ORD - MRY

$149 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 7/25. 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
$292
Typical prices: $610-$418
Multiple Airlines
Thu 10/15Mon 10/19
ORD - MRY • 2 stops
Cheapest non-stop
$430
United Airlines
Sat 6/6Sat 6/13
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 $302 (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

Thu, Oct 15 - Mon, Oct 19
Multiple Airlines Logo
2:46 pm - 3:20 pm
ORD
-
MRY
26h 34m
2 stops
Multiple Airlines Logo
4:39 pm - 5:42 am
MRY
-
ORD
11h 03m
1 stop
$292Multiple Airlines
Thu, Oct 15 - Mon, Oct 19
Multiple Airlines Logo
1:02 pm - 3:20 pm
ORD
-
MRY
28h 18m
1 stop
Multiple Airlines Logo
4:39 pm - 5:42 am
MRY
-
ORD
11h 03m
1 stop
$294Multiple Airlines
Wed, Sep 9 - Tue, Sep 15
Alaska Airlines Logo
2:22 pm - 11:59 pm
ORD
-
MRY
11h 37m
2 stops
Alaska Airlines Logo
2:43 pm - 11:57 pm
MRY
-
ORD
7h 14m
1 stop
$302Alaska Airlines
Tue, Jul 14 - Fri, Jul 17
Multiple Airlines Logo
1:50 pm - 1:34 pm
ORD
-
MRY
25h 44m
2 stops
Multiple Airlines Logo
10:00 pm - 5:28 am
MRY
-
ORD
29h 28m
1 stop
$306Multiple Airlines
Mon, Aug 17 - Thu, Aug 20
Alaska Airlines Logo
7:59 pm - 2:28 pm
ORD
-
MRY
20h 29m
1 stop
Alaska Airlines Logo
6:01 am - 7:03 pm
MRY
-
ORD
11h 02m
1 stop
$323Alaska Airlines
Tue, Jun 9 - Tue, Jun 16
Alaska Airlines Logo
2:10 pm - 11:33 pm
ORD
-
MRY
11h 23m
1 stop
Alaska Airlines Logo
3:05 pm - 11:36 pm
MRY
-
ORD
6h 31m
1 stop
$331Alaska Airlines
Wed, Sep 9 - Tue, Sep 15
Alaska Airlines Logo
2:22 pm - 11:59 pm
ORD
-
MRY
11h 37m
2 stops
Alaska Airlines Logo
2:43 pm - 6:22 am
MRY
-
ORD
13h 39m
2 stops
$333Alaska Airlines
Sat, Jul 11 - Wed, Jul 15
United Airlines Logo
9:05 am - 11:54 am
ORD
-
MRY
4h 49mnonstop
United Airlines Logo
3:30 pm - 12:59 am
MRY
-
ORD
7h 29m
1 stop
$339United Airlines
Sat, Oct 3 - Fri, Oct 9
Alaska Airlines Logo
2:21 pm - 10:52 pm
ORD
-
MRY
10h 31m
1 stop
Alaska Airlines Logo
2:44 pm - 11:59 pm
MRY
-
ORD
7h 15m
1 stop
$347Alaska Airlines
Wed, Nov 11 - Sat, Nov 14
Alaska Airlines Logo
7:25 am - 2:54 pm
ORD
-
MRY
9h 29m
1 stop
Alaska Airlines Logo
3:31 pm - 11:49 pm
MRY
-
ORD
6h 18m
1 stop
$349Alaska 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 October.

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 $371 (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 $542 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.

No, with an average price for the route of $461, prices are generally cheapest when you fly direct.

Good to know

Low seasonJuly
Cheapest flight$149
Best time to beat the crowds with an average 25% drop in price.
Most popular time to fly with an average 10% 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

  • 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 $149 for a one-way ticket and $292 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 $494 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 12383 reviews
7.0Entertainment
8.1Boarding
7.8Comfort
7.0Food
8.5Crew
Airline reviews

Flight delayed no communication. The gate was changed so many times.

6.0 GoodAnonymous, May 2026
SAN - SJC
Read more Alaska Airlines reviews

Flight delayed no communication. The gate was changed so many times.

It departed an hour and a half late because the crew got in late the previous night due to weather related problems. So we got into LA later than anticipated and traffic was much worse.

Good. I didn’t order food and there was no entertainment available.

It is a hassle to not have entertainment screens on the backs of the seats.

I had to cancel this trip due to medical reasons. I took out flight insurance but I was unable to cancel my reservation on either Kayak or Alaska. I need proof that I did not take this flight to get my refund. I have tried for a week and a half together that information from either Kayak or Alaska but so far I have gotten no response. I am very disappointed!

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!

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