$153+ 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 2/18. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MRY
Nov 4 — Nov 111
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 5, 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 5, 2026.
This United Airlines deal was found by Cheapflights users on 10/5. 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 11/66:20 pm -
1 stop7h 24m
Sun 11/85:20 am -
1 stop5h 55m
Deal found 10/5![United Airlines logo]()
$379
This Alaska Airlines deal was found by Cheapflights users on 10/2. 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 12/82:13 pm -
1 stop11h 33m
Tue 1/56:00 am -
2 stops15h 59m
Deal found 10/2![Alaska Airlines logo]()
$384
This American Airlines deal was found by Cheapflights users on 10/1. 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 10/315:00 am -
2 stops9h 19m
Sat 11/712:49 pm -
2 stops8h 26m
Deal found 10/1![American Airlines logo]()
$389
This Alaska Airlines deal was found by Cheapflights users on 10/5. 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 11/32:15 pm -
1 stop10h 16m
Sat 11/76:00 am -
1 stop10h 59m
Deal found 10/5![Alaska Airlines logo]()
$397
This Alaska Airlines deal was found by Cheapflights users on 10/5. 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 11/32:15 pm -
1 stop10h 16m
Fri 11/66:00 am -
1 stop29h 17m
Deal found 10/5![Alaska Airlines logo]()
$407
This American Airlines deal was found by Cheapflights users on 10/1. 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.
Sun 12/65:00 am -
1 stop9h 21m
Sun 12/2012:54 pm -
1 stop8h 09m
Deal found 10/1![American Airlines logo]()
$409
This Kiwi.com deal was found by Cheapflights users on 10/5. 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 -
2 stops31h 19m
Deal found 10/5![Multiple Airlines logo]()
$410
This Alaska Airlines deal was found by Cheapflights users on 10/5. 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 11/77:20 am -
1 stop9h 52m
Tue 11/103:49 pm -
1 stop25h 10m
Deal found 10/5![Alaska Airlines logo]()
$411
This Alaska Airlines deal was found by Cheapflights users on 10/4. 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 11/47:00 am -
2 stops17h 31m
Fri 11/66:00 am -
1 stop10h 59m
Deal found 10/4![Alaska Airlines logo]()
$414
This Alaska Airlines deal was found by Cheapflights users on 10/2. 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 11/42:15 pm -
1 stop10h 16m
Sat 11/76:00 am -
1 stop10h 59m
Deal found 10/2![Alaska Airlines logo]()
$443
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 5, 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 5, 2026.
This Alaska Airlines deal was found by Cheapflights users on 10/1. 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 10/222:21 pm -
1 stop10h 36m
Wed 10/286:03 am -
1 stop10h 50m
Deal found 10/1![Alaska Airlines logo]()
$379
This United Airlines deal was found by Cheapflights users on 10/1. 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 10/162:00 pm -
1 stop8h 01m
Tue 10/2011:59 am -
1 stop6h 23m
Deal found 10/1![United Airlines logo]()
$449
This Alaska Airlines deal was found by Cheapflights users on 10/5. 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 11/32:15 pm -
1 stop10h 16m
Sat 11/76:00 am -
1 stop10h 59m
Deal found 10/5![Alaska Airlines logo]()
$397
This Alaska Airlines deal was found by Cheapflights users on 10/5. 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 11/32:15 pm -
1 stop10h 16m
Fri 11/66:00 am -
1 stop29h 17m
Deal found 10/5![Alaska Airlines logo]()
$407
This United Airlines deal was found by Cheapflights users on 10/1. 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 10/175:59 am -
1 stop7h 19m
Wed 10/218:00 am -
1 stop7h 05m
Deal found 10/1![United Airlines logo]()
$449
This Alaska Airlines deal was found by Cheapflights users on 10/5. 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 11/42:15 pm -
1 stop10h 16m
Fri 11/66:00 am -
1 stop29h 17m
Deal found 10/5![Alaska Airlines logo]()
$407
This United Airlines deal was found by Cheapflights users on 10/5. 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 10/204:20 pm -
1 stop6h 45m
Sat 10/245:10 am -
1 stop8h 10m
Deal found 10/5![United Airlines logo]()
$449
This Alaska Airlines deal was found by Cheapflights users on 10/3. 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 2/108:00 am -
2 stops17h 55m
Mon 2/156:00 am -
1 stop5h 54m
Deal found 10/3![Alaska Airlines logo]()
$414
This Alaska Airlines deal was found by Cheapflights users on 10/5. 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 10/207:20 am -
1 stop8h 47m
Sat 10/242:44 pm -
2 stops12h 56m
Deal found 10/5![Alaska Airlines logo]()
$454
This Alaska Airlines deal was found by Cheapflights users on 10/1. 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 10/317:20 am -
1 stop8h 47m
Mon 11/26:00 am -
1 stop10h 59m
Deal found 10/1![Alaska Airlines logo]()
$461
Last-minute flights from Chicago to MontereyDiscover last-minute flight deals from Chicago to Monterey. Data last updated October 5, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Monterey. Data last updated October 5, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 10/2. 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.
