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$118+ 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 4/27. Fares are subject to change and may not be available on all flights or dates of travel.
SNA — CHI
Apr 8 — Apr 151
Tue 4/8
Tue 4/15
1 adult, Economy
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Cheapflights Tip: The best prices from Anaheim to Chicago are usually found in May or April, booked 57 days in advance, depart on a Tuesday or Wednesday and return on a Tuesday

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 April 3, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$289
(Delta)

One-way from

$118
(CheapOair)

Popular in

December

Cheapest in

May

Average price

$386
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.
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From Anaheim to Chicago (CHI)
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One-way flight from Anaheim to Chicago (CHI)
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Highest demand for flights based on searches. 2% potential increase in price ($9 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
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Average for round-trip flights in April 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 April 3, 2025.

This Delta deal was found by Cheapflights users on 4/2. 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 8/208:00 amSNA - MDW
1 stop8h 03mDelta
Sat 8/2310:35 amMDW - SNA
1 stop8h 59mDelta
Deal found 4/2$289
This FlightHub deal was found by Cheapflights users on 4/2. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/153:16 pmSNA - ORD
2 stops17h 39mSpirit Airlines
Tue 5/2011:50 amORD - SNA
1 stop11h 27mSpirit Airlines
Deal found 4/2$289
This CheapOair deal was found by Cheapflights users on 3/31. 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 4/103:32 pmSNA - MDW
1 stop11h 51mFrontier
Sun 4/278:01 pmMDW - SNA
1 stop17h 29mFrontier
Deal found 3/31$290
This American Airlines deal was found by Cheapflights users on 4/2. 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 4/1711:34 amSNA - ORD
Nonstop4h 03mAmerican Airlines
Wed 4/2311:45 amORD - SNA
Nonstop4h 29mAmerican Airlines
Deal found 4/2$294
This Travelocity deal was found by Cheapflights users on 4/2. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/303:21 pmSNA - ORD
1 stop13h 12mMultiple Airlines
Fri 5/29:51 amORD - SNA
Nonstop4h 29mMultiple Airlines
Deal found 4/2$295
This Alaska Airlines deal was found by Cheapflights users on 4/1. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/157:05 amSNA - ORD
1 stop9h 11mAlaska Airlines
Tue 4/226:58 pmORD - SNA
1 stop17h 21mAlaska Airlines
Deal found 4/1$297
This Frontier deal was found by Cheapflights users on 4/1. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/512:01 pmSNA - ORD
1 stop9h 58mFrontier
Wed 6/116:00 amORD - SNA
1 stop7h 16mFrontier
Deal found 4/1$298
This Delta deal was found by Cheapflights users on 4/1. 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 8/2011:55 amSNA - ORD
1 stop7h 26mDelta
Wed 8/277:15 amORD - SNA
1 stop6h 44mDelta
Deal found 4/1$303
This United Airlines deal was found by Cheapflights users on 4/1. 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 4/172:12 pmSNA - ORD
Nonstop4h 08mUnited Airlines
Sun 4/207:35 pmORD - SNA
Nonstop4h 42mUnited Airlines
Deal found 4/1$319
This Southwest deal was found by Cheapflights users on 4/1. 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 4/299:25 amSNA - MDW
1 stop5h 55mSouthwest
Tue 5/67:55 amMDW - SNA
1 stop8h 45mSouthwest
Deal found 4/1$323
This Mytrip deal was found by Cheapflights users on 4/1. 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.
Wed 5/217:58 pmSNA - RFD
1 stop13h 40mMultiple Airlines
Sun 5/2512:28 pmRFD - SNA
1 stop10h 49mMultiple Airlines
Deal found 4/1$325
This Hawaiian Airlines deal was found by Cheapflights users on 4/2. 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.
Mon 4/216:02 pmSNA - ORD
1 stop9h 57mHawaiian Airlines
Thu 4/249:00 amORD - SNA
1 stop9h 35mHawaiian Airlines
Deal found 4/2$367

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 April 3, 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 - MDW

