$180+ 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 12/16. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MRY
Sep 20 — Sep 271
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
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Best
Last-minute
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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 August 21, 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 August 21, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/18. 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 10/291:02 pm -
1 stop27h 49m
Mon 11/24:31 pm -
1 stop11h 04m
Deal found 8/18![Multiple Airlines logo]()
$322
This United Airlines deal was found by Cheapflights users on 8/17. 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 9/54:25 pm -
1 stop7h 34m
Sun 9/65:00 am -
1 stop6h 29m
Deal found 8/17![United Airlines logo]()
$354
This American Airlines deal was found by Cheapflights users on 8/17. 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.
Wed 9/93:18 pm -
1 stop9h 03m
Mon 9/144:20 pm -
1 stop6h 10m
Deal found 8/17![American Airlines logo]()
$359
This American Airlines deal was found by Cheapflights users on 8/21. 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 9/55:00 am -
1 stop9h 10m
Fri 9/1112:37 pm -
1 stop8h 53m
Deal found 8/21![American Airlines logo]()
$361
This Alaska Airlines deal was found by Cheapflights users on 8/18. 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 9/91:03 pm -
2 stops12h 56m
Tue 9/156:01 am -
2 stops15h 58m
Deal found 8/18![Alaska Airlines logo]()
$370
This United Airlines deal was found by Cheapflights users on 8/19. 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 10/221:00 pm -
1 stop6h 28m
Tue 10/272:25 pm -
1 stop6h 20m
Deal found 8/19![United Airlines logo]()
$381
This United Airlines deal was found by Cheapflights users on 8/19. 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 10/94:40 pm -
1 stop7h 10m
Tue 10/1310:30 am -
1 stop6h 35m
Deal found 8/19![United Airlines logo]()
$387
This Alaska Airlines deal was found by Cheapflights users on 8/18. 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 9/22:18 pm -
1 stop11h 41m
Sun 9/66:01 am -
1 stop11h 20m
Deal found 8/18![Alaska Airlines logo]()
$394
This Alaska Airlines deal was found by Cheapflights users on 8/18. 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 9/158:00 am -
2 stops17h 59m
Tue 9/226:01 am -
2 stops15h 58m
Deal found 8/18![Alaska Airlines logo]()
$404
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 August 21, 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 August 21, 2026.
This United Airlines deal was found by Cheapflights users on 8/19. 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 9/306:00 am -
1 stop7h 48m
Wed 10/71:53 pm -
1 stop7h 02m
Deal found 8/19![United Airlines logo]()
$359
This Alaska Airlines deal was found by Cheapflights users on 8/18. 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 9/192:18 pm -
1 stop11h 41m
Wed 9/236:01 am -
1 stop11h 20m
Deal found 8/18![Alaska Airlines logo]()
$359
This United Airlines deal was found by Cheapflights users on 8/20. 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 9/175:00 am -
1 stop7h 15m
Sun 9/203:36 pm -
1 stop7h 23m
Deal found 8/20![United Airlines logo]()
$359
This Alaska Airlines deal was found by Cheapflights users on 8/16. 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 9/156:00 am -
2 stops19h 59m
Mon 9/216:01 am -
1 stop11h 20m
Deal found 8/16![Alaska Airlines logo]()
$364
This United Airlines deal was found by Cheapflights users on 8/19. 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 10/221:00 pm -
1 stop6h 28m
Tue 10/272:25 pm -
1 stop6h 20m
Deal found 8/19![United Airlines logo]()
$381
This Alaska Airlines deal was found by Cheapflights users on 8/18. 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 9/29:00 am -
2 stops16h 59m
Sun 9/66:01 am -
1 stop11h 20m
Deal found 8/18![Alaska Airlines logo]()
$399
This Alaska Airlines deal was found by Cheapflights users on 8/16. 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.
Wed 10/219:00 am -
1 stop9h 51m
Sat 10/245:28 pm -
1 stop10h 12m
Deal found 8/16![Alaska Airlines logo]()
$429
This United Airlines deal was found by Cheapflights users on 8/16. 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.
Fri 9/114:26 pm -
1 stop6h 44m
Mon 9/146:45 pm -
1 stop8h 16m
Deal found 8/16![United Airlines logo]()
$459
This Booking.com deal was found by Cheapflights users on 8/16. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/42:03 pm -
2 stops11h 25m
Mon 12/73:06 pm -
2 stops13h 54m
Deal found 8/16![Alaska Airlines logo]()
$439
This Alaska Airlines deal was found by Cheapflights users on 8/20. 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
Tue 1/126:00 am -
1 stop14h 08m
Deal found 8/20![Alaska Airlines logo]()
$441
This Alaska Airlines deal was found by Cheapflights users on 8/19. 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 9/256:00 am -
2 stops19h 59m
Tue 9/292:43 pm -
2 stops13h 37m
Deal found 8/19![Alaska Airlines logo]()
$449
Last-minute flights from Chicago to MontereyDiscover last-minute flight deals from Chicago to Monterey. Data last updated August 21, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Monterey. Data last updated August 21, 2026 and is based on user searches.
