MRY - ORD

$175 Find Cheap Flights from Monterey to Chicago - Compare and Save

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 8/11. 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

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Everything you should know

Cheapest round-trip
$329
Typical prices: $435-$1,085
United Airlines
Sat 8/8Sat 8/15
MRY - ORD • Non-stop
Cheapest one-way
$175
Alaska Airlines
Tue 8/11
MRY - ORD • 1 stop
Nonstop flights
1 day a week
Sat
You can fly direct with United Airlines. Average duration is 4h 28m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top airlines
Cheapest • from $329 (round-trip)
Best reviews • 7.4 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Top layover airports
Cheapest • Avg $446 (round-trip)
Shortest trip • 6h 13m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 39% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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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

Sat, Aug 8 - Sat, Aug 15
United Airlines Logo
2:05 pm - 8:39 pm
MRY
-
ORD
4h 34mnonstop
United Airlines Logo
8:57 am - 11:43 am
ORD
-
MRY
4h 46mnonstop
$329United Airlines
Sat, Aug 15 - Wed, Aug 19
United Airlines Logo
2:05 pm - 8:27 pm
MRY
-
ORD
4h 22mnonstop
United Airlines Logo
4:00 pm - 9:59 pm
ORD
-
MRY
7h 59m
1 stop
$339United Airlines
Fri, Aug 14 - Fri, Aug 21
United Airlines Logo
1:51 pm - 11:05 pm
MRY
-
ORD
7h 14m
1 stop
United Airlines Logo
3:56 pm - 9:10 pm
ORD
-
MRY
7h 14m
1 stop
$349United Airlines
Mon, Aug 3 - Fri, Aug 7
Multiple Airlines Logo
10:00 pm - 5:37 am
MRY
-
ORD
29h 37m
1 stop
Multiple Airlines Logo
7:29 am - 9:14 pm
ORD
-
MRY
15h 45m
1 stop
$352Multiple Airlines
Wed, Aug 12 - Sat, Aug 15
American Airlines Logo
12:40 pm - 10:00 pm
MRY
-
ORD
7h 20m
1 stop
American Airlines Logo
5:00 am - 12:10 pm
ORD
-
MRY
9h 10m
2 stops
$354American Airlines
Mon, Aug 3 - Fri, Aug 7
Multiple Airlines Logo
10:00 pm - 8:52 pm
MRY
-
ORD
20h 52m
2 stops
Multiple Airlines Logo
7:29 am - 9:14 pm
ORD
-
MRY
15h 45m
1 stop
$365Multiple Airlines
Mon, Aug 10 - Tue, Aug 25
Alaska Airlines Logo
3:05 pm - 11:36 pm
MRY
-
ORD
6h 31m
1 stop
Alaska Airlines Logo
6:01 am - 2:06 pm
ORD
-
MRY
10h 05m
1 stop
$383Alaska Airlines
Wed, Aug 5 - Tue, Aug 25
Alaska Airlines Logo
3:05 pm - 11:36 pm
MRY
-
ORD
6h 31m
1 stop
Alaska Airlines Logo
6:01 am - 2:06 pm
ORD
-
MRY
10h 05m
1 stop
$384Alaska Airlines
Tue, Oct 27 - Sun, Nov 1
Alaska Airlines Logo
2:44 pm - 6:20 am
MRY
-
ORD
13h 36m
2 stops
Alaska Airlines Logo
7:56 pm - 2:54 pm
ORD
-
MRY
20h 58m
1 stop
$388Alaska Airlines
Sat, Aug 15 - Sat, Aug 29
Alaska Airlines Logo
6:00 am - 5:00 am
MRY
-
ORD
21h 00m
2 stops
Alaska Airlines Logo
6:00 am - 11:59 pm
ORD
-
MRY
19h 59m
2 stops
$393Alaska Airlines
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 is the cheapest month to fly from Monterey to Chicago O'Hare Intl Airport?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Monterey to Chicago O'Hare Intl Airport, 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 Monterey to Chicago O'Hare Intl Airport is September, where tickets cost $268 (return) on average. On the other hand, the most expensive months are June and May, where the average cost of round-trip tickets is $617 and $588 respectively.

Can I save money by flying with a layover from Monterey to Chicago O'Hare Intl Airport?

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 $435, prices are generally cheapest when you fly direct.

Good to know

Low season

March

Cheapest flight

$175
Best time to beat the crowds with an average 30% drop in price.
Most popular time to fly with an average 22% increase in price.
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

  • How many flights are there between Monterey and Chicago O'Hare Intl Airport per day?

    There is a maximum of 1 nonstop flight a day that takes off from Monterey and lands in Chicago O'Hare Intl Airport, with an average flight time of 4h 28m. The most common departure time is 2:00 pm and most flights take off in the afternoon. Each week, there are 1 flights.

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

    In the last 5 days, the lowest price for a flight from Monterey to Chicago O'Hare Intl Airport was $175 for a one-way ticket and $329 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?

