm
ORD
- SNA
1 stop13h 28m
Frontier
Sat 8/87:54 pm
SNA
- ORD
2 stops18h 14m
Frontier
Deal found 5/3![Frontier logo]()
$307
This American Airlines deal was found by Cheapflights users on 5/3. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/115:55 pm
ORD
- SNA
Nonstop4h 20m
American Airlines
Mon 8/177:45 am
SNA
- ORD
Nonstop4h 20m
American Airlines
Deal found 5/3![American Airlines logo]()
$309
This Frontier deal was found by Cheapflights users on 5/4. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/219:37 pm
ORD
- SNA
1 stop13h 32m
Frontier
Sun 5/249:54 am
SNA
- ORD
1 stop8h 38m
Frontier
Deal found 5/4![Frontier logo]()
$310
This Expedia deal was found by Cheapflights users on 5/3. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/209:48 pm
ORD
- SNA
1 stop12h 21m
Multiple Airlines
Fri 8/288:59 pm
SNA
- ORD
1 stop13h 08m
Multiple Airlines
Deal found 5/3![Multiple Airlines logo]()
$311
This Kiwi.com deal was found by Cheapflights users on 5/4. 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 5/217:49 pm
MDW
- SNA
1 stop18h 30m
Allegiant Air
Sat 5/234:15 pm
SNA
- MDW
1 stop24h 44m
Allegiant Air
Deal found 5/4![Allegiant Air logo]()
$314
This Frontier deal was found by Cheapflights users on 5/4. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/139:37 pm
ORD
- SNA
1 stop13h 32m
Frontier
Sat 5/169:54 am
SNA
- ORD
1 stop8h 38m
Frontier
Deal found 5/4![Frontier logo]()
$315
This Kiwi.com deal was found by Cheapflights users on 5/4. 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 7/47:20 am
ORD
- SNA
1 stop12h 25m
Multiple Airlines
Mon 7/67:54 pm
SNA
- ORD
1 stop7h 34m
Multiple Airlines
Deal found 5/4![Multiple Airlines logo]()
$317
This Kiwi.com deal was found by Cheapflights users on 5/4. 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.
Tue 8/111:50 pm
ORD
- SNA
2 stops29h 55m
Multiple Airlines
Sat 8/157:54 pm
SNA
- ORD
1 stop7h 34m
Multiple Airlines
Deal found 5/4![Multiple Airlines logo]()
$318
This Southwest deal was found by Cheapflights users on 5/5. 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 6/245:25 am
MDW
- SNA
1 stop6h 00m
Southwest
Wed 7/13:35 pm
SNA
- MDW
1 stop6h 30m
Southwest
Deal found 5/5![Southwest logo]()
$319
This American Airlines deal was found by Cheapflights users on 5/4. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/108:15 am
ORD
- SNA
Nonstop4h 32m
American Airlines
Tue 6/163:21 pm
SNA
- ORD
Nonstop4h 24m
American Airlines
Deal found 5/4![American Airlines logo]()
$320
This Southwest deal was found by Cheapflights users on 5/3. 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.
Wed 6/311:45 am
MDW
- SNA
1 stop6h 35m
Southwest
Sat 6/67:10 pm
SNA
- MDW
1 stop7h 50m
Southwest
Deal found 5/3![Southwest logo]()
$323
This United Airlines deal was found by Cheapflights users on 5/5. 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.
Tue 6/25:00 am
ORD
- SNA
1 stop6h 07m
United Airlines
Tue 6/94:00 pm
SNA
- ORD
1 stop6h 44m
United Airlines
Deal found 5/5![United Airlines logo]()
$324
Best flights from Chicago to AnaheimDiscover carefully curated flight deals from Chicago to Anaheim that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 8, 2026.
Discover carefully curated flight deals from Chicago to Anaheim that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 8, 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.
Tue 6/1611:45 am
MDW
- SNA
2 stops7h 00m
Southwest
Mon 6/226:00 pm
SNA
- MDW
1 stop5h 25m
Southwest
Deal found 5/8![Southwest logo]()
$344
This United Airlines deal was found by Cheapflights users on 5/6. 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.
