$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 4/15. 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
$284
Overall average: $347
Frontier
Thu 4/23Thu 4/30
ORD - SNA • 2 stops
Cheapest non-stop
$289
Typical prices: $290-$439
American Airlines
Wed 4/15Tue 4/21
ORD - SNA • Non-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

Thu, Apr 23 - Thu, Apr 30
Multiple Airlines Logo
5:20 am - 6:01 pm
ORD
-
SNA
14h 41m
2 stops
Multiple Airlines Logo
7:30 am - 6:08 am
SNA
-
ORD
20h 38m
1 stop
$284Multiple Airlines
Mon, Apr 13 - Sat, Apr 18
Spirit Airlines Logo
3:21 pm - 9:53 am
ORD
-
SNA
20h 32m
2 stops
Spirit Airlines Logo
3:23 pm - 5:25 am
SNA
-
ORD
12h 02m
1 stop
$285Spirit Airlines
Sat, May 2 - Sat, May 9
Southwest Logo
10:15 am - 5:35 pm
MDW
-
SNA
9h 20m
2 stops
Southwest Logo
6:45 am - 5:15 pm
SNA
-
MDW
8h 30m
2 stops
$285Southwest
Fri, Apr 10 - Wed, Apr 15
Spirit Airlines Logo
3:21 pm - 9:53 am
ORD
-
SNA
20h 32m
2 stops
Spirit Airlines Logo
3:23 pm - 5:25 am
SNA
-
ORD
12h 02m
1 stop
$286Spirit Airlines
Fri, Apr 24 - Mon, Apr 27
Multiple Airlines Logo
10:07 pm - 6:00 pm
ORD
-
SNA
21h 53m
1 stop
Multiple Airlines Logo
2:41 pm - 10:02 am
SNA
-
ORD
17h 21m
2 stops
$287Multiple Airlines
Sun, Apr 12 - Mon, Apr 13
Multiple Airlines Logo
4:41 pm - 9:53 am
ORD
-
SNA
19h 12m
2 stops
Multiple Airlines Logo
7:20 pm - 6:20 am
SNA
-
ORD
9h 00m
1 stop
$288Multiple Airlines
Fri, May 1 - Tue, May 5
Multiple Airlines Logo
8:58 pm - 6:00 pm
ORD
-
SNA
23h 02m
1 stop
Multiple Airlines Logo
7:30 am - 6:39 am
SNA
-
ORD
21h 09m
2 stops
$289Multiple Airlines
Fri, May 22 - Mon, May 25
Frontier Logo
9:30 am - 5:53 pm
ORD
-
SNA
10h 23m
1 stop
Frontier Logo
9:54 am - 8:37 pm
SNA
-
ORD
8h 43m
1 stop
$290Frontier
Wed, Apr 8 - Thu, Apr 16
Frontier Logo
3:29 pm - 11:34 am
ORD
-
SNA
22h 05m
1 stop
Frontier Logo
7:56 pm - 6:08 am
SNA
-
ORD
8h 12m
1 stop
$291Frontier
Fri, May 1 - Mon, May 4
Southwest Logo
4:10 pm - 8:20 pm
MDW
-
SNA
6h 10m
1 stop
Southwest Logo
8:10 pm - 6:00 am
SNA
-
MDW
7h 50m
1 stop
$297Southwest
Useful Info

Good to know

Low seasonNovember
Cheapest flight$145
Best time to beat the crowds but there is an average 1% increase in price.
Most popular time to fly and prices are also 9% 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 33m.

  • How many flights are there between Chicago and Anaheim?

    21 direct flights run between Chicago and Anaheim on a daily basis. On average, there are about 150 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 $72. Spirit Airlines offered a round-trip connection from $69 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 25 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.
8.0
SouthwestOverall score based on 4331 reviews
7.0Food
8.1Boarding
8.6Crew
8.0Comfort
7.5Entertainment
Airline reviews

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.

2.0 MediocreBeth, Mar 2026
MDW - PIT
Read more Southwest reviews

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.

The charges were ridiculous for an hour flight and the turbulence was very scary.

3 hour delay. Had to change plans and was still delayed.

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

The flight crew was extremely rude and especially not helpful when our flight was delayed.

Fine for a short flight. All went well. Snacks are lacking and I couldn’t hook up to wifi through the app, but it was fine.

Aircraft was freezing, cold air blowing on me the entire time and the individual fans were turned off.

Four hour delay. Missed our event. And they offered me $75. Absolutely shameful.

i canceled my flight from SEA to SFO, SNA to SEA and received full refund from Alaska Airlines. i am pleased with the customer service.

