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$144+ 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 3/11. Fares are subject to change and may not be available on all flights or dates of travel.
SNA — CHI
Jan 14 — Jan 211
Wed 1/14
Wed 1/21
1 adult, Economy
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Cheapflights Tip: The best prices from Anaheim to Chicago are usually found in August or September, booked 75 days in advance, depart on a Wednesday or Saturday and return on a Saturday

Cheap flight deals from Anaheim to Chicago

Cheapest flights from Anaheim to Chicago
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 December 15, 2025.

This CheapOair deal was found by Cheapflights users on 12/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/3011:53 amSNA - ORD
1 stop10h 19mFrontier
Sun 1/410:49 pmORD - SNA
1 stop22h 32mFrontier
Deal found 12/12$269
This Kiwi.com deal was found by Cheapflights users on 12/14. Clicking the “Pick Dates” 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 12/248:04 pmSNA - ORD
2 stops22h 19mMultiple Airlines
Thu 1/19:33 pmORD - SNA
1 stop12h 54mMultiple Airlines
Deal found 12/14$270
This CheapOair deal was found by Cheapflights users on 12/13. Clicking the “Pick Dates” 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 12/2511:52 amSNA - ORD
1 stop10h 20mFrontier
Sat 1/39:55 pmORD - SNA
1 stop12h 50mFrontier
Deal found 12/13$283
This CheapOair deal was found by Cheapflights users on 12/14. Clicking the “Pick Dates” 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 12/276:55 pmSNA - ORD
1 stop24h 44mFrontier
Sun 1/410:49 pmORD - SNA
1 stop22h 32mFrontier
Deal found 12/14$284
This CheapOair deal was found by Cheapflights users on 12/13. Clicking the “Pick Dates” 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 12/206:55 pmSNA - ORD
1 stop24h 44mFrontier
Sun 1/410:49 pmORD - SNA
1 stop22h 32mFrontier
Deal found 12/13$289
This Delta deal was found by Cheapflights users on 12/14. Clicking the “Pick Dates” 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 12/2412:05 pmSNA - ORD
1 stop9h 57mDelta
Thu 12/256:00 amORD - SNA
1 stop8h 44mDelta
Deal found 12/14$291
This CheapOair deal was found by Cheapflights users on 12/14. Clicking the “Pick Dates” 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 12/2110:35 amSNA - MDW
1 stop10h 46mFrontier
Sun 1/410:50 pmMDW - SNA
1 stop14h 18mFrontier
Deal found 12/14$293
This CheapOair deal was found by Cheapflights users on 12/15. Clicking the “Pick Dates” 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 12/2411:53 amSNA - ORD
1 stop10h 19mFrontier
Fri 1/94:30 pmORD - SNA
1 stop24h 03mFrontier
Deal found 12/15$293
This Kiwi.com deal was found by Cheapflights users on 12/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/236:45 amSNA - ORD
2 stops39h 27mMultiple Airlines
Sun 1/410:49 pmORD - SNA
1 stop13h 27mMultiple Airlines
Deal found 12/12$303
This United Airlines deal was found by Cheapflights users on 12/14. Clicking the “Pick Dates” 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 12/242:16 pmSNA - ORD
Nonstop4h 09mUnited Airlines
Thu 1/14:20 pmORD - SNA
Nonstop4h 36mUnited Airlines
Deal found 12/14$305
This United Airlines deal was found by Cheapflights users on 12/14. Clicking the “Pick Dates” 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 12/258:20 amSNA - ORD
1 stop8h 25mUnited Airlines
Thu 1/14:20 pmORD - SNA
Nonstop4h 36mUnited Airlines
Deal found 12/14$311
This American Airlines deal was found by Cheapflights users on 12/15. Clicking the “Pick Dates” 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 12/307:35 pmSNA - ORD
1 stop7h 59mAmerican Airlines
Wed 1/77:30 pmORD - SNA
Nonstop4h 31mAmerican Airlines
Deal found 12/15$314

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 December 15, 2025.

Most accurate provider

Justfly.com
3 stars

Most trusted provider

Justfly.com
3 stars

Round-trip from

$269
(American Airlines)

One-way from

$144
(Alaska Airlines)

Popular in

March

Cheapest in

August

Average price

$478
Provider with most accurate pricing for Los Angeles-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Los Angeles-Chicago (CHI) flights.
Search Deals
From Anaheim to Chicago (CHI)
Search Deals
One-way flight from Anaheim to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($28 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
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Average for round-trip flights in December 2025
Search Deals

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 December 15, 2025.
Use the filters below to find and compare flights from Anaheim to Chicago that are best for you.

