MRY - ORD

$103 Find Cheap Flights from Monterey to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Monterey to Chicago departing on 11/3. 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 Chicago O'Hare Intl Airport

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Monterey to Chicago, 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 Monterey to Chicago, as well as popular online travel agencies
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Everything you should know

Cheapest round-trip
$264
Multiple Airlines
Fri 12/12Mon 12/15
MRY - ORD • 2 stops
Cheapest one-way
$103
Typical prices: $484-$530
Multiple Airlines
Mon 11/3
MRY - ORD • 1 stop
Top airlines
Hawaiian Airlines
Cheapest • from $266 (round-trip)
United Airlines
Best reviews • 7.4 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
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We hope you love your trip to Chicago!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Monterey to Chicago (MRY-ORD)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Monterey to Chicago 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 Monterey to Chicago

Fri, Dec 12 - Mon, Dec 15
Multiple Airlines Logo
10:06 pm - 11:50 pmMRY-ORD
23h 44m2 stops
Multiple Airlines Logo
3:53 pm - 9:16 pmORD-MRY
7h 23m1 stop
$264Multiple Airlines
Find Deal
Thu, Nov 6 - Tue, Nov 11
Hawaiian Airlines Logo
6:00 am - 11:59 pmMRY-ORD
15h 59m1 stop
Hawaiian Airlines Logo
9:20 am - 11:32 pmORD-MRY
16h 12m1 stop
$266Hawaiian Airlines
Find Deal
Fri, Dec 12 - Mon, Dec 15
Hawaiian Airlines Logo
11:23 am - 10:30 pmMRY-ORD
9h 07m1 stop
Hawaiian Airlines Logo
8:55 am - 2:18 pmORD-MRY
7h 23m1 stop
$269Hawaiian Airlines
Find Deal
Thu, Dec 11 - Sun, Dec 14
Hawaiian Airlines Logo
2:55 pm - 11:50 pmMRY-ORD
6h 55m1 stop
Hawaiian Airlines Logo
8:59 pm - 2:18 pmORD-MRY
19h 19m1 stop
$272Hawaiian Airlines
Find Deal
Mon, Feb 23 - Sat, Feb 28
Alaska Airlines Logo
2:25 pm - 11:59 pmMRY-ORD
7h 34m1 stop
Alaska Airlines Logo
7:45 am - 1:35 pmORD-MRY
7h 50m1 stop
$277Alaska Airlines
Find Deal
Mon, Feb 23 - Fri, Feb 27
Alaska Airlines Logo
2:40 pm - 5:04 amMRY-ORD
12h 24m2 stops
Alaska Airlines Logo
7:45 am - 1:35 pmORD-MRY
7h 50m1 stop
$282Alaska Airlines
Find Deal
Tue, Nov 11 - Thu, Nov 13
Alaska Airlines Logo
6:00 am - 11:59 pmMRY-ORD
15h 59m1 stop
Alaska Airlines Logo
2:54 pm - 11:32 pmORD-MRY
10h 38m1 stop
$287Alaska Airlines
Find Deal
Sat, Nov 8 - Tue, Nov 11
Alaska Airlines Logo
11:14 am - 9:40 pmMRY-ORD
8h 26m1 stop
Alaska Airlines Logo
9:20 am - 11:32 pmORD-MRY
16h 12m1 stop
$297Alaska Airlines
Find Deal
Fri, Nov 7 - Mon, Nov 10
American Airlines Logo
12:31 pm - 11:37 pmMRY-ORD
9h 06m1 stop
American Airlines Logo
5:25 pm - 10:25 pmORD-MRY
7h 00m1 stop
$322American Airlines
Find Deal
Tue, Oct 28 - Mon, Nov 3
American Airlines Logo
6:07 am - 2:15 pmMRY-ORD
6h 08m1 stop
American Airlines Logo
7:00 am - 12:41 pmORD-MRY
7h 41m1 stop
$364American Airlines
Find Deal
Booking Insights

KAYAK's insights & trends for Monterey to Chicago flights

Get data-powered insights and trends into flights from Monterey to Chicago 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 Monterey to Chicago?

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

If your flying dates are flexible, you should consider flying to Chicago on a Friday, as we generally find the cheapest rates on that day for this route. On the other hand, Sunday is the most expensive day to fly from Monterey to Chicago. For your return ticket, we recommend flying on a Tuesday and avoiding Mondays for the best deals.

Good to know

Low seasonSeptember
Cheapest flight$103
Best time to beat the crowds with an average 55% drop in price.
Most popular time to fly and prices are also 24% lower on average.
Flight from Monterey to Chicago

When to book flights from Monterey to Chicago

Are your dates flexible? Find out the best times to travel from Monterey to Chicago 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 Monterey to Chicago flights

  • What is the cheapest flight from Monterey to Chicago O'Hare Intl Airport?

