$163+ 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 4/19. Fares are subject to change and may not be available on all flights or dates of travel.
SNA — CHI
Apr 24 — May 11
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 63 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 March 25, 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 March 25, 2026.
This Kiwi.com deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/167:30 am
SNA
- ORD
2 stops15h 22m
Multiple Airlines
Sun 4/198:58 pm
ORD
- SNA
1 stop13h 07m
Multiple Airlines
Deal found 3/20![Multiple Airlines logo]()
$292
This Mytrip deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/512:19 pm
SNA
- ORD
1 stop23h 00m
Frontier
Sat 4/118:00 am
ORD
- SNA
1 stop11h 37m
Frontier
Deal found 3/23![Frontier logo]()
$293
This Kiwi.com deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/137:20 pm
SNA
- ORD
1 stop9h 00m
Frontier
Thu 4/165:20 am
ORD
- SNA
2 stops14h 36m
Frontier
Deal found 3/20![Frontier logo]()
$294
This Southwest deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” 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 4/1812:00 pm
SNA
- ORD
1 stop8h 20m
Southwest
Tue 4/216:15 am
ORD
- SNA
2 stops10h 35m
Southwest
Deal found 3/23![Southwest logo]()
$295
This Kiwi.com deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/167:56 pm
SNA
- ORD
1 stop7h 29m
Multiple Airlines
Fri 4/178:58 pm
ORD
- SNA
1 stop19h 30m
Multiple Airlines
Deal found 3/20![Multiple Airlines logo]()
$296
This Southwest deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” 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 5/298:15 pm
SNA
- MDW
1 stop7h 30m
Southwest
Mon 6/16:25 pm
MDW
- SNA
1 stop5h 55m
Southwest
Deal found 3/23![Southwest logo]()
$297
This Trip.com deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/67:20 pm
SNA
- ORD
2 stops13h 24m
Frontier
Wed 4/83:29 pm
ORD
- SNA
1 stop22h 05m
Frontier
Deal found 3/20![Frontier logo]()
$297
This Kiwi.com deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” 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 4/810:48 am
SNA
- ORD
2 stops25h 28m
Multiple Airlines
Tue 4/148:58 pm
ORD
- SNA
1 stop23h 02m
Multiple Airlines
Deal found 3/21![Multiple Airlines logo]()
$298
This United Airlines deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/142:40 pm
SNA
- ORD
Nonstop4h 05m
United Airlines
Wed 4/156:25 am
ORD
- SNA
1 stop7h 53m
United Airlines
Deal found 3/20![United Airlines logo]()
$299
This Southwest deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” 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 5/3011:30 am
SNA
- ORD
2 stops8h 50m
Southwest
Tue 6/26:15 am
ORD
- SNA
2 stops10h 35m
Southwest
Deal found 3/23![Southwest logo]()
$300
This Kiwi.com deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” 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 4/67:20 pm
SNA
- ORD
2 stops13h 24m
Frontier
Mon 4/1312:50 pm
ORD
- SNA
1 stop8h 50m
Frontier
Deal found 3/21![Frontier logo]()
$301
This CheapOair deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” 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.
Thu 4/233:23 pm
SNA
- ORD
1 stop12h 02m
Spirit Airlines
Sun 4/2610:07 pm
ORD
- SNA
1 stop11h 58m
Spirit Airlines
Deal found 3/22![Spirit Airlines logo]()
$302
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 March 25, 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 March 25, 2026.