Fly from

Anaheim

Fly to

Chicago

Route

Depart

Return

Price

Santa AnaChicago

SNA - ORD

SNAORD

Santa Ana J. Wayne/Orange Cnty

Wed 1/21

2:16 pm-8:25 pm

Nonstop4h 09m

Chicago O'Hare Intl

Wed 1/28

9:04 am-11:51 am

Nonstop4h 47m

$269

Santa AnaChicago

SNA - ORD

SNAORD

Santa Ana J. Wayne/Orange Cnty

Sun 1/11

2:16 pm-8:25 pm

Nonstop4h 09m

Chicago O'Hare Intl

Sun 1/18

9:04 am-11:51 am

Nonstop4h 47m

$287

Santa AnaChicago

SNA - MDW

SNAMDW

Santa Ana J. Wayne/Orange Cnty

Thu 1/8

8:00 am-6:32 pm

1 stop8h 32m

Chicago Midway

Tue 1/13

1:49 pm-8:32 pm

1 stop8h 43m

$289

Santa AnaChicago

SNA - MDW

SNAMDW

Santa Ana J. Wayne/Orange Cnty

Wed 1/21

12:25 pm-8:40 pm

1 stop6h 15m

Chicago Midway

Wed 1/28

8:25 am-4:20 pm

1 stop9h 55m

$289

Santa AnaChicago

SNA - ORD

SNAORD

Santa Ana J. Wayne/Orange Cnty

Wed 1/7

6:45 am-5:10 pm

1 stop8h 25m

Chicago O'Hare Intl

Sat 1/10

8:00 am-2:46 pm

1 stop8h 46m

$289

Santa AnaChicago

SNA - MDW

SNAMDW

Santa Ana J. Wayne/Orange Cnty

Thu 1/8

11:45 am-10:07 pm

1 stop8h 22m

Chicago Midway

Sat 1/10

11:21 am-8:14 pm

1 stop10h 53m

$289

Santa AnaChicago

SNA - MDW

SNAMDW

Santa Ana J. Wayne/Orange Cnty

Thu 1/22

12:25 pm-8:40 pm

1 stop6h 15m

Chicago Midway

Thu 1/29

8:25 am-4:20 pm

1 stop9h 55m

$289

Santa AnaChicago

SNA - ORD

SNAORD

Santa Ana J. Wayne/Orange Cnty

Fri 1/16

12:33 pm-11:50 pm

1 stop9h 17m

Chicago O'Hare Intl

Sun 1/18

2:06 pm-8:19 pm

1 stop8h 13m

$289

Santa AnaChicago

SNA - MDW

SNAMDW

Santa Ana J. Wayne/Orange Cnty

Wed 1/7

11:45 am-10:07 pm

1 stop8h 22m

Chicago Midway

Sun 1/11

1:49 pm-8:32 pm

1 stop8h 43m

$289

Santa AnaChicago

SNA - MDW

SNAMDW

Santa Ana J. Wayne/Orange Cnty

Thu 1/15

2:25 pm-10:25 pm

1 stop6h 00m

Chicago Midway

Sun 1/18

10:05 am-4:05 pm

1 stop8h 00m

$289

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/14

Showing 1-10 of 55 results
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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.
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

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 December 12, 2025.

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, March is the cheapest month in which you can book a flight from Anaheim to Chicago (average of $77). Flying from Anaheim to Chicago in October is currently the most expensive (average of $147). 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 December 15, 2025.

Unlike in the morning, when flights are generally more expensive, you can save up to 29% on flights from Anaheim to Chicago by exploring options for tickets in the evening.

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 December 13, 2025.

Travelers seeking maximum savings on their Anaheim to Chicago flight should consider departing on Wednesday mornings when fares are most often at their lowest. Monday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated December 15, 2025.
Peruse reviews from past customers who have flown with Alaska Airlines, Southwest, and United 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.
Alaska Airlines
8.0
Very good
11,453 reviews

Boarding

8.1

Crew

8.5

Entertainment

7.0

Comfort

7.8

Overall

8.0

Food

7.1

Reviews

1 / 20
2.0
Mediocre

Art,Dec 2025

SAN - OGG

It was a five hour flight and my seat did not recline. I have had three back surgeries and I’m solid bone for my L3 vertebrae all the way to my tailbone. My body has never hurt so much. There was no TV on this flight and only a small can of soda was free.
Alaska Airlines
8.0
Very good
11,453 reviews
Alaska Airlines
8.0
Very good
11,453 reviews

