$145 Find Cheap Flights from Chicago to Anaheim

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Anaheim departing on 6/20. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$319
Typical prices: $457-$299
American Airlines
Wed 7/1Sat 7/11
ORD - SNA • Non-stop
Cheapest one-way
$145
Typical prices: $158-$318
Frontier
Sat 6/20
ORD - SNA • 1 stop
Arrival airport
You can't fly directly to Anaheim. It is served by Santa Ana (SNA), located 9.8 miles from Anaheim.
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Flight Deals
Useful Info
Flight Deals

Cheap Flights from Chicago to Anaheim (CHI-SNA)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Anaheim that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Chicago to Anaheim

Wed, Jul 1 - Sat, Jul 11
American Airlines Logo
12:00 pm - 2:31 pm
ORD
-
SNA
4h 31mnonstop
American Airlines Logo
3:11 pm - 9:50 pm
SNA
-
ORD
4h 39mnonstop
$319American Airlines
Fri, May 29 - Sun, May 31
Multiple Airlines Logo
7:40 am - 2:43 pm
ORD
-
SNA
9h 03m
1 stop
Multiple Airlines Logo
9:54 am - 8:32 pm
SNA
-
ORD
8h 38m
1 stop
$320Multiple Airlines
Wed, Aug 5 - Sat, Aug 8
Frontier Logo
1:50 pm - 1:42 pm
ORD
-
SNA
25h 52m
2 stops
Frontier Logo
7:54 pm - 5:28 am
SNA
-
ORD
7h 34m
1 stop
$323Frontier
Tue, Jun 16 - Tue, Jun 23
United Airlines Logo
5:00 am - 9:07 am
ORD
-
SNA
6h 07m
1 stop
United Airlines Logo
4:00 pm - 12:44 am
SNA
-
ORD
6h 44m
1 stop
$324United Airlines
Tue, Jun 30 - Wed, Jul 8
United Airlines Logo
8:40 am - 11:21 am
ORD
-
SNA
4h 41mnonstop
United Airlines Logo
4:00 pm - 12:44 am
SNA
-
ORD
6h 44m
1 stop
$325United Airlines
Fri, Jun 5 - Fri, Jun 12
Frontier Logo
9:37 pm - 9:09 am
ORD
-
SNA
13h 32m
1 stop
Frontier Logo
2:24 pm - 8:43 pm
SNA
-
ORD
28h 19m
2 stops
$327Frontier
Thu, Aug 6 - Sun, Aug 9
Multiple Airlines Logo
9:57 pm - 8:05 am
ORD
-
SNA
12h 08m
1 stop
Multiple Airlines Logo
6:03 pm - 4:08 pm
SNA
-
ORD
20h 05m
2 stops
$328Multiple Airlines
Tue, Jun 30 - Wed, Jul 8
Southwest Logo
2:55 pm - 8:20 pm
MDW
-
SNA
7h 25m
1 stop
Southwest Logo
3:35 pm - 12:05 am
SNA
-
MDW
6h 30m
1 stop
$329Southwest
Tue, Jun 2 - Tue, Jun 16
Delta Logo
7:12 am - 4:39 pm
ORD
-
SNA
11h 27m
1 stop
Delta Logo
11:20 am - 11:39 pm
SNA
-
ORD
10h 19m
1 stop
$329Delta
Thu, May 28 - Wed, Jun 3
Southwest Logo
4:50 pm - 9:10 pm
ORD
-
SNA
6h 20m
1 stop
Southwest Logo
10:00 am - 6:50 pm
SNA
-
ORD
6h 50m
1 stop
$333Southwest
Useful Info

Good to know

Low seasonNovember
Cheapest flight$145
Best time to beat the crowds with an average 1% drop in price.
Most popular time to fly and prices are also 13% lower on average.
Flight from Chicago O'Hare Airport to John Wayne (Santa Ana)

When to book flights from Chicago to Anaheim

Are your dates flexible? Find out the best times to travel from Chicago to Anaheim based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price

FAQs for booking flights from Chicago to Anaheim

  • Which airports will I be using when flying from Chicago to Anaheim?

    When flying out of Chicago you’ll be using one of these airports: Chicago Midway or Chicago O'Hare Intl. Anaheim does not have its own airport so you’ll be flying into nearby Santa Ana J. Wayne/Orange Cnty airport, which is 9.8 mi away.

  • How long does a flight from Chicago to Anaheim take?

    Direct flights cover the 1,734 miles separating Chicago and Anaheim in about 4h 24m.

  • How many flights are there between Chicago and Anaheim?

    29 direct flights run between Chicago and Anaheim on a daily basis. On average, there are about 206 departures each week.

  • What’s the cheapest day of the week to fly between Chicago and Anaheim?