This Kiwi.com deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/82:53 pm
SNA
- RFD
1 stop19h 07m
Multiple Airlines
Wed 4/152:51 pm
RFD
- SNA
1 stop19h 59m
Multiple Airlines
Deal found 3/20![Multiple Airlines logo]()
$308
This Southwest deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” 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 4/1412:55 pm
SNA
- ORD
2 stops9h 00m
Southwest
Fri 4/171:35 pm
ORD
- SNA
2 stops9h 40m
Southwest
Deal found 3/22![Southwest logo]()
$334
This United Airlines deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/96:45 am
SNA
- ORD
Nonstop4h 24m
United Airlines
Mon 7/135:00 am
ORD
- SNA
1 stop6h 07m
United Airlines
Deal found 3/20![United Airlines logo]()
$335
This Delta deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/276:45 am
SNA
- MDW
1 stop7h 27m
Delta
Mon 6/11:59 pm
MDW
- SNA
1 stop8h 35m
Delta
Deal found 3/20![Delta logo]()
$344
This Kiwi.com deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” 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 4/810:48 am
SNA
- RFD
1 stop23h 12m
Multiple Airlines
Sun 4/1212:50 pm
RFD
- SNA
1 stop23h 03m
Multiple Airlines
Deal found 3/21![Multiple Airlines logo]()
$318
This United Airlines deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/291:55 pm
SNA
- ORD
Nonstop4h 16m
United Airlines
Mon 6/15:00 am
ORD
- SNA
1 stop6h 07m
United Airlines
Deal found 3/20![United Airlines logo]()
$335
This Delta deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” 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 5/126:45 am
SNA
- ORD
1 stop9h 56m
Delta
Sat 5/165:00 pm
ORD
- SNA
1 stop6h 54m
Delta
Deal found 3/22![Delta logo]()
$349
This United Airlines deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” 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 4/1810:50 am
SNA
- ORD
Nonstop4h 05m
United Airlines
Tue 4/217:30 am
ORD
- SNA
1 stop8h 06m
United Airlines
Deal found 3/23![United Airlines logo]()
$339
This Southwest deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” 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 4/149:00 am
SNA
- MDW
2 stops8h 30m
Southwest
Fri 4/174:05 pm
MDW
- SNA
2 stops7h 50m
Southwest
Deal found 3/22![Southwest logo]()
$379
This United Airlines deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” 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 5/12:35 pm
SNA
- ORD
Nonstop4h 06m
United Airlines
Sun 5/105:30 am
ORD
- SNA
1 stop7h 41m
United Airlines
Deal found 3/21![United Airlines logo]()
$339
This Delta deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” 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 8/142:00 pm
SNA
- ORD
1 stop7h 57m
Delta
Fri 8/211:55 pm
ORD
- SNA
1 stop6h 18m
Delta
Deal found 3/21![Delta logo]()
$374
This Kiwi.com deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” 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 5/146:48 pm
SNA
- RFD
1 stop22h 57m
Multiple Airlines
Sun 5/1712:50 pm
RFD
- SNA
1 stop10h 55m
Multiple Airlines
Deal found 3/24![Multiple Airlines logo]()
$375
This Southwest deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/155:00 pm
SNA
- MDW
1 stop6h 25m
Southwest
Sun 6/215:15 am
MDW
- SNA
1 stop6h 45m
Southwest
Deal found 3/20![Southwest logo]()
$383
This United Airlines deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/214:00 pm
SNA
- ORD
1 stop6h 44m
United Airlines
Tue 7/285:00 am
ORD
- SNA
1 stop6h 07m
United Airlines
Deal found 3/20![United Airlines logo]()
$340
This Kiwi.com deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” 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 5/294:20 pm
SNA
- RFD
1 stop17h 51m
Multiple Airlines
Sun 5/311:11 pm
RFD
- SNA
1 stop7h 42m
Multiple Airlines
Deal found 3/23![Multiple Airlines logo]()
$380
This Southwest deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” 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 5/236:10 pm
SNA
- MDW
1 stop9h 30m
Southwest
Sun 5/316:55 am
MDW
- SNA
1 stop6h 40m
Southwest
Deal found 3/24![Southwest logo]()
$388
This United Airlines deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” 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 7/104:00 pm
SNA
- ORD
1 stop6h 44m
United Airlines
Mon 7/135:00 am
ORD
- SNA
1 stop6h 07m
United Airlines
Deal found 3/24![United Airlines logo]()
$340
This Kiwi.com deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” 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 7/96:03 pm
SNA
- RFD
1 stop24h 20m
Multiple Airlines
Mon 7/137:50 pm
RFD
- SNA
1 stop18h 25m
Multiple Airlines
Deal found 3/23![Multiple Airlines logo]()
$399
This Southwest deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” 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 5/236:45 am
SNA
- MDW
2 stops8h 30m
Southwest
Sun 5/2411:05 am
MDW
- SNA
1 stop9h 00m
Southwest
Deal found 3/21![Southwest logo]()
$412
This United Airlines deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” 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 5/83:35 pm
SNA
- ORD
1 stop7h 10m
United Airlines
Mon 5/117:52 pm
ORD
- SNA
Nonstop4h 43m
United Airlines
Deal found 3/24![United Airlines logo]()
$356
This Kiwi.com deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” 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 5/294:20 pm
SNA
- RFD
1 stop17h 51m
Multiple Airlines
Mon 6/19:13 pm
RFD
- SNA
2 stops19h 15m
Multiple Airlines