Fri 7/245:00 am
ORD
- SNA
1 stop6h 07m
United Airlines
Fri 7/312:10 pm
SNA
- ORD
Nonstop4h 16m
United Airlines
Deal found 5/6![United Airlines logo]()
$363
This Alaska Airlines deal was found by Cheapflights users on 5/6. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/278:15 am
ORD
- SNA
Nonstop4h 26m
Alaska Airlines
Sat 5/306:45 am
SNA
- ORD
1 stop10h 18m
Alaska Airlines
Deal found 5/6![Alaska Airlines logo]()
$439
This Delta deal was found by Cheapflights users on 5/4. 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.
Thu 5/287:12 am
ORD
- SNA
2 stops13h 03m
Delta
Sun 5/317:45 am
SNA
- ORD
1 stop7h 11m
Delta
Deal found 5/4![Delta logo]()
$510
This Southwest deal was found by Cheapflights users on 5/5. 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.
Fri 6/57:10 am
MDW
- SNA
1 stop6h 05m
Southwest
Fri 6/125:15 pm
SNA
- MDW
1 stop5h 20m
Southwest
Deal found 5/5![Southwest logo]()
$349
This Southwest deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” 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 7/174:15 pm
MDW
- SNA
1 stop7h 40m
Southwest
Sun 7/269:10 pm
SNA
- MDW
1 stop6h 35m
Southwest
Deal found 5/7![Southwest logo]()
$349
This United Airlines deal was found by Cheapflights users on 5/6. 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.
Fri 5/225:00 am
ORD
- SNA
1 stop6h 07m
United Airlines
Sun 5/244:12 pm
SNA
- ORD
1 stop6h 49m
United Airlines
Deal found 5/6![United Airlines logo]()
$414
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.
Wed 6/175:30 am
MDW
- SNA
1 stop6h 00m
Southwest
Tue 6/303:45 pm
SNA
- MDW
1 stop5h 50m
Southwest
Deal found 5/8![Southwest logo]()
$350
This Southwest deal was found by Cheapflights users on 5/6. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/1611:45 am
MDW
- SNA
2 stops7h 00m
Southwest
Tue 6/233:35 pm
SNA
- MDW
1 stop5h 30m
Southwest
Deal found 5/6![Southwest logo]()
$355
This Alaska Airlines deal was found by Cheapflights users on 5/4. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/256:44 pm
ORD
- SNA
Nonstop4h 22m
Alaska Airlines
Fri 7/313:11 pm
SNA
- ORD
Nonstop4h 39m
Alaska Airlines
Deal found 5/4![Alaska Airlines logo]()
$487
This Delta deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” 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 5/217:45 am
ORD
- SNA
1 stop6h 10m
Delta
Mon 5/252:00 pm
SNA
- ORD
1 stop7h 59m
Delta
Deal found 5/7![Delta logo]()
$519
This Southwest deal was found by Cheapflights users on 5/5. 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 7/295:25 am
MDW
- SNA
1 stop6h 00m
Southwest
Thu 8/68:50 pm
SNA
- MDW
1 stop6h 50m
Southwest
Deal found 5/5![Southwest logo]()
$360
This United Airlines deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” 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 5/207:52 pm
ORD
- SNA
Nonstop4h 43m
United Airlines
Tue 5/262:10 pm
SNA
- ORD
Nonstop4h 16m
United Airlines
Deal found 5/7![United Airlines logo]()
$483
This United Airlines deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” 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 5/287:58 pm
ORD
- SNA
Nonstop4h 34m
United Airlines
Thu 6/46:45 am
SNA
- ORD
Nonstop4h 24m
United Airlines
Deal found 5/7![United Airlines logo]()
$524
This Southwest deal was found by Cheapflights users on 5/3. 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 7/176:40 pm
MDW
- SNA
1 stop5h 45m
Southwest
Sat 7/257:10 pm
SNA
- MDW
1 stop7h 50m
Southwest
Deal found 5/3![Southwest logo]()
$407
This Southwest deal was found by Cheapflights users on 5/3. 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.
