Find cheap flights from Chicago to Monterey

CHI - MRY

Find cheap flights from Chicago to Monterey

Round-trip
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Chicago (CHI)
Monterey Regional
Wed 3/3
Wed 3/10
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Good to know

Low season

June Best time to beat the crowds with an average 33% drop in price.

High season

March Most popular time to fly with an average 33% increase in price.

Average price round-trip

$428 (avg. price over the last 2 weeks)

Good deal round-trip

$312 or less

Good deal one-way

$147 or less

When to book flights from Chicago to Monterey

Estimated round-trip price
Average price per month
Flight prices as travel date approaches

Top tips for finding a cheap flight

  • Looking for a cheap flight? 25% of our users found flights on this route for $147 or less one-way and $312 or less round-trip.
  • The cheapest flight from Chicago to Monterey was found 70 days before departure, on average.
  • Book at least 3 weeks 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 June.
  • Morning departure is around 121% more expensive than an evening flight, on average*.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

FAQs for booking flights from Chicago to Monterey

Are there Monterey travel restrictions currently due to Coronavirus?

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

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Top 3 airlines serving Chicago to Monterey Regional

Scores according to KAYAK customer reviews

8.3
Alaska Airlines
Overall score based on 29,264 reviews
8.5
Boarding
8.3
Comfort
8.8
Crew
7.9
Entertainment
7.9
Food
Airline reviews

Cons: "WiFi sucked"

Cons: "A little more room."

Cons: "It was a little chilly."

Cons: "Late departure"

Cons: "Plane delayed"

Cons: "Better snacks. No cost for checked first luggage"

Cons: "Nothing. I've flown on worse."

Pros: "Alaska is a great airline."
Cons: "Free food would be awesome."

Pros: "Average"
Cons: "Seat back screens. More space."

Cons: "Equipment problem that delayed our departure"

Pros: "Timing-Fasrer than scheduled"

Pros: "Great! Decent."

Cons: "Delayed. Flue season folks. If your sick just don’t travel!"

Pros: "Everything went smooth and was great besides the boarding."
Cons: "Boarding seemed to take quite quite awhile, not sure what the deal was but once we were boarded they kicked it into high gear"

Cons: "Dog allowed to sit next to me. It should be ina crate or at least on the lap of the owner"

Pros: "All good"

Cons: "Delayed"

Cons: "The delay due to mechanical failure and not being compensated"

Pros: "Promptness."
Cons: "Only beverages. Perhaps a little something, like nuts"

Pros: "I love Virgin America and was surprised I was getting on one of their planes. I later found out Alaska bought VA out. The moon lighting and easy access to food/drink choices on touch screen is a plus."

Pros: "Nice movies Comfortable seats"
Cons: "Noisy air con Seat not reclining Headphone jack not working No storage space"

Pros: "The staff was so helpful and *human*... all of my interactions with them were absolutely wonderful."
Cons: "Cabin could have been a little cleaner. There was some candy/gum stuck to my seat and my tray table had juice spilled on it."

Cons: "Nothing"

Pros: "Comfort and quality of the airline is top notch, like its sister company Virgin."
Cons: "A little hard to get onto the WiFi, but once on, it was fine. Hey ... it’s free so overall, still great"

Cons: "The USB charger on my seat was broken"

Pros: "Excellent experience all around on all flights."

Pros: "Professional flight attendants"
Cons: "N/A"

Pros: "The flight attendants went above and beyond!"

Pros: "Great flight. On time, good weather"

Pros: "Everything"
Cons: "Nothing"

Pros: "Love the amount of space availabile for my legs!!"

Pros: "Friendliness"

Pros: "Mood lighting"
Cons: "No free snacks and $25 per bag surcharge"

Pros: "Plane had a delayed boarding and no explanation for the delay eas given"

Pros: "Cancelled"
Cons: "Cancelled"

Cons: "I will never fly with Alaska again."

Pros: "Efficient and comfortable"

Pros: "The plane was new but with no bells let alone whistles."
Cons: "No monitors/screens at all on plane."

Pros: "Very accommodating staff"

Cons: "We were asked to exit the plane at Tarmac and I was traveling with 2 little children. There were a lot of stairs to get off the plane and then walk back to terminal and then a lot of stairs were there to get back to terminal. I was hurting in my knee and my kids ears were hurting badly because the pressure was not controlled while landing. It was a very bad experience and I will definitely think twice about flying Alaska again."

Pros: "New equipment"
Cons: "Sparse food."

Pros: "Great service and extremely friendly staff. Brand new plane. More economy legroom then other carriers"

Cons: "This flight was first delayed, then not listed on the reader board. Then the flight added a stop over in Seattle for the the only reason that the crew was maximizing their allowed time to work. This delayed arrival at final destination. They could have brought on a fresh crew in Chicago but they did not do that."