Deal found 3/23![Multiple Airlines logo]()
$403
This Delta deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1012:20 pm
SNA
- MDW
1 stop7h 26m
Delta
Mon 9/142:00 pm
MDW
- SNA
1 stop8h 33m
Delta
Deal found 3/20![Delta logo]()
$489
This Southwest deal was found by Cheapflights users on 3/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/17:45 pm
SNA
- MDW
1 stop7h 40m
Southwest
Tue 7/76:20 am
MDW
- SNA
1 stop6h 10m
Southwest
Deal found 3/25![Southwest logo]()
$417
This United Airlines deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” 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 4/89:00 am
SNA
- ORD
1 stop7h 59m
United Airlines
Tue 4/144:05 pm
ORD
- SNA
Nonstop4h 41m
United Airlines
Deal found 3/21![United Airlines logo]()
$374
This Kiwi.com deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” 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 9/37:30 am
SNA
- RFD
1 stop11h 09m
Multiple Airlines
Sun 9/69:29 pm
RFD
- SNA
1 stop16h 31m
Multiple Airlines
Deal found 3/23![Multiple Airlines logo]()
$417
This Southwest deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” 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 4/77:40 pm
SNA
- MDW
1 stop7h 45m
Southwest
Fri 4/104:10 pm
MDW
- SNA
1 stop7h 25m
Southwest
Deal found 3/24![Southwest logo]()
$419
This Kiwi.com deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” 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 7/211:00 pm
SNA
- RFD
1 stop18h 13m
Multiple Airlines
Sat 7/2512:58 pm
RFD
- SNA
1 stop23h 45m
Multiple Airlines
Deal found 3/21![Multiple Airlines logo]()
$428
This Southwest deal was found by Cheapflights users on 3/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/57:05 am
SNA
- MDW
2 stops8h 00m
Southwest
Sun 6/75:00 am
MDW
- SNA
1 stop5h 40m
Southwest
Deal found 3/25![Southwest logo]()
$430
This Kiwi.com deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” 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 6/149:35 pm
SNA
- RFD
1 stop20h 45m
Multiple Airlines
Sun 6/211:13 pm
RFD
- SNA
1 stop10h 02m
Multiple Airlines
Deal found 3/23![Multiple Airlines logo]()
$448
This Southwest deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” 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 4/289:45 am
SNA
- MDW
2 stops8h 25m
Southwest
Mon 5/410:20 am
MDW
- SNA
2 stops8h 05m
Southwest
Deal found 3/23![Southwest logo]()
$469
Last-minute flights from Anaheim to ChicagoDiscover last-minute flight deals from Anaheim to Chicago. Data last updated March 25, 2026 and is based on user searches.
Discover last-minute flight deals from Anaheim to Chicago. Data last updated March 25, 2026 and is based on user searches.
This Mytrip deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/512:19 pm
SNA
- ORD
1 stop23h 00m
Frontier
Sat 4/118:00 am
ORD
- SNA
1 stop11h 37m
Frontier
Deal found 3/23![Frontier logo]()
$293
This Trip.com deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/67:20 pm
SNA
- ORD
2 stops13h 24m
Frontier
Wed 4/83:29 pm
ORD
- SNA
1 stop22h 05m
Frontier
Deal found 3/20![Frontier logo]()
$297
This Kiwi.com deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” 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 4/67:20 pm
SNA
- ORD
2 stops13h 24m
Frontier
Mon 4/1312:50 pm
ORD
- SNA
1 stop8h 50m
Frontier
Deal found 3/21![Frontier logo]()
$301
This Kiwi.com deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” 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 4/810:48 am
SNA
- ORD
2 stops25h 28m
Multiple Airlines
Tue 4/148:58 pm
ORD
- SNA
1 stop23h 02m
Multiple Airlines
Deal found 3/21![Multiple Airlines logo]()
$298
This Kiwi.com deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/82:53 pm
SNA
- RFD
1 stop19h 07m
Multiple Airlines
Wed 4/152:51 pm
RFD
- SNA
1 stop19h 59m
Multiple Airlines
Deal found 3/20![Multiple Airlines logo]()
$308
This American Airlines deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/93:12 pm
SNA
- ORD
Nonstop4h 17m
American Airlines
Tue 4/1411:21 am
ORD
- SNA
Nonstop4h 35m
American Airlines
Deal found 3/20![American Airlines logo]()
$303
This Kiwi.com deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/137:20 pm
SNA
- ORD
1 stop9h 00m
Frontier
Thu 4/165:20 am
ORD
- SNA
2 stops14h 36m
Frontier
Deal found 3/20![Frontier logo]()
$294
This United Airlines deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/142:40 pm
SNA
- ORD
Nonstop4h 05m
United Airlines
Wed 4/156:25 am
ORD
- SNA
1 stop7h 53m
United Airlines
Deal found 3/20![United Airlines logo]()
$299
This Kiwi.com deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/167:30 am
SNA
- ORD
2 stops15h 22m
Multiple Airlines
Sun 4/198:58 pm
ORD
- SNA
1 stop13h 07m
Multiple Airlines
Deal found 3/20![Multiple Airlines logo]()
$292
This Kiwi.com deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/167:56 pm
SNA
- ORD
1 stop7h 29m
Multiple Airlines
Fri 4/178:58 pm
ORD
- SNA
1 stop19h 30m
Multiple Airlines
Deal found 3/20![Multiple Airlines logo]()
$296
This Southwest deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” 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 4/1812:00 pm
SNA
- ORD
1 stop8h 20m
Southwest
Tue 4/216:15 am
ORD
- SNA
2 stops10h 35m
Southwest
Deal found 3/23![Southwest logo]()
$295
This CheapOair deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” 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.