    In the last 3 days, the lowest price for a flight from Monterey to Chicago O'Hare Intl Airport was $103 for a one-way ticket and $264 for a round-trip.

  • Do I need a passport to fly between Monterey and Chicago?

    Even though you are not required to have a passport, keep in mind that an official ID is needed to board the airplane.

  • Which airports will I be using when flying from Monterey to Chicago?

    Monterey and Chicago are both served by 1 main airport. You will leave Monterey from Monterey Regional and will be arriving at Chicago O'Hare Intl.

  • Which aircraft models fly most regularly from Monterey to Chicago?

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

  • Which airline alliances offer flights from Monterey to Chicago?

    oneworld, and Star Alliance are the airline alliances operating flights between Monterey and Chicago, with oneworld being the most commonly used for this route.

  • Which is the best airline for flights from Monterey to Chicago, United Airlines or American Airlines?

    The two airlines most popular with KAYAK users for flights from Monterey to Chicago are United Airlines and American Airlines. With an average price for the route of $676 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 $449 and an overall rating of 7.2.

  • How does KAYAK find such low prices on flights from Monterey to Chicago?

    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 Monterey to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Monterey to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Monterey 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 Monterey to Chicago?

    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 Chicago with an airline and back to Monterey with another airline. Booking your flights between Monterey and ORD 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 Monterey to Chicago?

    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 Chicago from Monterey 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 Monterey to Chicago

 
See real verified KAYAK customer reviews for airlines flying from Monterey to Chicago. 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 Monterey to Chicago? 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 8968 reviews
7.3Comfort
6.6Food
7.1Entertainment
8.1Crew
7.7Boarding
Airline reviews

Trip was great. A wild landing in Ottawa with the wind and rain, but the pilot did a great job. Always love flying United.👍

8.0 ExcellentAnonymous, Oct 2025MEM - ORD
Read more United Airlines reviews

Trip was great. A wild landing in Ottawa with the wind and rain, but the pilot did a great job. Always love flying United.👍

Excellent experience. Starting with the agent at the Premier bag drop who noticed I was very early for my scheduled flight and offered to rebook me on an earlier flight with my seat preference. She would not let me leave the counter until she knew that all of the changes and new boarding pass showed up on my United app. At the gate, the flight boarded quickly such that we departed early and the flight was smooth. We arrived 20 minutes early at ORD and I was able to be home in time for dinner. One of the best flights I've had.

Salina to travers city was great! But the sept 24 Tranverse city was not! Traverse city to chichago was cancelled, i went to Denver & got to Salina 6 hours later!

See previous note about the passenger in Denver who threw my husband's bag out of the overhead bin in order to maker room for his own. And the flight attendant back up the new passenger.

Flight attendant in first class gave poor service (like he didn't want to be there) and food was awful. We sat waiting for gate upon arrival over 45 mins.

Weather delay in Chicago?. No sense of urgency to make connection in Chicago for our connecting flight that wasn't delayed. Connection was missed.

Overall it was good. I missed my connection but I was put on another flight.

Overall a very poor experience - booked premium economy tickets but due to last minute flight delays , all my itinery went for a toss and had to fly economy class with no access to lounge or any compensation by united airlines to make up for the flight delays . i had expected better experience than that from united.

It was fine, definitely older planes with no charging or anything. There’s no entertainment set up on board, but it is nice that they allow you to access the in flight entertainment from your phone without having to pay for the Wi-Fi and they do offer free texting.

I liked that the flight was nonstop from ORD to CIU for $200 round trip.

After we landed we sat on the tarmac for 1.5 hours waiting to get to our gate. Ridiculous.

Terrible. Flight delayed for more than 8 hours with only a $12 meal voucher provided for the inconvenience. The airplane did not have breaks on arrival yet they still made us go through the motions and board on time knowing we could not take off then sit for 40+ minutes before having to get of the time. A complete waste of my time. I cannot believe they can stay business with these shenanigans. I’ll avoid this company like the plague moving forward as the lack of accountability is disgraceful.

This was the best 2 flights I have had with American out of SGF. Great crew both flights.

Excellent - explanations were clear staff was nice and flight was comfortable

Lost bag and 2 days no word leaving for cruise no clothes or stuff

Any flight to ORD after about 2pm this summer has been challenging. Flight was delayed getting in (coming from ORD) and that led to it not leaving before a ground stop due to lightening before they could fuel the plane, and so forth. They made up some time but we were still late in arriving at ORD, and that led to missed connections.

Food was ok, but not as good as I have had before on AA.

Pretty good. The food was just mediocre, the boarding and crew were good.

My flight got switched and my prepaid bag didnt transfer over properly so I paid to check ANOTHER BAG. I was placed in a middle seat and it was just miserable. At least it was a bulkhead row so I had legroom. The flight just never seem3d to end

Was not able to watch most shows on the entertainment site. They would not load

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

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