This Alaska Airlines deal was found by Cheapflights users on 8/18. 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 9/22:18 pm -
1 stop11h 41m
Sun 9/66:01 am -
1 stop11h 20m
Deal found 8/18![Alaska Airlines logo]()
$394
This United Airlines deal was found by Cheapflights users on 8/20. 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 9/44:25 pm -
1 stop7h 34m
Tue 9/83:38 pm -
1 stop7h 21m
Deal found 8/20![United Airlines logo]()
$429
This Alaska Airlines deal was found by Cheapflights users on 8/18. 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 9/43:43 pm -
1 stop28h 03m
Tue 9/86:01 am -
1 stop11h 20m
Deal found 8/18![Alaska Airlines logo]()
$439
This United Airlines deal was found by Cheapflights users on 8/17. 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 9/54:25 pm -
1 stop7h 34m
Sun 9/65:00 am -
1 stop6h 29m
Deal found 8/17![United Airlines logo]()
$354
This American Airlines deal was found by Cheapflights users on 8/21. 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 9/55:00 am -
1 stop9h 10m
Fri 9/1112:37 pm -
1 stop8h 53m
Deal found 8/21![American Airlines logo]()
$361
This American Airlines deal was found by Cheapflights users on 8/17. 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.
Wed 9/93:18 pm -
1 stop9h 03m
Mon 9/144:20 pm -
1 stop6h 10m
Deal found 8/17![American Airlines logo]()
$359
This Alaska Airlines deal was found by Cheapflights users on 8/18. 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 9/91:03 pm -
2 stops12h 56m
Tue 9/156:01 am -
2 stops15h 58m
Deal found 8/18![Alaska Airlines logo]()
$370
This United Airlines deal was found by Cheapflights users on 8/18. 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 9/114:26 pm -
1 stop6h 44m
Tue 9/158:00 am -
1 stop7h 05m
Deal found 8/18![United Airlines logo]()
$459
This Alaska Airlines deal was found by Cheapflights users on 8/18. 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 9/158:00 am -
2 stops17h 59m
Tue 9/226:01 am -
2 stops15h 58m
Deal found 8/18![Alaska Airlines logo]()
$404
This Alaska Airlines deal was found by Cheapflights users on 8/20. 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 9/258:00 am -
2 stops17h 59m
Tue 9/296:01 am -
2 stops15h 58m
Deal found 8/20![Alaska Airlines logo]()
$449
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 August 21, 2026.
Search for one-way flight options from Chicago to Monterey. Find affordable one-way fares based on user searches. Data last updated August 21, 2026.
This Alaska Airlines deal was found by Cheapflights users on 8/21. 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 12/169:20 am -
1 stop7h 13m
Deal found 8/21![Alaska Airlines logo]()
$180
This Expedia deal was found by Cheapflights users on 8/20. 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 9/306:00 am -
2 stops19h 59m
Deal found 8/20![Alaska Airlines logo]()
$191
This Alaska Airlines deal was found by Cheapflights users on 8/19. 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 10/149:00 am -
2 stops15h 57m
Deal found 8/19![Alaska Airlines logo]()
$220
This Alaska Airlines deal was found by Cheapflights users on 8/18. 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 8/296:05 am -
1 stop10h 01m
Deal found 8/18![Alaska Airlines logo]()
$260
This Alaska Airlines deal was found by Cheapflights users on 8/19. 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 8/261:03 pm -
2 stops12h 56m
Deal found 8/19![Alaska Airlines logo]()
$265
This Alaska Airlines deal was found by Cheapflights users on 8/18. 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 8/276:05 am -
1 stop10h 01m
Deal found 8/18![Alaska Airlines logo]()
$295
This Alaska Airlines deal was found by Cheapflights users on 8/21. 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 10/57:49 pm -
1 stop29h 08m
Deal found 8/21![Alaska Airlines logo]()
$297
This Alaska Airlines deal was found by Cheapflights users on 8/18. 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 10/97:20 am -
1 stop17h 37m
Deal found 8/18![Alaska Airlines logo]()
$309
This Alaska Airlines deal was found by Cheapflights users on 8/19. 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 10/47:20 am -
1 stop17h 37m
