What are the cheapest airlines to fly from Chicago to Anaheim one-way?

For one-way options, check prices for Frontier. According to our data, you can fly for as low as $82. Users have also found prices from $144 and $144 on Southwest and American Airlines, respectively.

Weekly flight availability from Chicago to Anaheim

The most flights from CHI to AN4 are scheduled on a Tuesday (19 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (10 on average).

In terms of precipitation, rainfall in Anaheim ranges from 0.0 - 3.1 inches per month. February is typically the wettest month, when rainfall can reach 3.1 in. July is typically the driest time to visit Anaheim when rainfall is around 0.0 in.

If weather is an important factor for your trip to Anaheim, use this chart to help with planning. For those seeking warmer temperatures, August 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 55.4 F).

What are the cheapest flights from Chicago to Anaheim?

On average you can expect to pay $807 for a flight from Chicago to Anaheim. The cheapest flight overall is $144 while the most popular route, (Chicago O'Hare Intl - Santa Ana J. Wayne/Orange Cnty) is currently priced at $265.

What are the most reliable airlines from Chicago to Anaheim?

Before booking your flight to Anaheim from Chicago, check out the most reliable airlines to get you to your destination on time: United Airlines (79%), Brussels Airlines (77%), Air Canada( 75%).

What are the most popular airlines that fly from Chicago to Anaheim?

The most popular airlines flying from Chicago to Anaheim are American Airlines, United Airlines and Alaska Airlines. Something to consider prior to booking your flight.

Can I find deals for flights from Chicago to Anaheim that include hotel bookings?

Yes. In addition to deals on Chicago to Anaheim flights, Cheapflights offers vacation packages that include both flights and hotel.

How can I find direct flights from Chicago to Anaheim?

After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Anaheim.

Can I find deals for business class flights from Chicago to Anaheim?

Yes. Cheapflights offers flight deals from Chicago to Anaheim by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

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Cheapflights Tip: The best prices from Chicago to Anaheim are usually found in January or April, booked 61 days in advance, depart on a Saturday or Tuesday and return on a Saturday

Find flight deals from Chicago to Anaheim

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Popular in	June
Cheapest in	January
Average price	$432

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Highest demand for flights based on searches. 1% potential increase in price ($8 potential increase over avg. RT price).

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Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).

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Average for round-trip flights in September 2026

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Everything you need to know about your flight from Chicago to Anaheim

Prices

Airlines

What is the cheapest time of day to fly from CHI to AN4?

It’s typically best to fly out from Chicago to Anaheim in the morning. Doing so could potentially save you 16% on the flight price compared to flying in the evening, which is usually more expensive.

What is the cheapest day to fly from Chicago to Anaheim?

Travelers seeking maximum savings on their Chicago to Anaheim flight should consider departing on Monday evenings when fares are most often at their lowest. Sunday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

Reviews of airlines servicing Anaheim

Peruse reviews from past customers who have flown with Southwest,Alaska Airlines, andUnited Airlines from Chicago to Anaheim 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.

Southwest

8.0

Very good

4,199 reviews

Reviews

1 / 20

10.0

Excellent

Walter,May 2026

LAS - BUR

Short but excellent flight. Everyone was friendly and professional it was a great flight!

Southwest

8.0

Very good

4,199 reviews

Southwest

8.0

Very good

4,199 reviews

Reviews

1 / 20

10.0

Excellent

Walter,May 2026

LAS - BUR

Short but excellent flight. Everyone was friendly and professional it was a great flight!

Alaska Airlines

7.9

Good

12,962 reviews

Southwest

8.0

Very good

4,199 reviews

Reviews

1 / 20

10.0

Excellent

Walter,May 2026

LAS - BUR

Short but excellent flight. Everyone was friendly and professional it was a great flight!

United Airlines

7.4

Good

10,233 reviews

Southwest

8.0

Very good

4,199 reviews

Reviews

1 / 20

10.0

Excellent

Walter,May 2026

LAS - BUR

Short but excellent flight. Everyone was friendly and professional it was a great flight!

American Airlines

7.0

Good

12,074 reviews

Southwest

8.0

Very good

4,199 reviews

Reviews

1 / 20

10.0

Excellent

Walter,May 2026

LAS - BUR

Short but excellent flight. Everyone was friendly and professional it was a great flight!

