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 5/27. 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
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$280
Typical prices: $1,323-$366
Multiple Airlines
ven. 7/31lun. 8/10
ORD - MRY • 1 stop
Cheapest non-stop
$329
United Airlines
sam. 5/23sam. 5/30
ORD - MRY • Non-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 $313 (round-trip)
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Top layover airports
Cheapest • Avg $427 (round-trip)
Shortest trip • 6h 49m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 24% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
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

ven., juil. 31 - lun., août 10
Multiple Airlines Logo
7:15 am - 9:10 pm
ORD
-
MRY
15h 55m
1 stop
Multiple Airlines Logo
10:04 pm - 5:28 am
MRY
-
ORD
29h 24m
1 stop
$280Multiple Airlines
ven., août 7 - lun., août 10
Multiple Airlines Logo
7:15 am - 9:14 pm
ORD
-
MRY
15h 59m
1 stop
Multiple Airlines Logo
10:04 pm - 5:28 am
MRY
-
ORD
29h 24m
1 stop
$288Multiple Airlines
lun., août 3 - lun., août 10
Multiple Airlines Logo
7:15 am - 9:10 pm
ORD
-
MRY
15h 55m
1 stop
Multiple Airlines Logo
10:04 pm - 5:28 am
MRY
-
ORD
29h 24m
1 stop
$296Multiple Airlines
mar., juin 2 - mar., juin 9
Alaska Airlines Logo
9:00 am - 2:18 pm
ORD
-
MRY
7h 18m
1 stop
Alaska Airlines Logo
2:55 pm - 1:21 pm
MRY
-
ORD
20h 26m
1 stop
$313Alaska Airlines
jeu., août 6 - lun., août 10
Multiple Airlines Logo
5:46 pm - 9:14 pm
ORD
-
MRY
29h 28m
2 stops
Multiple Airlines Logo
10:04 pm - 5:28 am
MRY
-
ORD
29h 24m
1 stop
$317Multiple Airlines
sam., mai 30 - sam., sept. 19
Alaska Airlines Logo
9:00 am - 2:18 pm
ORD
-
MRY
7h 18m
1 stop
Alaska Airlines Logo
6:26 pm - 6:22 am
MRY
-
ORD
9h 56m
1 stop
$326Alaska Airlines
sam., mai 23 - sam., mai 30
United Airlines Logo
8:40 am - 11:29 am
ORD
-
MRY
4h 49mnonstop
United Airlines Logo
2:06 pm - 8:40 pm
MRY
-
ORD
4h 34mnonstop
$329United Airlines
jeu., mai 28 - mar., juin 2
Alaska Airlines Logo
9:00 am - 2:18 pm
ORD
-
MRY
7h 18m
1 stop
Alaska Airlines Logo
2:55 pm - 1:14 pm
MRY
-
ORD
20h 19m
1 stop
$331Alaska Airlines
jeu., mai 28 - mar., juin 2
Alaska Airlines Logo
3:28 pm - 2:18 pm
ORD
-
MRY
24h 50m
2 stops
Alaska Airlines Logo
2:55 pm - 1:14 pm
MRY
-
ORD
20h 19m
1 stop
$336Alaska Airlines
sam., mai 30 - mer., juin 3
United Airlines Logo
8:40 am - 11:29 am
ORD
-
MRY
4h 49mnonstop
United Airlines Logo
1:54 pm - 1:15 am
MRY
-
ORD
9h 21m
1 stop
$339United 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.

How much is a round-trip flight from Chicago O'Hare Intl Airport to Monterey?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Chicago O'Hare Intl Airport to Monterey departing in July.

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 May, where tickets cost $367 (return) on average. On the other hand, the most expensive months are March and October, where the average cost of round-trip tickets is $684 and $527 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 $527 on average.

Good to know

Low seasonMarch
Cheapest flight$152
Best time to beat the crowds but there is an average 41% increase in price.
Most popular time to fly with an average 8% increase 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 8:00 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 3 days, the lowest price for a flight from Chicago O'Hare Intl Airport to Monterey was $152 for a one-way ticket and $280 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 MAX 8 is the aircraft model that flies most regularly on the Chicago to Monterey flight route.

  • Which airline alliances offer flights from Chicago to Monterey?

    Star Alliance, and oneworld are the airline alliances operating flights between Chicago and Monterey, with Star Alliance 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 $458 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.

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 12319 reviews
8.1Boarding
7.8Comfort
8.5Crew
7.0Entertainment
7.1Food
Airline reviews

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!

10.0 ExcellentMary Kay, Apr 2026
STS - PSP
Read more Alaska Airlines reviews

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

Alaska Airlines staff go out of their way to accommodate my fragile musical instrument, every time. They are unlike any other airline. I've experienced this can-do attitude on several flights with different staff, so this must be the culture of their company. I appreciate Alaska!

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.

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.

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

Information on your arrival and departure airports