Cons: "A child crying the whole trip behind my seat. No effort by mother to stop child from crying"

Cons: "Should not have to pay for movies other air lines they are free"

Pros: "Got there earlier than expected. Staff didn't charge me for one drink"

Pros: "Exelet"
Cons: "Exelente"

Pros: "Friendly, caring, and knowledgable staff"
Cons: "No hot food choice on 6+ hour flight."

Pros: "Boeing plane was so comfortable and modern and new."

Pros: "Clean environment of the terminals and the speed of the shuttle."
Cons: "no comment."

Pros: "It took off on time and life was good."

Pros: "Great service!"

Pros: "Everything"

Cons: "Same as previous response."

Pros: "The entertainment was amazing"
Cons: "We were delayed multiple times and landed extremely late"

Pros: "Very affordable! Traveling can be difficult, especially from Chicago O'hare - one of the busiest airports in the country - but everything was made easy for me and was a breeze!"
Cons: "No complaints here!"

Cons: "bag got lost checking it at the gate in dtw, bag went to santa barbara, completely wrong airport. huge inconvenience"

Pros: "Almost always on time, captain keeps us updated, friendly airline staff"
Cons: "Nothing"

Pros: "On time"

Pros: "Everyone was polite, helpful, and courteous."

Pros: "There were too many gate changes ."

Pros: "I like that they have complimentary snacks"

Cons: "Delay boarding and then dropped us off at a remote runway and had to wait 45 minutes for a bus to main terminal!"

Cons: "Due to the delay which caused us to miss our connection we had to get a hotel, which we had to pay for. It also caused me to miss work the following day."

Pros: "Nothing"
Cons: "4 hora de retraso ni una cortesía empleados bien carnepuercos"

Pros: "Price space, time"
Cons: "Waiting.. but better to be early than late"

Pros: "Everything was pretty decent.. Best part was the price.. Boarding was good staff was good"
Cons: "Wasn't enough room.. kind of tight.. Couple more inches all around would have been perfect though"

Pros: "Ease of travel"

Pros: "Everything"
Cons: "No dislikes"

Pros: "No complaints"

Pros: "N/A"
Cons: "The flights were delayed multiple times. No communication at your gates. Oh and I think my favorite was changing terminals and gates 5 TIMES within 1 hour at DFW! RIDICULOUS AND UNACCEPTABLE. NEVER AGAIN!"

Pros: "All personnel where polite,helpful, and respectful. Greg to have wifi and power chargers."
Cons: "There was no real entertainment on the screens. No movies."

Pros: "Everybody was nice my ride was comfortable and they treat me with respect"
Cons: "I like everything"

Pros: "On time."

Pros: "very good no problems.."
Cons: "all good thanks much"

Pros: "My back is probably even more worst than what it is ,I had poor back support...u had to sit up the wholetime and no pillows.Wish you all had reclining seats and a Lil pillow or something.Everytime I travel I'm never comfortable sleeping,if the trip is far."
Cons: "The seats,no cushion ,no pillows."

Pros: "Left on time arrived on time."
Cons: "We went to the gate early and it was printed on our boarding passes. We left to get some food and came back and tried to board. The gate agent was incredibly rude and sarcastic about telling us that the gate had been changed. They also tried to sell us 3 upgrades when we were trying to get our boarding passes."

Pros: "The ride was smooth the airplane was the food was OK the stewardess were kind"
Cons: "The ride was smooth the airplane was the food was OK the stewardess were kind"

Pros: "Staff friensly"
Cons: "Multiple delays and gate changes the last when we were already were to start boarding Aircraft seating had some issues."

Pros: "I loved the entertainment options"
Cons: "I did not like"

Pros: "It was a good nice ride. The employee was nice."

Cons: "No AC or USB charging ports, no individual entertainment screens."

Cons: "We wait to long for the connection"

Pros: "Rough landing"

Pros: "Everyone was friendly and helpful"

Pros: "Price no delays"
Cons: "Nothing"

Pros: "Customer service was great"
Cons: "The landing to New York was very scary,"

Cons: "Out of certain food items that should have been available"

Pros: "The chairs where comfortable and there was a free movie"
Cons: "The sound for the movie didn't work, the atenders dI'd not do any thing tI make uo for it. There was no complimentary snack. Loading on was a mess, not organized well."

Pros: "Everything"
Cons: "Nothing"

Pros: "We had a small technical glitch and the pilot kept us updated. Nothing is more difficult than not knowing what is going on."

Cons: "I don't know, I've yet to actually make it to Fort Lauderdale!"

Cons: "Horrible delays and many gate changes"

Cons: "There's no room for non skinny people. It was awful"

Cons: "They have taken all the joy out of flying. Cramming more seats on planes, makes them uncomfortable for anyone over 5'9""

Cons: "Decided to have a glass of wine -- had to ask the F.A. twice for my change. Dont feel they( F.A.s) were especially friendly."

Cons: "Delayed as well!!!"