Frontier

5.6

Fair

2,578 reviews

Southwest

8.0

Very good

4,199 reviews

Reviews

1 / 20

10.0

Excellent

Walter,May 2026

LAS - BUR

Short but excellent flight. Everyone was friendly and professional it was a great flight!

Related info for your journey

What are the cheapest airlines to fly from Chicago to Anaheim one-way?
For one-way options, check prices for Frontier. According to our data, you can fly for as low as $82. Users have also found prices from $144 and $144 on Southwest and American Airlines, respectively.
What are the most reliable airlines from Chicago to Anaheim?
Before booking your flight to Anaheim from Chicago, check out the most reliable airlines to get you to your destination on time: United Airlines (79%), Brussels Airlines (77%), Air Canada( 75%).
What are the cheapest flights from Chicago to Anaheim?
On average you can expect to pay $807 for a flight from Chicago to Anaheim. The cheapest flight overall is $144 while the most popular route, (Chicago O'Hare Intl - Santa Ana J. Wayne/Orange Cnty) is currently priced at $265.
Can I find deals for flights from Chicago to Anaheim that include hotel bookings?
Yes. In addition to deals on Chicago to Anaheim flights, Cheapflights offers vacation packages that include both flights and hotel.
How can I find direct flights from Chicago to Anaheim?
After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Anaheim.
Can I find deals for business class flights from Chicago to Anaheim?
Yes. Cheapflights offers flight deals from Chicago to Anaheim by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

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Top 7 airlines flying from Chicago to Anaheim

Airline	Cheapest	Average	Flexibility	On-time
Frontier	Cheapest$100	Average$282	FlexibilityNo cancel fee	On-time62%
Delta	Cheapest$118	Average$342	FlexibilityNo cancel fee	On-timeN/A
United Airlines	Cheapest$190	Average$420	FlexibilityNo cancel fee	On-time69%
JetBlue	Cheapest$194	Average$326	FlexibilityNo cancel fee	On-time62%
American Airlines	Cheapest$197	Average$396	FlexibilityNo cancel fee	On-time71%
Southwest	Cheapest$236	Average$462	FlexibilityNo cancel fee	On-time63%
Alaska Airlines	Cheapest$359	Average$469	FlexibilityNo cancel fee	On-time75%

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Cheap flights from Chicago (CHI) to Anaheim, CA

Find cheap flights from Chicago to Anaheim with Cheapflights

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3. Compare prices and book

Find flight deals from Chicago to Anaheim

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Cheapflights Insights

What is the cheapest time of day to fly from CHI to AN4?

It’s typically best to fly out from Chicago to Anaheim in the morning. Doing so could potentially save you 16% on the flight price compared to flying in the evening, which is usually more expensive.

What is the cheapest day to fly from Chicago to Anaheim?

Travelers seeking maximum savings on their Chicago to Anaheim flight should consider departing on Monday evenings when fares are most often at their lowest. Sunday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Chicago to Anaheim

The most flights from CHI to AN4 are scheduled on a Tuesday (19 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (10 on average).

Reviews of airlines servicing Anaheim

Peruse reviews from past customers who have flown with Southwest,Alaska Airlines, andUnited Airlines from Chicago to Anaheim 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.

Related info for your journey

What are the cheapest airlines to fly from Chicago to Anaheim one-way?

What are the most reliable airlines from Chicago to Anaheim?

What are the cheapest flights from Chicago to Anaheim?

Can I find deals for flights from Chicago to Anaheim that include hotel bookings?

How can I find direct flights from Chicago to Anaheim?

Can I find deals for business class flights from Chicago to Anaheim?

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 Chicago to Anaheim

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Complete your trip

Complete your trip to Anaheim by adding a car rental and/or hotel reservation to your travel itinerary.

Search flights from Chicago to Anaheim by cabin class

Find flights from Chicago to Anaheim, based on your preferred cabin class, be it economy, premium economy, business, or first class.

Chicago and Anaheim flights

Browse other Chicago and Anaheim flight options. Last updated on September 24, 2026.

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Top 7 airlines flying from Chicago to Anaheim

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