Thu 7/166:40 pm
MDW
- SNA
1 stop5h 45m
Southwest
Sun 7/269:10 pm
SNA
- MDW
1 stop6h 35m
Southwest
Deal found 5/3![Southwest logo]()
$407
This United Airlines deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” 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 5/208:55 am
ORD
- SNA
Nonstop4h 46m
United Airlines
Fri 5/2210:37 am
SNA
- ORD
Nonstop4h 16m
United Airlines
Deal found 5/7![United Airlines logo]()
$547
This Southwest deal was found by Cheapflights users on 5/3. 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.
Thu 7/1610:00 am
MDW
- SNA
2 stops7h 40m
Southwest
Sat 7/257:10 pm
SNA
- MDW
1 stop7h 50m
Southwest
Deal found 5/3![Southwest logo]()
$412
This Southwest deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” 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 8/112:00 pm
MDW
- SNA
2 stops9h 25m
Southwest
Fri 8/76:45 am
SNA
- MDW
2 stops8h 15m
Southwest
Deal found 5/7![Southwest logo]()
$417
This Southwest deal was found by Cheapflights users on 5/4. 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.
Tue 5/196:10 am
MDW
- SNA
1 stop6h 25m
Southwest
Sat 5/237:25 pm
SNA
- MDW
1 stop8h 00m
Southwest
Deal found 5/4![Southwest logo]()
$419
This Southwest deal was found by Cheapflights users on 5/5. 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.
Tue 5/196:15 am
ORD
- SNA
2 stops10h 35m
Southwest
Thu 5/2812:15 pm
SNA
- ORD
2 stops8h 40m
Southwest
Deal found 5/5![Southwest logo]()
$491
This Southwest deal was found by Cheapflights users on 5/3. 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.
Sun 5/176:15 am
ORD
- SNA
1 stop8h 00m
Southwest
Tue 5/194:15 pm
SNA
- ORD
1 stop5h 40m
Southwest
Deal found 5/3![Southwest logo]()
$565
Last-minute flights from Chicago to AnaheimDiscover last-minute flight deals from Chicago to Anaheim. Data last updated May 8, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Anaheim. Data last updated May 8, 2026 and is based on user searches.
This Frontier deal was found by Cheapflights users on 5/4. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/139:37 pm
ORD
- SNA
1 stop13h 32m
Frontier
Sat 5/169:54 am
SNA
- ORD
1 stop8h 38m
Frontier
Deal found 5/4![Frontier logo]()
$315
This Frontier deal was found by Cheapflights users on 5/4. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/219:37 pm
ORD
- SNA
1 stop13h 32m
Frontier
Sun 5/249:54 am
SNA
- ORD
1 stop8h 38m
Frontier
Deal found 5/4![Frontier logo]()
$310
This Kiwi.com deal was found by Cheapflights users on 5/4. 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 5/217:49 pm
MDW
- SNA
1 stop18h 30m
Allegiant Air
Sat 5/234:15 pm
SNA
- MDW
1 stop24h 44m
Allegiant Air
Deal found 5/4![Allegiant Air logo]()
$314
This United Airlines deal was found by Cheapflights users on 5/4. 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.
Sun 5/245:00 am
ORD
- SNA
1 stop6h 07m
United Airlines
Tue 6/210:20 am
SNA
- ORD
1 stop6h 31m
United Airlines
Deal found 5/4![United Airlines logo]()
$325
This United Airlines deal was found by Cheapflights users on 5/5. 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.
Tue 6/25:00 am
ORD
- SNA
1 stop6h 07m
United Airlines
Tue 6/94:00 pm
SNA
- ORD
1 stop6h 44m
United Airlines
Deal found 5/5![United Airlines logo]()
$324
This Kiwi.com deal was found by Cheapflights users on 5/4. 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.
