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$117+ 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 2/5. Fares are subject to change and may not be available on all flights or dates of travel.
SNA — CHI
Feb 27 — Mar 61
Fri 2/27
Fri 3/6
1 adult, Economy
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Cheapflights Tip: The best prices from Anaheim to Chicago are usually found in August or September, booked 51 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 January 28, 2026.

This United Airlines deal was found by Cheapflights users on 1/27. 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 2/192:22 pm
SNA
-
ORD
Nonstop4h 03m
United Airlines
Mon 2/237:44 pm
ORD
-
SNA
Nonstop4h 46m
United Airlines
Deal found 1/27$269
This Kiwi.com deal was found by Cheapflights users on 1/26. 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 3/297:53 pm
SNA
-
ORD
2 stops37h 28m
Multiple Airlines
Sat 4/45:53 pm
ORD
-
SNA
1 stop19h 41m
Multiple Airlines
Deal found 1/26$270
This Kiwi.com deal was found by Cheapflights users on 1/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/54:37 pm
SNA
-
ORD
1 stop10h 54m
Multiple Airlines
Mon 5/117:43 am
ORD
-
SNA
1 stop8h 01m
Multiple Airlines
Deal found 1/26$271
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 2/124:37 pm
SNA
-
ORD
1 stop22h 49m
Multiple Airlines
Mon 2/167:19 pm
ORD
-
SNA
1 stop19h 06m
Multiple Airlines
Deal found 1/27$272
This CheapOair deal was found by Cheapflights users on 1/26. 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 1/2911:53 am
SNA
-
ORD
1 stop21h 04m
Frontier
Mon 2/29:00 am
ORD
-
SNA
1 stop7h 11m
Frontier
Deal found 1/26$273
This American Airlines deal was found by Cheapflights users on 1/26. 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 5/57:45 am
SNA
-
ORD
Nonstop4h 12m
American Airlines
Tue 5/1211:45 am
ORD
-
SNA
Nonstop4h 37m
American Airlines
Deal found 1/26$274
This Kiwi.com deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/149:50 am
SNA
-
MDW
1 stop10h 55m
Multiple Airlines
Mon 3/169:51 pm
MDW
-
SNA
2 stops19h 47m
Multiple Airlines
Deal found 1/27$275
This CheapOair deal was found by Cheapflights users on 1/27. 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 5/174:37 pm
SNA
-
ORD
1 stop10h 54m
Spirit Airlines
Wed 5/207:41 am
ORD
-
SNA
2 stops15h 16m
Spirit Airlines
Deal found 1/27$275
This Kiwi.com deal was found by Cheapflights users on 1/26. 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 5/48:20 pm
SNA
-
ORD
1 stop7h 11m
Multiple Airlines
Tue 9/18:53 pm
ORD
-
SNA
1 stop17h 32m
Multiple Airlines
Deal found 1/26$276
This Kiwi.com deal was found by Cheapflights users on 1/26. 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 2/1912:46 pm
SNA
-
MDW
1 stop8h 55m
Frontier
Sun 2/223:21 pm
MDW
-
SNA
2 stops18h 52m
Frontier
Deal found 1/26$278
This Kiwi.com deal was found by Cheapflights users on 1/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/54:37 pm
SNA
-
ORD
2 stops16h 07m
Multiple Airlines
Sat 5/98:43 am
ORD
-
SNA
1 stop7h 01m
Multiple Airlines
Deal found 1/26$278
This United Airlines deal was found by Cheapflights users on 1/27. 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 2/186:45 am
SNA
-
ORD
Nonstop4h 10m
United Airlines
Mon 2/232:02 pm
ORD
-
SNA
1 stop8h 47m
United Airlines
Deal found 1/27$279

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 January 28, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$269
(United Airlines)

One-way from

$117
(CheapOair)

Popular in

January

Cheapest in

August

Average price

$465
Provider with most accurate pricing for Los Angeles-Chicago (CHI) flight deals.
Search Deals
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. 8% potential increase in price ($37 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($7 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
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 January 28, 2026.
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 2/18

