$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 10/29. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MRY
Oct 18 — Oct 251
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 September 18, 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 September 18, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 11/55:15 pm -
1 stop22h 28m
Mon 11/93:02 pm -
1 stop12h 11m
Deal found 9/16![Multiple Airlines logo]()
$315
This American Airlines deal was found by Cheapflights users on 9/15. 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.
Thu 10/225:00 am -
1 stop9h 19m
Tue 10/279:54 am -
1 stop9h 06m
Deal found 9/15![American Airlines logo]()
$379
This Expedia deal was found by Cheapflights users on 9/15. 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 10/222:21 pm -
1 stop10h 36m
Tue 10/276:03 am -
2 stops21h 37m
Deal found 9/15![Alaska Airlines logo]()
$384
This Alaska Airlines deal was found by Cheapflights users on 9/14. 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 10/249:00 am -
2 stops15h 57m
Wed 10/282:44 pm -
2 stops12h 56m
Deal found 9/14![Alaska Airlines logo]()
$389
This United Airlines deal was found by Cheapflights users on 9/13. 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.
Thu 10/81:00 pm -
1 stop6h 28m
Tue 10/1310:30 am -
1 stop8h 10m
Deal found 9/13![United Airlines logo]()
$409
This United Airlines deal was found by Cheapflights users on 9/15. 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.
Sat 10/35:59 am -
1 stop7h 19m
Tue 10/62:25 pm -
1 stop6h 35m
Deal found 9/15![United Airlines logo]()
$414
This American Airlines deal was found by Cheapflights users on 9/17. 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 10/37:09 am -
2 stops10h 40m
Fri 10/94:12 pm -
1 stop6h 23m
Deal found 9/17![American Airlines logo]()
$419
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 11/85:15 pm -
1 stop22h 57m
Fri 11/132:33 pm -
2 stops17h 02m
Deal found 9/14![Multiple Airlines logo]()
$423
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 10/18:55 pm -
1 stop20h 25m
Mon 10/54:41 pm -
2 stops29h 42m
Deal found 9/16![Multiple Airlines logo]()
$428
This Expedia deal was found by Cheapflights users on 9/17. 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 11/12:15 pm -
1 stop11h 44m
Fri 11/66:00 am -
1 stop10h 59m
Deal found 9/17![Alaska Airlines logo]()
$429
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 September 18, 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 September 18, 2026.
This American Airlines deal was found by Cheapflights users on 9/14. 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.
Thu 10/291:26 pm -
1 stop7h 17m
Thu 11/57:22 pm -
1 stop7h 38m
Deal found 9/14![American Airlines logo]()
$379
This United Airlines deal was found by Cheapflights users on 9/14. 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.
Sat 10/244:20 pm -
1 stop6h 45m
Wed 10/282:05 pm -
1 stop6h 54m
Deal found 9/14![United Airlines logo]()
$379
This Alaska Airlines deal was found by Cheapflights users on 9/14. 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 10/299:00 am -
1 stop9h 51m
Thu 11/56:00 am -
2 stops15h 59m
Deal found 9/14![Alaska Airlines logo]()
$419
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 10/18:55 pm -
1 stop20h 25m
Mon 10/54:41 pm -
2 stops29h 42m
Deal found 9/16![Multiple Airlines logo]()
$428
This United Airlines deal was found by Cheapflights users on 9/17. 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.
Thu 10/11:00 pm -
1 stop6h 28m
Mon 10/53:31 pm -
1 stop7h 24m
Deal found 9/17![United Airlines logo]()
$449
This United Airlines deal was found by Cheapflights users on 9/17. 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.
Sat 10/38:40 am -
1 stop6h 26m
Wed 10/73:31 pm -
1 stop7h 24m
Deal found 9/17![United Airlines logo]()
$449
This Alaska Airlines deal was found by Cheapflights users on 9/15. 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 9/257:00 pm -
2 stops21h 06m
Tue 9/292:43 pm -
2 stops13h 37m
Deal found 9/15![Alaska Airlines logo]()
$505
This United Airlines deal was found by Cheapflights users on 9/14. 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.