    The Boeing 737-800 is the aircraft model that flies most regularly on the Monterey to Chicago flight 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.

  • On which days can I fly direct from Monterey to Chicago?

    You can catch a nonstop flight from Monterey to Chicago on Saturday.

  • 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 $484 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 $488 and an overall rating of 7.1.

  • 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.

KAYAK’s top tips for finding a cheap flight from Monterey to Chicago O'Hare Intl Airport

  • Looking for a cheap flight? 25% of our users found flights on this route for $329 or less round-trip.

Prefer to fly direct from Monterey to Chicago?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Monterey Regional to Chicago O'Hare Intl.
Find which airlines fly direct from Monterey Regional Airport to Chicago O'Hare Intl Airport, which days they fly and book direct flights.

Direct departures

Monterey Regional to Chicago O'Hare Intl

Saturday

United Airlines

United Airlines

See more direct flights

Direct returns

Chicago O'Hare Intl to Monterey Regional

Saturday

United Airlines

United Airlines

See more direct flights

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 10006 reviews
7.7Boarding
7.3Comfort
7.1Entertainment
6.6Food
8.1Crew
Airline reviews

Crew was great (professional, attentive, prompt). Snacks for 4 hrs flight is deplorable.

8.0 ExcellentDarly, Feb 2026
LAX - ORD
Read more United Airlines reviews

Crew was great (professional, attentive, prompt). Snacks for 4 hrs flight is deplorable.

It was a pretty standard flight... until the almost hour and a half spent on the taxi way. I get that the weather has been poor but the delay had nothing to do with the weather and more to do with a plane with several issues tying up the gate. I get that that happens from time to time but this has been EVERY flight I've been on for the past 5 years and I fly 3 to 5 times a year. This isn't just United... it's American, it's Delta. It's an issue with the entire industry. I work for UPS and packages on a cargo plane get better service than people do these days. Anymore I HATE flying.

While the staff was pleasant and helpful, the following observations are for your awareness. There was some delay on the tarmac on take off and landing. The paid lunch/food offerings were limited. Entertainment was only available on WiFi at a cost.

The first flight was better in terms of the aircraft.

As usual, United scheduling is completely misleading. A 54-minute layover at O’Hare is too short to make a lot of connections, especially since the flight landed “on time” but had to wait on the taxiway 15 minutes for a gate to open up. Then it takes another 10 minutes to exit the plane before one can run to another concourse to catch a connecting flight.

when you can say you don't remember being at any point upset during a flight, the airline is winning .

I had a great flight. Everything went smoothly and the flight arrived early.

United WiFi is consistently unusable (it can take 10 mins to load a single web page). If you need Wifi to do work, be prepared to lose half a day of productivity.

The Palm Springs to Chicago O’Hare was on Time and Palm Springs airport is easier navigate. As our connection was only an approximately 50 minutes, we asked staff for insights for the Chicago airport in terms of transferring into the other terminal from which our flight left, and they were unhelpful. However, the United App was very helpful in terms of notifications and even providing directions. The Chicago to Detroit flight was significantly delayed which we all know does happen. However, there were very few updates or notifications as to why this was happening when we would actually arrive. It took nearly 30 minutes for bags to make it to baggage claim. We arrived nearly 1 hour late on a 40 minute flight.

Wifi did not work. Cut off on and off every 10 min

The flight from LA to Chicago was smooth and service was very good overall.

The chicken wrap was tiny ($13 for what looked like a 1/3 of a normal wrap?) and disgusting.

We flew in first class. The crew did not offer drinks before the flight took off, but they treated us well during the flight. The food was excellent. There was actually too much food served, but it was nice to have all the options.

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

The plane was late and then sat on the runway for almost 45 minutes before taking off.

Had to wait on pilot and crew to depart and had to wait to arrive at the gate because they only had 2 crews working. Delays, delays....Planes just keep getting smaller and tighter and they nickle and dime for everything. When will an airline actually wake up and make flying more enjoyable?

It was nice being on a flight that had working wifi. The boarding was quick - why don’t all airlines have small boarding groups window to aisle? Makes so much sense!!! I was disappointed to be the first person stopped to have to gate check my carryon. Especially when there was plenty of overhead space at the back! But I get it…keeps it moving. Crew was nice.

The flight encountered a delay exceeding 4 hours. The food voucher issued was valued at $12, insufficient to cover our meal expenses. Consequently, I was unable to take my medication, leading to a drop in blood sugar levels and exacerbating my anxiety.

The flight was uneventful. What was a problem was I was delayed getting home one entire day because the flight from Sacramento was delayed. That made getting to my connecting flight impossible. I had to stay another night at the hotel and incur that expense as a result.

Seats were very uncomfortable. I paid extra for a seat with more leg room, the seat was no different than a seat at the back of the plane. Flight attendant was rude.

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

Information on your arrival and departure airports