ORD - MRY

$179 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 4/22. 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
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
$265
Overall average: $362
Alaska Airlines
Sat 4/18Wed 4/22
ORD - MRY • 1 stop
Cheapest non-stop
$359
United Airlines
Sat 5/23Sat 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
Alaska Airlines
Cheapest • from $265 (round-trip)
United Airlines
Best reviews • 7.4 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Top layover airports
San Francisco (SFO)
Cheapest • Avg $442 (round-trip)
Denver (DEN)
Shortest trip • 6h 47m (one-way)
Insights
Insights
Insights
Insights
When to travel
April
Cheapest • 33% price drop
October
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

Sat, Apr 18 - Wed, Apr 22
Alaska Airlines Logo
4:10 pm - 11:48 pm
ORD
-
MRY
9h 38m
1 stop
Alaska Airlines Logo
6:02 am - 7:03 pm
MRY
-
ORD
11h 01m
1 stop
$265Alaska Airlines
Tue, May 12 - Tue, May 19
Alaska Airlines Logo
3:52 pm - 11:59 pm
ORD
-
MRY
10h 07m
1 stop
Alaska Airlines Logo
2:55 pm - 1:14 pm
MRY
-
ORD
20h 19m
1 stop
$274Alaska Airlines
Sat, Apr 18 - Wed, Apr 22
Alaska Airlines Logo
4:10 pm - 11:48 pm
ORD
-
MRY
9h 38m
1 stop
Alaska Airlines Logo
6:02 am - 11:59 pm
MRY
-
ORD
15h 57m
2 stops
$282Alaska Airlines
Mon, May 11 - Tue, May 19
Alaska Airlines Logo
3:52 pm - 11:59 pm
ORD
-
MRY
10h 07m
1 stop
Alaska Airlines Logo
2:55 pm - 1:14 pm
MRY
-
ORD
20h 19m
1 stop
$286Alaska Airlines
Wed, May 27 - Tue, Jun 2
United Airlines Logo
6:00 am - 11:41 am
ORD
-
MRY
7h 41m
1 stop
United Airlines Logo
3:30 pm - 12:59 am
MRY
-
ORD
7h 29m
1 stop
$289United Airlines
Mon, Apr 27 - Thu, Apr 30
Alaska Airlines Logo
6:00 am - 11:59 pm
ORD
-
MRY
19h 59m
2 stops
Alaska Airlines Logo
6:02 am - 7:03 pm
MRY
-
ORD
11h 01m
1 stop
$294Alaska Airlines
Sat, May 2 - Wed, May 6
Alaska Airlines Logo
3:52 pm - 11:59 pm
ORD
-
MRY
10h 07m
1 stop
Alaska Airlines Logo
6:02 am - 7:03 pm
MRY
-
ORD
11h 01m
1 stop
$304Alaska Airlines
Thu, Apr 9 - Mon, Apr 13
United Airlines Logo
4:40 pm - 10:19 pm
ORD
-
MRY
7h 39m
1 stop
United Airlines Logo
7:00 pm - 5:27 am
MRY
-
ORD
8h 27m
1 stop
$306United Airlines
Fri, May 1 - Mon, May 4
United Airlines Logo
1:20 pm - 6:11 pm
ORD
-
MRY
6h 51m
1 stop
United Airlines Logo
1:58 pm - 11:28 pm
MRY
-
ORD
7h 30m
1 stop
$310United Airlines
Wed, Apr 1 - Wed, Apr 8
Alaska Airlines Logo
4:13 pm - 11:48 pm
ORD
-
MRY
9h 35m
1 stop
Alaska Airlines Logo
6:00 am - 7:02 pm
MRY
-
ORD
11h 02m
1 stop
$311Alaska 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 April, where tickets cost $362 (return) on average. On the other hand, the most expensive months are March and August, where the average cost of round-trip tickets is $933 and $828 respectively.

Good to know

Low seasonMay
Cheapest flight$133
Best time to beat the crowds with an average 29% drop in price.
Most popular time to fly with an average 2% 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 $133 for a one-way ticket and $265 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.

  • 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 $502 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 $512 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 9377 reviews
6.6Food
7.3Comfort
8.1Crew
7.1Entertainment
7.7Boarding
Airline reviews

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.

4.0 OkayDr. Joseph, Feb 2026
ORD - IAH
Read more United Airlines reviews

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.

We were delayed for about an hour from taking off due to traffic control procedures at the destination airport. But once in the air, the flight went well. The crew members were great and provided cabin service despite moderate turbulence during much of the flight.

Short flight, but no drink/snack service. The flights both going and coming were delayed.

Not being stranded in Chicago for her airport to 11:30 tomorrow morning the 3rd

I was fully checked in the prior night and i was unchecked and then didn’t have a seat when I boarded. Instead of an aisle seat, I was out in the middle seat of the very last row of the plane.

In overall it was a good experience, the only down point was that the entertainment screen was working properly.

They lost my luggage, so, not happy. The crew was nice but my suitcases never made it, still trying to find out what happened!

I understand weather is an issue, but making us chase our plane down at five scheduled gates across three terminals in an airport the size of O'Hare was unfair. They'd have probably been better off to leave gates as TBD until the inbound plane is in final approach instead of running us all over the place. Also, props to the consistently-unprepared ground crew in Richmond for once again leaving my lane parked short of the gate because they couldn't have a crew in place on time with 2 hours notice...

cabin crew was OK, food was OK, the trip from the US to Munich was actually pretty bad comfort wise. Noisy aircraft, lights never dimmed even in Business class (night flight) barely sufficient amenities for the price. I have millions of miles with United but TBH American is gaining ground and Delta has always been marginally better then United although on paper United has more longes and cheaper upgrades.

Essy to get on. The hostess gave very little pop, the plane was late getting in, and we are still waiting for our bags. This sucks. :/

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.

No Snacks or Entertainment. The flight was short, snacks should still be given.

See prior comment about how Kayak mishandled my reservation and delayed my arrival by 6 hours.

Boarding delayed 20 minutes for no reason, no wifi, in flight entertainment, or snacks / waters?

Delayed an hour due to operational issues. Minimal apologies or care for the significant inconvenience caused. Landed at nearly 1am and they still couldn’t find ground staff to get us off the plane promptly.

The aircraft had several problems - from excess fuel to non operational ac. Two hours of delay in Chicago could have been avoided with proper planning and aircraft maintenance.

Crew in Columbia was not prepared for landing. It was a bit of a disaster and getting bags took forever.

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

Information on your arrival and departure airports