Tue 6/24:05 pm
ORD
- SNA
2 stops27h 40m
Multiple Airlines
Sat 6/69:54 am
SNA
- ORD
1 stop8h 38m
Multiple Airlines
Deal found 5/4![Multiple Airlines logo]()
$327
This Kiwi.com deal was found by Cheapflights users on 5/5. 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 6/25:11 pm
ORD
- SNA
1 stop21h 14m
Multiple Airlines
Sun 6/78:10 pm
SNA
- ORD
2 stops22h 22m
Multiple Airlines
Deal found 5/5![Multiple Airlines logo]()
$328
This American Airlines deal was found by Cheapflights users on 5/3. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/312:00 pm
ORD
- SNA
Nonstop4h 24m
American Airlines
Sat 6/63:21 pm
SNA
- ORD
Nonstop4h 24m
American Airlines
Deal found 5/3![American Airlines logo]()
$309
This Southwest deal was found by Cheapflights users on 5/3. 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.
Wed 6/311:45 am
MDW
- SNA
1 stop6h 35m
Southwest
Sat 6/67:10 pm
SNA
- MDW
1 stop7h 50m
Southwest
Deal found 5/3![Southwest logo]()
$323
This United Airlines deal was found by Cheapflights users on 5/3. 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.
Fri 6/54:20 pm
ORD
- SNA
Nonstop4h 32m
United Airlines
Tue 6/92:47 pm
SNA
- ORD
1 stop8h 12m
United Airlines
Deal found 5/3![United Airlines logo]()
$319
This American Airlines deal was found by Cheapflights users on 5/4. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/108:15 am
ORD
- SNA
Nonstop4h 32m
American Airlines
Tue 6/163:21 pm
SNA
- ORD
Nonstop4h 24m
American Airlines
Deal found 5/4![American Airlines logo]()
$320
This Southwest deal was found by Cheapflights users on 5/5. 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 6/245:25 am
MDW
- SNA
1 stop6h 00m
Southwest
Wed 7/13:35 pm
SNA
- MDW
1 stop6h 30m
Southwest
Deal found 5/5![Southwest logo]()
$319
One-way flights from Chicago to AnaheimSearch for one-way flight options from Chicago to Anaheim. Find affordable one-way fares based on user searches. Data last updated May 8, 2026.
Search for one-way flight options from Chicago to Anaheim. Find affordable one-way fares based on user searches. Data last updated May 8, 2026.
This Frontier deal was found by Cheapflights users on 5/6. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/207:20 am
ORD
- SNA
1 stop7h 14m
Frontier
Deal found 5/6![Frontier logo]()
$145
This Kiwi.com deal was found by Cheapflights users on 5/5. 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.
Wed 8/51:50 pm
ORD
- SNA
2 stops25h 52m
Frontier
Deal found 5/5![Frontier logo]()
$146
This Kiwi.com deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” 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 6/29:37 pm
ORD
- SNA
2 stops40h 42m
Frontier
Deal found 5/7![Frontier logo]()
$147
This Kiwi.com deal was found by Cheapflights users on 5/4. 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.
Wed 7/221:50 pm
ORD
- SNA
2 stops24h 46m
Frontier
Deal found 5/4![Frontier logo]()
$148
This United Airlines deal was found by Cheapflights users on 5/4. 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.
Tue 5/265:00 am
ORD
- SNA
1 stop6h 07m
United Airlines
Deal found 5/4![United Airlines logo]()
$150
This CheapOair deal was found by Cheapflights users on 5/6. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/319:37 pm
ORD
- SNA
1 stop13h 32m
Frontier
Deal found 5/6![Frontier logo]()
$151
This Kiwi.com deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” 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 7/238:11 pm
MDW
- SNA
1 stop14h 42m
Allegiant Air
Deal found 5/7![Allegiant Air logo]()
$151
This Kiwi.com deal was found by Cheapflights users on 5/5. 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 7/219:57 pm
ORD
- SNA
2 stops41h 45m
Frontier
Deal found 5/5![Frontier logo]()
$152
This Kiwi.com deal was found by Cheapflights users on 5/4. 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.
