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 5/30. 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
$303
Typical prices: $399-$348
Alaska Airlines
ti. 5/5lø. 5/9
ORD - MRY • 1 stop
Cheapest non-stop
$329
United Airlines
lø. 5/23lø. 5/30
ORD - MRY • Non-stop
Nonstop flights
1 day a week
Sat
You can fly direct with United Airlines. Average duration is 0
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top airlines
Cheapest • from $303 (round-trip)
Best reviews • 7.4 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 • 27% 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

ti., mai 5 - lø., mai 9
Alaska Airlines Logo
3:52 pm - 11:59 pm
ORD
-
MRY
10h 07m
1 stop
Alaska Airlines Logo
2:51 pm - 1:13 pm
MRY
-
ORD
20h 22m
1 stop
$303Alaska Airlines
fr., jun. 5 - ma., jun. 8
Multiple Airlines Logo
7:15 am - 9:11 pm
ORD
-
MRY
15h 56m
2 stops
Multiple Airlines Logo
10:01 pm - 5:32 am
MRY
-
ORD
29h 31m
1 stop
$315Multiple Airlines
on., apr. 29 - sø., mai 3
Multiple Airlines Logo
11:07 am - 4:19 pm
ORD
-
MRY
31h 12m
2 stops
Multiple Airlines Logo
5:09 pm - 5:25 am
MRY
-
ORD
10h 16m
1 stop
$317Multiple Airlines
to., mai 7 - ti., mai 12
Alaska Airlines Logo
3:52 pm - 11:59 pm
ORD
-
MRY
10h 07m
1 stop
Alaska Airlines Logo
2:51 pm - 1:14 pm
MRY
-
ORD
20h 23m
1 stop
$326Alaska Airlines
on., apr. 29 - sø., mai 3
Multiple Airlines Logo
8:58 pm - 4:19 pm
ORD
-
MRY
21h 21m
1 stop
Multiple Airlines Logo
5:09 pm - 5:25 am
MRY
-
ORD
10h 16m
1 stop
$327Multiple Airlines
lø., mai 23 - lø., mai 30
United Airlines Logo
8:40 am - 11:29 am
ORD
-
MRY
4h 49mnonstop
United Airlines Logo
2:01 pm - 8:35 pm
MRY
-
ORD
4h 34mnonstop
$329United Airlines
ti., mai 5 - lø., mai 9
Alaska Airlines Logo
3:52 pm - 11:59 pm
ORD
-
MRY
10h 07m
1 stop
Alaska Airlines Logo
2:51 pm - 6:40 am
MRY
-
ORD
13h 49m
2 stops
$331Alaska Airlines
lø., jul. 11 - on., 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
on., sep. 9 - ti., sep. 15
Alaska Airlines Logo
6:00 am - 5:49 pm
ORD
-
MRY
13h 49m
1 stop
Alaska Airlines Logo
6:01 am - 7:03 pm
MRY
-
ORD
11h 02m
1 stop
$349Alaska Airlines
to., mai 28 - ti., jun. 2
Alaska Airlines Logo
9:00 am - 2:18 pm
ORD
-
MRY
7h 18m
1 stop
Alaska Airlines Logo
6:00 am - 10:59 pm
MRY
-
ORD
14h 59m
2 stops
$354Alaska 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 May.

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 $348 (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 $556 respectively.

Good to know

Low seasonMarch
Cheapest flight$152
Best time to beat the crowds but there is an average 44% increase in price.
Most popular time to fly with an average 17% 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 $152 for a one-way ticket and $303 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?

    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, United Airlines or American Airlines?

    The two airlines most popular with KAYAK users for flights from Chicago to Monterey are United Airlines and American Airlines. With an average price for the route of $458 and an overall rating of 7.4, United Airlines is the most popular choice. American Airlines is also a great choice for the route, with an average price of $501 and an overall rating of 7.1.

  • 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 airlines flying 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.
7.4
United AirlinesOverall score based on 9605 reviews
7.7Boarding
8.1Crew
6.6Food
7.3Comfort
7.1Entertainment
Airline reviews

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.

6.0 GoodAlejandro, Apr 2026
ORD - LNK
Read more United Airlines reviews

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!

Efficient boarding and early departure. Very smooth flight. Early arrival in ATL. Great flight.

Smooth and easy boarding, comfortable for the entire 5 hour flight, and the seat back entertainment was great! I appreciated all the features, from location info and maps, movies, the ability to connect with Bluetooth headphones, and good selection of movies. Food was good, normal airline snacks (I didn’t purchase anything)

Awful. No counter attendants. No dinner offered due to delays.

This trip did not start off well. The inbound flight was delayed about 20 minutes. Then, after initial onboarding, the passengers had to deplane due to a mechanical problem. That took about 30 minutes to fix and be cleared. Then, reboarding was chaotic. It took a long time to sort passengers and two passengers on standby were ticketed but there was no seat. So, they had to deplane. One of the flight crew was trying to help passengers figure out a place to put their carry-on bags and that took more time. In the end, our scheduled 10:30 am departure did not actually take off until about 12:05 pm CST. The flight itself was long but we got to Houston. Some passengers missed their connecting flights and had to rebook. Not the best of flights I've had.

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.

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.

Flight to Tampa was delayed taking off due to plane arriving late but no other issues

As previously stated the delay I experienced flying from Wichita to Chicago caused a host of issues. When I finally was able to be booked on the last remaining American flight from Chicago to Cincinnati, the gate changed four times with the last change occurring very near the scheduled boarding time. While I didn't have a problem moving from gate to gate, I did notice and make note of others that had mobility issues and had to move each time for the gate change.

Maintenance took a very long time and then we were in a holding pattern. While a one-off maintenance issue is standard, there were delays on both of my flights for this trip based on maintenance issues with the planes, which delayed both flights over 45 minutes. Thankfully, I didn't have any connections but it wasn't an experience that would make me pick AA if I have other options.

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

Information on your arrival and departure airports