I have been flying commercial for decades. I was in one of the ladder boarding groups, had my bag tagged because they thought there was not going to be enough space for it in the overhead bins. I politely asked one of the attendance if I could try to find a space- she said I could and I did. I then took the bag tag off and gave it to one of the other attendants as I was told to do by the first one. He, in a curt, anal, and disrespectful manner, told me that I needed to take my bag down from the overhead bin and check it. This was a situation I’ve never encountered before. The attendant’s attitude was confrontational and belittling in front of other onlooking passengers as if daring me to challenge him. I am a physician who takes care of patients day in and day out. Not wanting to make a scene, I calmly told him, “do what you need to do.” he took my bag down from the overhead bin, put the back tag back on it, and checked it only to make room for another bag that was also supposed to be technically checked by a following passenger. The same male attendant later came up to me and said “you shouldn’t have showed me the bag tag,” as if conveying that he was just following protocol was a justification for treating me like a kid out of line. I cared about this because it took 15 minutes from my life to then retrieve the bag at baggage claim and it also felt like really poor customer service. I understand the need for protocols. This is also a service industry, and we the passengers are the clients. We should be made to feel welcome and respected and our life in transit made as easy as it can be within reason. This attendant clearly needs to be reminded of that. Of note, an older female fellow passenger sitting next to me agreed with this assessment.

Departing flight for our weekend trip was cancelled due to weather which meant our return flight was useless. The whole thing was difficult to get support through but Alaska did recover and was able to reimburse us for the flights yesterday. For some reason, Kayak was not kept in the loop, adding to the confusion.

i canceled my return flight package with Alaska Airlines. Customer Service was excellent and assisted me to cancelled both of our reservations and returned the payment in full. that is excellent service and understanding and empathy of the customers' needs. i like Alaska Airlines and recommend AS to everyone.

You sent me an email saying boarding was at 9:29 and AA sent one that was 8:29 on Sunday morning. I had to call AA to get that it was indeed 8:29.

The airport crew and on board experience was fine. The problem with Alaska air is that there is zero customer service over the phone when you’re trying to buy your ticket or change anything.

The front desk attendant was rude to everyone in an absolutely careless way.

This trip did not start off well. The inbound flight was delayed about 20 minutes. Then, after initial onboarding, the passengers had to deplane due to a mechanical problem. That took about 30 minutes to fix and be cleared. Then, reboarding was chaotic. It took a long time to sort passengers and two passengers on standby were ticketed but there was no seat. So, they had to deplane. One of the flight crew was trying to help passengers figure out a place to put their carry-on bags and that took more time. In the end, our scheduled 10:30 am departure did not actually take off until about 12:05 pm CST. The flight itself was long but we got to Houston. Some passengers missed their connecting flights and had to rebook. Not the best of flights I've had.

We were delayed for about an hour from taking off due to traffic control procedures at the destination airport. But once in the air, the flight went well. The crew members were great and provided cabin service despite moderate turbulence during much of the flight.

Short flight, but no drink/snack service. The flights both going and coming were delayed.

Not being stranded in Chicago for her airport to 11:30 tomorrow morning the 3rd

I was fully checked in the prior night and i was unchecked and then didn’t have a seat when I boarded. Instead of an aisle seat, I was out in the middle seat of the very last row of the plane.

In overall it was a good experience, the only down point was that the entertainment screen was working properly.

They lost my luggage, so, not happy. The crew was nice but my suitcases never made it, still trying to find out what happened!

I understand weather is an issue, but making us chase our plane down at five scheduled gates across three terminals in an airport the size of O'Hare was unfair. They'd have probably been better off to leave gates as TBD until the inbound plane is in final approach instead of running us all over the place. Also, props to the consistently-unprepared ground crew in Richmond for once again leaving my lane parked short of the gate because they couldn't have a crew in place on time with 2 hours notice...

cabin crew was OK, food was OK, the trip from the US to Munich was actually pretty bad comfort wise. Noisy aircraft, lights never dimmed even in Business class (night flight) barely sufficient amenities for the price. I have millions of miles with United but TBH American is gaining ground and Delta has always been marginally better then United although on paper United has more longes and cheaper upgrades.

Essy to get on. The hostess gave very little pop, the plane was late getting in, and we are still waiting for our bags. This sucks. :/

Pretty awful. 2 hours late due to operational issues and finally deboarded around 2am.

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

As previously stated the delay I experienced flying from Wichita to Chicago caused a host of issues. When I finally was able to be booked on the last remaining American flight from Chicago to Cincinnati, the gate changed four times with the last change occurring very near the scheduled boarding time. While I didn't have a problem moving from gate to gate, I did notice and make note of others that had mobility issues and had to move each time for the gate change.

Maintenance took a very long time and then we were in a holding pattern. While a one-off maintenance issue is standard, there were delays on both of my flights for this trip based on maintenance issues with the planes, which delayed both flights over 45 minutes. Thankfully, I didn't have any connections but it wasn't an experience that would make me pick AA if I have other options.

No Snacks or Entertainment. The flight was short, snacks should still be given.

See prior comment about how Kayak mishandled my reservation and delayed my arrival by 6 hours.

Boarding delayed 20 minutes for no reason, no wifi, in flight entertainment, or snacks / waters?

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.

My flight was cancelled I missed time at work and got a parking ticket

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

Crew was very nice. Take off and landing were great. Economy seats are not comfortable. Extra cost for snacks.

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

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