    Consider leaving on a Friday and avoid Saturdays if you are looking for the best rates. For your return to Chicago, you’ll find the best rates on Mondays and the most expensive ones on Saturdays.

  • How does KAYAK find such low prices on flights from Chicago to Anaheim?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to Anaheim.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Anaheim?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Anaheim from Chicago is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago to Anaheim?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Anaheim with an airline and back to Chicago with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Anaheim?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Anaheim from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • Which airlines provide the cheapest flights from Chicago to Anaheim?

    In the last 72 hours, the cheapest one-way ticket between Chicago and Anaheim found on KAYAK was with Frontier for $76. Spirit Airlines offered a round-trip connection from $85 and Frontier from $129.

Top tips for finding cheap flights from Chicago to Anaheim

  • There is no airport in Anaheim. Instead, you’ll be flying into John Wayne Airport, OC when flying between Chicago and Anaheim.
  • The cheapest flight from Chicago to Anaheim was found 26 days before departure, on average.
  • Book at least 1 week before departure in order to get a below-average price.
  • High season is considered to be February, March and April. The cheapest month to fly is September.

Reviews of the top 5 airlines serving Chicago to Anaheim

 
Need help choosing which airline to fly with from Chicago to Anaheim? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.9
Alaska AirlinesOverall score based on 12353 reviews
7.0Food
8.1Boarding
7.8Comfort
7.0Entertainment
8.5Crew
Airline reviews

I had to cancel this trip due to medical reasons. I took out flight insurance but I was unable to cancel my reservation on either Kayak or Alaska. I need proof that I did not take this flight to get my refund. I have tried for a week and a half together that information from either Kayak or Alaska but so far I have gotten no response. I am very disappointed!

2.0 MediocreDave, May 2026
SEA - PSP
Read more Alaska Airlines reviews

I had to cancel this trip due to medical reasons. I took out flight insurance but I was unable to cancel my reservation on either Kayak or Alaska. I need proof that I did not take this flight to get my refund. I have tried for a week and a half together that information from either Kayak or Alaska but so far I have gotten no response. I am very disappointed!

I had to change my flight last minute due to a medical emergency. Their agent was compassionate and extremely helpful. This airlines really cares about making travel, for fun, work, or an emergency a customer-focused experience. Thank you!

See what I wrote in the previous section. This was a terrible experience. I would like refund.. I even paid an extra $70 for an aisle seat closer to the front to ensure that I got off early enough to catch the next flight. The fact that the plane did not wait, and even left eearlier, knowing that the first flight came in late, and was moved to a terminal three train stops away is appalling. My friend that flew JetBlue, their flight was delayed and came in later and the connecting flight WAITED for them. How is it that JetBlue could do that, and Alaska could not.

The seat on the plane out was broken and would not lean back. I have back problems and sitting up straight was hard on my lower back and caused pain for over half the flight. Since I paid extra for First Class so I would not have these issues. This needs to be addressed.

No headphones provided. No gf food. Only 1 beverage cart run sAN to HNL. Rarely saw crew members

Thanks for all you do to keep us safe and on time!

The check-in crew for Alaska was rude, unhelpful, and the opposite of customer-centric. We arrived 50 minutes before our flight and were told it was too late to check baggage. When I asked what the cutoff was, the agent started speaking in codes “D50” and yelling to their manager who also spoke in codes. They then tried to speak to me using these codes and all I wanted to know was the time of the cutoff, which they would not — or could not — articulate. They booked me and my family on the next flight while smirking.

Generally Good. Outbound flight was marred by a continuously s creaming baby. Fortunately the flight was only 90 mins long it would be nice if people traveling with small childres could be centered in one part of the plane. Also, you need to adapt your servey to include a "not applicable " option for things like food and entertainment, which are not offered on shorter flights. I fily Alaska by choice as given all the cirumstances, I fel\el you do a good job.

A solidly good experience, but would’ve appreciated more communication with regards to travel delays.

I wasn’t aware that we needed to supply our own screens for entertainment

Plane was clean and comfortable. Flight attendants and gate staff were professional, friendly and efficient. Boarding and deplaning were orderly and efficient. All in all, the typical excellent Southwest experience.

Not having a five hour delay with little notice! The crew was very kind, though, and just as tired as we passengers were. The flight didn't depart until nearly 1 am...and no reason was ever given.

This leg was much better, but we did have to have a 3 hour lay o er after coming from a very exhausting hiccup with our flight from BNA to Den

The Air hostess were very rude on my flight from Houston to Austin . Their regular communication itself felt a they are shouting at people.

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

Boarding was easy. The seats are small and fairly uncomfortable

The problem with the seat assignments is that there were a lot of rows in the front that were empty but my row at the back was full. Just not so pleasant.

No food or entertainment, just a quick 40 minute flight. A little bumpy due to Santa Ana winds but pilot has no control over that. Good flight and landing!

