$124+ 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 5/31. Fares are subject to change and may not be available on all flights or dates of travel.
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 May or September, 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 abril 29, 2025.
Most accurate provider | CheapOair 3 stars |
|---|---|
Most trusted provider | CheapOair 3 stars |
Round-trip from | $271 (CheapOair) |
One-way from | $124 (Alaska Airlines) |
Popular in | December |
Cheapest in | May |
Average price | $385 |
Find flight deals from Anaheim to Chicago
Cheapest flights from Anaheim to ChicagoExplore 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 abril 29, 2025.
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 abril 29, 2025.
This CheapOair deal was found by Cheapflights users on 4/28. 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.
This Orbitz deal was found by Cheapflights users on 4/28. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Delta deal was found by Cheapflights users on 4/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This CheapOair deal was found by Cheapflights users on 4/28. 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.
This United Airlines deal was found by Cheapflights users on 4/28. 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.
This Mytrip deal was found by Cheapflights users on 4/28. 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.
This Delta deal was found by Cheapflights users on 4/28. 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.
This CheapOair deal was found by Cheapflights users on 4/28. 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.
This American Airlines deal was found by Cheapflights users on 4/29. 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.
This Alaska Airlines deal was found by Cheapflights users on 4/28. 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.
This Southwest deal was found by Cheapflights users on 4/28. 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.
This Mytrip deal was found by Cheapflights users on 4/28. 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.
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 abril 29, 2025.
Use the filters below to find and compare flights from Anaheim to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Price
Santa AnaChicago
SNA - MDW
SNAMDW
Santa Ana J. Wayne/Orange Cnty
mar. 5/27
12:01 pm-8:53 pm
1 stop6h 52m
Chicago Midway
sáb. 5/31
2:44 pm-11:16 am
1 stop22h 32m
Santa AnaChicago
SNA - ORD
SNAORD
Santa Ana J. Wayne/Orange Cnty
mié. 5/14
3:16 pm-10:55 am
2 stops17h 39m
Chicago O'Hare Intl
vie. 5/23
3:15 pm-7:35 pm
1 stop6h 20m
Santa AnaChicago
SNA - MDW
SNAMDW
Santa Ana J. Wayne/Orange Cnty
mié. 5/28
11:46 am-9:27 pm
1 stop7h 41m
Chicago Midway
jue. 6/5
6:00 am-1:05 pm
1 stop9h 05m
Santa AnaChicago
SNA - ORD
SNAORD
Santa Ana J. Wayne/Orange Cnty
sáb. 5/17
3:16 pm-5:25 am
2 stops12h 09m
Chicago O'Hare Intl
mar. 5/20
9:14 pm-10:52 am
2 stops15h 38m
Santa AnaChicago
SNA - ORD
SNAORD
Santa Ana J. Wayne/Orange Cnty
mié. 6/4
10:35 am-4:46 pm
Nonstop4h 11m
Chicago O'Hare Intl
sáb. 6/7
5:02 am-9:14 am
1 stop6h 12m
Santa AnaChicago
SNA - MDW
SNAMDW
Santa Ana J. Wayne/Orange Cnty
dom. 5/11
6:47 pm-10:09 am
1 stop13h 22m
Chicago Midway
jue. 5/15
3:03 pm-1:08 pm
1 stop24h 05m
Santa AnaChicago
SNA - ORD
SNAORD
Santa Ana J. Wayne/Orange Cnty
lun. 5/12
12:51 pm-11:41 pm
1 stop8h 50m
Chicago O'Hare Intl
jue. 5/15
8:14 pm-6:31 pm
1 stop24h 17m
Santa AnaChicago
SNA - ORD
SNAORD
Santa Ana J. Wayne/Orange Cnty
mar. 7/1
9:46 am-6:25 pm
1 stop6h 39m
Chicago O'Hare Intl
mar. 7/8
7:40 am-11:50 am
1 stop6h 10m
Santa AnaChicago
SNA - ORD
SNAORD
Santa Ana J. Wayne/Orange Cnty
vie. 6/13
11:32 am-5:43 pm
Nonstop4h 11m
Chicago O'Hare Intl
lun. 6/23
7:09 am-9:25 am
Nonstop4h 16m
Santa AnaChicago
SNA - ORD
SNAORD
Santa Ana J. Wayne/Orange Cnty
vie. 10/17
6:10 pm-5:04 am
1 stop8h 54m
Chicago O'Hare Intl
lun. 10/20
10:00 am-5:15 pm
1 stop9h 15m
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.
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 25, 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 abril 29, 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 abril 29, 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 (6 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 abril 29, 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.
Boarding
Comfort
Food
Entertainment
Crew
Overall
Reviews
James,Apr 2025
LAX - SFO
Boarding
Comfort
Food
Entertainment
Crew
Overall
Reviews
James,Apr 2025
LAX - SFO
Boarding
Comfort
Food
Entertainment
Crew
Overall
Reviews
James,Apr 2025
LAX - SFO
Boarding
Comfort
Food
Entertainment
Crew
Overall
Reviews
James,Apr 2025
LAX - SFO
Boarding
Comfort
Food
Entertainment
Crew
Overall
Reviews
James,Apr 2025
LAX - SFO
Boarding
Comfort
Food
Entertainment
Crew
Overall
Reviews
James,Apr 2025
LAX - SFO
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.
Traveling to a place near Anaheim?
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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 abril 29, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$49 | Average$120 | FlexibilityNo cancel fee | On-time88% | |
| Cheapest$74 | Average$210 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$88 | Average$217 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$130 | Average$330 | FlexibilityNo cancel fee | On-time83% | |
| Cheapest$157 | Average$430 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$161 | Average$428 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$179 | Average$391 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$181 | Average$374 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$236 | Average$433 | FlexibilityNo cancel fee | On-timeN/A |