Boarding

8.1

Crew

8.5

Entertainment

7.0

Comfort

7.8

Overall

8.0

Food

7.1

Reviews

1 / 20
2.0
Mediocre

Art,Dec 2025

SAN - OGG

It was a five hour flight and my seat did not recline. I have had three back surgeries and I’m solid bone for my L3 vertebrae all the way to my tailbone. My body has never hurt so much. There was no TV on this flight and only a small can of soda was free.
Southwest
7.9
Good
4,249 reviews
Alaska Airlines
8.0
Very good
11,453 reviews

Boarding

8.1

Crew

8.5

Entertainment

7.0

Comfort

7.8

Overall

8.0

Food

7.1

Reviews

1 / 20
2.0
Mediocre

Art,Dec 2025

SAN - OGG

It was a five hour flight and my seat did not recline. I have had three back surgeries and I’m solid bone for my L3 vertebrae all the way to my tailbone. My body has never hurt so much. There was no TV on this flight and only a small can of soda was free.
United Airlines
7.4
Good
9,093 reviews
Alaska Airlines
8.0
Very good
11,453 reviews

Boarding

8.1

Crew

8.5

Entertainment

7.0

Comfort

7.8

Overall

8.0

Food

7.1

Reviews

1 / 20
2.0
Mediocre

Art,Dec 2025

SAN - OGG

It was a five hour flight and my seat did not recline. I have had three back surgeries and I’m solid bone for my L3 vertebrae all the way to my tailbone. My body has never hurt so much. There was no TV on this flight and only a small can of soda was free.
American Airlines
7.2
Good
11,048 reviews
Alaska Airlines
8.0
Very good
11,453 reviews

Boarding

8.1

Crew

8.5

Entertainment

7.0

Comfort

7.8

Overall

8.0

Food

7.1

Reviews

1 / 20
2.0
Mediocre

Art,Dec 2025

SAN - OGG

It was a five hour flight and my seat did not recline. I have had three back surgeries and I’m solid bone for my L3 vertebrae all the way to my tailbone. My body has never hurt so much. There was no TV on this flight and only a small can of soda was free.
Spirit Airlines
6.3
Okay
8,188 reviews
Alaska Airlines
8.0
Very good
11,453 reviews

Boarding

8.1

Crew

8.5

Entertainment

7.0

Comfort

7.8

Overall

8.0

Food

7.1

Reviews

1 / 20
2.0
Mediocre

Art,Dec 2025

SAN - OGG

It was a five hour flight and my seat did not recline. I have had three back surgeries and I’m solid bone for my L3 vertebrae all the way to my tailbone. My body has never hurt so much. There was no TV on this flight and only a small can of soda was free.

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.

  • How long is the flight from Anaheim to Chicago?

    For as low as $269, United Airlines can have you in Chicago from Anaheim in 4h 09m. The distance from Anaheim to Chicago is about 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 Anaheim to Chicago one-way?

    The cheapest airlines for a one-way flight from Anaheim to Chicago are Frontier ($55), Spirit Airlines ($67), and Delta ($128).

  • What are the most popular routes from Anaheim to Chicago?

    Most travelers choose Santa Ana J. Wayne/Orange Cnty - Chicago O'Hare Intl, Santa Ana J. Wayne/Orange Cnty - Chicago Midway or Santa Ana J. Wayne/Orange Cnty - Chicago Greater Rockford when deciding on the best route from Anaheim to Chicago.

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

    Consider Aer Lingus (84%), Brussels Airlines (84%) or Qatar Airways (82%) when booking your flight. These represent the most reliable airlines when flying from Anaheim to Chicago.

  • What are the cheapest flights from Anaheim to Chicago?

    The cheapest flight price from Anaheim to Chicago is $153. On average you can expect to pay $1,132. The most popular route, (Santa Ana J. Wayne/Orange Cnty - Chicago O'Hare Intl), can usually be booked for $144.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Anaheim to Chicago 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 Anaheim to Chicago?

    Currently, March is the cheapest month in which you can book a flight from Anaheim to Chicago (average of $77). Flying from Anaheim to Chicago in October is currently the most expensive (average of $147). 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

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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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.
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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 December 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$77Average$199FlexibilityNo cancel feeOn-time65%
FrontierCheapest$88Average$228FlexibilityNo cancel feeOn-time62%
Sun Country AirCheapest$130Average$330FlexibilityNo cancel feeOn-time83%
SouthwestCheapest$179Average$412FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$182Average$383FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$190Average$441FlexibilityNo cancel feeOn-time75%
American AirlinesCheapest$199Average$392FlexibilityNo cancel feeOn-time71%
DeltaCheapest$218Average$363FlexibilityNo cancel feeOn-timeN/A

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