Good but I prefer choose your own seat. With the new assigned seats they should board from the back I see no advantage to this new boarding. Just like every other airline

Mediocre. Boarding is now unpleasant. The employees, once friendly and nice, are now regularly speaking sternly to passengers, badgering them to do things right so they can take off on time and gate check bags because they don't have enough overhead bin space. The pretzel snack was crushed flat and broken into even smaller pieces, which happens frequently lately. Drink service was suspended before they reached my row.

A long delay. Don't travel late in the day.

Super friendly with lots of drink options an entertainment. Friendly crew.

The crew was great. Very friendly and responsive. The plane was old, small and tight. We ran out of overhead space and I had to check. Middle seat was particularly tight.

Several missed and almost missed connections. It felt like everything was being patched together last minute without enough resources and it ended up being an extremely stressful experience that basically ruined our weekend on the west coast. What a waste.

Crew was friendly. Seats are too narrow, particularly when a big person is in the adjacent seat, but I understand this is due to smaller planes usually flight into Lincoln. I have experienced several flight delays going out and coming into Lincoln airport, I say maybe 50% or higher of the flights I've taken out of this airport have been delayed.

Great flight. Boarded efficiently. Arrived early at CLT. There was no in flight entertainment on this aircraft. Great crew.

The seat was comfortable. There was a lot of turbulence. If it weren't for that,it would have been okay.

Poor communication, flight was delayed for preventable reasons. I missed my connection.

No meal service to the back of the plane as it started late or was too slow to get it out before it was time to land.

Terrible, if possible won't be flying again anytime soon!

The airplane was an old model, the overhead didn’t have enough room for people’s items and made boarding and boarding disappointing and stressful. Crew allowed passengers to bring more than the permitted baggage sizes.

Original flight was on time, then late, then changed gates...4 times. Once our newest plane came in, it was fine.

I almost missed my flight and they helped me out enormously

Delays experienced in boarding/take off due to incoming plane delayed. However, the boarding time/depart time in the app was significantly delayed in providing these updates. Usually not updated until an hour after we should have already boarded. Poorly managed.

Moved to earlier flight which unexpectedly had maintenance issues initially indicated as quick fix to ultimately plane changes. Moved back to original flight, also delayed. In all cases customer updates and communication very unclear, no updates on drivers for delays.

Typical AA - late by 90+ mn. Gate changed twice... Changed the departure time 6 times No explanation, no communication on reasons for delay I travel with AA twice a year... and it is consistently very poor.. I will continue to use AA only when i have to.

The gate got changed several times and the flight was delayed over an hour. Awful experience

American continues to decline in their customer service and its beyond disappointing.

It was an older plane. First Class was not especially roomy or comfortable. It was a short flight so there were no meal but they did offer mixed nuts which used to be normal but now is rare. Crew member was very polite and professional.

Flight to Tampa was delayed taking off due to plane arriving late but no other issues

The airline cancel mi flight, lost a lot of money!!!

They cancelled our flight. 2 hours before we were supposed to take off and offered us nothing! We got our money back and that was it. No other flight to get to our cruise no working with another airline or with us to get there. Terrible customer service, no apology.

No WiFi, no outlets to charge phones, no complimentary beverages on a 6 hour flight

Flight was delayed more than 3 hours, and the metro had stopped running by the time we got to the terminal well past midnight, so I was stranded, alone, with no way to get home until the metro started up the next morning.

We get stuck in the plane when landed during 45min and no communication from the crew People were listening to their phone and music out loud and nobody told them anything I definitely want stop booking spirit flight it is a disaster

Good: It was cheap and they got us to our destination safely. Not so Good: Gates experience with many, many nauseatingly (almost) threatening announcements about bags size and how much they were going to charge us if our bag was too big, even to the point of having a gate agent roaming around through the passengers eyeballing bags size and making people go check their bags in the sizers.

Terrible. The flight was randomly delayed in Chicago causing us to miss our connection and they offered us a flight the next day at 6 am and it would have taken till 345 to get to Pensacola. They didn’t cover any fees. Our bags also supposedly were on the flight to Pensacola and we tried to get them yesterday after driving 6 hours and nobody was available. Worst company ever and will never use them again. Had to pay for a rental. Spirit is claiming in climate weather for the delay but there wasn’t any weather issuesz it’s a bunch of bullshit and I am not happy

Checking in at desk in Chicago was horrible. Person was not friendly never smiled and said my flight was not paid for so I had to give another credit card. Then it ended up that I was charged twice. Then after arriving at my destination had to wait on the phone a long time to speak to a person to fix the double charge! Thank goodness the flight was perfect.

Flight was delayed for 12 h. They should stop overlooking flights.

All of our flights were canceled, though every other airline was flying out and in

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

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