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$113+ 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 11/7. Fares are subject to change and may not be available on all flights or dates of travel.
SNA — CHI
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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Cheapflights Tip: The best prices from Anaheim to Chicago are usually found in September or August, booked 81 days in advance, depart on a Wednesday or Tuesday and return on a Saturday

Cheap flight deals from Anaheim to Chicago

Keep the following information in mind while searching for Anaheim to Chicago flight deals. Data was last updated September 11, 2025.

Round-trip from

$269
(United Airlines)

One-way from

$113
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$349
From Anaheim to Chicago (CHI)
Search Deals
One-way flight from Anaheim to Chicago (CHI)
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Highest demand for flights based on searches. 9% potential increase in price ($39 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($8 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find 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 September 11, 2025.

This United Airlines deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/31:48 pmSNA - ORD
Nonstop4h 11mUnited Airlines
Tue 10/77:58 pmORD - SNA
Nonstop4h 32mUnited Airlines
Deal found 9/9$269
This CheapOair deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/106:45 amSNA - ORD
2 stops11h 18mSpirit Airlines
Tue 10/146:40 amORD - SNA
1 stop14h 34mSpirit Airlines
Deal found 9/10$270
This CheapOair deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/77:38 pmSNA - ORD
2 stops26h 34mFrontier
Sun 11/910:43 pmORD - SNA
2 stops19h 04mFrontier
Deal found 9/9$271
This Southwest deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/1910:30 amSNA - MDW
1 stop6h 45mSouthwest
Wed 11/264:20 pmMDW - SNA
1 stop8h 00mSouthwest
Deal found 9/10$272
This Kiwi.com deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/162:15 pmSNA - ORD
2 stops18h 25mMultiple Airlines
Thu 9/186:00 amORD - SNA
1 stop7h 07mMultiple Airlines
Deal found 9/8$272
This Trip.com deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/166:45 amSNA - MDW
2 stops39h 39mMultiple Airlines
Sun 10/1912:09 pmMDW - SNA
2 stops35h 54mMultiple Airlines
Deal found 9/9$273
This CheapOair deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/145:46 pmSNA - ORD
1 stop10h 39mSpirit Airlines
Sun 11/167:35 amORD - SNA
2 stops15h 24mSpirit Airlines
Deal found 9/9$273
This Kiwi.com deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/1012:01 pmSNA - MDW
1 stop10h 23mMultiple Airlines
Tue 10/148:05 amMDW - SNA
2 stops37h 09mMultiple Airlines
Deal found 9/9$274
This CheapOair deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/166:45 amSNA - ORD
2 stops11h 18mSpirit Airlines
Mon 10/206:35 amORD - SNA
1 stop14h 39mSpirit Airlines
Deal found 9/9$274
This United Airlines deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/16:45 amSNA - ORD
Nonstop4h 23mUnited Airlines
Tue 10/75:01 amORD - SNA
1 stop6h 16mUnited Airlines
Deal found 9/10$275
This Southwest deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/253:25 pmSNA - MDW
1 stop6h 40mSouthwest
Wed 10/18:25 amMDW - SNA
1 stop7h 25mSouthwest
Deal found 9/10$276
This Hawaiian Airlines deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Hawaiian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/166:24 pmSNA - ORD
1 stop8h 37mHawaiian Airlines
Tue 10/212:04 pmORD - SNA
1 stop8h 18mHawaiian Airlines
Deal found 9/11$276

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 September 11, 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 10/15

