ORD - MRY

$138 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 10/14. 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

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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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

Tue, Oct 7 - Sat, Oct 11
Hawaiian Airlines Logo
3:50 pm - 10:51 pmORD-MRY
9h 01m1 stop
Hawaiian Airlines Logo
7:57 pm - 6:24 amMRY-ORD
8h 27m1 stop
$276Hawaiian Airlines
Find Deal
Tue, Nov 11 - Wed, Dec 3
American Airlines Logo
5:00 am - 12:41 pmORD-MRY
9h 41m1 stop
American Airlines Logo
4:23 pm - 12:31 amMRY-ORD
6h 08m1 stop
$277American Airlines
Find Deal
Mon, Sep 29 - Fri, Oct 3
 Logo
9:00 am - 8:35 pmORD-MRY
13h 35m1 stop
 Logo
10:10 pm - 11:51 amMRY-ORD
11h 41m1 stop
Tue, Nov 11 - Wed, Dec 3
American Airlines Logo
11:46 am - 6:41 pmORD-MRY
8h 55m2 stops
American Airlines Logo
12:45 pm - 9:01 pmMRY-ORD
6h 16m1 stop
$282American Airlines
Find Deal
Thu, Dec 4 - Sun, Dec 7
Alaska Airlines Logo
6:00 am - 11:34 pmORD-MRY
19h 34m2 stops
Alaska Airlines Logo
6:00 am - 10:30 pmMRY-ORD
14h 30m2 stops
$287Alaska Airlines
Find Deal
Mon, Sep 29 - Fri, Oct 3
 Logo
6:15 am - 8:35 pmORD-MRY
16h 20m1 stop
 Logo
10:10 pm - 9:28 pmMRY-ORD
21h 18m2 stops
Sat, Dec 13 - Mon, Jan 12
Alaska Airlines Logo
3:05 pm - 11:34 pmORD-MRY
10h 29m1 stop
Alaska Airlines Logo
2:40 pm - 11:10 pmMRY-ORD
6h 30m1 stop
$307Alaska Airlines
Find Deal
Sat, Nov 22 - Mon, Dec 1
Alaska Airlines Logo
3:51 pm - 11:33 pmORD-MRY
9h 42m1 stop
Alaska Airlines Logo
7:46 pm - 10:30 pmMRY-ORD
24h 44m1 stop
$321Alaska Airlines
Find Deal
Wed, Oct 1 - Wed, Oct 8
United Airlines Logo
3:40 pm - 9:53 pmORD-MRY
8h 13m1 stop
United Airlines Logo
8:01 am - 5:10 pmMRY-ORD
7h 09m1 stop
$364United Airlines
Find Deal
Fri, Oct 17 - Mon, Oct 20
United Airlines Logo
4:40 pm - 9:53 pmORD-MRY
7h 13m1 stop
United Airlines Logo
6:30 pm - 5:06 amMRY-ORD
8h 36m1 stop
$367United Airlines
Find Deal

Everything you should know

Top airlines
Hawaiian Airlines
Cheapest • from $276 (round-trip)
United Airlines
Best reviews • 7.4 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to travel
February
Cheapest • 43% price drop
October
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Cheapest round-trip
$276
Overall average: $482
Hawaiian Airlines
Tue 10/7Sat 10/11
ORD - MRY • 1 stop
Cheapest one-way
$138
Typical prices: $232-346
Alaska Airlines
Tue 10/14
ORD - MRY • 1 stop
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We hope you love your trip to Monterey!
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’s the cheapest day of the week to fly from Chicago to Monterey?

The average price of all round-trip flights from Chicago O'Hare Intl Airport to Monterey clicked on KAYAK for each day over the last 12 months.

For Chicago to Monterey, Tuesday is the cheapest day to fly on average and Monday is the most expensive. Flying from Monterey back to Chicago, the best deals are generally found on Friday, with Sunday being the most expensive.