Pros: "Great service."
Cons: "Seats to small lol"

Cons: "We were not allowed to check bags because our booking had less than an hour between flights! We were going on a 12 day trip from Chicago to Italy and at the airport we're advised we can bring our luggage!"

Cons: "Seats were hard, worst I've ever experienced. Seat power outlets were inconvenient."

Pros: "The directTV was great."

Pros: "Loved the Great Falls airport!! Who goes to an airport that has leather couches that you can lay down on and take a quick nap!! Beautiful airport!!"

Cons: "You are required to pay to watch the tv. It's free with Delta."

Pros: "Excellent all the way!"
Cons: "It took about 30 minutes to get luggage in Atlanta"

Pros: "easy transfer"
Cons: "had to transfer"

Cons: "Left about 15 minutes late."

Pros: "Excellent service and friendly staff"
Cons: "Absolutely not enough room to stretch your legs"

Pros: "same as above"
Cons: "same as above"

Pros: "Getting to Charlotte"
Cons: "Plane dirty. Windows dirty. Extremely bumpy. Seats clostraphobic. Sat too long leaving"

Pros: "ontime"
Cons: "At least one check-in baggage should be free for the price."

Pros: "Overall service."
Cons: "Impolite Lady Gate Agent."

Cons: "Too cramped, fligjt delay of over an hour"

Cons: "lost our bag, crying babies, uncomfortable plane"

Cons: "Delayed almost an hour."

Pros: "Everything was on time"

Pros: "Overall fine"

Cons: "Why should I have to pay to watch tv? I know you don't have to pay on Southwest, Virgin America or Jet Blue. Not sure that a very (and I mean VERY SMALL) snack can be considered food"

Pros: "On time, gates were close together"

Cons: "I had originally booked an isle or window seat and ended up in the middle This made it very uncomfortable"

Cons: "The delay"

Pros: "Getting from point a to point b."
Cons: "Lack of good free snacks. Not getting free bag checked."

Cons: "Deverted to Newark to get to portland"

Pros: "Good"

Cons: "Never made it so I can't rate it"

Pros: "Everything went smoothly"

Pros: "Large plane very comfortable"
Cons: "Nothing"

Pros: "Staff was great"
Cons: "Second delay in a row"

Cons: "Delays both ways"

Pros: "Everything!"

Pros: "Smoothly and on time"

Pros: "Willingness to check carry ons for sold out flights"
Cons: "Choosing of seats process. My traveling partner and I did not get to sit together on way home. Everyone was nice and got a free upgrade but would have been nice to sit together"

Cons: "Fine until the unexpected stop but has to be done"

Pros: "Very respectful and loved all the smiling facez"
Cons: "N/A"

Pros: "Excellent choices, comparisons, easy to use, updates"

Pros: "Bigger planes"

Pros: "On time."

Cons: "Prices to watch Tv"

Pros: "Overall nice service and nice plane united is on my top list for flying to mexico. Liked the free snack and added culture."
Cons: "Didnt like having to pay for tv. At least have a free channel or cheaper."

Pros: "All went as planned"
Cons: "Coffee"

Pros: "American Airlines saved the day!"

Pros: "Excellent"

Pros: "On time"

Pros: "Same as above."
Cons: "Same as above."

Pros: "Seats were fairly comfortable"
Cons: "Only one free snack option and I don't like ranch flavor. A bag of popped corn is $4"

Cons: "The seats didnt have a lot or room."

Pros: "I liked getting to my destination safe and back safe."
Cons: "I didn't like the pulling off or the landing or the rocking while flying."

Cons: "We landed in Msp and waited 1 hour for our hate it was horrible!!"

Cons: "United airlines.. Terrible"

Cons: "When about to get on plane, carry on taken to checked bags; 5 people already on plane were required to come back off and check bags. I begged not to have to check because I was flying to Nicaragua and was worried my only bag would get lost. I was right -- it did not arrive in Nicaragua until the next day. We sat on runway for 45 minutes before departure so United could fix BOTH sets of the plane's wings lights. Why did they not discover that at any time BEFORE we all boarded or while we were boarding -- NOT first when deciding to pull away from gate. Delay caused many to miss connections."

Read more about Alaska Airlines
COVID-19 information

Safety measures for airlines flying from Chicago to Monterey

Airlines flying from Chicago to Monterey have enacted additional safety measures and adjusted policies to better accommodate travelers. Policies vary by airline.

Heightened sanitation

Daily cleaning, installation of cabin HEPA filters on flights from Chicago to Monterey

Mandatory masks

Masks required on board, masks provided on flights from Chicago to Monterey

Social distancing seating

Middle seats unavailable to book on flights from Chicago to Monterey

Pre-flight testing

Testing for antibodies, testing for symptoms for flights from Chicago to Monterey

Book cheap flights from Chicago to Monterey

Recent round-trip flight deals

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