$190+ Cheap flights from Chicago (CHI) to Monterey (MRY)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/16. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MRY
Nov 30 — Dec 71
Round-trip
1 adult, Economy
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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
Cheapest
Best
Last-minute
One-way
Cheapest flights from Chicago to MontereyExplore 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 October 31, 2026.
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 October 31, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 12/36:21 am -
1 stop30h 20m
Mon 12/711:31 am -
1 stop15h 30m
Deal found 10/28![Multiple Airlines logo]()
$273
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 12/174:08 pm -
2 stops30h 02m
Fri 1/811:22 am -
1 stop16h 38m
Deal found 10/28![Multiple Airlines logo]()
$355
This Kiwi.com deal was found by Cheapflights users on 10/28. 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.
Fri 12/185:40 am -
2 stops16h 30m
Fri 1/811:22 am -
1 stop16h 38m
Deal found 10/28![Multiple Airlines logo]()
$361
This Delta deal was found by Cheapflights users on 10/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/193:00 pm -
1 stop7h 20m
Tue 1/511:03 am -
1 stop9h 05m
Deal found 10/28![Delta logo]()
$379
This Delta deal was found by Cheapflights users on 10/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/193:00 pm -
1 stop7h 20m
Wed 1/67:20 am -
2 stops12h 16m
Deal found 10/28![Delta logo]()
$384
This American Airlines deal was found by Cheapflights users on 10/28. 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.
Sat 12/1210:34 am -
2 stops10h 05m
Sat 1/91:14 pm -
2 stops8h 45m
Deal found 10/28![American Airlines logo]()
$389
This Alaska Airlines deal was found by Cheapflights users on 10/28. 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 12/157:27 am -
1 stop9h 48m
Tue 1/56:00 am -
1 stop14h 08m
Deal found 10/28![Alaska Airlines logo]()
$391
This Alaska Airlines deal was found by Cheapflights users on 10/27. 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.
Thu 11/197:00 am -
2 stops18h 59m
Tue 12/16:00 am -
1 stop11h 00m
Deal found 10/27![Alaska Airlines logo]()
$394
This Kiwi.com deal was found by Cheapflights users on 10/28. 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.
Sun 12/207:45 am -
2 stops39h 39m
Fri 1/811:22 am -
1 stop16h 38m
Deal found 10/28![Multiple Airlines logo]()
$396
This Expedia deal was found by Cheapflights users on 10/26. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/146:00 am -
2 stops19h 46m
Wed 12/166:00 am -
2 stops15h 59m
Deal found 10/26![Alaska Airlines logo]()
$399
This Alaska Airlines deal was found by Cheapflights users on 10/28. 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 12/157:27 am -
1 stop9h 48m
Fri 1/86:00 am -
1 stop14h 08m
Deal found 10/28![Alaska Airlines logo]()
$401
Best flights from Chicago to MontereyDiscover carefully curated flight deals from Chicago to Monterey that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 31, 2026.
Discover carefully curated flight deals from Chicago to Monterey that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 31, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/28. 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.
Fri 1/157:30 am -
1 stop9h 39m
Mon 1/183:59 pm -
2 stops22h 56m
Deal found 10/28![Multiple Airlines logo]()
$319
This United Airlines deal was found by Cheapflights users on 10/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/183:56 pm -
1 stop7h 16m
Sun 11/222:25 pm -
1 stop7h 02m
Deal found 10/28![United Airlines logo]()
$379
This Alaska Airlines deal was found by Cheapflights users on 10/30. 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.
Thu 2/42:13 pm -
1 stop11h 42m
Sun 2/76:00 am -
1 stop14h 08m
Deal found 10/30![Alaska Airlines logo]()
$379
This United Airlines deal was found by Cheapflights users on 10/26. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/186:25 am -
1 stop6h 49m
Thu 4/228:20 pm -
1 stop6h 41m
Deal found 10/26![United Airlines logo]()
$379
This Alaska Airlines deal was found by Cheapflights users on 10/29. 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 1/97:40 am -
1 stop8h 21m
Wed 1/132:38 pm -
1 stop29h 30m
Deal found 10/29![Alaska Airlines logo]()
$391
This United Airlines deal was found by Cheapflights users on 10/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/152:33 pm -
1 stop6h 51m
Mon 1/183:30 pm -
1 stop7h 44m
Deal found 10/28![United Airlines logo]()
$379
This Expedia deal was found by Cheapflights users on 10/26. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/146:00 am -
2 stops19h 46m
Wed 12/166:00 am -
2 stops15h 59m
Deal found 10/26![Alaska Airlines logo]()
$399
This United Airlines deal was found by Cheapflights users on 10/30. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/234:20 pm -
1 stop7h 17m
Mon 4/262:00 pm -
1 stop7h 02m
Deal found 10/30![United Airlines logo]()
$379
Last-minute flights from Chicago to MontereyDiscover last-minute flight deals from Chicago to Monterey. Data last updated October 31, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Monterey. Data last updated October 31, 2026 and is based on user searches.
