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 ($83), Southwest ($144), and Alaska Airlines ($144).

Weekly flight availability from Anaheim to Chicago

The most flights from AN4 to CHI are scheduled on a Tuesday (25 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (11 on average).

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.

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).

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 cheapest flights from Anaheim to Chicago?

The cheapest flight price from Anaheim to Chicago is $171. On average you can expect to pay $1,273. The most popular route, (Santa Ana J. Wayne/Orange Cnty - Chicago O'Hare Intl), can usually be booked for $244.

What are the most reliable airlines from Anaheim to Chicago?

Consider Brussels Airlines (84%), British Airways (83%) or Aer Lingus (83%) when booking your flight. These represent the most reliable airlines when flying from Anaheim to Chicago.

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

When booking a flight from Anaheim to Chicago, you may want to consider flying on American Airlines, United Airlines or Alaska Airlines as they are the most popular for this route.

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.

Find Cheap Flights from Anaheim to Chicago

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Cheapflights Tip: The best prices from Anaheim to Chicago are usually found in October or November, booked 79 days in advance, depart on a Saturday or Wednesday and return on a Saturday

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Average price	$440

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Highest demand for flights based on searches. 3% potential increase in price ($15 potential increase over avg. 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 Anaheim to Chicago

Prices

Airlines

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

Unlike at noon, when flights are generally more expensive, you can save up to 18% on flights from Anaheim to Chicago by exploring options for tickets in the afternoon.

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

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

Reviews of airlines servicing Chicago

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

Southwest

8.0

Very good

4,199 reviews

Reviews

1 / 20

6.0

Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers

Southwest

8.0

Very good

4,199 reviews

Southwest

8.0

Very good

4,199 reviews

Reviews

1 / 20

6.0

Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers

Alaska Airlines

7.9

Good

12,962 reviews

Southwest

8.0

Very good

4,199 reviews

Reviews

1 / 20

6.0

Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers

United Airlines

7.4

Good

10,233 reviews

Southwest

8.0

Very good

4,199 reviews

Reviews

1 / 20

6.0

Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers

American Airlines

7.0

Good

12,074 reviews

Southwest

8.0

Very good

4,199 reviews

Reviews

1 / 20

6.0

Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers

Frontier

5.6

Fair

2,578 reviews

Southwest

8.0

Very good

4,199 reviews

Reviews

1 / 20

6.0

Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers

Related info for your journey

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 ($83), Southwest ($144), and Alaska Airlines ($144).
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 Brussels Airlines (84%), British Airways (83%) or Aer Lingus (83%) 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 $171. On average you can expect to pay $1,273. The most popular route, (Santa Ana J. Wayne/Orange Cnty - Chicago O'Hare Intl), can usually be booked for $244.
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.

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Top 7 airlines flying from Anaheim to Chicago

Airline	Cheapest	Average	Flexibility	On-time
Frontier	Cheapest$100	Average$288	FlexibilityNo cancel fee	On-time62%
JetBlue	Cheapest$166	Average$384	FlexibilityNo cancel fee	On-time62%
United Airlines	Cheapest$182	Average$449	FlexibilityNo cancel fee	On-time69%
Delta	Cheapest$190	Average$357	FlexibilityNo cancel fee	On-timeN/A
American Airlines	Cheapest$216	Average$421	FlexibilityNo cancel fee	On-time71%
Southwest	Cheapest$233	Average$454	FlexibilityNo cancel fee	On-time63%
Alaska Airlines	Cheapest$288	Average$499	FlexibilityNo cancel fee	On-time75%

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Cheap flights from Anaheim, CA to Chicago (CHI)

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3. Compare prices and book

Find flight deals from Anaheim to Chicago

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Popular in

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Cheapflights Insights

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

Unlike at noon, when flights are generally more expensive, you can save up to 18% on flights from Anaheim to Chicago by exploring options for tickets in the afternoon.

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

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

Weekly flight availability from Anaheim to Chicago

The most flights from AN4 to CHI are scheduled on a Tuesday (25 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

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

Related info for your journey

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

What are the most popular routes from Anaheim to Chicago?

What are the most reliable airlines from Anaheim to Chicago?

What are the cheapest flights from Anaheim to Chicago?

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

How can I find direct flights from Anaheim to Chicago?

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

Traveling to a place near Chicago?

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Other flights to Chicago

Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on September 23, 2026.

Complete your trip

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Top 7 airlines flying from Anaheim to Chicago

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