Sun 10/185:00 am -
1 stop8h 54m
Wed 10/2112:44 pm -
1 stop8h 16m
Deal found 10/2![American Airlines logo]()
$449
This Alaska Airlines deal was found by Cheapflights users on 10/1. 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 10/222:21 pm -
1 stop10h 36m
Wed 10/282:44 pm -
2 stops12h 56m
Deal found 10/1![Alaska Airlines logo]()
$384
This American Airlines deal was found by Cheapflights users on 10/1. 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 10/315:00 am -
2 stops9h 19m
Sat 11/712:49 pm -
2 stops8h 26m
Deal found 10/1![American Airlines logo]()
$389
This Alaska Airlines deal was found by Cheapflights users on 10/5. 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 11/32:15 pm -
1 stop10h 16m
Sat 11/76:00 am -
1 stop10h 59m
Deal found 10/5![Alaska Airlines logo]()
$397
This Alaska Airlines deal was found by Cheapflights users on 10/5. 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 11/32:15 pm -
1 stop10h 16m
Fri 11/66:00 am -
1 stop29h 17m
Deal found 10/5![Alaska Airlines logo]()
$407
This Alaska Airlines deal was found by Cheapflights users on 10/4. 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 11/47:00 am -
2 stops17h 31m
Fri 11/66:00 am -
1 stop10h 59m
Deal found 10/4![Alaska Airlines logo]()
$414
This Alaska Airlines deal was found by Cheapflights users on 10/5. 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 11/42:15 pm -
1 stop10h 16m
Sat 11/76:00 am -
1 stop10h 59m
Deal found 10/5![Alaska Airlines logo]()
$443
This Kiwi.com deal was found by Cheapflights users on 10/5. 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 -
2 stops31h 19m
Deal found 10/5![Multiple Airlines logo]()
$410
This United Airlines deal was found by Cheapflights users on 10/5. 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 11/66:20 pm -
1 stop7h 24m
Sun 11/85:20 am -
1 stop5h 55m
Deal found 10/5![United Airlines logo]()
$379
This Alaska Airlines deal was found by Cheapflights users on 10/5. 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 11/77:20 am -
1 stop9h 52m
Tue 11/103:49 pm -
1 stop25h 10m
Deal found 10/5![Alaska Airlines logo]()
$411
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 5, 2026.
Search for one-way flight options from Chicago to Monterey. Find affordable one-way fares based on user searches. Data last updated October 5, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/4. 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 2/185:40 am -
2 stops35h 34m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/4![Multiple Airlines logo]()
$153
This Alaska Airlines deal was found by Cheapflights users on 10/1. 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 10/1![Alaska Airlines logo]()
$190
This Alaska Airlines deal was found by Cheapflights users on 10/5. 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 10/207:20 am -
1 stop8h 47m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/5![Alaska Airlines logo]()
$225
This United Airlines deal was found by Cheapflights users on 10/4. 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 11/202:00 pm -
1 stop8h 29m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/4![United Airlines logo]()
$250
This Kiwi.com deal was found by Cheapflights users on 9/30. 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.
