$99 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 11/5. 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.
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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

Fri, Sep 5 - Sun, Sep 7
Frontier Logo
9:54 pm - 6:27 pmORD-SNA
22h 33m1 stop
Frontier Logo
7:16 pm - 8:59 pmSNA-ORD
23h 43m1 stop
$251Frontier
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Sat, Sep 13 - Sat, Sep 20
 Logo
8:25 am - 11:07 amORD-SNA
28h 42m1 stop
 Logo
2:15 pm - 10:42 amSNA-ORD
18h 27m2 stops
Fri, Sep 5 - Sun, Sep 7
Frontier Logo
4:48 pm - 12:13 pmMDW-SNA
21h 25m1 stop
Frontier Logo
11:52 am - 3:53 pmSNA-MDW
26h 01m1 stop
$253Frontier
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Wed, Oct 8 - Thu, Oct 16
Spirit Airlines Logo
7:25 am - 10:03 pmORD-SNA
16h 38m2 stops
Spirit Airlines Logo
8:09 pm - 2:41 pmSNA-ORD
16h 32m2 stops
$254Spirit Airlines
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Mon, Sep 8 - Fri, Sep 12
Spirit Airlines Logo
9:00 am - 10:05 pmORD-SNA
15h 05m1 stop
Spirit Airlines Logo
6:45 am - 10:42 amSNA-ORD
25h 57m3 stops
$255Spirit Airlines
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Fri, Sep 19 - Sat, Sep 27
Alaska Airlines Logo
1:01 pm - 9:42 pmORD-SNA
10h 41m1 stop
Alaska Airlines Logo
2:03 pm - 12:04 amSNA-ORD
8h 01m1 stop
$268Alaska Airlines
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Thu, Oct 23 - Sat, Oct 25
American Airlines Logo
7:00 am - 9:28 amORD-SNA
4h 28mnonstop
American Airlines Logo
7:55 am - 2:04 pmSNA-ORD
4h 09mnonstop
$269American Airlines
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Sat, Oct 25 - Wed, Oct 29
United Airlines Logo
5:01 am - 9:17 amORD-SNA
6h 16m1 stop
United Airlines Logo
6:45 am - 12:56 pmSNA-ORD
4h 11mnonstop
$275United Airlines
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Fri, Sep 12 - Mon, Sep 15
United Airlines Logo
7:58 pm - 10:30 pmORD-SNA
4h 32mnonstop
United Airlines Logo
6:45 am - 1:08 pmSNA-ORD
4h 23mnonstop
$294United Airlines
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Fri, Sep 5 - Fri, Sep 12
American Airlines Logo
6:50 am - 9:10 amORD-SNA
4h 20mnonstop
American Airlines Logo
3:10 pm - 9:18 pmSNA-ORD
4h 08mnonstop
$295American Airlines
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Good to know

Low seasonJanuary
Cheapest flight$99
Best time to beat the crowds but there is an average 8% increase in price.
Most popular time to fly with an average 24% increase in price.
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 28m.

  • How many flights are there between Chicago and Anaheim?

    26 direct flights run between Chicago and Anaheim on a daily basis. On average, there are about 187 departures each week.

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

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

  • 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 Spirit Airlines for $99. Frontier offered a round-trip connection from $251 and Spirit Airlines from $254.

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 78 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
Alaska AirlinesOverall score based on 10000 reviews
8.1Boarding
7.8Comfort
8.5Crew
7.0Entertainment
7.1Food
Airline reviews

Agent boarding us in San Diego lectured me on showing up on time for the flight, and said that if I had been three minutes later, he would have denied myself and my wife boarding. Our trusted traveler numbers were not in the system, even though I entered them when I bought the tickets. Our food orders were not in the system, even though I entered them prior to the flight. My wife requires a wheelchair, and that was delayed on both flights.

4.0 OkayAnonymous, Aug 2025SEA - SAN
Read more Alaska Airlines reviews

Agent boarding us in San Diego lectured me on showing up on time for the flight, and said that if I had been three minutes later, he would have denied myself and my wife boarding. Our trusted traveler numbers were not in the system, even though I entered them when I bought the tickets. Our food orders were not in the system, even though I entered them prior to the flight. My wife requires a wheelchair, and that was delayed on both flights.

