$190+ Cheap flights from Monterey (MRY) to Chicago (CHI)
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 1/9. Fares are subject to change and may not be available on all flights or dates of travel.
MRY — CHI
Nov 16 — Nov 231
Round-trip
1 adult, Economy
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Find cheap flights from Monterey to Chicago with Cheapflights
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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
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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 Monterey to Chicago
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Cheapest flights from Monterey to ChicagoExplore the most affordable flight options available from Monterey to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 17, 2026.
Explore the most affordable flight options available from Monterey to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 17, 2026.
This United Airlines deal was found by Cheapflights users on 10/12. 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.
Mon 11/22:25 pm -
1 stop7h 02m
Wed 11/412:42 pm -
1 stop6h 36m
Deal found 10/12![United Airlines logo]()
$379
This American Airlines deal was found by Cheapflights users on 10/12. 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.
Mon 11/212:49 pm -
2 stops9h 10m
Wed 11/45:00 am -
1 stop9h 19m
Deal found 10/12![American Airlines logo]()
$384
This Expedia deal was found by Cheapflights users on 10/16. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/126:00 am -
2 stops15h 59m
Mon 11/162:15 pm -
1 stop11h 44m
Deal found 10/16![Alaska Airlines logo]()
$394
This United Airlines deal was found by Cheapflights users on 10/15. 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.
Tue 11/247:00 pm -
1 stop6h 02m
Fri 11/275:52 pm -
1 stop6h 27m
Deal found 10/15![United Airlines logo]()
$411
This United Airlines deal was found by Cheapflights users on 10/13. 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.
Sat 11/212:00 pm -
1 stop7h 02m
Tue 11/243:47 pm -
1 stop6h 42m
Deal found 10/13![United Airlines logo]()
$412
This American Airlines deal was found by Cheapflights users on 10/16. 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.
Thu 11/57:22 pm -
1 stop7h 38m
Sun 11/85:00 am -
1 stop9h 19m
Deal found 10/16![American Airlines logo]()
$414
This Alaska Airlines deal was found by Cheapflights users on 10/14. 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 11/56:00 am -
1 stop10h 59m
Tue 11/102:15 pm -
1 stop10h 16m
Deal found 10/14![Alaska Airlines logo]()
$424
This Alaska Airlines deal was found by Cheapflights users on 10/12. 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 11/146:00 am -
1 stop10h 59m
Wed 11/187:20 am -
1 stop9h 52m
Deal found 10/12![Alaska Airlines logo]()
$431
This Expedia deal was found by Cheapflights users on 10/13. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/256:04 am -
1 stop11h 59m
Mon 11/309:01 pm -
1 stop20h 14m
Deal found 10/13![Alaska Airlines logo]()
$439
This American Airlines deal was found by Cheapflights users on 10/12. 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 10/284:12 pm -
1 stop6h 23m
Fri 10/306:48 am -
1 stop7h 31m
Deal found 10/12![American Airlines logo]()
$449
Best flights from Monterey to ChicagoDiscover carefully curated flight deals from Monterey to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 17, 2026.
Discover carefully curated flight deals from Monterey to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 17, 2026.
This United Airlines deal was found by Cheapflights users on 10/12. 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.
Mon 11/22:25 pm -
1 stop7h 02m
Wed 11/412:42 pm -
1 stop6h 36m
Deal found 10/12![United Airlines logo]()
$379
This Alaska Airlines deal was found by Cheapflights users on 10/16. 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.
Fri 2/126:00 am -
1 stop5h 54m
Fri 2/198:00 am -
1 stop12h 09m
Deal found 10/16![Alaska Airlines logo]()
$424
This United Airlines deal was found by Cheapflights users on 10/17. 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.
Tue 11/242:25 pm -
1 stop7h 02m
Fri 11/276:00 am -
1 stop6h 55m
Deal found 10/17![United Airlines logo]()
$379
This Alaska Airlines deal was found by Cheapflights users on 10/14. 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 11/56:00 am -
1 stop10h 59m
Tue 11/102:15 pm -
1 stop10h 16m
Deal found 10/14![Alaska Airlines logo]()
$424
This United Airlines deal was found by Cheapflights users on 10/13. 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.
Sat 11/212:00 pm -
1 stop7h 02m
Tue 11/243:47 pm -
1 stop6h 42m
Deal found 10/13![United Airlines logo]()
$412
This Alaska Airlines deal was found by Cheapflights users on 10/12. 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 11/146:00 am -
1 stop10h 59m
Wed 11/187:20 am -
1 stop9h 52m
Deal found 10/12![Alaska Airlines logo]()
$431
This United Airlines deal was found by Cheapflights users on 10/16. 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.