Sun 6/148:03 pm
MDW
- SNA
1 stop14h 02m
Multiple Airlines
Deal found 5/4![Multiple Airlines logo]()
$152
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.
Wed 6/37:49 pm
ORD
- SNA
1 stop16h 19m
Alaska Airlines
Deal found 5/8![Alaska Airlines logo]()
$155
This Delta deal was found by Cheapflights users on 5/4. 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.
Wed 5/2710:59 am
MDW
- SNA
1 stop9h 34m
Delta
Deal found 5/4![Delta logo]()
$155
This Kiwi.com deal was found by Cheapflights users on 5/5. 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 5/268:46 pm
ORD
- SNA
2 stops44h 49m
Frontier
Deal found 5/5![Frontier logo]()
$156
Find flight deals from Chicago to Anaheim
Keep the following information in mind while searching for Chicago to Anaheim flight deals. Data was last updated May 8, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $307 (Kiwi.com) |
One-way from | $145 (Frontier) |
Popular in | March |
Cheapest in | September |
Average price | $343 |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Anaheim 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 8, 2026.
Use the filters below to find and compare flights from Chicago to Anaheim that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoSanta Ana
MDW - SNA
MDWSNA
Chicago Midway
Tue 6/16
11:45 am-4:45 pm
2 stops7h 00m
Santa Ana J. Wayne/Orange Cnty
Mon 6/22
6:00 pm-1:25 am
1 stop5h 25m
$344
ChicagoSanta Ana
MDW - SNA
MDWSNA
Chicago Midway
Fri 6/5
7:10 am-11:15 am
1 stop6h 05m
Santa Ana J. Wayne/Orange Cnty
Fri 6/12
5:15 pm-12:35 am
1 stop5h 20m
$349
ChicagoSanta Ana
MDW - SNA
MDWSNA
Chicago Midway
Fri 7/17
4:15 pm-9:55 pm
1 stop7h 40m
Santa Ana J. Wayne/Orange Cnty
Sun 7/26
9:10 pm-5:45 am
1 stop6h 35m
$349
ChicagoSanta Ana
MDW - SNA
MDWSNA
Chicago Midway
Wed 6/17
5:30 am-9:30 am
1 stop6h 00m
Santa Ana J. Wayne/Orange Cnty
Tue 6/30
3:45 pm-11:35 pm
1 stop5h 50m
$350
ChicagoSanta Ana
MDW - SNA
MDWSNA
Chicago Midway
Tue 6/16
11:45 am-4:45 pm
2 stops7h 00m
Santa Ana J. Wayne/Orange Cnty
Tue 6/23
3:35 pm-11:05 pm
1 stop5h 30m
$355
ChicagoSanta Ana
MDW - SNA
MDWSNA
Chicago Midway
Wed 7/29
5:25 am-9:25 am
1 stop6h 00m
Santa Ana J. Wayne/Orange Cnty
Thu 8/6
8:50 pm-5:40 am
1 stop6h 50m
$360
ChicagoSanta Ana
ORD - SNA
ORDSNA
Chicago O'Hare Intl
Fri 7/24
5:00 am-9:07 am
1 stop6h 07m
Santa Ana J. Wayne/Orange Cnty
Fri 7/31
2:10 pm-8:26 pm
Nonstop4h 16m
$363
ChicagoSanta Ana
MDW - SNA
MDWSNA
Chicago Midway
Fri 7/17
6:40 pm-10:25 pm
1 stop5h 45m
Santa Ana J. Wayne/Orange Cnty
Sat 7/25
7:10 pm-5:00 am
1 stop7h 50m
$407
ChicagoSanta Ana
MDW - SNA
MDWSNA
Chicago Midway
Thu 7/16
6:40 pm-10:25 pm
1 stop5h 45m
Santa Ana J. Wayne/Orange Cnty
Sun 7/26
9:10 pm-5:45 am
1 stop6h 35m
$407
ChicagoSanta Ana
MDW - SNA
MDWSNA
Chicago Midway
Thu 7/16
10:00 am-3:40 pm
2 stops7h 40m
Santa Ana J. Wayne/Orange Cnty
Sat 7/25
7:10 pm-5:00 am
1 stop7h 50m
$412
Showing 1-10 of 45 resultsSorted by cheapest first
Best time to book a flight from Chicago to Anaheim
Have a flexible travel schedule? Discover the best time to fly to Anaheim from Chicago with our price prediction graph.
