Chicago

$114+ 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 4/9. Fares are subject to change and may not be available on all flights or dates of travel.
SNA — CHI
Dec 28 — Jan 41
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The best prices from Anaheim to Chicago are usually found in February or May, booked 57 days in advance, depart on a Wednesday or Saturday and return on a Saturday

Cheap flight deals from Anaheim to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Anaheim (AN4) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated December 23, 2024.

Round-trip from

$293
(Frontier)

One-way from

$114
(Frontier)

Popular in

December

Cheapest in

February

Average price

$503
From Anaheim to Chicago (CHI)
One-way flight from Anaheim to Chicago (CHI)
High demand for flights, 2% potential price rise
Best time to find cheap flights, 1% potential price drop
Average for round-trip flights in December 2024

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 December 23, 2024.

This CheapOair deal was found by Cheapflights users on 12/21. 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 12/311:48 pmSNA - ORD
1 stop13h 42mSpirit Airlines
Sat 1/49:54 pmORD - SNA
1 stop12h 17mSpirit Airlines
Deal found 12/21$335
This Frontier deal was found by Cheapflights users on 12/21. 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.
Fri 12/279:15 amSNA - ORD
1 stop12h 31mFrontier
Wed 1/16:00 amORD - SNA
1 stop12h 16mFrontier
Deal found 12/21$428
This Cheapflightsfares deal was found by Cheapflights users on 12/21. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/284:07 pmSNA - MDW
1 stop6h 20mFrontier
Sat 1/47:00 amMDW - SNA
1 stop6h 39mFrontier
Deal found 12/21$449
This Booking.com deal was found by Cheapflights users on 12/22. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/307:51 pmSNA - ORD
1 stop7h 39mMultiple Airlines
Thu 1/28:34 pmORD - SNA
1 stop13h 41mMultiple Airlines
Deal found 12/22$473
This American Airlines deal was found by Cheapflights users on 12/22. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/307:50 amSNA - ORD
Nonstop4h 06mAmerican Airlines
Mon 12/307:28 pmORD - SNA
Nonstop4h 31mAmerican Airlines
Deal found 12/22$679
This Delta deal was found by Cheapflights users on 12/21. 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.
Mon 12/308:00 amSNA - MDW
1 stop7h 44mDelta
Fri 1/36:00 amMDW - SNA
1 stop7h 47mDelta
Deal found 12/21$698
This Delta deal was found by Cheapflights users on 12/22. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/318:00 amSNA - ORD
1 stop7h 09mDelta
Sat 1/45:40 amORD - SNA
1 stop8h 07mDelta
Deal found 12/22$698
This Alaska Airlines deal was found by Cheapflights users on 12/22. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/277:00 amSNA - ORD
1 stop9h 36mAlaska Airlines
Sat 1/46:00 amORD - SNA
1 stop10h 15mAlaska Airlines
Deal found 12/22$732
This United Airlines deal was found by Cheapflights users on 12/22. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/3010:40 amSNA - ORD
Nonstop4h 09mUnited Airlines
Mon 12/307:40 pmORD - SNA
Nonstop4h 35mUnited Airlines
Deal found 12/22$764
This Southwest deal was found by Cheapflights users on 12/21. 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.
Sun 12/299:20 amSNA - MDW
1 stop6h 50mSouthwest
Thu 1/29:25 amMDW - SNA
1 stop6h 30mSouthwest
Deal found 12/21$892

Find flights from Anaheim to Chicago within your budget

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 23, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

