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$54+ 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 1/15. Fares are subject to change and may not be available on all flights or dates of travel.
SNA — CHI
Nov 9 — Nov 161
1 adult
Sat 11/9
Sat 11/16
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The best prices from Anaheim to Chicago are usually found in February or April, booked 57 days in advance, depart on a Wednesday or Friday 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 November 4, 2024.

Popular in

December

Cheapest in

February

Round-trip from

$108
(Frontier)

One-way from

$54
(Frontier)
High demand for flights, 12% potential price rise
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Best time to find cheap flights, 21% potential price drop
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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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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 November 4, 2024.

This FlightHub deal was found by Cheapflights users on 11/3. 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.
Sun 11/242:20 pmSNA - ORD
1 stop8h 46mMultiple Airlines
Mon 12/28:27 pmORD - SNA
2 stops21h 29mMultiple Airlines
Deal found 11/3$267
This CheapOair deal was found by Cheapflights users on 11/4. 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 11/264:51 pmSNA - ORD
1 stop9h 44mSpirit Airlines
Wed 12/49:10 pmORD - SNA
2 stops17h 43mSpirit Airlines
Deal found 11/4$269
This CheapOair deal was found by Cheapflights users on 11/4. 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.
Mon 12/236:00 pmSNA - MDW
1 stop9h 33mFrontier
Fri 12/278:41 pmMDW - SNA
1 stop14h 04mFrontier
Deal found 11/4$273
This CheapOair deal was found by Cheapflights users on 11/4. 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.
Sat 11/911:10 amSNA - ORD
1 stop19h 22mFrontier
Fri 11/1511:32 amORD - SNA
1 stop24h 48mFrontier
Deal found 11/4$318
This Delta deal was found by Cheapflights users on 11/3. 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 12/2412:50 pmSNA - MDW
1 stop7h 16mDelta
Fri 1/36:00 amMDW - SNA
1 stop7h 47mDelta
Deal found 11/3$320
This Delta deal was found by Cheapflights users on 11/3. 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 12/2412:50 pmSNA - ORD
1 stop9h 06mDelta
Fri 1/35:40 amORD - SNA
1 stop9h 32mDelta
Deal found 11/3$320
This United Airlines deal was found by Cheapflights users on 11/4. 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 12/52:15 pmSNA - ORD
Nonstop4h 07mUnited Airlines
Tue 12/107:45 pmORD - SNA
Nonstop4h 37mUnited Airlines
Deal found 11/4$329
This American Airlines deal was found by Cheapflights users on 11/3. 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.
Sun 11/241:29 pmSNA - ORD
Nonstop4h 06mAmerican Airlines
Thu 11/2810:02 amORD - SNA
Nonstop4h 37mAmerican Airlines
Deal found 11/3$373
This Southwest deal was found by Cheapflights users on 11/2. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/62:25 pmSNA - MDW
1 stop6h 00mSouthwest
Mon 12/94:20 pmMDW - SNA
1 stop7h 05mSouthwest
Deal found 11/2$440
This Mytrip deal was found by Cheapflights users on 11/3. 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.
Sat 11/238:37 pmSNA - RFD
1 stop14h 21mMultiple Airlines
Sat 11/3012:13 pmRFD - SNA
1 stop12h 07mMultiple Airlines
Deal found 11/3$512
This Mytrip deal was found by Cheapflights users on 11/2. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/1512:18 pmSNA - MDW
2 stops19h 10mMultiple Airlines
Mon 11/184:51 pmMDW - SNA
3 stops20h 32mMultiple Airlines
Deal found 11/2$675

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 2,455,398 searches. Data last updated November 4, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

Santa AnaChicago

SNA - MDW

SNAMDW

Santa Ana J. Wayne/Orange Cnty

Wed 2/19

7:12 pm-11:52 am

1 stop14h 40m

$109

Santa AnaChicago

SNA - ORD

SNAORD

Santa Ana J. Wayne/Orange Cnty

Fri 12/6

8:11 pm-5:40 pm

2 stops19h 29m

$109

Santa AnaChicago

SNA - RFD

SNARFD

Santa Ana J. Wayne/Orange Cnty

Sat 11/23

8:37 pm-12:58 pm

1 stop14h 21m

$110

Santa AnaChicago

SNA - MDW

SNAMDW

Santa Ana J. Wayne/Orange Cnty

Thu 3/6

8:33 pm-10:42 am

1 stop12h 09m

$116

Santa AnaChicago

SNA - MDW

SNAMDW

Santa Ana J. Wayne/Orange Cnty

Sat 1/11

8:00 am-5:47 pm

1 stop7h 47m

$150

Santa AnaChicago

SNA - ORD

SNAORD

Santa Ana J. Wayne/Orange Cnty

Mon 3/3

7:06 pm-5:53 am

1 stop8h 47m

$154

Santa AnaChicago

SNA - ORD

SNAORD

Santa Ana J. Wayne/Orange Cnty

Tue 12/31

11:30 am-8:02 pm

1 stop6h 32m

$174

Santa AnaChicago

SNA - ORD

SNAORD

Santa Ana J. Wayne/Orange Cnty

Tue 11/26

1:29 pm-7:35 pm

Nonstop4h 06m

$209

Santa AnaChicago

SNA - MDW

SNAMDW

Santa Ana J. Wayne/Orange Cnty

Tue 12/31

3:25 pm-11:25 pm

1 stop6h 00m

$220

Santa AnaChicago

SNA - ORD

SNAORD

Santa Ana J. Wayne/Orange Cnty

Mon 12/23

9:15 am-11:46 pm

1 stop12h 31m

$139

Flights are sorted by cheapest first

Deals found on 11/3

Showing 1-10 of 27 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 November 1, 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.