Deal found 8/19![Alaska Airlines logo]()
$317
This Alaska Airlines deal was found by Cheapflights users on 8/21. 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 11/247:57 pm -
1 stop29h 41m
Deal found 8/21![Alaska Airlines logo]()
$336
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 August 21, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $322 (Kiwi.com) |
One-way from | $180 (Alaska Airlines) |
Popular in | May |
Cheapest in | July |
Average price | $556 |
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 August 21, 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 9/30
6:00 am-11:48 am
1 stop7h 48m
Monterey Regional
Wed 10/7
1:53 pm-10:55 pm
1 stop7h 02m
$359
ChicagoMonterey
ORD Chicago O'Hare Intl - MRY Monterey Regional
ORDMRY
Chicago O'Hare Intl
Sat 9/19
2:18 pm-11:59 pm
1 stop11h 41m
Monterey Regional
Wed 9/23
6:01 am-7:21 pm
1 stop11h 20m
$359
ChicagoMonterey
ORD Chicago O'Hare Intl - MRY Monterey Regional
ORDMRY
Chicago O'Hare Intl
Thu 9/17
5:00 am-10:15 am
1 stop7h 15m
Monterey Regional
Sun 9/20
3:36 pm-12:59 am
1 stop7h 23m
$359
ChicagoMonterey
ORD Chicago O'Hare Intl - MRY Monterey Regional
ORDMRY
Chicago O'Hare Intl
Tue 9/15
6:00 am-11:59 pm
2 stops19h 59m
Monterey Regional
Mon 9/21
6:01 am-7:21 pm
1 stop11h 20m
$364
Quickest round-trip
ChicagoMonterey
ORD Chicago O'Hare Intl - MRY Monterey Regional
ORDMRY
Chicago O'Hare Intl
Thu 10/22
1:00 pm-5:28 pm
1 stop6h 28m
Monterey Regional
Tue 10/27
2:25 pm-10:45 pm
1 stop6h 20m
$381
ChicagoMonterey
ORD Chicago O'Hare Intl - MRY Monterey Regional
ORDMRY
Chicago O'Hare Intl
Wed 9/2
9:00 am-11:59 pm
2 stops16h 59m
Monterey Regional
Sun 9/6
6:01 am-7:21 pm
1 stop11h 20m
$399
ChicagoMonterey
ORD Chicago O'Hare Intl - MRY Monterey Regional
ORDMRY
Chicago O'Hare Intl
Wed 10/21
9:00 am-4:51 pm
1 stop9h 51m
Monterey Regional
Sat 10/24
5:28 pm-5:40 am
1 stop10h 12m
$429
ChicagoMonterey
ORD Chicago O'Hare Intl - MRY Monterey Regional
ORDMRY
Chicago O'Hare Intl
Fri 12/4
2:03 pm-11:28 pm
2 stops11h 25m
Monterey Regional
Mon 12/7
3:06 pm-7:00 am
2 stops13h 54m
$439
ChicagoMonterey
ORD Chicago O'Hare Intl - MRY Monterey Regional
ORDMRY
Chicago O'Hare Intl
Sat 1/9
7:40 am-2:01 pm
1 stop8h 21m
Monterey Regional
Tue 1/12
6:00 am-10:08 pm
1 stop14h 08m
$441
ChicagoMonterey
ORD Chicago O'Hare Intl - MRY Monterey Regional
ORDMRY
Chicago O'Hare Intl
Fri 9/25
6:00 am-11:59 pm
2 stops19h 59m
Monterey Regional
Tue 9/29
2:43 pm-6:20 am
2 stops13h 37m
$449
Showing 1-10 of 16 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 August.
| 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, November is the cheapest month in which you can book a flight from Chicago to Monterey (average of $410). Flying from Chicago to Monterey in September is currently the most expensive (average of $630). 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 21, 2026.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago to Monterey as you normally would.
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 21, 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.
Boarding
7.7
Overall
7.4
Crew
8.1
Food
6.7
Comfort
7.3
Entertainment
7.1
Reviews
1 / 20
2.0
MediocreDawn,Aug 2026
ORD - DEN
Boarding
7.7
Overall
7.4
Crew
8.1
Food
6.7
Comfort
7.3
Entertainment
7.1
Reviews
1 / 20
2.0
MediocreDawn,Aug 2026
ORD - DEN
Boarding
7.7
Overall
7.4
Crew
8.1
Food
6.7
Comfort
7.3
Entertainment
7.1
Reviews
1 / 20
2.0
MediocreDawn,Aug 2026
ORD - DEN
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.
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Other flights to Monterey
Explore flights to Monterey departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on August 21, 2026.
Chicago and Monterey flights
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Top 3 airlines flying from Chicago to Monterey
Discover the top 3 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 7,457,451 searches. Data last updated August 21, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$276 | Average$509 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$289 | Average$468 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$352 | Average$458 | FlexibilityNo cancel fee | On-time75% |