Tue 11/243:00 pm -
1 stop7h 29m
Fri 11/2710:20 am -
1 stop6h 36m
Deal found 9/14![United Airlines logo]()
$459
This Alaska Airlines deal was found by Cheapflights users on 9/13. 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 11/87:00 am -
2 stops18h 59m
Fri 11/136:00 am -
2 stops15h 59m
Deal found 9/13![Alaska Airlines logo]()
$532
This United Airlines deal was found by Cheapflights users on 9/17. 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 10/23:35 pm -
1 stop8h 15m
Thu 10/810:30 am -
1 stop6h 35m
Deal found 9/17![United Airlines logo]()
$477
This United Airlines deal was found by Cheapflights users on 9/15. 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.
Thu 10/291:00 pm -
1 stop6h 35m
Sun 11/15:20 am -
1 stop6h 09m
Deal found 9/15![United Airlines logo]()
$479
Last-minute flights from Chicago to MontereyDiscover last-minute flight deals from Chicago to Monterey. Data last updated September 18, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Monterey. Data last updated September 18, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 10/18:55 pm -
1 stop20h 25m
Mon 10/54:41 pm -
2 stops29h 42m
Deal found 9/16![Multiple Airlines logo]()
$428
This United Airlines deal was found by Cheapflights users on 9/15. 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.
Sat 10/35:59 am -
1 stop7h 19m
Tue 10/62:25 pm -
1 stop6h 35m
Deal found 9/15![United Airlines logo]()
$414
This American Airlines deal was found by Cheapflights users on 9/17. 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 10/37:09 am -
2 stops10h 40m
Fri 10/94:12 pm -
1 stop6h 23m
Deal found 9/17![American Airlines logo]()
$419
This United Airlines deal was found by Cheapflights users on 9/16. 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.
Sat 10/33:50 pm -
1 stop7h 15m
Mon 10/51:53 pm -
1 stop7h 02m
Deal found 9/16![United Airlines logo]()
$449
This American Airlines deal was found by Cheapflights users on 9/16. 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 10/31:46 pm -
2 stops10h 35m
Mon 10/512:44 pm -
1 stop8h 16m
Deal found 9/16![American Airlines logo]()
$454
This United Airlines deal was found by Cheapflights users on 9/13. 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.
Thu 10/81:00 pm -
1 stop6h 28m
Tue 10/1310:30 am -
1 stop8h 10m
Deal found 9/13![United Airlines logo]()
$409
This Expedia deal was found by Cheapflights users on 9/17. 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.
Tue 10/209:00 am -
2 stops15h 57m
Sat 10/242:44 pm -
2 stops12h 56m
Deal found 9/17![Alaska Airlines logo]()
$459
This American Airlines deal was found by Cheapflights users on 9/15. 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.
Thu 10/225:00 am -
1 stop9h 19m
Tue 10/279:54 am -
1 stop9h 06m
Deal found 9/15![American Airlines logo]()
$379
This Expedia deal was found by Cheapflights users on 9/15. 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 10/222:21 pm -
1 stop10h 36m
Tue 10/276:03 am -
2 stops21h 37m
Deal found 9/15![Alaska Airlines logo]()
$384
This Alaska Airlines deal was found by Cheapflights users on 9/14. 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 10/249:00 am -
2 stops15h 57m
Wed 10/282:44 pm -
2 stops12h 56m
Deal found 9/14![Alaska Airlines logo]()
$389
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 September 18, 2026.
Search for one-way flight options from Chicago to Monterey. Find affordable one-way fares based on user searches. Data last updated September 18, 2026.
This Alaska Airlines deal was found by Cheapflights users on 9/17. 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 10/299:00 am -
1 stop9h 51m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Alaska Airlines logo]()
$190
This Expedia deal was found by Cheapflights users on 9/14. 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.