It was fine—the seats are not very comfortable and the aisles are very narrow. Nothing different from other airlines

Unfortunately 4 hour 40 minute delay because of airport then one hour into flight diverted back to Kona elderly man on plane got heart attack trying to get home some how

Seats are so small now that it's very hard even for a medium-sized person to be comfortable!!!

My experience would’ve been great because we were on a new plane, but they said as we boarded that the plane would be too new to have WiFi, which to me is unreasonable - newer planes should def have WiFi! It was a 5 hour flight from Anchorage to San Fran and because there was no WiFi, I had to take an unexpected half day off work, which was super annoying because I had a lot to do and we only found out a few minutes before takeoff.

Such great crew, from checkin to the plane. So friendly and helpful, I was genuinely impressed.

Hawaiian Airlines, like most US-based ones, constantly provide sub-par service and pack their planes to the max with all kinds of last-minute-purchase schemes. As a result, it makes every flight so uncomfortable and generates high health risk for its passengers. In one word, GREED rules the day!

Well the flight being delayed multiple time really was frustrating. But the crew and flight was good.

Staff at Gate desk were helpful. My connecting flight from the first part of my trip Kona to Seattle was late. I had to run through SeaTac Seattle to catch my flight to San Jose. They made an exception to let me board. On my return trip San Jose to San Diego and San Diego to Honolulu the same thing happened. One flight arrived late and I had to run through the terminal to catch my connection. There are no Gluten-free & Vegan options meals and snacks to purchase.

generally good. No snacks or drinks on the flight 3379 from Portland to San Jose, CA. Sad.

Once we got in the air the pilot made up some of the time of the delay. So that was really nice.

Excellent flight. Boarding was efficient and departure was on time. Smooth flight with on time arrival. Deplaning was also efficient.

It was delayed instead of departing at 9:20pm, we departed at 11pm… putting us in Columbus after 2am! It was awful. Had I known about the delay, I could have spent some time in the United Lounge… I was starving because I started my journey in Budapest… so I was exhausted and hungry. Plus I had to make new arrangements to be picked up at the airport in Columbus, instead of midnight it was 2:30 am after getting luggage and out of airport. Not feasible. I would have just stayed in Chicago for the night and gotten a morning flight.

It was great, I’m very grateful for the pilots and crew flight attendants for everything.

Evidently, my seat had the only broken TV. I couldn’t plug it in, get it to come on, or watch anything, and of course, no one could fix it while we were on the plane. The service was good and the boarding was quick

I was charged for my daughters bag when I am supposed to receive two free checked bags with my United Explorer card.

The schedule to Moline changed 5 times. The gate changed 6 times. That is a pathetic way to run an airline. No wonder that no one in our company flies on United Express to or from Moline. Changes happen most of the time. I learned my lesson on this trip…never again!

Flight was great. Efficient boarding. Short flight. Early arrival. Friendly flight crew. The entertainment system did not work well. Could not access it until the aircraft reached 10K feet or more. Lots of glitches.

A bit rush for transit. Food and entertainment are not available

Smooth boarding process. Early departure, smooth flight, early arrival. The entertainment package has very good recent movie options. The flight crew were friendly and professional.

3 hour weather delay followed by 1 hour (and counting) maintenance delay. UGH!

After we'd boarded , they canceled the flight. The crew didn't even know , we just all received text messages. Then after they deplaned us , AA was just like "too bad, go F your self, we sure ain't gonna help you"

After a two hour delay, my flight was CANCELLED! No pilot available. Such BS.

Amazing food, great staff, with one noticable detail missing ...but no seat entertainment in any of aircraft ...I am not a fan

I wish American Airlines would change the airline industry by loading the plane back to front instead of front to back. Planes would board so much more smoothly and quickly.

I have long legs, my foot was out in the aisle and when a flight attendant came walking by and I didn't notice, instead of saying "excuse me" or anything like that, she kicked my foot. Extremely rude

Excellent! The gate agents were kind enough to rebook me on an earlier flight saving me from a 6 hour layover. Even my luggage made it despite the fact that the connection was technically too narrow. The flight itself was very comfortable, roomy, and clean. Plenty of space for my carryon items with plugs to charge my phone. After a long international flight of 14 hours, this was an excellent way to end my travels!

