HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Monterey

$135+ Cheap flights from Chicago (CHI) to Monterey (MRY)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/22. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MRY
Aug 31 — Sep 71
Sun 8/31
Sun 9/7
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Chicago to Monterey with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Chicago to Monterey

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Monterey (MRY). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated August 26, 2025.

Round-trip from

$257
(Hawaiian Airlines)

One-way from

$135
(United Airlines)

Popular in

March

Cheapest in

October

Average price

$593
From Chicago (CHI) to Monterey Regional
Search Deals
One-way flight from Chicago (CHI) to Monterey Regional
Search Deals
Highest demand for flights based on searches. 13% potential increase in price ($93 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($25 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in August 2025
Search Deals

Find flight deals from Chicago to Monterey

Cheapest flights from Chicago to Monterey
Explore the most affordable flight options available from Chicago to Monterey. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 26, 2025.

This Hawaiian Airlines deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Hawaiian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/83:50 pmORD - MRY
1 stop9h 01mHawaiian Airlines
Wed 10/156:00 amMRY - ORD
1 stop6h 50mHawaiian Airlines
Deal found 8/26$257
This Alaska Airlines deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/2712:05 pmORD - MRY
1 stop9h 09mAlaska Airlines
Sat 10/46:00 amMRY - ORD
1 stop6h 50mAlaska Airlines
Deal found 8/26$269
This American Airlines deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/710:32 amORD - MRY
2 stops9h 55mAmerican Airlines
Sat 10/114:07 pmMRY - ORD
1 stop6h 23mAmerican Airlines
Deal found 8/25$274
This Alaska Airlines deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/163:20 pmORD - MRY
2 stops28h 52mAlaska Airlines
Tue 9/236:00 amMRY - ORD
2 stops14h 07mAlaska Airlines
Deal found 8/24$279
This Alaska Airlines deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/127:59 pmORD - MRY
1 stop29h 33mAlaska Airlines
Tue 12/211:23 amMRY - ORD
1 stop9h 07mAlaska Airlines
Deal found 8/25$287
This Mytrip deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/36:35 amORD - MRY
1 stop16h 38mMultiple Airlines
Mon 12/810:06 pmMRY - ORD
2 stops9h 38mMultiple Airlines
Deal found 8/25$295
This Mytrip deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/226:15 amORD - MRY
1 stop16h 20mMultiple Airlines
Mon 9/299:25 pmMRY - ORD
2 stops13h 44mMultiple Airlines
Deal found 8/25$296
This Hawaiian Airlines deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Hawaiian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/223:50 pmORD - MRY
1 stop9h 01mHawaiian Airlines
Sun 10/266:00 amMRY - ORD
1 stop5h 54mHawaiian Airlines
Deal found 8/26$301
This Hawaiian Airlines deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Hawaiian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/163:50 pmORD - MRY
1 stop9h 47mHawaiian Airlines
Mon 10/207:57 pmMRY - ORD
1 stop8h 27mHawaiian Airlines
Deal found 8/24$306
This Alaska Airlines deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/83:50 pmORD - MRY
1 stop9h 01mAlaska Airlines
Wed 10/156:00 amMRY - ORD
2 stops15h 59mAlaska Airlines
Deal found 8/24$307
This Alaska Airlines deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/113:50 pmORD - MRY
1 stop9h 01mAlaska Airlines
Mon 10/136:00 amMRY - ORD
1 stop6h 50mAlaska Airlines
Deal found 8/24$314
This Kiwi.com deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/161:26 pmORD - MRY
2 stops33h 54mMultiple Airlines
Mon 10/209:19 pmMRY - ORD
1 stop15h 08mMultiple Airlines
Deal found 8/24$317

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Monterey that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 26, 2025.
Use the filters below to find and compare flights from Chicago to Monterey that are best for you.