Sun 11/15:20 am -
1 stop6h 10m
Thu 11/52:30 pm -
1 stop6h 49m
Deal found 10/16![United Airlines logo]()
$449
Last-minute flights from Monterey to ChicagoDiscover last-minute flight deals from Monterey to Chicago. Data last updated October 17, 2026 and is based on user searches.
Discover last-minute flight deals from Monterey to Chicago. Data last updated October 17, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 10/12. 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 10/284:12 pm -
1 stop6h 23m
Fri 10/306:48 am -
1 stop7h 31m
Deal found 10/12![American Airlines logo]()
$449
This United Airlines deal was found by Cheapflights users on 10/12. 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.
Mon 11/22:25 pm -
1 stop7h 02m
Wed 11/412:42 pm -
1 stop6h 36m
Deal found 10/12![United Airlines logo]()
$379
This American Airlines deal was found by Cheapflights users on 10/12. 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.
Mon 11/212:49 pm -
2 stops9h 10m
Wed 11/45:00 am -
1 stop9h 19m
Deal found 10/12![American Airlines logo]()
$384
This American Airlines deal was found by Cheapflights users on 10/16. 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.
Thu 11/57:22 pm -
1 stop7h 38m
Sun 11/85:00 am -
1 stop9h 19m
Deal found 10/16![American Airlines logo]()
$414
This Alaska Airlines deal was found by Cheapflights users on 10/14. 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 11/56:00 am -
1 stop10h 59m
Tue 11/102:15 pm -
1 stop10h 16m
Deal found 10/14![Alaska Airlines logo]()
$424
This Expedia deal was found by Cheapflights users on 10/16. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/126:00 am -
2 stops15h 59m
Mon 11/162:15 pm -
1 stop11h 44m
Deal found 10/16![Alaska Airlines logo]()
$394
This Alaska Airlines deal was found by Cheapflights users on 10/12. 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 11/146:00 am -
1 stop10h 59m
Wed 11/187:20 am -
1 stop9h 52m
Deal found 10/12![Alaska Airlines logo]()
$431
This United Airlines deal was found by Cheapflights users on 10/13. 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.
Sat 11/212:00 pm -
1 stop7h 02m
Tue 11/243:47 pm -
1 stop6h 42m
Deal found 10/13![United Airlines logo]()
$412
This United Airlines deal was found by Cheapflights users on 10/15. 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.
Tue 11/247:00 pm -
1 stop6h 02m
Fri 11/275:52 pm -
1 stop6h 27m
Deal found 10/15![United Airlines logo]()
$411
This Expedia deal was found by Cheapflights users on 10/13. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/256:04 am -
1 stop11h 59m
Mon 11/309:01 pm -
1 stop20h 14m
Deal found 10/13![Alaska Airlines logo]()
$439
One-way flights from Monterey to ChicagoSearch for one-way flight options from Monterey to Chicago. Find affordable one-way fares based on user searches. Data last updated October 17, 2026.
Search for one-way flight options from Monterey to Chicago. Find affordable one-way fares based on user searches. Data last updated October 17, 2026.
This Delta deal was found by Cheapflights users on 10/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/911:15 am -
1 stop8h 38m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/16![Delta logo]()
$190
This Delta deal was found by Cheapflights users on 10/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/1011:15 am -
1 stop8h 38m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/16![Delta logo]()
$220
This Delta deal was found by Cheapflights users on 10/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/411:15 am -
1 stop8h 38m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/14![Delta logo]()
$230
This United Airlines deal was found by Cheapflights users on 10/16. 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 10/307:00 am -
1 stop8h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/16![United Airlines logo]()
$235
This Delta deal was found by Cheapflights users on 10/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/311:15 am -
1 stop8h 38m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/14![Delta logo]()
$250
This United Airlines deal was found by Cheapflights users on 10/15. 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 11/510:20 am -
1 stop6h 36m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/15![United Airlines logo]()
$260
This United Airlines deal was found by Cheapflights users on 10/15. 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.
Sun 1/172:06 pm -
2 stops7h 52m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/15![United Airlines logo]()
$265
This Kiwi.com deal was found by Cheapflights users on 10/16. 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.
Fri 10/303:41 pm -
2 stops24h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/16![Multiple Airlines logo]()
$282
This United Airlines deal was found by Cheapflights users on 10/14. 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.
Thu 10/2210:30 am -
1 stop8h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/14![United Airlines logo]()
$340
This Alaska Airlines deal was found by Cheapflights users on 10/16. 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.
Sat 1/24:46 pm -
1 stop29h 13m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/16![Alaska Airlines logo]()
$377
This United Airlines deal was found by Cheapflights users on 10/16. 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.
Sun 1/102:06 pm -
2 stops7h 52m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/16![United Airlines logo]()
$378
Find flight deals from Monterey to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from Monterey (MRY) to Chicago (CHI). 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 17, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $379 (United Airlines) |
One-way from | $190 (Delta) |
Popular in | December |
Cheapest in | March |
Average price | $498 |
Cheapflights Fare Finder
Customize your flight search to find flights from Monterey to Chicago 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 17, 2026.
