HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$99+ 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 10/14. Fares are subject to change and may not be available on all flights or dates of travel.
SNA — CHI
Aug 5 — Aug 121
Tue 8/5
Tue 8/12
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Anaheim to Chicago with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheapflights Tip: The best prices from Anaheim to Chicago are usually found in August or September, booked 57 days in advance, depart on a Wednesday or Tuesday and return on a Wednesday

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 July 31, 2025.

Round-trip from

$269
(American Airlines)

One-way from

$99
(CheapOair)

Popular in

December

Cheapest in

August

Average price

$412
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 ($38 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2025
Search Deals

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 July 31, 2025.

This American Airlines deal was found by Cheapflights users on 7/29. 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.
Wed 8/2011:34 amSNA - ORD
Nonstop4h 14mAmerican Airlines
Sat 8/238:25 amORD - SNA
Nonstop4h 19mAmerican Airlines
Deal found 7/29$269
This Booking.com deal was found by Cheapflights users on 7/30. 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.
Fri 11/712:01 pmSNA - MDW
1 stop8h 37mFrontier
Sun 11/94:29 pmMDW - SNA
1 stop20h 47mFrontier
Deal found 7/30$270
This Booking.com deal was found by Cheapflights users on 7/29. 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.
Tue 8/57:58 pmSNA - ORD
1 stop8h 05mSpirit Airlines
Mon 8/113:18 pmORD - SNA
1 stop5h 45mSpirit Airlines
Deal found 7/29$270
This United Airlines deal was found by Cheapflights users on 7/30. 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 9/261:48 pmSNA - ORD
Nonstop4h 11mUnited Airlines
Mon 9/295:01 amORD - SNA
1 stop6h 16mUnited Airlines
Deal found 7/30$275
This Alaska Airlines deal was found by Cheapflights users on 7/31. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/79:25 pmSNA - ORD
1 stop29h 36mAlaska Airlines
Sun 11/98:05 amORD - SNA
Nonstop4h 37mAlaska Airlines
Deal found 7/31$277
This Delta deal was found by Cheapflights users on 7/30. 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 8/278:00 amSNA - MDW
1 stop7h 37mDelta
Wed 9/36:00 amMDW - SNA
1 stop8h 42mDelta
Deal found 7/30$279
This Delta deal was found by Cheapflights users on 7/31. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/2711:28 amSNA - ORD
1 stop6h 55mDelta
Wed 9/37:45 amORD - SNA
1 stop6h 08mDelta
Deal found 7/31$279
This CheapOair deal was found by Cheapflights users on 7/29. 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 8/511:56 amSNA - ORD
1 stop10h 36mMultiple Airlines
Thu 8/73:18 pmORD - SNA
1 stop5h 45mMultiple Airlines
Deal found 7/29$285
This Frontier deal was found by Cheapflights users on 7/30. 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.
Tue 8/511:56 amSNA - ORD
1 stop10h 36mFrontier
Fri 8/82:15 pmORD - SNA
1 stop7h 31mFrontier
Deal found 7/30$288
This Southwest deal was found by Cheapflights users on 7/31. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2911:30 amSNA - MDW
1 stop6h 15mSouthwest
Wed 9/38:40 amMDW - SNA
1 stop8h 10mSouthwest
Deal found 7/31$289
This Mytrip deal was found by Cheapflights users on 7/31. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/158:04 pmSNA - RFD
1 stop14h 50mMultiple Airlines
Fri 10/173:08 pmRFD - SNA
3 stops32h 57mMultiple Airlines
Deal found 7/31$314

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 July 31, 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 8/20