Great experience. Flight boarded easily. Departed early. Smooth flight. Great arrival in DC--almost no taxing! Almost direct to gate from runway. Crew was terrific. Same cookies and beverages in main cabin. I did not use the entertainment system on this flight.

Most of the delay was due to weather which is not what was at issue here. One delay was due to a missing flashlight and in the end the flashlight was actually found on the plane. The entertainment system is very limited. Live TV options offer only a few channels that are not very appealing. Boarding and deplaning are always difficult. It just takes too much time to get on and off the plane. On the plus side, I missed my connecting flight, but was easily able to book a later flight from the app while enroute.

You were more on time than United. I'm so over united delays.

Late departure by 1:45min. No explanation why. During boarding inconsistent policing of their baggage rules. Before takeoff and lamdimg strange obsession with window shade and armrest positions. Don't know why they care. 15 min tarmac delay on arrival, they blamed airport congestion but we were the o lh flight waiting, it was clear it was due to poor staff planning (only one ground crew to receive airplanes and multiple arrivals) Got there but was rrally lame the whole trip.

It was very bad it got delayed by 2 hours.Never going to travel with spirit airlines in future.

The flight times got delayed multiple times due to weather which is understandable, but later the time got prepared 30min. Made to the flight barely but got stressed too much.

Boarding was a breeze, however, two of the flights that I boarded with Spirit did not have Wi-Fi available.

Very good. Nothing more or less than expected. No complaints.

My experience with the spirit as a first time it was OK, but the seats need a little cushion, the problem I had the most impacted me was when checking in the scales were so off and wrong. It will tell that you would have more weight, which was not true. The scale was say that it had Thirty Eight Pounds, when get in the labels when we send the luggage into the band. It says that it was overweight. I really really dislike that because the scales are not accurate. If I use Spirit and I have that issue again. That will be my last time flying with the spirit, even though I like so much to service the planes, and everything else

hahaha we are delayed for one hour plus.. but thx we arrived San Diego safe

Worst airline ever! The guy weighing my bag had his foot on the metal plate and when I called him out on it, I got this stupid little smirk. La is a scam and so is Spirit Airlines. All the flight attendants looked like they hated our flight just as much as we did.

Very dissatisfied with spirit airlines after buying my ticket's they cancelled our flights with no reasoning.

Unclear pricing; ended up being charged an extra $52 just to get onboard

Great for the price. No wifi or entertainment, but gate agents and crew were fantastic and we boarded quickly and left on time.

sluggish boarding and arrival procedures, fake nice flight attendants, and lots of delays.

Disaster. They lied every step of the way. We ended up being delayed due to crew and then allegedly abandoned the flight because of a curfew at LGA. No rebooking to LGA at any reasonable time. No hotel. No meal vouchers. Had to sleep in the airport and fly to Newark instead. Will never fly Frontier again.

What I expected, nickeled and dined and a frontier flight attendant loudly complained about her job and lack of communication as she headed to the gate on her cell phone. Not professional.

As every law enforcement agency I could imagine surrounded the plane and we didn’t disembark for 2 hours and then had to stick around for another hour to go get our personal belongings after leaving them behind and being bused away from the plane, it was scary and inconvenient. We were given no information as to why this was happening. Lack of communication with passengers was disappointing.

After boarding and un-boarding twice over 6+hours, the flight was canceled.

Severe turbulence. Captain never came on to reassure passengers after things settled down.

My first flight was delayed 5 hours. The 2nd flight was canceled til the next day and the never even tried to compensate for it. Worse I was delayed again on the flight the rebooked me on.

Boarding in Orlando was not good. Giant mob at the gate, should have been lines.

Decent clean onboard experience. Okay discount airline experience. Unfortunately, any customer service interactions are difficult and unhelpful. There is no service. Also, a premium seat only gets you premium boarding if you line up first. Once they start general boarding you must go to the back of the line. Not very premium

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