Use the filters below to find and compare flights from Monterey to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
MontereyChicago
MRY Monterey Regional - ORD Chicago O'Hare Intl
MRYORD
Monterey Regional
Sat 1/9
11:15 am-9:53 pm
1 stop8h 38m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$190
MontereyChicago
MRY Monterey Regional - ORD Chicago O'Hare Intl
MRYORD
Monterey Regional
Sun 4/4
11:15 am-9:53 pm
1 stop8h 38m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$230
MontereyChicago
MRY Monterey Regional - ORD Chicago O'Hare Intl
MRYORD
Monterey Regional
Fri 10/30
7:00 am-5:00 pm
1 stop8h 00m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$235
MontereyChicago
MRY Monterey Regional - ORD Chicago O'Hare Intl
MRYORD
Monterey Regional
Sat 4/3
11:15 am-9:53 pm
1 stop8h 38m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$250
Quickest round-trip
MontereyChicago
MRY Monterey Regional - ORD Chicago O'Hare Intl
MRYORD
Monterey Regional
Thu 11/5
10:20 am-6:56 pm
1 stop6h 36m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$260
MontereyChicago
MRY Monterey Regional - ORD Chicago O'Hare Intl
MRYORD
Monterey Regional
Mon 1/18
3:30 pm-1:14 am
1 stop7h 44m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$260
MontereyChicago
MRY Monterey Regional - ORD Chicago O'Hare Intl
MRYORD
Monterey Regional
Thu 10/22
10:30 am-8:40 pm
1 stop8h 10m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$340
MontereyChicago
MRY Monterey Regional - ORD Chicago O'Hare Intl
MRYORD
Monterey Regional
Sun 1/10
2:06 pm-11:58 pm
2 stops7h 52m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$378
MontereyChicago
MRY Monterey Regional - ORD Chicago O'Hare Intl
MRYORD
Monterey Regional
Mon 11/2
2:25 pm-11:27 pm
1 stop7h 02m
Chicago O'Hare Intl
Wed 11/4
12:42 pm-5:18 pm
1 stop6h 36m
$379
MontereyChicago
MRY Monterey Regional - ORD Chicago O'Hare Intl
MRYORD
Monterey Regional
Tue 11/24
2:25 pm-11:27 pm
1 stop7h 02m
Chicago O'Hare Intl
Fri 11/27
6:00 am-10:55 am
1 stop6h 55m
$379
Showing 1-10 of 17 resultsSorted by cheapest first
- Most accurate provider: When it comes to deals on Monterey-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Monterey-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Monterey-Chicago flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Monterey-Chicago 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 Monterey-Chicago 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 Monterey to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Monterey with our price prediction graph.
MRY-CHI
MRY-ORD
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 Monterey to Chicago
MRY-CHI
MRY-ORD
What is the cheapest month to book a flight from Monterey to Chicago?
Currently, March is the cheapest month in which you can book a flight from Monterey to Chicago (average of $313). Flying from Monterey to Chicago in September is currently the most expensive (average of $608). 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 Monterey to Chicago?
Airfare is below average for this route at the moment.
Monterey to Chicago flights typically cost between $432 and $513 in November.The cheapest round-trip price found within the last 5 days was $379 on United Airlines (Nov 2-Nov 4).
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated October 17, 2026.
Read through reviews of airlines operating flights from Monterey to Chicago, such as Alaska Airlines,United Airlines, andAmerican Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.5
Entertainment
7.0
Comfort
7.8
Food
7.0
Overall
7.9
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
Crew
8.5
Entertainment
7.0
Comfort
7.8
Food
7.0
Overall
7.9
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
Crew
8.5
Entertainment
7.0
Comfort
7.8
Food
7.0
Overall
7.9
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
Crew
8.5
Entertainment
7.0
Comfort
7.8
Food
7.0
Overall
7.9
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
Related info for your journey
Find useful and relevant information for your journey from Monterey to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Merrillville
Lansing
Valparaiso
Hammond
Saint Joseph
Porter
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Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
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Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on October 17, 2026.
Complete your trip
Complete your trip to Chicago by adding a car rental and/or hotel reservation to your travel itinerary.
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Find flights from Monterey to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Monterey and Chicago flights
Browse other Monterey and Chicago flight options. Last updated on October 17, 2026.
Other flights from Monterey
Browse through other flights departing from Monterey. Flights are based on user searches made on Cheapflights and were last updated on October 17, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top airline flying from Monterey to Chicago
Discover the top airline that operate flights from Monterey to Chicago. 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 17, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$298 | Average$479 | FlexibilityNo cancel fee | On-time69% |