Fly from

Chicago

Fly to

Monterey

Route

Depart

Return

Price

ChicagoMonterey

ORD - MRY

ORDMRY

Chicago O'Hare Intl

Wed 10/8

3:50 pm-10:51 pm

1 stop9h 01m

Monterey Regional

Wed 10/15

6:00 am-2:50 pm

1 stop6h 50m

$257

ChicagoMonterey

ORD - MRY

ORDMRY

Chicago O'Hare Intl

Mon 9/22

3:35 pm-8:18 pm

1 stop6h 43m

Monterey Regional

Mon 9/29

6:30 pm-5:06 am

1 stop8h 36m

$269

ChicagoMonterey

ORD - MRY

ORDMRY

Chicago O'Hare Intl

Tue 9/16

6:00 am-11:39 am

1 stop7h 39m

Monterey Regional

Tue 9/23

12:46 pm-10:24 pm

1 stop7h 38m

$269

ChicagoMonterey

ORD - MRY

ORDMRY

Chicago O'Hare Intl

Wed 10/8

3:50 pm-10:51 pm

1 stop9h 01m

Monterey Regional

Wed 10/15

6:00 am-2:50 pm

1 stop6h 50m

$269

ChicagoMonterey

ORD - MRY

ORDMRY

Chicago O'Hare Intl

Thu 9/25

2:35 pm-9:53 pm

1 stop9h 18m

Monterey Regional

Mon 9/29

6:30 pm-6:10 am

1 stop9h 40m

$269

ChicagoMonterey

ORD - MRY

ORDMRY

Chicago O'Hare Intl

Sat 9/27

12:05 pm-7:14 pm

1 stop9h 09m

Monterey Regional

Mon 10/6

7:57 pm-6:24 am

1 stop8h 27m

$269

ChicagoMonterey

ORD - MRY

ORDMRY

Chicago O'Hare Intl

Mon 11/3

5:18 am-11:41 am

1 stop8h 23m

Monterey Regional

Mon 12/8

4:23 pm-12:31 am

1 stop6h 08m

$269

ChicagoMonterey

ORD - MRY

ORDMRY

Chicago O'Hare Intl

Tue 10/7

3:50 pm-10:51 pm

1 stop9h 01m

Monterey Regional

Sat 10/11

7:57 pm-6:24 am

1 stop8h 27m

$269

ChicagoMonterey

ORD - MRY

ORDMRY

Chicago O'Hare Intl

Fri 9/19

2:25 pm-9:48 pm

1 stop9h 23m

Monterey Regional

Sun 9/21

6:01 am-2:35 pm

1 stop6h 34m

$269

ChicagoMonterey

ORD - MRY

ORDMRY

Chicago O'Hare Intl

Sat 9/27

12:05 pm-7:14 pm

1 stop9h 09m

Monterey Regional

Sat 10/4

6:00 am-2:50 pm

1 stop6h 50m

$269

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/24

Showing 1-10 of 21 results
1
2
3

Best time to book a flight from Chicago to Monterey

Have a flexible travel schedule? Discover the best time to fly to Monterey from Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

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

What is the cheapest month to book a flight from Chicago to Monterey?

Currently, January is the cheapest month in which you can book a flight from Chicago to Monterey (average of $376). Flying from Chicago to Monterey in June is currently the most expensive (average of $488). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from CHI to MRY?

Find hourly flight availability from Chicago to Monterey. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 26, 2025.

One of the essential ways to save on airfare from Chicago to Monterey is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight in the afternoon could potentially save you up to 20% on airfare.

Reviews of airlines servicing Monterey

Get insights into the airlines that provide service to Monterey. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Monterey. Reviews last updated August 26, 2025.
See what other customers who have flown with United Airlines and American Airlines from Chicago to Monterey have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
8,943 reviews

Overall

7.4

Comfort

7.3

Boarding

7.7

Entertainment

7.1

Crew

8.1

Food

6.6

Reviews

1 / 20
8.0
Excellent

Ruth,Dec 2024

ORD - AMS

United Airlines flights seem to always use a bus to/from the boarding gate to the plane. Can they not get their own gate? This time there was no lift when leaving the plane and people in wheelchairs somehow had to climb down the steps to the ground to get to the bus. I udon’t know how some managed that!
United Airlines
7.4
Good
8,943 reviews
United Airlines
7.4
Good
8,943 reviews

Overall

7.4

Comfort

7.3

Boarding

7.7

Entertainment

7.1

Crew

8.1

Food

6.6

Reviews

1 / 20
8.0
Excellent

Ruth,Dec 2024

ORD - AMS

United Airlines flights seem to always use a bus to/from the boarding gate to the plane. Can they not get their own gate? This time there was no lift when leaving the plane and people in wheelchairs somehow had to climb down the steps to the ground to get to the bus. I udon’t know how some managed that!
American Airlines
7.2
Good
10,000 reviews
United Airlines
7.4
Good
8,943 reviews

Overall

7.4

Comfort

7.3

Boarding

7.7

Entertainment

7.1

Crew

8.1

Food

6.6

Reviews

1 / 20
8.0
Excellent

Ruth,Dec 2024

ORD - AMS

United Airlines flights seem to always use a bus to/from the boarding gate to the plane. Can they not get their own gate? This time there was no lift when leaving the plane and people in wheelchairs somehow had to climb down the steps to the ground to get to the bus. I udon’t know how some managed that!