6:45 am-1:08 pm

Nonstop4h 23m

Chicago O'Hare Intl

Tue 10/21

4:20 pm-6:46 pm

Nonstop4h 26m

$269

Santa AnaChicago

SNA - ORD

SNAORD

Santa Ana J. Wayne/Orange Cnty

Sat 10/4

10:39 am-4:50 pm

Nonstop4h 11m

Chicago O'Hare Intl

Tue 10/7

7:58 pm-10:30 pm

Nonstop4h 32m

$269

Santa AnaChicago

SNA - ORD

SNAORD

Santa Ana J. Wayne/Orange Cnty

Fri 10/3

1:48 pm-7:59 pm

Nonstop4h 11m

Chicago O'Hare Intl

Tue 10/7

7:58 pm-10:30 pm

Nonstop4h 32m

$269

Santa AnaChicago

SNA - ORD

SNAORD

Santa Ana J. Wayne/Orange Cnty

Fri 10/10

1:48 pm-7:59 pm

Nonstop4h 11m

Chicago O'Hare Intl

Sat 10/25

5:01 am-9:17 am

1 stop6h 16m

$275

Santa AnaChicago

SNA - MDW

SNAMDW

Santa Ana J. Wayne/Orange Cnty

Thu 9/25

3:25 pm-12:05 am

1 stop6h 40m

Chicago Midway

Wed 10/1

8:25 am-1:50 pm

1 stop7h 25m

$276

Santa AnaChicago

SNA - ORD

SNAORD

Santa Ana J. Wayne/Orange Cnty

Thu 10/16

6:24 pm-5:01 am

1 stop8h 37m

Chicago O'Hare Intl

Tue 10/21

2:04 pm-8:22 pm

1 stop8h 18m

$276

Santa AnaChicago

SNA - ORD

SNAORD

Santa Ana J. Wayne/Orange Cnty

Fri 12/12

2:15 pm-8:20 pm

Nonstop4h 05m

Chicago O'Hare Intl

Mon 12/15

6:55 am-12:17 pm

1 stop7h 22m

$279

Santa AnaChicago

SNA - MDW

SNAMDW

Santa Ana J. Wayne/Orange Cnty

Fri 2/20

8:50 pm-5:05 am

1 stop6h 15m

Chicago Midway

Sun 2/22

8:00 am-1:55 pm

1 stop7h 55m

$283

Santa AnaChicago

SNA - ORD

SNAORD

Santa Ana J. Wayne/Orange Cnty

Thu 10/16

6:24 pm-5:01 am

1 stop8h 37m

Chicago O'Hare Intl

Tue 10/21

6:00 am-2:17 pm

1 stop10h 17m

$289

Santa AnaChicago

SNA - ORD

SNAORD

Santa Ana J. Wayne/Orange Cnty

Thu 9/25

10:39 am-4:50 pm

Nonstop4h 11m

Chicago O'Hare Intl

Wed 10/1

7:58 pm-10:30 pm

Nonstop4h 32m

$294

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/9

Showing 1-10 of 60 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 August 29, 2025.

Booking 81 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, August is the cheapest month in which you can book a flight from Anaheim to Chicago (average of $245). Flying from Anaheim to Chicago in March is currently the most expensive (average of $321). 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 September 11, 2025.

When flying from Anaheim to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 September 7, 2025.

Travelers seeking maximum savings on their Anaheim to Chicago flight should consider departing on Wednesday evenings when fares are most often at their lowest. Sunday at noon 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 September 11, 2025.

The most flights from AN4 to CHI are scheduled on a Thursday (27 on average). You will have fewer flight options on Friday, which is when the least amount of flights are scheduled (20 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 September 11, 2025.
Peruse reviews from past customers who have flown with Alaska Airlines, United Airlines, and American 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
10,000 reviews

Crew

8.5

Boarding

8.1

Entertainment

7.0

Overall

8.0

Food

7.1

Comfort

7.8

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Boarding

8.1

Entertainment

7.0

Overall

8.0

Food

7.1

Comfort

7.8

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
United Airlines
7.4
Good
8,937 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Boarding

8.1

Entertainment

7.0

Overall

8.0

Food

7.1

Comfort

7.8

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Boarding

8.1

Entertainment

7.0

Overall

8.0

Food

7.1

Comfort

7.8

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
Spirit Airlines
6.3
Okay
8,023 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Boarding

8.1

Entertainment

7.0

Overall

8.0

Food

7.1

Comfort

7.8

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
Frontier
5.8
Fair
3,177 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Boarding

8.1

Entertainment

7.0

Overall

8.0

Food

7.1

Comfort

7.8

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.

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 23m. 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 Spirit Airlines ($116), Southwest ($121), and Alaska Airlines ($124).

  • 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 Brussels Airlines (90%), Emirates (87%) or United Airlines (84%) 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 $160. On average you can expect to pay $933. The most popular route, (Santa Ana J. Wayne/Orange Cnty - Chicago O'Hare Intl), can usually be booked for $120.

  • 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, August is the cheapest month in which you can book a flight from Anaheim to Chicago (average of $245). Flying from Anaheim to Chicago in March is currently the most expensive (average of $321). 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
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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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 September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$90Average$229FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$97Average$192FlexibilityNo cancel feeOn-time65%
Sun Country AirCheapest$130Average$330FlexibilityNo cancel feeOn-time83%
United AirlinesCheapest$149Average$400FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$157Average$421FlexibilityNo cancel feeOn-time63%
Alaska AirlinesCheapest$190Average$422FlexibilityNo cancel feeOn-time75%
American AirlinesCheapest$192Average$403FlexibilityNo cancel feeOn-time71%
DeltaCheapest$218Average$396FlexibilityNo cancel feeOn-timeN/A

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