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$134+ 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 6/18. Fares are subject to change and may not be available on all flights or dates of travel.
SNA — CHI
Apr 29 — May 61
Tue 4/29
Tue 5/6
1 adult, Economy
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Cheapflights Tip: The best prices from Anaheim to Chicago are usually found in May or April, booked 76 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 24, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$271
(Mytrip)

One-way from

$134
(CheapOair)

Popular in

December

Cheapest in

May

Average price

$383
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. 3% potential increase in price ($15 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 24, 2025.

This Mytrip deal was found by Cheapflights users on 4/23. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/76:45 amSNA - ORD
1 stop20h 40mSpirit Airlines
Sat 5/104:35 pmORD - SNA
2 stops20h 17mSpirit Airlines
Deal found 4/23$271
This Expedia deal was found by Cheapflights users on 4/23. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/67:46 amSNA - ORD
1 stop8h 15mMultiple Airlines
Wed 5/286:00 amORD - SNA
1 stop7h 11mMultiple Airlines
Deal found 4/23$273
This Mytrip deal was found by Cheapflights users on 4/23. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/86:45 amSNA - RFD
1 stop12h 01mMultiple Airlines
Sun 5/119:36 pmRFD - SNA
2 stops19h 56mMultiple Airlines
Deal found 4/23$280
This Delta deal was found by Cheapflights users on 4/23. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/142:15 pmSNA - ORD
1 stop7h 43mDelta
Sat 5/175:30 amORD - SNA
1 stop7h 31mDelta
Deal found 4/23$286
This Frontier deal was found by Cheapflights users on 4/23. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/196:10 pmSNA - ORD
1 stop9h 00mFrontier
Thu 5/226:00 amORD - SNA
1 stop7h 11mFrontier
Deal found 4/23$287
This Hawaiian Airlines deal was found by Cheapflights users on 4/22. 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.
Sat 10/47:00 pmSNA - ORD
1 stop8h 04mHawaiian Airlines
Wed 10/82:00 pmORD - SNA
1 stop10h 30mHawaiian Airlines
Deal found 4/22$288
This Delta deal was found by Cheapflights users on 4/23. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/268:00 amSNA - MDW
1 stop8h 03mDelta
Sat 8/92:00 pmMDW - SNA
1 stop8h 28mDelta
Deal found 4/23$289
This American Airlines deal was found by Cheapflights users on 4/23. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/87:45 amSNA - ORD
Nonstop4h 09mAmerican Airlines
Thu 5/297:05 amORD - SNA
Nonstop4h 29mAmerican Airlines
Deal found 4/23$294
This Alaska Airlines deal was found by Cheapflights users on 4/23. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/77:01 amSNA - ORD
1 stop9h 19mAlaska Airlines
Tue 5/139:00 amORD - SNA
1 stop9h 55mAlaska Airlines
Deal found 4/23$298
This United Airlines deal was found by Cheapflights users on 4/23. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/231:57 pmSNA - ORD
Nonstop4h 11mUnited Airlines
Thu 5/295:02 amORD - SNA
1 stop6h 12mUnited Airlines
Deal found 4/23$299
This CheapOair deal was found by Cheapflights users on 4/23. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/276:27 pmSNA - MDW
1 stop18h 24mFrontier
Sun 5/48:03 pmMDW - SNA
1 stop17h 58mFrontier
Deal found 4/23$301
This Southwest deal was found by Cheapflights users on 4/23. 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.
Mon 6/163:30 pmSNA - MDW
1 stop7h 00mSouthwest
Thu 6/195:00 pmMDW - SNA
1 stop6h 10mSouthwest
Deal found 4/23$363

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 24, 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 5/7