6:45 am-12:55 pm

Nonstop4h 10m

Chicago O'Hare Intl

Mon 2/23

7:44 pm-10:30 pm

Nonstop4h 46m

$269

Santa AnaChicago

SNA - ORD

SNAORD

Santa Ana J. Wayne/Orange Cnty

Thu 2/26

2:22 pm-8:25 pm

Nonstop4h 03m

Chicago O'Hare Intl

Sat 2/28

12:46 pm-8:50 pm

1 stop10h 04m

$279

Santa AnaChicago

SNA - ORD

SNAORD

Santa Ana J. Wayne/Orange Cnty

Fri 5/29

4:00 pm-12:44 am

1 stop6h 44m

Chicago O'Hare Intl

Tue 6/2

5:00 am-9:05 am

1 stop6h 05m

$285

Santa AnaChicago

SNA - ORD

SNAORD

Santa Ana J. Wayne/Orange Cnty

Fri 4/17

2:20 pm-8:25 pm

Nonstop4h 05m

Chicago O'Hare Intl

Mon 4/27

7:49 pm-10:30 pm

Nonstop4h 41m

$288

Santa AnaChicago

SNA - MDW

SNAMDW

Santa Ana J. Wayne/Orange Cnty

Thu 2/19

7:30 pm-5:05 am

1 stop7h 35m

Chicago Midway

Mon 2/23

8:10 am-4:00 pm

1 stop9h 50m

$289

Santa AnaChicago

SNA - ORD

SNAORD

Santa Ana J. Wayne/Orange Cnty

Wed 5/20

6:45 am-7:03 pm

1 stop10h 18m

Chicago O'Hare Intl

Tue 6/2

6:00 am-2:18 pm

1 stop10h 18m

$289

Santa AnaChicago

SNA - ORD

SNAORD

Santa Ana J. Wayne/Orange Cnty

Thu 3/19

7:05 am-6:05 pm

1 stop9h 00m

Chicago O'Hare Intl

Wed 3/25

1:19 pm-6:10 pm

1 stop6h 51m

$289

Santa AnaChicago

SNA - ORD

SNAORD

Santa Ana J. Wayne/Orange Cnty

Fri 5/22

9:20 pm-8:34 am

1 stop9h 14m

Chicago O'Hare Intl

Fri 5/29

3:50 pm-8:33 pm

1 stop6h 43m

$289

Santa AnaChicago

SNA - ORD

SNAORD

Santa Ana J. Wayne/Orange Cnty

Wed 5/20

10:15 am-6:01 pm

1 stop5h 46m

Chicago O'Hare Intl

Fri 5/29

1:15 pm-10:18 pm

1 stop11h 03m

$289

Santa AnaChicago

SNA - ORD

SNAORD

Santa Ana J. Wayne/Orange Cnty

Mon 5/18

9:20 pm-8:34 am

1 stop9h 14m

Chicago O'Hare Intl

Sat 5/30

3:50 pm-8:33 pm

1 stop6h 43m

$289

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/26

Showing 1-10 of 57 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 January 23, 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, 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 January 28, 2026.

Unlike at noon, when flights are generally more expensive, you can save up to 25% 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 January 24, 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. Saturday 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 January 28, 2026.

The most flights from AN4 to CHI are scheduled on a Monday (24 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (11 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 January 28, 2026.
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
11,805 reviews

Food

7.1

Entertainment

7.0

Overall

8.0

Crew

8.5

Boarding

8.1

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading
Alaska Airlines
8.0
Very good
11,805 reviews
Alaska Airlines
8.0
Very good
11,805 reviews

Food

7.1

Entertainment

7.0

Overall

8.0

Crew

8.5

Boarding

8.1

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading
Southwest
8.0
Very good
4,267 reviews
Alaska Airlines
8.0
Very good
11,805 reviews

Food

7.1

Entertainment

7.0

Overall

8.0

Crew

8.5

Boarding

8.1

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading
United Airlines
7.4
Good
9,213 reviews
Alaska Airlines
8.0
Very good
11,805 reviews

Food

7.1

Entertainment

7.0

Overall

8.0

Crew

8.5

Boarding

8.1

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading
American Airlines
7.2
Good
11,199 reviews
Alaska Airlines
8.0
Very good
11,805 reviews

Food

7.1

Entertainment

7.0

Overall

8.0

Crew

8.5

Boarding

8.1

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading
Spirit Airlines
6.3
Okay
8,388 reviews
Alaska Airlines
8.0
Very good
11,805 reviews

Food

7.1

Entertainment

7.0

Overall

8.0

Crew

8.5

Boarding

8.1

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading

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 10m. 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 ($67), Frontier ($74), and Delta ($129).

  • 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 Royal Jordanian (90%), Brussels Airlines (85%) or United Airlines (83%) 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 $158. On average you can expect to pay $997. The most popular route, (Santa Ana J. Wayne/Orange Cnty - Chicago O'Hare Intl), can usually be booked for $147.

  • 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 9 airlines flying from Anaheim to Chicago

Discover the top 9 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 January 28, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$77Average$196FlexibilityNo cancel feeOn-time65%
FrontierCheapest$86Average$230FlexibilityNo cancel feeOn-time62%
Sun Country AirCheapest$130Average$323FlexibilityNo cancel feeOn-time83%
JetBlueCheapest$166Average$204FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$179Average$405FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$182Average$404FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$190Average$443FlexibilityNo cancel feeOn-time75%
American AirlinesCheapest$203Average$380FlexibilityNo cancel feeOn-time71%
DeltaCheapest$218Average$363FlexibilityNo cancel feeOn-timeN/A

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