ORD - MRY

$152 Find Cheap Flights from Chicago to Monterey

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 Monterey departing on 7/22. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Monterey

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Monterey, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Monterey, as well as popular online travel agencies
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Everything you should know

Cheapest round-trip
$329
Typical prices: $348-$2,142
United Airlines
Sat 8/8Sat 8/15
ORD - MRY • Non-stop
Cheapest one-way
$152
Typical prices: $318-$409
Multiple Airlines
Wed 7/22
ORD - MRY • 1 stop
Nonstop flights
1 day a week
Sat
You can fly direct with United Airlines. Average duration is 4h 49m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top airlines
Cheapest • from $329 (round-trip)
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Top layover airports
Cheapest • Avg $414 (round-trip)
Shortest trip • 6h 49m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 23% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Monterey!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Chicago to Monterey (ORD-MRY)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Monterey 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 Monterey

Sat, Aug 8 - Sat, Aug 15
United Airlines Logo
10:00 am - 12:49 pm
ORD
-
MRY
4h 49mnonstop
United Airlines Logo
2:05 pm - 8:27 pm
MRY
-
ORD
4h 22mnonstop
$329United Airlines
Sat, Aug 8 - Sat, Aug 15
United Airlines Logo
8:50 am - 2:55 pm
ORD
-
MRY
8h 05m
1 stop
United Airlines Logo
2:05 pm - 8:27 pm
MRY
-
ORD
4h 22mnonstop
$339United Airlines
Sat, Aug 8 - Sat, Aug 15
United Airlines Logo
6:00 am - 11:42 am
ORD
-
MRY
7h 42m
1 stop
United Airlines Logo
3:36 pm - 12:59 am
MRY
-
ORD
7h 23m
1 stop
$349United Airlines
Sat, Aug 8 - Sat, Aug 15
American Airlines Logo
6:00 am - 11:42 am
ORD
-
MRY
7h 42m
1 stop
American Airlines Logo
12:40 pm - 11:30 pm
MRY
-
ORD
8h 50m
1 stop
$350American Airlines
Tue, Aug 18 - Thu, Aug 27
American Airlines Logo
5:00 am - 12:10 pm
ORD
-
MRY
9h 10m
2 stops
American Airlines Logo
12:40 pm - 11:30 pm
MRY
-
ORD
8h 50m
1 stop
$354American Airlines
Wed, Oct 7 - Wed, Oct 14
Alaska Airlines Logo
6:00 am - 10:52 pm
ORD
-
MRY
18h 52m
2 stops
Alaska Airlines Logo
6:03 am - 11:59 pm
MRY
-
ORD
15h 56m
2 stops
$359Alaska Airlines
Sat, Jul 25 - Sat, Aug 1
United Airlines Logo
2:33 pm - 9:10 pm
ORD
-
MRY
8h 37m
1 stop
United Airlines Logo
2:05 pm - 8:39 pm
MRY
-
ORD
4h 34mnonstop
$370United Airlines
Sat, Aug 8 - Sat, Aug 15
United Airlines Logo
2:30 pm - 7:59 pm
ORD
-
MRY
7h 29m
1 stop
United Airlines Logo
2:05 pm - 8:27 pm
MRY
-
ORD
4h 22mnonstop
$371United Airlines
Sat, Oct 3 - Fri, Oct 9
United Airlines Logo
6:07 am - 11:18 am
ORD
-
MRY
7h 11m
1 stop
United Airlines Logo
3:31 pm - 12:59 am
MRY
-
ORD
7h 28m
1 stop
$380United Airlines
Wed, Nov 4 - Sun, Nov 8
United Airlines Logo
6:00 am - 10:32 am
ORD
-
MRY
6h 32m
1 stop
United Airlines Logo
5:07 am - 1:31 pm
MRY
-
ORD
6h 24m
1 stop
$381United Airlines
Booking Insights

KAYAK's insights & trends for Chicago to Monterey flights

Get data-powered insights and trends into flights from Chicago to Monterey to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest month to fly from Chicago O'Hare Intl Airport to Monterey?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago O'Hare Intl Airport to Monterey, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago O'Hare Intl Airport to Monterey is July, where tickets cost $402 (return) on average. On the other hand, the most expensive months are March and November, where the average cost of round-trip tickets is $1,016 and $530 respectively.

Can I save money by flying with a layover from Chicago O'Hare Intl Airport to Monterey?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $413 on average.

Good to know

Low seasonJune
Cheapest flight$152
Best time to beat the crowds with an average 10% drop in price.
Flight from Chicago to Monterey

When to book flights from Chicago to Monterey

Are your dates flexible? Find out the best times to travel from Chicago to Monterey based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Chicago to Monterey flights

  • How many flights are there between Chicago O'Hare Intl Airport and Monterey per day?

    There is a maximum of 1 nonstop flight a day that takes off from Chicago O'Hare Intl Airport and lands in Monterey, with an average flight time of 4h 49m. The most common departure time is 10:00 am and most flights take off in the morning. Each week, there are 1 flights.