Find deals

What is the cheapest month to book a flight from Anaheim to Chicago?

Currently, September is the cheapest month in which you can book a flight from Anaheim to Chicago (average of $232). Flying from Anaheim to Chicago in June is currently the most expensive (average of $308). 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 November 4, 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 October 27, 2024.

Travelers seeking maximum savings on their Anaheim to Chicago flight should consider departing on Friday 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.

Find deals

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 November 4, 2024.

The most flights from AN4 to CHI are scheduled on a Sunday (20 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (2 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 November 4, 2024.
See what other customers who have flown with Spirit Airlines, Frontier 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.
Southwest
8.1
Very good
5,089 reviews

Boarding

8.3

Entertainment

7.7

Overall

8.1

Comfort

8.1

Crew

8.7

Food

7.2

Reviews

1 / 10

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

Southwest
8.1
Very good
5,089 reviews
Southwest
8.1
Very good
5,089 reviews

Boarding

8.3

Entertainment

7.7

Overall

8.1

Comfort

8.1

Crew

8.7

Food

7.2

Reviews

1 / 10

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

Alaska Airlines
8.0
Very good
9,423 reviews
Southwest
8.1
Very good
5,089 reviews

Boarding

8.3

Entertainment

7.7

Overall

8.1

Comfort

8.1

Crew

8.7

Food

7.2

Reviews

1 / 10

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

Delta
8.0
Very good
8,829 reviews
Southwest
8.1
Very good
5,089 reviews

Boarding

8.3

Entertainment

7.7

Overall

8.1

Comfort

8.1

Crew

8.7

Food

7.2

Reviews

1 / 10

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

United Airlines
7.4
Good
9,226 reviews
Southwest
8.1
Very good
5,089 reviews

Boarding

8.3

Entertainment

7.7

Overall

8.1

Comfort

8.1

Crew

8.7

Food

7.2

Reviews

1 / 10

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

WestJet
7.3
Good
2,803 reviews
Southwest
8.1
Very good
5,089 reviews

Boarding

8.3

Entertainment

7.7

Overall

8.1

Comfort

8.1

Crew

8.7

Food

7.2

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.

  • Can I find flights from Anaheim to Chicago for under $200 on Cheapflights?

    Yes, there are multiple flights from Anaheim to Chicago for under $200. The cheapest flight booked recently is on Frontier for just $108, but on average you can expect to pay $302.

  • Are there nonstop flights from Anaheim to Chicago for under $400 on Cheapflights?

    Cheapflights has at least 3 direct flights from Anaheim to Chicago under $400. A good price for a nonstop flight from Anaheim to Chicago is less than $447.

  • Are there last-minute flights available from Anaheim to Chicago for under $300?

    There are currently 11+ open flights from Anaheim to Chicago within the next 7 days for less than $300.

  • 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 ($54), Spirit Airlines ($56), and Allegiant Air ($116).

  • 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 Emirates (95%), Brussels Airlines (95%) or United Airlines (94%) 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 $133. On average you can expect to pay $884. The most popular route, (Santa Ana J. Wayne/Orange Cnty - Chicago O'Hare Intl), can usually be booked for $114.

  • What does SNA to ORD mean?

    This is defined as Santa Ana J. Wayne/Orange Cnty Airport (SNA) and Chicago O'Hare Intl Airport (ORD). Codes like Chicago O'Hare Intl Airport are often used to just call airports uniquely. While you’re still figuring out your travel plans, it’s not a bad idea to learn the names and codes of other airports around these areas: Chicago Midway Airport (MDW), Chicago Greater Rockford Airport (RFD).

  • Can I find deals for flights from Anaheim to Chicago that include extra baggage allowance?

    The amount of baggage you can bring on your Anaheim to Chicago flight depends on the airline and the type of fare you've chosen. After entering your flight details, you'll be able to view the specific baggage policies for each deal in the search results. Keep in mind that certain deals may offer additional baggage allowance.

  • Can I find deals on flights from Anaheim to Chicago with specific airlines?

    Yes, Cheapflights allows you to browse and filter Anaheim to Chicago flight deals by airline. After entering your origin and destination, use the available filters to view flights offered by airlines.

  • 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.

  • Can I find deals for flights from Anaheim to Chicago that allow pets onboard?

    Many airlines flying from Anaheim to Chicago offer the option to travel with pets. After selecting a flight deal, you can find more information about the airline's pet policy on their official website or by contacting the airline directly. Please note that additional fees and restrictions may apply.

  • Can I find deals on last-minute flights from Anaheim to Chicago?

    Yes, you can often find last-minute deals on Anaheim to Chicago flights on Cheapflights. However, these deals can vary and may not always be available. We recommend checking back frequently or signing up for price alerts for the most up-to-date deals.

  • How recently were the Anaheim to Chicago flight deals updated?

    The Anaheim to Chicago flight deals you see on this page were last updated on 11/4.

  • What is the cheapest month to book a flight from Anaheim to Chicago?

    Currently, September is the cheapest month in which you can book a flight from Anaheim to Chicago (average of $232). Flying from Anaheim to Chicago in June is currently the most expensive (average of $308). 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.
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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 2,455,398 searches. Data last updated November 4, 2024.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$49Average$120FlexibilityNo cancel feeOn-time88%
Alaska AirlinesCheapest$68Average$421FlexibilityNo cancel feeOn-time75%
Spirit AirlinesCheapest$88Average$216FlexibilityNo cancel feeOn-time65%
FrontierCheapest$101Average$206FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$178Average$432FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$179Average$427FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$191Average$380FlexibilityNo cancel feeOn-time71%
DeltaCheapest$199Average$474FlexibilityNo cancel feeOn-timeN/A
Sun Country AirCheapest$313Average$362FlexibilityNo cancel feeOn-time83%
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