11:34 am-5:48 pm

Nonstop4h 14m

Chicago O'Hare Intl

Sat 8/23

8:25 am-10:44 am

Nonstop4h 19m

$269

Santa AnaChicago

SNA - MDW

SNAMDW

Santa Ana J. Wayne/Orange Cnty

Fri 11/7

12:01 pm-10:38 pm

1 stop8h 37m

Chicago Midway

Sun 11/9

4:29 pm-11:16 am

1 stop20h 47m

$270

Santa AnaChicago

SNA - ORD

SNAORD

Santa Ana J. Wayne/Orange Cnty

Tue 8/5

7:58 pm-6:03 am

1 stop8h 05m

Chicago O'Hare Intl

Mon 8/11

3:18 pm-7:03 pm

1 stop5h 45m

$270

Santa AnaChicago

SNA - ORD

SNAORD

Santa Ana J. Wayne/Orange Cnty

Fri 10/3

1:48 pm-7:59 pm

Nonstop4h 11m

Chicago O'Hare Intl

Sun 10/5

5:01 am-9:17 am

1 stop6h 16m

$275

Santa AnaChicago

SNA - MDW

SNAMDW

Santa Ana J. Wayne/Orange Cnty

Wed 8/27

8:00 am-5:37 pm

1 stop7h 37m

Chicago Midway

Wed 9/3

6:00 am-12:42 pm

1 stop8h 42m

$279

Santa AnaChicago

SNA - ORD

SNAORD

Santa Ana J. Wayne/Orange Cnty

Wed 8/27

11:28 am-8:23 pm

1 stop6h 55m

Chicago O'Hare Intl

Wed 9/3

7:45 am-11:53 am

1 stop6h 08m

$279

Santa AnaChicago

SNA - ORD

SNAORD

Santa Ana J. Wayne/Orange Cnty

Wed 8/6

7:58 pm-5:10 pm

2 stops19h 12m

Chicago O'Hare Intl

Fri 8/8

2:15 pm-7:46 pm

1 stop7h 31m

$283

Santa AnaChicago

SNA - ORD

SNAORD

Santa Ana J. Wayne/Orange Cnty

Tue 8/5

11:56 am-12:32 am

1 stop10h 36m

Chicago O'Hare Intl

Fri 8/8

2:15 pm-7:46 pm

1 stop7h 31m

$288

Santa AnaChicago

SNA - MDW

SNAMDW

Santa Ana J. Wayne/Orange Cnty

Fri 8/29

11:30 am-7:45 pm

1 stop6h 15m

Chicago Midway

Wed 9/3

8:40 am-2:50 pm

1 stop8h 10m

$289

Santa AnaChicago

SNA - ORD

SNAORD

Santa Ana J. Wayne/Orange Cnty

Fri 9/26

6:17 pm-5:00 am

1 stop8h 43m

Chicago O'Hare Intl

Tue 9/30

10:00 am-7:16 pm

2 stops11h 16m

$311

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/30

Showing 1-10 of 20 results
1
2

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 July 25, 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 July 31, 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 July 27, 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. 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 July 31, 2025.

The most flights from AN4 to CHI are scheduled on a Thursday (30 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (11 on average).

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 July 31, 2025.
Peruse reviews from past customers who have flown with Alaska Airlines, Southwest, and Delta 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
10,000 reviews

Overall

8.0

Boarding

8.1

Food

7.1

Entertainment

7.1

Comfort

7.8

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Boarding

8.1

Food

7.1

Entertainment

7.1

Comfort

7.8

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Southwest
8.0
Very good
4,246 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Boarding

8.1

Food

7.1

Entertainment

7.1

Comfort

7.8

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Delta
8.0
Very good
7,981 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Boarding

8.1

Food

7.1

Entertainment

7.1

Comfort

7.8

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
United Airlines
7.4
Good
8,900 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Boarding

8.1

Food

7.1

Entertainment

7.1

Comfort

7.8

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Boarding

8.1

Food

7.1

Entertainment

7.1

Comfort

7.8

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

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 ($99), Frontier ($109), and Alaska Airlines ($124).

  • 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 (93%), Brussels Airlines (93%) or United Airlines (88%) 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 $1,222. The most popular route, (Santa Ana J. Wayne/Orange Cnty - Chicago O'Hare Intl), can usually be booked for $140.

  • 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 Chicago?

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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Anaheim to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Los Angeles to O'Hare Intl flights
San Francisco to O'Hare Intl flights
Ontario to O'Hare Intl flights
Santa Ana to O'Hare Intl flights
Burbank to O'Hare Intl flights
San Diego to O'Hare Intl flights
San Jose to O'Hare Intl flights
Oakland to O'Hare Intl flights
Los Angeles to Midway flights
San Francisco to Midway flights
Las Vegas to O'Hare Intl flights
Sacramento to O'Hare Intl flights
Ontario to Midway flights
San Jose to Midway flights
San Francisco to St. Louis flights
San Diego to Midway flights
Los Angeles to St. Louis flights
Las Vegas to Midway flights
Long Beach to O'Hare Intl flights
Santa Ana to Midway flights
Fresno to O'Hare Intl flights
Palm Springs to O'Hare Intl flights
Burbank to Midway flights
Oakland to Midway flights
Ontario to St. Louis flights
San Diego to Moline flights
San Diego to St. Louis flights
Sacramento to Midway flights
Reno to O'Hare Intl flights
Reno to St. Louis flights
Fresno to Midway flights
Monterey to O'Hare Intl flights
Santa Barbara to O'Hare Intl flights
Burbank to St. Louis flights
San Diego to Peoria flights
Sacramento to St. Louis flights
Reno to Midway flights
San Jose to St. Louis flights
Santa Ana to St. Louis flights
Los Angeles to Rockford flights
Las Vegas to St. Louis flights
Los Angeles to Peoria flights
Oakland to St. Louis flights
Palm Springs to Midway flights
Long Beach to Midway flights
San Luis Obispo to O'Hare Intl flights
Long Beach to St. Louis flights
Santa Rosa to O'Hare Intl flights
San Francisco to Moline flights
Los Angeles to Moline flights

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 July 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$44Average$130FlexibilityNo cancel feeOn-time88%
Spirit AirlinesCheapest$67Average$196FlexibilityNo cancel feeOn-time65%
FrontierCheapest$96Average$219FlexibilityNo cancel feeOn-time62%
Sun Country AirCheapest$130Average$330FlexibilityNo cancel feeOn-time83%
United AirlinesCheapest$149Average$387FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$157Average$422FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$183Average$403FlexibilityNo cancel feeOn-time71%
Alaska AirlinesCheapest$190Average$418FlexibilityNo cancel feeOn-time75%
DeltaCheapest$236Average$402FlexibilityNo cancel feeOn-timeN/A

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.