  • What is the cheapest flight from Chicago O'Hare Intl Airport to Monterey?

    In the last 5 days, the lowest price for a flight from Chicago O'Hare Intl Airport to Monterey was $152 for a one-way ticket and $329 for a round-trip.

  • Do I need a passport to fly between Chicago and Monterey?

    A passport is not required to fly from Chicago to Monterey.

  • Which aircraft models fly most regularly from Chicago to Monterey?

    The Boeing 737-800 is the aircraft model that flies most regularly on the Chicago to Monterey flight route.

  • Which airline alliances offer flights from Chicago to Monterey?

    oneworld, and Star Alliance are the airline alliances operating flights between Chicago and Monterey, with oneworld being the most commonly used for this route.

  • On which days can I fly direct from Chicago to Monterey?

    You can catch a nonstop flight from Chicago to Monterey on Saturday.

  • Which is the best airline for flights from Chicago to Monterey, Alaska Airlines or United Airlines?

    The two airlines most popular with KAYAK users for flights from Chicago to Monterey are Alaska Airlines and United Airlines. With an average price for the route of $458 and an overall rating of 7.9, Alaska Airlines is the most popular choice. United Airlines is also a great choice for the route, with an average price of $478 and an overall rating of 7.4.

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

    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 Monterey.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Monterey 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 Monterey?

    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 Monterey with an airline and back to Chicago with another airline. Booking your flights between Chicago and MRY can sometimes prove cheaper using this method.

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

    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 Monterey from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Chicago O'Hare Intl Airport to Monterey

  • Looking for a cheap flight? 25% of our users found flights on this route for $248 or less one-way.

Prefer to fly direct from Chicago to Monterey?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Chicago O'Hare Intl to Monterey Regional.
Find which airlines fly direct from Chicago O'Hare Intl Airport to Monterey Regional Airport, which days they fly and book direct flights.

Direct departures

Chicago O'Hare Intl to Monterey Regional

Saturday

United Airlines

United Airlines

See more direct flights

Direct returns

Monterey Regional to Chicago O'Hare Intl

Saturday

United Airlines

United Airlines

See more direct flights

Reviews of the top 3 airlines serving from Chicago to Monterey

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Monterey. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Chicago to Monterey? 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 12583 reviews
7.8Comfort
8.5Crew
8.1Boarding
7.0Entertainment
7.0Food
Airline reviews

Good as usual. Just wished my seat was assigned at online check in. Thanks anyways

8.0 ExcellentAnonymous, Mar 2026
SAN - MRY
Read more Alaska Airlines reviews

Good as usual. Just wished my seat was assigned at online check in. Thanks anyways

No WiFi. Terrible food. Very long walk to the gate and from the gate after landing. Gate changed without notice.

I really hate the seat assignment at the gate. I understand it is so families can sit together but it caused me and others a lot of unnecessary stress and confusion, enough for me to not fly Alaska again. The app is so awful that it did not even update my seat assignment on the boarding pass but sent me a notification of my seat... it showed in Apple Wallet but not in the Alaska app itself. That only made the stress worse. I think most people like myself prefer to know where they are seated at check in 24 hours before so they don't have to anxiously hang out at the gate the entire time. This is not a good use of your agents time either to be dealing with all of us asking where we are sitting. You should automatically assign the multiple seat purchases to be together before they check in and fill us solo travelers in those gaps as we check in.

The flight was delayed so we didn’t get into San Diego until almost 1 AM. Otherwise, it was lovely.

My flight got canceled never left san diego and miss out my fam event

would have been nice for flight to not be delayed by 2 hours so that we had to pay $80 to get home since BART had shut down. i thought a 10pm arrival would leave enough time to account for delays but i was wrong.

I like that volunteers were asked to check in their carryons for free. And then they come out of the carousels within 20 minutes as promised.

The landing was a little rough - but a good flight overall! :)

The issue was not alaska airlines. The ticket you printed was innacurate.

Pretty terrible. The aisles on this flight were too narrow so we had to carry our baby, care seat, luggage, travel stroller step by step down the aisle slowing down a lot of passengers in the process. Not only was this a safety hazard but remember that scene from game of thrones where Cersei walks naked through the streets? It felt about as excruciating as that except both me and my husband were carrying 50lbs of weight while everyone from the flight attendants and passengers dolled out comments like “that stroller doesn’t fit in the overhead compartment and you should check it at the gate” when it is a travel stroller that absolutely fits and did fit in the overhead compartment. The flight said it was 30 min delayed but in actuality we did not take off until 1.5 hours past the original time. It was absolutely terrible. Alaska also charged us 200 dollars just in baggage fees even tho we took the time to buy two check on baggages via their app and bought an extra seat for our child and they still refused to overlook our first time flying with them. Everyone in general looked super miserable and traveling with them with a child is pretty much untenable. Lastly I originally thought I had booked an AM flight for my family but it was a PM flight which I knew was not going to end well since we had a 1.5 year old with us on a flight that gets in 9p. I ended up calling Alaska to try to change the first leg for a change fee, and would even have accepted half of a refund to book a completely different flight but of course they refused and absolutely allowed no flexibility to plans so I guess my revenge was our baby cried for 3 out of the four hour flight and hopefully convinced every miserable person on that flight to never fly Alaska again 🤷🏻‍♀️

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.