This Expedia deal was found by Cheapflights users on 10/26. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/57:20 am -
1 stop9h 52m
Sat 11/74:51 pm -
1 stop10h 49m
Deal found 10/26![Alaska Airlines logo]()
$539
This United Airlines deal was found by Cheapflights users on 10/26. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/111:00 pm -
1 stop6h 35m
Sun 11/157:55 pm -
1 stop7h 52m
Deal found 10/26![United Airlines logo]()
$449
This Alaska Airlines deal was found by Cheapflights users on 10/30. 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 11/147:00 am -
2 stops18h 31m
Wed 11/184:51 pm -
1 stop10h 49m
Deal found 10/30![Alaska Airlines logo]()
$454
This United Airlines deal was found by Cheapflights users on 10/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/157:00 am -
1 stop6h 47m
Thu 11/192:00 pm -
1 stop6h 59m
Deal found 10/28![United Airlines logo]()
$414
This Expedia deal was found by Cheapflights users on 10/28. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/157:00 am -
1 stop11h 09m
Thu 11/196:00 am -
2 stops15h 59m
Deal found 10/28![Alaska Airlines logo]()
$419
This Expedia deal was found by Cheapflights users on 10/28. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/189:30 am -
2 stops15h 01m
Sun 11/226:04 am -
1 stop11h 59m
Deal found 10/28![Alaska Airlines logo]()
$384
This Alaska Airlines deal was found by Cheapflights users on 10/27. 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.
Thu 11/197:00 am -
2 stops18h 59m
Tue 12/16:00 am -
1 stop11h 00m
Deal found 10/27![Alaska Airlines logo]()
$394
This Alaska Airlines deal was found by Cheapflights users on 10/28. 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.
Fri 11/209:01 pm -
1 stop19h 29m
Mon 11/236:04 am -
1 stop11h 59m
Deal found 10/28![Alaska Airlines logo]()
$379
This Kiwi.com deal was found by Cheapflights users on 10/30. 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.
Fri 11/205:25 am -
2 stops16h 14m
Mon 11/238:29 pm -
1 stop6h 41m
Deal found 10/30![Multiple Airlines logo]()
$409
This Alaska Airlines deal was found by Cheapflights users on 10/26. 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.
Sun 11/229:01 pm -
1 stop19h 29m
Fri 11/276:04 am -
1 stop15h 45m
Deal found 10/26![Alaska Airlines logo]()
$478
This Alaska Airlines deal was found by Cheapflights users on 10/26. 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.
Mon 11/237:26 am -
1 stop9h 04m
Fri 11/276:04 am -
1 stop15h 45m
Deal found 10/26![Alaska Airlines logo]()
$456
This Alaska Airlines deal was found by Cheapflights users on 10/28. 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 11/252:16 pm -
1 stop29h 13m
Wed 12/26:00 am -
2 stops15h 59m
Deal found 10/28![Alaska Airlines logo]()
$510
One-way flights from Chicago to MontereySearch for one-way flight options from Chicago to Monterey. Find affordable one-way fares based on user searches. Data last updated October 31, 2026.
Search for one-way flight options from Chicago to Monterey. Find affordable one-way fares based on user searches. Data last updated October 31, 2026.
This Alaska Airlines deal was found by Cheapflights users on 10/30. 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 12/167:27 am -
1 stop9h 48m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/30![Alaska Airlines logo]()
$190
This Orbitz deal was found by Cheapflights users on 10/27. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/179:30 am -
2 stops15h 01m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![Alaska Airlines logo]()
$195
This Delta deal was found by Cheapflights users on 10/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/193:00 pm -
1 stop7h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/30![Delta logo]()
$220
This Alaska Airlines deal was found by Cheapflights users on 10/30. 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.
Thu 11/197:00 am -
1 stop11h 09m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/30![Alaska Airlines logo]()
$225
This Kiwi.com deal was found by Cheapflights users on 10/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/255:40 am -
2 stops40h 27m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![Multiple Airlines logo]()
$234
This Alaska Airlines deal was found by Cheapflights users on 10/29. 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.
Thu 11/127:20 am -
1 stop9h 52m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/29![Alaska Airlines logo]()
$235
This United Airlines deal was found by Cheapflights users on 10/29. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/36:00 am -
1 stop7h 42m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/29![United Airlines logo]()
$237
This Kiwi.com deal was found by Cheapflights users on 10/29. 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.
Fri 1/14:08 pm -
2 stops29h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/29![Multiple Airlines logo]()
$238
This Alaska Airlines deal was found by Cheapflights users on 10/28. 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.
Thu 12/177:00 am -
1 stop18h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![Alaska Airlines logo]()
$247
This American Airlines deal was found by Cheapflights users on 10/30. 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.