Santa AnaChicago

SNA - ORD

SNAORD

Santa Ana J. Wayne/Orange Cnty

Sun 1/5

5:29 pm-5:40 am

1 stop10h 11m

Chicago O'Hare Intl

Sun 1/12

6:20 am-4:11 pm

1 stop11h 51m

$293

Santa AnaChicago

SNA - ORD

SNAORD

Santa Ana J. Wayne/Orange Cnty

Wed 1/8

1:48 pm-10:01 am

2 stops18h 13m

Chicago O'Hare Intl

Sun 1/12

10:34 am-9:44 pm

2 stops13h 10m

$294

Santa AnaChicago

SNA - ORD

SNAORD

Santa Ana J. Wayne/Orange Cnty

Fri 1/24

7:20 pm-1:30 pm

1 stop16h 10m

Chicago O'Hare Intl

Wed 1/29

2:25 pm-10:30 pm

1 stop10h 05m

$298

Santa AnaChicago

SNA - ORD

SNAORD

Santa Ana J. Wayne/Orange Cnty

Thu 1/30

7:00 am-4:27 pm

1 stop7h 27m

Chicago O'Hare Intl

Tue 2/4

7:45 am-2:08 pm

1 stop8h 23m

$299

Santa AnaChicago

SNA - MDW

SNAMDW

Santa Ana J. Wayne/Orange Cnty

Fri 1/10

8:00 am-5:47 pm

1 stop7h 47m

Chicago Midway

Sat 1/11

10:57 am-7:43 pm

1 stop10h 46m

$300

Santa AnaChicago

SNA - MDW

SNAMDW

Santa Ana J. Wayne/Orange Cnty

Sat 1/4

4:07 pm-12:27 am

1 stop6h 20m

Chicago Midway

Mon 1/6

10:04 pm-1:18 pm

1 stop17h 14m

$314

Santa AnaChicago

SNA - RFD

SNARFD

Santa Ana J. Wayne/Orange Cnty

Sat 1/11

9:23 am-11:54 am

2 stops24h 31m

Chicago Greater Rockford

Thu 1/16

12:44 pm-9:44 pm

1 stop11h 00m

$330

Santa AnaChicago

SNA - ORD

SNAORD

Santa Ana J. Wayne/Orange Cnty

Sun 1/12

4:59 pm-12:30 pm

2 stops17h 31m

Chicago O'Hare Intl

Fri 1/24

2:07 pm-9:30 pm

1 stop9h 23m

$331

Santa AnaChicago

SNA - ORD

SNAORD

Santa Ana J. Wayne/Orange Cnty

Sat 1/18

11:01 am-5:10 pm

Nonstop4h 09m

Chicago O'Hare Intl

Sat 1/25

9:05 am-11:46 am

Nonstop4h 41m

$349

Santa AnaChicago

SNA - MDW

SNAMDW

Santa Ana J. Wayne/Orange Cnty

Sun 1/12

12:36 pm-11:48 am

2 stops21h 12m

Chicago Midway

Sat 1/18

5:05 pm-9:20 am

2 stops18h 15m

$349

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/22

Showing 1-10 of 28 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.

Travel insights for flights from Anaheim to Chicago

Get recent, data-driven insights about flights from Anaheim to Chicago including ideal travel times, pricing trends, and more.

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 20, 2024.

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 $317). 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 23, 2024.

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 December 16, 2024.

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 December 23, 2024.

The most flights from AN4 to CHI are scheduled on a Monday (22 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (9 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 December 23, 2024.
See what other customers who have flown with Frontier, Spirit Airlines and Alaska Airlines from Anaheim to Chicago have to say. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
8.1
Very good
4,780 reviews

Overall

8.1

Crew

8.7

Comfort

8.1

Food

7.2

Boarding

8.2

Entertainment

7.7

Reviews

1 / 10

My original flight was delayed so they found this flight for me so I could arrive at a reasonable time

8.1
Very good
4,780 reviews
8.1
Very good
4,780 reviews

Overall

8.1

Crew

8.7

Comfort

8.1

Food

7.2

Boarding

8.2

Entertainment

7.7

Reviews

1 / 10

My original flight was delayed so they found this flight for me so I could arrive at a reasonable time

8.0
Very good
9,549 reviews
8.1
Very good
4,780 reviews

Overall

8.1

Crew

8.7

Comfort

8.1

Food

7.2

Boarding

8.2

Entertainment

7.7

Reviews

1 / 10

My original flight was delayed so they found this flight for me so I could arrive at a reasonable time

8.0
Very good
8,594 reviews
8.1
Very good
4,780 reviews

Overall

8.1

Crew

8.7

Comfort

8.1

Food

7.2

Boarding

8.2

Entertainment

7.7

Reviews

1 / 10

My original flight was delayed so they found this flight for me so I could arrive at a reasonable time

7.4
Good
9,028 reviews
8.1
Very good
4,780 reviews

Overall

8.1

Crew

8.7

Comfort

8.1

Food

7.2

Boarding

8.2

Entertainment

7.7

Reviews

1 / 10

My original flight was delayed so they found this flight for me so I could arrive at a reasonable time

7.4
Good
823 reviews
8.1
Very good
4,780 reviews

Overall

8.1

Crew

8.7

Comfort

8.1

Food

7.2

Boarding

8.2

Entertainment

7.7

Reviews

1 / 10

My original flight was delayed so they found this flight for me so I could arrive at a reasonable time

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 Frontier ($114), Spirit Airlines ($115), and Allegiant Air ($121).

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

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

    Consider Royal Jordanian (97%), Brussels Airlines (95%) or Qatar Airways (95%) 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 $146. On average you can expect to pay $943. The most popular route, (Santa Ana J. Wayne/Orange Cnty - Chicago O'Hare Intl), can usually be booked for $128.

  • 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 $317). 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

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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.

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 December 23, 2024.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$49Average$120FlexibilityNo cancel feeOn-time88%
Spirit AirlinesCheapest$82Average$214FlexibilityNo cancel feeOn-time65%
FrontierCheapest$105Average$204FlexibilityNo cancel feeOn-time62%
Sun Country AirCheapest$149Average$362FlexibilityNo cancel feeOn-time83%
United AirlinesCheapest$179Average$423FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$182Average$389FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$185Average$460FlexibilityNo cancel feeOn-time63%
DeltaCheapest$199Average$475FlexibilityNo cancel feeOn-timeN/A
Alaska AirlinesCheapest$221Average$412FlexibilityNo cancel feeOn-time75%
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