Anaheim

$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 5/19. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SNA
Apr 22 — Apr 291
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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 Tuesday and return on a Wednesday

Cheap flight deals from Chicago to Anaheim

Cheapest flights from Chicago to Anaheim
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 March 23, 2026.

This Kiwi.com deal was found by Cheapflights users on 3/18. Clicking the “Pick Dates” 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 4/139:06 pm
ORD
-
SNA
1 stop20h 27m
Multiple Airlines
Sun 4/197:56 pm
SNA
-
ORD
2 stops27h 13m
Multiple Airlines
Deal found 3/18$284
This CheapOair deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” 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 4/133:21 pm
ORD
-
SNA
2 stops20h 32m
Spirit Airlines
Sat 4/183:23 pm
SNA
-
ORD
1 stop12h 02m
Spirit Airlines
Deal found 3/19$285
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 5/210:15 am
MDW
-
SNA
2 stops9h 20m
Southwest
Sat 5/96:45 am
SNA
-
MDW
2 stops8h 30m
Southwest
Deal found 3/23$285
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/103:21 pm
ORD
-
SNA
2 stops20h 32m
Spirit Airlines
Wed 4/153:23 pm
SNA
-
ORD
1 stop12h 02m
Spirit Airlines
Deal found 3/21$286
This Kiwi.com deal was found by Cheapflights users on 3/18. Clicking the “Pick Dates” 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 4/158:58 pm
ORD
-
SNA
1 stop22h 58m
Multiple Airlines
Tue 4/217:30 am
SNA
-
ORD
1 stop20h 38m
Multiple Airlines
Deal found 3/18$287
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 4/124:41 pm
ORD
-
SNA
2 stops19h 12m
Multiple Airlines
Mon 4/137:20 pm
SNA
-
ORD
1 stop9h 00m
Multiple Airlines
Deal found 3/23$288
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.
Wed 4/156:40 pm
ORD
-
SNA
Nonstop4h 33m
American Airlines
Tue 4/211:36 pm
SNA
-
ORD
Nonstop4h 23m
American Airlines
Deal found 3/20$289
This CheapOair deal was found by Cheapflights users on 3/18. Clicking the “Pick Dates” 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.
Sat 5/169:42 pm
ORD
-
SNA
1 stop13h 27m
Multiple Airlines
Wed 5/203:23 pm
SNA
-
ORD
1 stop12h 02m
Multiple Airlines
Deal found 3/18$290
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/308:48 pm
ORD
-
SNA
1 stop15h 37m
Multiple Airlines
Sun 5/32:42 pm
SNA
-
ORD
1 stop13h 26m
Multiple Airlines
Deal found 3/21$291
This Kiwi.com deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” 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 4/158:58 pm
ORD
-
SNA
1 stop22h 58m
Multiple Airlines
Sat 4/187:30 am
SNA
-
ORD
2 stops13h 57m
Multiple Airlines
Deal found 3/19$292
This Booking.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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/612:50 pm
ORD
-
SNA
1 stop8h 50m
Multiple Airlines
Thu 4/92:53 pm
SNA
-
ORD
2 stops21h 23m
Multiple Airlines
Deal found 3/23$293
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.
Mon 4/612:50 pm
ORD
-
SNA
1 stop8h 50m
Frontier
Mon 4/137:20 pm
SNA
-
ORD
2 stops32h 30m
Frontier
Deal found 3/23$294

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 March 23, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$284
(Kiwi.com)

One-way from

$145
(American Airlines)

Popular in

March

Cheapest in

September

Average price

$454
Provider with most accurate pricing for Chicago (CHI)-Los Angeles Los Angeles flight deals.
Provider most trusted by Cheapflights users for Chicago (CHI)-Los Angeles Los Angeles flights.
From Chicago (CHI) to Anaheim
One-way flight from Chicago (CHI) to Anaheim
Highest demand for flights based on searches. 10% potential increase in price ($42 potential increase over avg. RT price).
Cheapest flight prices on average. 1% potential price decrease ($8 potential savings vs. average RT price).
Average for round-trip flights in March 2026

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 March 23, 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