Fri 12/185:00 am -
1 stop9h 04m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/30![American Airlines logo]()
$250
This Kiwi.com deal was found by Cheapflights users on 10/29. 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.
Sat 1/27:35 am -
1 stop14h 32m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/29![Multiple Airlines logo]()
$251
Find 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 October 31, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $273 (Kiwi.com) |
One-way from | $190 (Alaska Airlines) |
Popular in | September |
Cheapest in | July |
Average price | $453 |
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 7,457,451 searches. Data last updated October 31, 2026.
Use the filters below to find and compare flights from Chicago to Monterey that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoMonterey
ORD Chicago O'Hare Intl - MRY Monterey Regional
ORDMRY
Chicago O'Hare Intl
Wed 12/16
9:00 am-5:32 pm
1 stop10h 32m
Monterey Regional
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$190
ChicagoMonterey
ORD Chicago O'Hare Intl - MRY Monterey Regional
ORDMRY
Chicago O'Hare Intl
Tue 11/17
9:30 am-10:31 pm
2 stops15h 01m
Monterey Regional
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$195
Quickest round-trip
ChicagoMonterey
ORD Chicago O'Hare Intl - MRY Monterey Regional
ORDMRY
Chicago O'Hare Intl
Sat 12/19
3:00 pm-8:20 pm
1 stop7h 20m
Monterey Regional
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$220
ChicagoMonterey
ORD Chicago O'Hare Intl - MRY Monterey Regional
ORDMRY
Chicago O'Hare Intl
Thu 11/19
7:00 am-4:09 pm
1 stop11h 09m
Monterey Regional
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$225
ChicagoMonterey
ORD Chicago O'Hare Intl - MRY Monterey Regional
ORDMRY
Chicago O'Hare Intl
Thu 11/12
7:20 am-3:12 pm
1 stop9h 52m
Monterey Regional
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$235
ChicagoMonterey
ORD Chicago O'Hare Intl - MRY Monterey Regional
ORDMRY
Chicago O'Hare Intl
Thu 12/17
7:58 pm-4:29 pm
1 stop22h 31m
Monterey Regional
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$247
ChicagoMonterey
ORD Chicago O'Hare Intl - MRY Monterey Regional
ORDMRY
Chicago O'Hare Intl
Fri 1/15
7:30 am-3:09 pm
1 stop9h 39m
Monterey Regional
Mon 1/18
3:59 pm-4:55 pm
2 stops22h 56m
$319
ChicagoMonterey
ORD Chicago O'Hare Intl - MRY Monterey Regional
ORDMRY
Chicago O'Hare Intl
Wed 11/18
3:56 pm-9:12 pm
1 stop7h 16m
Monterey Regional
Sun 11/22
2:25 pm-11:27 pm
1 stop7h 02m
$379
ChicagoMonterey
ORD Chicago O'Hare Intl - MRY Monterey Regional
ORDMRY
Chicago O'Hare Intl
Thu 2/4
2:13 pm-11:55 pm
1 stop11h 42m
Monterey Regional
Sun 2/7
6:00 am-10:08 pm
1 stop14h 08m
$379
ChicagoMonterey
ORD Chicago O'Hare Intl - MRY Monterey Regional
ORDMRY
Chicago O'Hare Intl
Sun 4/18
6:25 am-11:14 am
1 stop6h 49m
Monterey Regional
Thu 4/22
8:20 pm-5:01 am
1 stop6h 41m
$379
Showing 1-10 of 14 resultsSorted by cheapest first
Compare providers for flights from Chicago to Monterey
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to Monterey in October.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Chicago-Monterey flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Monterey flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Monterey flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago-Monterey flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-Monterey flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
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.
CHI-MRY
ORD-MRY
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
CHI-MRY
ORD-MRY
What is the cheapest month to book a flight from Chicago to Monterey?
Currently, August is the cheapest month in which you can book a flight from Chicago to Monterey (average of $348). Flying from Chicago to Monterey in September is currently the most expensive (average of $656). 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.
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 October 31, 2026.
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.
Overall
7.3
Comfort
7.3
Food
6.7
Crew
8.1
Entertainment
7.1
Boarding
7.7
Reviews
1 / 20
2.0
MediocreDawn,Aug 2026
ORD - DEN
Overall
7.3
Comfort
7.3
Food
6.7
Crew
8.1
Entertainment
7.1
Boarding
7.7
Reviews
1 / 20
2.0
MediocreDawn,Aug 2026
ORD - DEN
Overall
7.3
Comfort
7.3
Food
6.7
Crew
8.1
Entertainment
7.1
Boarding
7.7
Reviews
1 / 20
2.0
MediocreDawn,Aug 2026
ORD - DEN
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| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$289 | Average$458 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$352 | Average$448 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$423 | Average$533 | FlexibilityNo cancel fee | On-time71% |