Sun 11/227:55 am -
3 stops37h 44m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![Multiple Airlines logo]()
$251
This United Airlines deal was found by Cheapflights users on 10/4. 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 11/276:00 am -
1 stop9h 04m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/4![United Airlines logo]()
$285
This Alaska Airlines deal was found by Cheapflights users on 10/5. 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 10/137:20 am -
1 stop8h 47m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/5![Alaska Airlines logo]()
$305
This Kiwi.com deal was found by Cheapflights users on 10/2. 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.
Wed 12/167:32 pm -
3 stops50h 38m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/2![Multiple Airlines logo]()
$312
This United Airlines deal was found by Cheapflights users on 10/2. 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 10/255:55 am -
1 stop7h 52m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/2![United Airlines logo]()
$330
This United Airlines deal was found by Cheapflights users on 10/4. 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 11/281:00 pm -
1 stop9h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/4![United Airlines logo]()
$449
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 5, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $374 (United Airlines) |
One-way from | $153 (Kiwi.com) |
Popular in | September |
Cheapest in | July |
Average price | $450 |
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 5, 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
Thu 2/18
5:40 am-3:14 pm
2 stops35h 34m
Monterey Regional
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$153
ChicagoMonterey
ORD Chicago O'Hare Intl - MRY Monterey Regional
ORDMRY
Chicago O'Hare Intl
Wed 12/16
7:27 am-3:15 pm
1 stop9h 48m
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
6:50 am-12:21 pm
1 stop7h 31m
Monterey Regional
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$190
Quickest round-trip
ChicagoMonterey
ORD Chicago O'Hare Intl - MRY Monterey Regional
ORDMRY
Chicago O'Hare Intl
Sun 11/22
1:00 pm-5:32 pm
1 stop6h 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
5:00 am-12:19 pm
1 stop9h 19m
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 12/8
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
Thu 10/22
2:21 pm-10:57 pm
1 stop10h 36m
Monterey Regional
Wed 10/28
6:03 am-6:53 pm
1 stop10h 50m
$379
ChicagoMonterey
ORD Chicago O'Hare Intl - MRY Monterey Regional
ORDMRY
Chicago O'Hare Intl
Tue 11/3
2:15 pm-10:31 pm
1 stop10h 16m
Monterey Regional
Sat 11/7
6:00 am-6:59 pm
1 stop10h 59m
$397
ChicagoMonterey
ORD Chicago O'Hare Intl - MRY Monterey Regional
ORDMRY
Chicago O'Hare Intl
Tue 11/3
2:15 pm-10:31 pm
1 stop10h 16m
Monterey Regional
Fri 11/6
6:00 am-1:17 pm
1 stop29h 17m
$407
ChicagoMonterey
ORD Chicago O'Hare Intl - MRY Monterey Regional
ORDMRY
Chicago O'Hare Intl
Wed 11/4
2:15 pm-10:31 pm
1 stop10h 16m
Monterey Regional
Fri 11/6
6:00 am-1:17 pm
1 stop29h 17m
$407
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 October.
| 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 $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.
How much does it cost to fly round-trip from Chicago to Monterey?
Airfare is below average for this route at the moment.
Chicago to Monterey flights typically cost between $413 and $453 in February.The cheapest round-trip price found within the last 5 days was $379 on Alaska Airlines (Feb 10-Feb 15).
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 5, 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.
Food
6.7
Overall
7.4
Crew
8.1
Comfort
7.3
Boarding
7.7
Entertainment
7.1
Reviews
1 / 20
2.0
MediocreDawn,Aug 2026
ORD - DEN
Food
6.7
Overall
7.4
Crew
8.1
Comfort
7.3
Boarding
7.7
Entertainment
7.1
Reviews
1 / 20
2.0
MediocreDawn,Aug 2026
ORD - DEN
Food
6.7
Overall
7.4
Crew
8.1
Comfort
7.3
Boarding
7.7
Entertainment
7.1
Reviews
1 / 20
2.0
MediocreDawn,Aug 2026
ORD - DEN
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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 October 5, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$289 | Average$450 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$352 | Average$458 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$405 | Average$556 | FlexibilityNo cancel fee | On-time71% |