Price

Cheapest round-trip

ChicagoSanta Ana

MDW - SNA

MDWSNA

Chicago Midway

Sat 4/18

6:55 am-10:50 am

1 stop5h 55m

Santa Ana J. Wayne/Orange Cnty

Tue 4/21

7:40 pm-5:00 am

1 stop7h 20m

$323

ChicagoSanta Ana

ORD - SNA

ORDSNA

Chicago O'Hare Intl

Mon 4/20

7:54 pm-10:35 pm

Nonstop4h 41m

Santa Ana J. Wayne/Orange Cnty

Mon 4/27

3:29 pm-12:45 am

1 stop7h 16m

$339

ChicagoSanta Ana

ORD - SNA

ORDSNA

Chicago O'Hare Intl

Sat 4/11

6:25 am-2:08 pm

1 stop9h 43m

Santa Ana J. Wayne/Orange Cnty

Wed 4/15

2:40 pm-8:45 pm

Nonstop4h 05m

$339

ChicagoSanta Ana

ORD - SNA

ORDSNA

Chicago O'Hare Intl

Fri 6/5

3:47 pm-8:34 pm

1 stop6h 47m

Santa Ana J. Wayne/Orange Cnty

Mon 6/8

2:00 pm-11:59 pm

1 stop7h 59m

$349

ChicagoSanta Ana

ORD - SNA

ORDSNA

Chicago O'Hare Intl

Fri 4/17

6:25 am-12:34 pm

1 stop8h 09m

Santa Ana J. Wayne/Orange Cnty

Tue 4/21

9:54 am-6:04 pm

1 stop6h 10m

$349

ChicagoSanta Ana

ORD - SNA

ORDSNA

Chicago O'Hare Intl

Tue 4/14

2:09 pm-6:06 pm

1 stop5h 57m

Santa Ana J. Wayne/Orange Cnty

Tue 4/21

9:54 am-6:04 pm

1 stop6h 10m

$349

ChicagoSanta Ana

MDW - SNA

MDWSNA

Chicago Midway

Sat 8/15

4:30 pm-10:14 pm

1 stop7h 44m

Santa Ana J. Wayne/Orange Cnty

Tue 8/18

12:20 pm-9:46 pm

1 stop7h 26m

$349

ChicagoSanta Ana

MDW - SNA

MDWSNA

Chicago Midway

Sat 9/5

4:30 pm-10:14 pm

1 stop7h 44m

Santa Ana J. Wayne/Orange Cnty

Sat 9/12

8:00 am-6:05 pm

1 stop8h 05m

$349

ChicagoSanta Ana

MDW - SNA

MDWSNA

Chicago Midway

Fri 4/17

4:05 pm-9:55 pm

2 stops7h 50m

Santa Ana J. Wayne/Orange Cnty

Mon 4/20

9:10 pm-5:00 am

1 stop5h 50m

$354

ChicagoSanta Ana

ORD - SNA

ORDSNA

Chicago O'Hare Intl

Tue 4/7

7:20 am-12:20 pm

1 stop7h 00m

Santa Ana J. Wayne/Orange Cnty

Wed 4/15

6:45 am-6:35 pm

1 stop9h 50m

$364

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/20

Showing 1-10 of 43 resultsSorted by cheapest first
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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.
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

How far ahead should I book a flight from Chicago to Anaheim?

Use this chart to determine the optimal time to book a round-trip flight from Chicago to Anaheim. Price data was last updated on March 13, 2026.

The price you pay for your flight from Chicago to Anaheim may vary depending on when you book. For the best chance of a lower fare, look to book 25 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

What is the cheapest month to book a flight from Chicago to Anaheim?

Currently, April is the cheapest month in which you can book a flight from Chicago to Anaheim (average of $67). Flying from Chicago to Anaheim in March is currently the most expensive (average of $166). 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 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 March 23, 2026.

It’s typically best to fly out from Chicago to Anaheim in the evening. Doing so could potentially save you 16% on the flight price compared to flying at noon, 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 March 14, 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 March 23, 2026.

The most flights from CHI to AN4 are scheduled on a Monday (20 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (13 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 March 23, 2026.
Peruse reviews from past customers who have flown with Southwest,Alaska Airlines, 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.

Comfort

8.0

Food

7.0

Boarding

8.1

Entertainment

7.5

Overall

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

Comfort

8.0

Food

7.0

Boarding

8.1

Entertainment

7.5

Overall

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

Comfort

8.0

Food

7.0

Boarding

8.1

Entertainment

7.5

Overall

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

Comfort

8.0

Food

7.0

Boarding

8.1

Entertainment

7.5

Overall

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

Comfort

8.0

Food

7.0

Boarding

8.1

Entertainment

7.5

Overall

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

Comfort

8.0

Food

7.0

Boarding

8.1

Entertainment

7.5

Overall

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

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.
  • How long is the flight from Chicago to Anaheim?

    Airlines like Southwest, United Airlines, and Delta fly from Chicago to Anaheim in about 4h 41m. The time it takes to get you to your destination can typically vary by up to 3h 49m. Airlines will cover a distance of 1721 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines to fly from Chicago to Anaheim one-way?

    For one-way options, check prices for Frontier. According to our data, you can fly for as low as $72. Users have also found prices from $86 and $128 on Spirit Airlines and Delta, respectively.

  • What are the most reliable airlines from Chicago to Anaheim?

    Before booking your flight to Anaheim from Chicago, check out the most reliable airlines to get you to your destination on time: Emirates (80%), Alaska Airlines (76%), Qatar Airways( 74%).

  • What are the cheapest flights from Chicago to Anaheim?

    On average you can expect to pay $535 for a flight from Chicago to Anaheim. The cheapest flight overall is $168 while the most popular route, (Chicago O'Hare Intl - Santa Ana J. Wayne/Orange Cnty) is currently priced at $204.

  • Can I find deals for flights from Chicago to Anaheim that include hotel bookings?

    Yes. In addition to deals on Chicago to Anaheim flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Anaheim?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Anaheim.

  • Can I find deals for business class flights from Chicago to Anaheim?

    Yes. Cheapflights offers flight deals from Chicago to Anaheim by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago to Anaheim?

    Currently, April is the cheapest month in which you can book a flight from Chicago to Anaheim (average of $67). Flying from Chicago to Anaheim in March is currently the most expensive (average of $166). 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.

See more FAQs

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Alternative routes for Chicago to Anaheim

See prices for flight routes from nearby airports that may be better suited for you.

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 March 23, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$69Average$175FlexibilityNo cancel feeOn-time65%
FrontierCheapest$82Average$238FlexibilityNo cancel feeOn-time62%
DeltaCheapest$128Average$345FlexibilityNo cancel feeOn-timeN/A
Alaska AirlinesCheapest$139Average$493FlexibilityNo cancel feeOn-time75%
United AirlinesCheapest$174Average$400FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$190Average$391FlexibilityNo cancel feeOn-time71%
JetBlueCheapest$199Average$321FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$213Average$460FlexibilityNo cancel feeOn-time63%

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