ORD-SNA
MDW-SNA
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 Chicago to Anaheim
CHI-AN4
ORD-SNA
MDW-SNA
What is the cheapest time of day to fly from CHI to AN4?
Find hourly flight availability from Chicago to Anaheim. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated May 8, 2026.
It’s typically best to fly out from Chicago to Anaheim in the evening. Doing so could potentially save you 15% on the flight price compared to flying in the afternoon, which is usually more expensive.
What is the cheapest day to fly from Chicago to Anaheim?
Use this chart to determine the cheapest time to fly round-trip from Chicago to Anaheim. Price data was last updated on May 2, 2026.
Travelers seeking maximum savings on their Chicago to Anaheim flight should consider departing on Monday evenings 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.
Weekly flight availability from Chicago to Anaheim
Explore weekly flight availability from Chicago to Anaheim. 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 8, 2026.
The most flights from CHI to AN4 are scheduled on a Monday (20 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (15 on average).
How much does it cost to fly round-trip from Chicago to Anaheim?
Reviews of airlines servicing Anaheim
Get insights into the airlines that provide service to Anaheim. 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 Anaheim. Reviews last updated May 8, 2026.
Peruse reviews from past customers who have flown with Alaska Airlines,Southwest, andUnited Airlines from Chicago to Anaheim 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.
Entertainment
7.0
Boarding
8.1
Crew
8.5
Overall
7.9
Comfort
7.8
Food
7.1
Reviews
1 / 20
10.0
Excellentrobert,Feb 2026
LAS - SAN
Entertainment
7.0
Boarding
8.1
Crew
8.5
Overall
7.9
Comfort
7.8
Food
7.1
Reviews
1 / 20
10.0
Excellentrobert,Feb 2026
LAS - SAN
Entertainment
7.0
Boarding
8.1
Crew
8.5
Overall
7.9
Comfort
7.8
Food
7.1
Reviews
1 / 20
10.0
Excellentrobert,Feb 2026
LAS - SAN
Entertainment
7.0
Boarding
8.1
Crew
8.5
Overall
7.9
Comfort
7.8
Food
7.1
Reviews
1 / 20
10.0
Excellentrobert,Feb 2026
LAS - SAN
Entertainment
7.0
Boarding
8.1
Crew
8.5
Overall
7.9
Comfort
7.8
Food
7.1
Reviews
1 / 20
10.0
Excellentrobert,Feb 2026
LAS - SAN
Entertainment
7.0
Boarding
8.1
Crew
8.5
Overall
7.9
Comfort
7.8
Food
7.1
Reviews
1 / 20
10.0
Excellentrobert,Feb 2026
LAS - SAN
Related info for your journey
Find useful and relevant information for your journey from Chicago to Anaheim. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Chicago to Anaheim
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Complete your trip
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Search flights from Chicago to Anaheim by cabin class
Find flights from Chicago to Anaheim, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and Anaheim flights
Browse other Chicago and Anaheim flight options. Last updated on May 8, 2026.
Other flights from Chicago
Browse through other flights departing from Chicago. Flights are based on user searches made on Cheapflights and were last updated on May 8, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Chicago to Anaheim flights
Consider these flights traveling from Chicago to Anaheim.
Top 8 airlines flying from Chicago to Anaheim
Discover the top 8 airlines that operate flights from Chicago to Anaheim. 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 8, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$84 | Average$241 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$85 | Average$175 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$128 | Average$350 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$139 | Average$541 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$177 | Average$417 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$194 | Average$396 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$199 | Average$321 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$213 | Average$463 | FlexibilityNo cancel fee | On-time63% |