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 February, where tickets cost $328 (return) on average. On the other hand, the most expensive months are March and November, where the average cost of round-trip tickets is $850 and $790 respectively.

Good to know

Low seasonDecember
Cheapest flight$138
Best time to beat the crowds with an average 13% drop in price.
Most popular time to fly and prices are also 16% lower on average.
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 $138 for a one-way ticket and $276 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?

    We unfortunately don’t have that data for this specific 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.

  • 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 $532 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 $552 and an overall rating of 7.2.

  • 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.

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 8929 reviews
7.1Entertainment
7.3Comfort
7.7Boarding
8.1Crew
6.6Food
Airline reviews

Once we got in the air the pilot made up some of the time of the delay. So that was really nice.

10.0 ExcellentAnonymous, Aug 2025ORD - MEM
Read more United Airlines reviews

Once we got in the air the pilot made up some of the time of the delay. So that was really nice.

Excellent flight. Boarding was efficient and departure was on time. Smooth flight with on time arrival. Deplaning was also efficient.

It was delayed instead of departing at 9:20pm, we departed at 11pm… putting us in Columbus after 2am! It was awful. Had I known about the delay, I could have spent some time in the United Lounge… I was starving because I started my journey in Budapest… so I was exhausted and hungry. Plus I had to make new arrangements to be picked up at the airport in Columbus, instead of midnight it was 2:30 am after getting luggage and out of airport. Not feasible. I would have just stayed in Chicago for the night and gotten a morning flight.

It was great, I’m very grateful for the pilots and crew flight attendants for everything.

Evidently, my seat had the only broken TV. I couldn’t plug it in, get it to come on, or watch anything, and of course, no one could fix it while we were on the plane. The service was good and the boarding was quick

I was charged for my daughters bag when I am supposed to receive two free checked bags with my United Explorer card.

The schedule to Moline changed 5 times. The gate changed 6 times. That is a pathetic way to run an airline. No wonder that no one in our company flies on United Express to or from Moline. Changes happen most of the time. I learned my lesson on this trip…never again!

Flight was great. Efficient boarding. Short flight. Early arrival. Friendly flight crew. The entertainment system did not work well. Could not access it until the aircraft reached 10K feet or more. Lots of glitches.

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

Smooth boarding process. Early departure, smooth flight, early arrival. The entertainment package has very good recent movie options. The flight crew were friendly and professional.

3 hour weather delay followed by 1 hour (and counting) maintenance delay. UGH!

After we'd boarded , they canceled the flight. The crew didn't even know , we just all received text messages. Then after they deplaned us , AA was just like "too bad, go F your self, we sure ain't gonna help you"

After a two hour delay, my flight was CANCELLED! No pilot available. Such BS.

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

I wish American Airlines would change the airline industry by loading the plane back to front instead of front to back. Planes would board so much more smoothly and quickly.

I have long legs, my foot was out in the aisle and when a flight attendant came walking by and I didn't notice, instead of saying "excuse me" or anything like that, she kicked my foot. Extremely rude

Excellent! The gate agents were kind enough to rebook me on an earlier flight saving me from a 6 hour layover. Even my luggage made it despite the fact that the connection was technically too narrow. The flight itself was very comfortable, roomy, and clean. Plenty of space for my carryon items with plugs to charge my phone. After a long international flight of 14 hours, this was an excellent way to end my travels!

Great experience. Flight boarded easily. Departed early. Smooth flight. Great arrival in DC--almost no taxing! Almost direct to gate from runway. Crew was terrific. Same cookies and beverages in main cabin. I did not use the entertainment system on this flight.

Most of the delay was due to weather which is not what was at issue here. One delay was due to a missing flashlight and in the end the flashlight was actually found on the plane. The entertainment system is very limited. Live TV options offer only a few channels that are not very appealing. Boarding and deplaning are always difficult. It just takes too much time to get on and off the plane. On the plus side, I missed my connecting flight, but was easily able to book a later flight from the app while enroute.

You were more on time than United. I'm so over united delays.

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

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