Related info for your journey

Find useful and relevant information for your journey from Chicago to Monterey. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Monterey from Chicago?

    Monterey Regional (MRY), located 3.2 mi from the city center, is the airport you fly into when you book flights from Chicago to Monterey. 2 airlines have flights to Monterey Regional from Chicago on a regular basis. Booking flights from Chicago to Monterey Regional should not be difficult; the airport handles an average of 0 inbound flights from Chicago per day.

  • How long is the flight from Chicago to Monterey?

    Airlines like Hawaiian Airlines, United Airlines, and American Airlines fly from Chicago to Monterey in about 6h 43m. The time it takes to get you to your destination can typically vary by up to 2h 18m. Chicago and Monterey are separated by a distance of 1839 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines flying from Chicago to Monterey round-trip?

    Flying on American Airlines is currently your cheapest option to Monterey, with prices starting at $268. Another option worth looking into is United Airlines, starting at $358 round trip. American Airlines is 53% cheaper than the average price of flights available within the next 90 days to this destination.

  • What are the cheapest airlines to fly from Chicago to Monterey one-way?

    The cheapest airline one-way is United Airlines, with whom users have recently found tickets for as low as $135. However, be on the lookout for offers from Hawaiian Airlines and American Airlines, as they are both options that can get you from Chicago to Monterey for a low price.

  • Can I find deals for flights from Chicago to Monterey that include hotel bookings?

    Yes. In addition to deals on Chicago to Monterey flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Monterey?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Monterey.

  • Can I find deals for business class flights from Chicago to Monterey?

    Yes. Cheapflights offers flight deals from Chicago to Monterey by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago to Monterey?

    Currently, January is the cheapest month in which you can book a flight from Chicago to Monterey (average of $376). Flying from Chicago to Monterey in June is currently the most expensive (average of $488). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Chicago to Monterey

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Las Vegas flights
O'Hare Intl to Los Angeles flights
Midway to Las Vegas flights
O'Hare Intl to San Francisco flights
O'Hare Intl to Ontario flights
O'Hare Intl to Santa Ana flights
O'Hare Intl to San Diego flights
St. Louis to Las Vegas flights
Midway to Los Angeles flights
O'Hare Intl to Burbank flights
Midway to San Francisco flights
O'Hare Intl to Palm Springs flights
O'Hare Intl to San Jose flights
O'Hare Intl to Sacramento flights
O'Hare Intl to Oakland flights
Midway to San Diego flights
St. Louis to Los Angeles flights
O'Hare Intl to Reno flights
St. Louis to San Francisco flights
St. Louis to San Diego flights
Rockford to Las Vegas flights
Midway to Ontario flights
Midway to San Jose flights
Midway to Santa Ana flights
O'Hare Intl to Fresno flights
Midway to Palm Springs flights
Peoria to Las Vegas flights
St. Louis to Reno flights
St. Louis to Ontario flights
Moline to Las Vegas flights
Midway to Oakland flights
St. Louis to Sacramento flights
O'Hare Intl to Santa Barbara flights
O'Hare Intl to Long Beach flights
Peoria to Santa Ana flights
Midway to Sacramento flights
Midway to Reno flights
St. Louis to Santa Ana flights
Bloomington to Las Vegas flights
St. Louis to Palm Springs flights
Moline to San Jose flights
O'Hare Intl to Monterey flights
Midway to Burbank flights
Evansville to Las Vegas flights
O'Hare Intl to San Luis Obispo flights
St. Louis to Long Beach flights
Moline to Palm Springs flights
Peoria to San Diego flights
St. Louis to Fresno flights
Moline to Los Angeles flights

Top 2 airlines flying from Chicago to Monterey

Discover the top 2 airlines that operate flights from Chicago to Monterey. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 26, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$268Average$554FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$358Average$503FlexibilityNo cancel feeOn-time69%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.