SNAMDW

Santa Ana J. Wayne/Orange Cnty

Wed 8/20

8:00 am-6:03 pm

1 stop8h 03m

Chicago Midway

Sat 8/23

10:35 am-5:34 pm

1 stop8h 59m

$289

Santa AnaChicago

SNA - ORD

SNAORD

Santa Ana J. Wayne/Orange Cnty

Thu 5/15

3:16 pm-10:55 am

2 stops17h 39m

Chicago O'Hare Intl

Tue 5/20

11:50 am-9:17 pm

1 stop11h 27m

$289

Santa AnaChicago

SNA - ORD

SNAORD

Santa Ana J. Wayne/Orange Cnty

Thu 4/17

11:34 am-5:37 pm

Nonstop4h 03m

Chicago O'Hare Intl

Wed 4/23

8:10 am-10:44 am

Nonstop4h 34m

$294

Santa AnaChicago

SNA - ORD

SNAORD

Santa Ana J. Wayne/Orange Cnty

Wed 4/30

3:21 pm-6:33 am

1 stop13h 12m

Chicago O'Hare Intl

Fri 5/2

9:51 am-12:20 pm

Nonstop4h 29m

$295

Santa AnaChicago

SNA - RFD

SNARFD

Santa Ana J. Wayne/Orange Cnty

Wed 4/23

10:30 am-8:46 pm

2 stops32h 16m

Chicago Greater Rockford

Sun 4/27

9:36 pm-2:26 pm

2 stops18h 50m

$296

Santa AnaChicago

SNA - ORD

SNAORD

Santa Ana J. Wayne/Orange Cnty

Tue 4/15

7:05 am-6:16 pm

1 stop9h 11m

Chicago O'Hare Intl

Tue 4/22

6:58 pm-10:19 am

1 stop17h 21m

$297

Santa AnaChicago

SNA - ORD

SNAORD

Santa Ana J. Wayne/Orange Cnty

Thu 6/5

12:01 pm-11:59 pm

1 stop9h 58m

Chicago O'Hare Intl

Wed 6/11

6:00 am-11:16 am

1 stop7h 16m

$298

Santa AnaChicago

SNA - MDW

SNAMDW

Santa Ana J. Wayne/Orange Cnty

Thu 6/5

12:01 pm-8:53 pm

1 stop6h 52m

Chicago Midway

Mon 6/9

6:25 am-6:54 pm

1 stop14h 29m

$300

Santa AnaChicago

SNA - ORD

SNAORD

Santa Ana J. Wayne/Orange Cnty

Wed 8/20

11:55 am-9:21 pm

1 stop7h 26m

Chicago O'Hare Intl

Mon 8/25

7:15 am-11:59 am

1 stop6h 44m

$303

Santa AnaChicago

SNA - ORD

SNAORD

Santa Ana J. Wayne/Orange Cnty

Thu 4/17

2:12 pm-8:20 pm

Nonstop4h 08m

Chicago O'Hare Intl

Sun 4/20

7:35 pm-10:17 pm

Nonstop4h 42m

$319

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/1

Showing 1-10 of 30 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 March 28, 2025.

Booking 57 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 April 3, 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 March 30, 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. Monday mornings 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 April 3, 2025.

The most flights from AN4 to CHI are scheduled on a Thursday (26 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (4 on average).

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 April 3, 2025.
See what other customers who have flown with Alaska Airlines, Southwest and Delta from Anaheim to Chicago have to say. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
9,825 reviews

Comfort

7.9

Overall

8.0

Food

7.1

Crew

8.5

Entertainment

7.1

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Alaska Airlines
8.0
Very good
9,825 reviews
Alaska Airlines
8.0
Very good
9,825 reviews

Comfort

7.9

Overall

8.0

Food

7.1

Crew

8.5

Entertainment

7.1

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Southwest
8.0
Very good
4,274 reviews
Alaska Airlines
8.0
Very good
9,825 reviews

Comfort

7.9

Overall

8.0

Food

7.1

Crew

8.5

Entertainment

7.1

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Delta
8.0
Very good
7,897 reviews
Alaska Airlines
8.0
Very good
9,825 reviews

Comfort

7.9

Overall

8.0

Food

7.1

Crew

8.5

Entertainment

7.1

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Hawaiian Airlines
7.9
Good
2,344 reviews
Alaska Airlines
8.0
Very good
9,825 reviews

Comfort

7.9

Overall

8.0

Food

7.1

Crew

8.5

Entertainment

7.1

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
United Airlines
7.4
Good
8,619 reviews
Alaska Airlines
8.0
Very good
9,825 reviews

Comfort

7.9

Overall

8.0

Food

7.1

Crew

8.5

Entertainment

7.1

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

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.

  • 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 ($118), Frontier ($119), and Allegiant Air ($123).

  • 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 United Airlines (89%), Qatar Airways (85%) or Air Canada (85%) 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 $142. On average you can expect to pay $906. The most popular route, (Santa Ana J. Wayne/Orange Cnty - Chicago O'Hare Intl), can usually be booked for $170.

  • 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 Anaheim?

Book flights to Anaheim if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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Alternative routes for Anaheim to Chicago

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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 April 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$49Average$120FlexibilityNo cancel feeOn-time88%
Spirit AirlinesCheapest$74Average$211FlexibilityNo cancel feeOn-time65%
FrontierCheapest$89Average$213FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$157Average$426FlexibilityNo cancel feeOn-time63%
Alaska AirlinesCheapest$161Average$429FlexibilityNo cancel feeOn-time75%
United AirlinesCheapest$179Average$398FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$183Average$377FlexibilityNo cancel feeOn-time71%
DeltaCheapest$236Average$469FlexibilityNo cancel feeOn-timeN/A

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