Fri 12/115:29 pm -
2 stops32h 17m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![Alaska Airlines logo]()
$206
This Alaska Airlines deal was found by Cheapflights users on 9/17. 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 10/309:00 am -
1 stop9h 51m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Alaska Airlines logo]()
$225
This Alaska Airlines deal was found by Cheapflights users on 9/17. 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 12/162:08 pm -
2 stops11h 38m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Alaska Airlines logo]()
$230
This Alaska Airlines deal was found by Cheapflights users on 9/15. 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 10/137:00 am -
2 stops17h 57m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Alaska Airlines logo]()
$236
This Alaska Airlines deal was found by Cheapflights users on 9/16. 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 9/297:20 am -
1 stop8h 46m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Alaska Airlines logo]()
$270
This Expedia deal was found by Cheapflights users on 9/15. 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 10/46:00 am -
2 stops18h 57m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Alaska Airlines logo]()
$281
This Alaska Airlines deal was found by Cheapflights users on 9/16. 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 10/57:20 am -
1 stop8h 47m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Alaska Airlines logo]()
$305
This KAYAK deal was found by Cheapflights users on 9/17. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/307:20 am -
1 stop8h 46m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Alaska Airlines logo]()
$314
This Expedia deal was found by Cheapflights users on 9/17. 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 10/77:20 am -
1 stop17h 37m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Alaska Airlines logo]()
$320
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 September 18, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $315 (Kiwi.com) |
One-way from | $190 (Alaska Airlines) |
Popular in | May |
Cheapest in | July |
Average price | $656 |
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 September 18, 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 11/4
7:20 am-3:12 pm
1 stop9h 52m
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
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
$225
ChicagoMonterey
ORD Chicago O'Hare Intl - MRY Monterey Regional
ORDMRY
Chicago O'Hare Intl
Sat 10/3
9:00 am-10:57 pm
2 stops15h 57m
Monterey Regional
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$230
ChicagoMonterey
ORD Chicago O'Hare Intl - MRY Monterey Regional
ORDMRY
Chicago O'Hare Intl
Tue 10/13
7:00 am-10:57 pm
2 stops17h 57m
Monterey Regional
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$236
ChicagoMonterey
ORD Chicago O'Hare Intl - MRY Monterey Regional
ORDMRY
Chicago O'Hare Intl
Sun 11/22
9:00 am-5:43 pm
1 stop10h 43m
Monterey Regional
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$270
Quickest round-trip
ChicagoMonterey
ORD Chicago O'Hare Intl - MRY Monterey Regional
ORDMRY
Chicago O'Hare Intl
Tue 9/22
7:20 am-2:06 pm
1 stop8h 46m
Monterey Regional
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$305
ChicagoMonterey
ORD Chicago O'Hare Intl - MRY Monterey Regional
ORDMRY
Chicago O'Hare Intl
Thu 10/29
1:26 pm-6:43 pm
1 stop7h 17m
Monterey Regional
Thu 11/5
7:22 pm-5:00 am
1 stop7h 38m
$379
ChicagoMonterey
ORD Chicago O'Hare Intl - MRY Monterey Regional
ORDMRY
Chicago O'Hare Intl
Sat 10/24
4:20 pm-9:05 pm
1 stop6h 45m
Monterey Regional
Wed 10/28
2:05 pm-10:59 pm
1 stop6h 54m
$379
ChicagoMonterey
ORD Chicago O'Hare Intl - MRY Monterey Regional
ORDMRY
Chicago O'Hare Intl
Thu 10/29
9:00 am-4:51 pm
1 stop9h 51m
Monterey Regional
Thu 11/5
6:00 am-11:59 pm
2 stops15h 59m
$419
ChicagoMonterey
ORD Chicago O'Hare Intl - MRY Monterey Regional
ORDMRY
Chicago O'Hare Intl
Thu 10/1
8:55 pm-3:20 pm
1 stop20h 25m
Monterey Regional
Mon 10/5
4:41 pm-12:23 am
2 stops29h 42m
$428
Showing 1-10 of 17 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 September.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 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 $647). 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 September 18, 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.
Crew
8.1
Food
6.7
Boarding
7.7
Comfort
7.3
Entertainment
7.1
Overall
7.4
Reviews
1 / 20
2.0
MediocreDawn,Aug 2026
ORD - DEN
Crew
8.1
Food
6.7
Boarding
7.7
Comfort
7.3
Entertainment
7.1
Overall
7.4
Reviews
1 / 20
2.0
MediocreDawn,Aug 2026
ORD - DEN
Crew
8.1
Food
6.7
Boarding
7.7
Comfort
7.3
Entertainment
7.1
Overall
7.4
Reviews
1 / 20
2.0
MediocreDawn,Aug 2026
ORD - DEN
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| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$276 | Average$515 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$289 | Average$458 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$352 | Average$458 | FlexibilityNo cancel fee | On-time75% |