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

Subject: Formal Complaint: Discriminatory and Unprofessional Conduct – Request for Immediate Action & Compensation Dear [Airline Customer Relations Team], I am writing to file a formal complaint regarding my recent travel experience with [Airline], which was by far the worst I have ever encountered. What occurred was not only unprofessional, but in several instances discriminatory, unsafe, and unacceptable. On the first leg of my trip, I arrived only four minutes past check-in. Instead of making any attempt to resolve the matter, your representative flatly denied me boarding and made me wait while she attended to passengers who arrived after me. By the time a manager intervened, it was too late to board, costing me time, money, and unnecessary frustration. The second leg of my trip (Chicago–San Francisco) raised even more serious concerns. From the outset, it was apparent that the staff—particularly two attendants—prioritized Caucasian passengers while dismissing African American and minority passengers. • When a Caucasian passenger in the exit row refused to comply with federal safety requirements, I, as a first responder, immediately offered to switch seats and assume the responsibility. My offer was blatantly ignored, and instead, a Caucasian passenger seated further up was chosen. This was discriminatory and deeply insulting, especially as I was actively de-escalating the situation that could have delayed the flight further. • During a lengthy tarmac delay of over 90 minutes, passengers were given conflicting and unreasonable instructions that created unnecessary distress and tension. • Throughout the flight, a visibly intoxicated passenger directly in front of me was disruptive, rude to others, failed to comply with seatbelt and electronic device rules, and yet faced no enforcement from the crew. In stark contrast, I was singled out for repeated compliance checks even though I was following every rule. This unequal treatment was so obvious that multiple passengers around me spoke up in my defense. This pattern of behavior demonstrated a clear lack of professionalism, disregard for passenger safety, and discriminatory treatment. I expect far better from an airline of your stature. As a paying customer subjected to this unacceptable treatment, I am formally requesting: 1. A full investigation into the conduct of the staff on both flights. 2. A written apology acknowledging the discriminatory and unprofessional behavior I endured. 3. Appropriate compensation for the distress, inconvenience, and mishandling of my travel. If this matter is not addressed promptly and thoroughly, I will have no choice but to escalate my complaint further, including filing with the U.S. Department of Transportation and sharing my experience through other channels. I trust [Airline] will take this complaint seriously and provide a timely resolution.

Check in was quick and easy during early hours. Flight was on time, and customer services was a plus.

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

We arrived early and finally made it to our gate almost an hour after.

Was a pain having to leave the plane and reboard but glad the plane was fixed

My flight was delayed for a whole day, so I lost a day of my vacation.

Flighty delayed on boarding - then group 1 had to check their carry on bags but groups 3 and beyond could carry bags on - very inconvenient for weekend business trip with no checked baggage. Then delayed on the runway - before take off. No communication from pilot on why or how long. Wifi/Entertainment didn't work for 4+ flight. Upon arrival, attendants announced wrong carousel for baggage claim - everyone was waiting at the wrong place for their checked bags. This was a mess united!

It was so much better than expected, Ohare is not such a pleasant experience but American Airlines with the new, clean aeroplane and free Wi-Fi was outstanding and the crew so pleasant and helpful.

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

My boarding pass wouldn't pull up in the app very easily and had to really dig through my email. That caused a delay in TSA..

Baby cried a lot. Nothing anyone could do about it. Just part of flying.

The flight crew was fantastic! Which the seats had a small TV.

My husband and I pre-ordered our food, but they did not have my husband’s order, and my cheese plate was very average. I asked for a blanket and was told they don’t carry blankets on domestic routs. The flight was on time and smooth!

5 hour flight - full flight - not enough room to use my computer - slightly delayed - Admirals club was excellent quality food, drink made up for flight seating. No food offerred on flight, you ahd to prebook.

Boarding was a mess - the agent basically called every group in rapid succession, so there was no organization at all. The economy seats are a joke, and main cabin extra seats were sold out when I purchased my flight. As such, I was locked in the same position for four hours. Being 6’6”, it was impossible to get my bag out from under the seat in front of me, and I couldn’t have used my laptop even if my bag were accessible due to the minuscule seat pitch. Also the wifi was broken. American is a joke - can’t wait until they merge with Spirit.

Horrible scam. Make you pay extra for more leg room then switch your seat as you’re boarding to a regular seat. Never fly American!

It was a smooth, uneventful ride. The staff was very friendly. The overhead compartments were a little small for my hiking style backpack, but I made it work.

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

Information on your arrival and departure airports