Thu 4/233:23 pm
SNA
- ORD
1 stop12h 02m
Spirit Airlines
Sun 4/2610:07 pm
ORD
- SNA
1 stop11h 58m
Spirit Airlines
Deal found 3/22![Spirit Airlines logo]()
$302
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 March 25, 2026.
Search for one-way flight options from Anaheim to Chicago. Find affordable one-way fares based on user searches. Data last updated March 25, 2026.
This Kiwi.com deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” 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 4/197:56 pm
SNA
- ORD
2 stops31h 54m
Frontier
Deal found 3/23![Frontier logo]()
$163
This Kiwi.com deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” 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 4/202:41 pm
SNA
- MDW
2 stops29h 33m
Frontier
Deal found 3/22![Frontier logo]()
$164
This CheapOair deal was found by Cheapflights users on 3/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/92:53 pm
SNA
- ORD
2 stops21h 23m
Spirit Airlines
Deal found 3/25![Spirit Airlines logo]()
$164
This Kiwi.com deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/810:48 am
SNA
- RFD
1 stop23h 12m
Multiple Airlines
Deal found 3/20![Multiple Airlines logo]()
$165
This Kiwi.com deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” 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 6/121:50 pm
SNA
- RFD
1 stop20h 24m
Multiple Airlines
Deal found 3/21![Multiple Airlines logo]()
$166
This Kiwi.com deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” 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 5/224:20 pm
SNA
- ORD
2 stops26h 17m
Frontier
Deal found 3/24![Frontier logo]()
$166
This Kiwi.com deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” 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 7/126:03 pm
SNA
- RFD
1 stop24h 20m
Allegiant Air
Deal found 3/24![Allegiant Air logo]()
$167
This CheapOair deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” 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 5/247:48 pm
SNA
- ORD
1 stop7h 37m
Spirit Airlines
Deal found 3/23![Spirit Airlines logo]()
$167
This Kiwi.com deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” 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 4/67:20 pm
SNA
- ORD
2 stops13h 24m
Frontier
Deal found 3/21![Frontier logo]()
$168
This Kiwi.com deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” 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 4/246:45 am
SNA
- MDW
2 stops33h 52m
Multiple Airlines
Deal found 3/24![Multiple Airlines logo]()
$169
This Delta deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/2312:25 pm
SNA
- ORD
1 stop7h 21m
Delta
Deal found 3/20![Delta logo]()
$169
This Kiwi.com deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” 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 6/188:10 pm
SNA
- ORD
1 stop14h 49m
Multiple Airlines
Deal found 3/24![Multiple Airlines logo]()
$170
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 March 25, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $292 (Kiwi.com) |
One-way from | $163 (Kiwi.com) |
Popular in | January |
Cheapest in | August |
Average price | $449 |
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 March 25, 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 - RFD
SNARFD
Santa Ana J. Wayne/Orange Cnty
Wed 4/8
2:53 pm-12:00 pm
1 stop19h 07m
Chicago Greater Rockford
Wed 4/15
2:51 pm-8:50 am
1 stop19h 59m
$308
Santa AnaChicago
SNA - RFD
SNARFD
Santa Ana J. Wayne/Orange Cnty
Wed 4/8
10:48 am-12:00 pm
1 stop23h 12m
Chicago Greater Rockford
Sun 4/12
12:50 pm-9:53 am
1 stop23h 03m
$318
Santa AnaChicago
SNA - ORD
SNAORD
Santa Ana J. Wayne/Orange Cnty
Tue 4/14
12:55 pm-11:55 pm
2 stops9h 00m
Chicago O'Hare Intl
Fri 4/17
1:35 pm-9:15 pm
2 stops9h 40m
$334
Santa AnaChicago
SNA - ORD
SNAORD
Santa Ana J. Wayne/Orange Cnty
Thu 7/9
6:45 am-1:09 pm
Nonstop4h 24m
Chicago O'Hare Intl
Mon 7/13
5:00 am-9:07 am
1 stop6h 07m
$335
Quickest round-trip
Santa AnaChicago
SNA - ORD
SNAORD
Santa Ana J. Wayne/Orange Cnty
Fri 5/29
1:55 pm-8:11 pm
Nonstop4h 16m
Chicago O'Hare Intl