6:45 am-5:25 am

1 stop20h 40m

Chicago O'Hare Intl

Sat 5/10

4:35 pm-10:52 am

2 stops20h 17m

$271

Santa AnaChicago

SNA - ORD

SNAORD

Santa Ana J. Wayne/Orange Cnty

Fri 5/30

7:58 pm-11:50 am

2 stops13h 52m

Chicago O'Hare Intl

Mon 6/2

3:18 pm-7:42 pm

1 stop6h 24m

$272

Santa AnaChicago

SNA - RFD

SNARFD

Santa Ana J. Wayne/Orange Cnty

Thu 5/8

6:45 am-8:46 pm

1 stop12h 01m

Chicago Greater Rockford

Sun 5/11

9:36 pm-3:32 pm

2 stops19h 56m

$280

Santa AnaChicago

SNA - ORD

SNAORD

Santa Ana J. Wayne/Orange Cnty

Wed 5/14

2:15 pm-11:58 pm

1 stop7h 43m

Chicago O'Hare Intl

Sat 5/17

5:30 am-11:01 am

1 stop7h 31m

$286

Santa AnaChicago

SNA - ORD

SNAORD

Santa Ana J. Wayne/Orange Cnty

Mon 5/19

6:10 pm-5:10 am

1 stop9h 00m

Chicago O'Hare Intl

Thu 5/22

6:00 am-11:11 am

1 stop7h 11m

$287

Santa AnaChicago

SNA - ORD

SNAORD

Santa Ana J. Wayne/Orange Cnty

Sat 10/4

7:00 pm-5:04 am

1 stop8h 04m

Chicago O'Hare Intl

Wed 10/8

2:00 pm-10:30 pm

1 stop10h 30m

$288

Santa AnaChicago

SNA - MDW

SNAMDW

Santa Ana J. Wayne/Orange Cnty

Sat 7/26

8:00 am-6:03 pm

1 stop8h 03m

Chicago Midway

Sat 8/9

2:00 pm-8:28 pm

1 stop8h 28m

$289

Santa AnaChicago

SNA - ORD

SNAORD

Santa Ana J. Wayne/Orange Cnty

Thu 5/8

7:45 am-1:54 pm

Nonstop4h 09m

Chicago O'Hare Intl

Thu 5/29

7:05 am-9:34 am

Nonstop4h 29m

$294

Santa AnaChicago

SNA - ORD

SNAORD

Santa Ana J. Wayne/Orange Cnty

Wed 5/7

7:01 am-6:20 pm

1 stop9h 19m

Chicago O'Hare Intl

Tue 5/13

9:00 am-4:55 pm

1 stop9h 55m

$298

Santa AnaChicago

SNA - ORD

SNAORD

Santa Ana J. Wayne/Orange Cnty

Fri 5/23

1:57 pm-8:08 pm

Nonstop4h 11m

Chicago O'Hare Intl

Thu 5/29

5:02 am-9:14 am

1 stop6h 12m

$299

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/23

Showing 1-10 of 26 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 April 18, 2025.

Booking 76 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 24, 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 24, 2025.

The most flights from AN4 to CHI are scheduled on a Monday (30 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (15 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 24, 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
9,918 reviews

Boarding

8.2

Comfort

7.9

Crew

8.5

Entertainment

7.1

Overall

8.0

Food

7.1

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
9,918 reviews
Alaska Airlines
8.0
Very good
9,918 reviews

Boarding

8.2

Comfort

7.9

Crew

8.5

Entertainment

7.1

Overall

8.0

Food

7.1

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
4,287 reviews
Alaska Airlines
8.0
Very good
9,918 reviews

Boarding

8.2

Comfort

7.9

Crew

8.5

Entertainment

7.1

Overall

8.0

Food

7.1

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
7,920 reviews
Alaska Airlines
8.0
Very good
9,918 reviews

Boarding

8.2

Comfort

7.9

Crew

8.5

Entertainment

7.1

Overall

8.0

Food

7.1

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
2,393 reviews
Alaska Airlines
8.0
Very good
9,918 reviews

Boarding

8.2

Comfort

7.9

Crew

8.5

Entertainment

7.1

Overall

8.0

Food

7.1

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
8,685 reviews
Alaska Airlines
8.0
Very good
9,918 reviews

Boarding

8.2

Comfort

7.9

Crew

8.5

Entertainment

7.1

Overall

8.0

Food

7.1

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 ($134), Delta ($142), and Frontier ($148).

  • 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 (89%), Emirates (87%) or United Airlines (87%) 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 $148. On average you can expect to pay $836. The most popular route, (Santa Ana J. Wayne/Orange Cnty - Chicago O'Hare Intl), can usually be booked for $159.

  • 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
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
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 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 April 24, 2025.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$49Average$120FlexibilityNo cancel feeOn-time88%
Spirit AirlinesCheapest$74Average$208FlexibilityNo cancel feeOn-time65%
FrontierCheapest$90Average$215FlexibilityNo cancel feeOn-time62%
Sun Country AirCheapest$130Average$330FlexibilityNo cancel feeOn-time83%
SouthwestCheapest$157Average$428FlexibilityNo cancel feeOn-time63%
Alaska AirlinesCheapest$161Average$430FlexibilityNo cancel feeOn-time75%
United AirlinesCheapest$179Average$394FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$182Average$376FlexibilityNo cancel feeOn-time71%
DeltaCheapest$236Average$476FlexibilityNo cancel feeOn-timeN/A

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