Mon 6/1
5:00 am-9:07 am
1 stop6h 07m
$335
Santa AnaChicago
SNA - ORD
SNAORD
Santa Ana J. Wayne/Orange Cnty
Sat 4/18
10:50 am-4:55 pm
Nonstop4h 05m
Chicago O'Hare Intl
Tue 4/21
7:30 am-1:36 pm
1 stop8h 06m
$339
Santa AnaChicago
SNA - ORD
SNAORD
Santa Ana J. Wayne/Orange Cnty
Fri 5/1
2:35 pm-8:41 pm
Nonstop4h 06m
Chicago O'Hare Intl
Sun 5/10
5:30 am-11:11 am
1 stop7h 41m
$339
Santa AnaChicago
SNA - ORD
SNAORD
Santa Ana J. Wayne/Orange Cnty
Tue 7/21
4:00 pm-12:44 am
1 stop6h 44m
Chicago O'Hare Intl
Tue 7/28
5:00 am-9:07 am
1 stop6h 07m
$340
Santa AnaChicago
SNA - ORD
SNAORD
Santa Ana J. Wayne/Orange Cnty
Fri 7/10
4:00 pm-12:44 am
1 stop6h 44m
Chicago O'Hare Intl
Mon 7/13
5:00 am-9:07 am
1 stop6h 07m
$340
Santa AnaChicago
SNA - MDW
SNAMDW
Santa Ana J. Wayne/Orange Cnty
Wed 5/27
6:45 am-4:12 pm
1 stop7h 27m
Chicago Midway
Mon 6/1
1:59 pm-8:34 pm
1 stop8h 35m
$344
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-ORD
SNA-MDW
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-ORD
SNA-MDW
SNA-RFD
How far ahead should I book a flight from Anaheim to Chicago?
Use this chart to determine the optimal time to book a round-trip flight from Anaheim to Chicago. Price data was last updated on March 13, 2026.
Booking 22 days in advance of your planned departure date is, on average, the best time to get cheap flights from Anaheim to Chicago. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
What is the cheapest month to book a flight from Anaheim to Chicago?
Currently, April is the cheapest month in which you can book a flight from Anaheim to Chicago (average of $97). Flying from Anaheim to Chicago in February is currently the most expensive (average of $198). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from 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 March 25, 2026.
Unlike at noon, when flights are generally more expensive, you can save up to 27% 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 March 23, 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 March 25, 2026.
The most flights from AN4 to CHI are scheduled on a Monday (22 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (6 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 March 25, 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.
Food
7.0
Entertainment
7.5
Overall
8.0
Comfort
8.0
Crew
8.6
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
Food
7.0
Entertainment
7.5
Overall
8.0
Comfort
8.0
Crew
8.6
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
Food
7.0
Entertainment
7.5
Overall
8.0
Comfort
8.0
Crew
8.6
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
Food
7.0
Entertainment
7.5
Overall
8.0
Comfort
8.0
Crew
8.6
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
Food
7.0
Entertainment
7.5
Overall
8.0
Comfort
8.0
Crew
8.6
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
Food
7.0
Entertainment
7.5
Overall
8.0
Comfort
8.0
Crew
8.6
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
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 locationsLansing
Merrillville
Hammond
Porter
Benton Harbor
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
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Alternative routes for Anaheim to Chicago
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 March 25, 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 March 25, 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 March 25, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$89 | Average$239 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$103 | Average$196 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$166 | Average$302 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$179 | Average$402 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$182 | Average$408 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$190 | Average$446 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$201 | Average$391 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$216 | Average$342 | FlexibilityNo cancel fee | On-timeN/A |