$180+ Cheap flights from Monterey (MRY) to Chicago (CHI)
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 10/1. Fares are subject to change and may not be available on all flights or dates of travel.
MRY — CHI
Sep 22 — Sep 291
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 August 23, 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 August 23, 2026.
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.
Sat 9/1910:30 am -
1 stop6h 35m
Fri 9/254:05 pm -
1 stop7h 54m
Deal found 8/20![United Airlines logo]()
$359
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.
Thu 9/246:01 am -
1 stop11h 20m
Sat 9/261:03 pm -
2 stops12h 56m
Deal found 8/19![Alaska Airlines logo]()
$364
This Alaska 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/266:23 pm -
1 stop9h 57m
Tue 9/297:20 am -
1 stop8h 46m
Deal found 8/17![Alaska Airlines logo]()
$394
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.
Fri 10/166:03 am -
1 stop10h 50m
Mon 10/197:16 pm -
2 stops20h 51m
Deal found 8/21![Alaska Airlines logo]()
$399
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 11/66:00 am -
2 stops15h 59m
Sat 11/149:30 am -
2 stops15h 01m
Deal found 8/19![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.
Sat 9/196:23 pm -
1 stop9h 57m
Wed 9/237:20 am -
1 stop18h 39m
Deal found 8/20![Alaska Airlines logo]()
$411
This Alaska Airlines deal was found by Cheapflights users on 8/22. 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 10/275:28 pm -
1 stop10h 12m
Wed 10/289:00 am -
1 stop9h 51m
Deal found 8/22![Alaska Airlines logo]()
$423
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.
Fri 9/412:32 pm -
1 stop9h 46m
Sun 9/63:18 pm -
1 stop9h 16m
Deal found 8/21![American Airlines logo]()
$429
This Alaska Airlines deal was found by Cheapflights users on 8/22. 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 9/26:01 am -
1 stop11h 20m
Sun 9/62:18 pm -
1 stop11h 41m
Deal found 8/22![Alaska Airlines logo]()
$439
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 August 23, 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 August 23, 2026.
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/183:36 pm -
1 stop7h 23m
Mon 9/215:00 am -
1 stop7h 15m
Deal found 8/21![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.
Fri 12/116:00 am -
1 stop5h 54m
Mon 12/149:20 am -
1 stop7h 13m
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.
Sat 9/195:00 am -
1 stop6h 21m
Tue 9/2212:58 pm -
1 stop7h 00m
Deal found 8/20![United Airlines logo]()
$359
This Alaska Airlines deal was found by Cheapflights users on 8/22. 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 2/192:54 pm -
1 stop10h 34m
Deal found 8/22![Alaska Airlines logo]()
$394
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.
Sat 9/52:43 pm -
2 stops20h 43m
Fri 9/113:52 pm -
2 stops24h 14m
Deal found 8/19![Alaska Airlines logo]()
$429
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 9/412:15 pm -
1 stop7h 19m
Tue 9/812:58 pm -
1 stop7h 00m
Deal found 8/20![United Airlines logo]()
$453
This Alaska Airlines deal was found by Cheapflights users on 8/22. 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 10/225:28 pm -
1 stop10h 12m
Sat 10/247:20 am -
1 stop8h 47m
Deal found 8/22![Alaska Airlines logo]()
$429
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.
Sat 10/106:03 am -
2 stops21h 37m
Mon 10/127:49 pm -
1 stop20h 18m
Deal found 8/21![Alaska Airlines logo]()
$434
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 9/196:23 pm -
1 stop9h 57m
Wed 9/237:20 am -
1 stop18h 39m
Deal found 8/18![Alaska Airlines logo]()
$446
Last-minute flights from Monterey to ChicagoDiscover last-minute flight deals from Monterey to Chicago. Data last updated August 23, 2026 and is based on user searches.
Discover last-minute flight deals from Monterey to Chicago. Data last updated August 23, 2026 and is based on user searches.
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 9/26:01 am -
2 stops15h 58m
Sun 9/62:18 pm -
1 stop11h 41m
Deal found 8/19![Alaska Airlines logo]()
$399
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.
Fri 9/412:32 pm -
1 stop9h 46m
Sun 9/63:18 pm -
1 stop9h 16m
Deal found 8/21![American Airlines logo]()
$429
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 9/512:40 pm -
2 stops9h 38m
Wed 9/95:00 am -
2 stops9h 18m
Deal found 8/21![American Airlines logo]()
$404
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.
Sat 9/1910:30 am -
1 stop6h 35m
Fri 9/254:05 pm -
1 stop7h 54m
Deal found 8/20![United Airlines logo]()
$359
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 9/196:23 pm -
1 stop9h 57m
Wed 9/237:20 am -
1 stop18h 39m
Deal found 8/20![Alaska Airlines logo]()
$411
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.
Thu 9/246:01 am -
1 stop11h 20m
Sat 9/261:03 pm -
2 stops12h 56m
Deal found 8/19![Alaska Airlines logo]()
$364
This Alaska 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/266:23 pm -
1 stop9h 57m
Tue 9/297:20 am -
1 stop8h 46m
Deal found 8/17![Alaska Airlines logo]()
$394
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 August 23, 2026.
Search for one-way flight options from Monterey to Chicago. Find affordable one-way fares based on user searches. Data last updated August 23, 2026.
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 10/12:43 pm -
1 stop7h 16m
Deal found 8/18![Alaska Airlines logo]()
$180
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 9/182:43 pm -
1 stop7h 16m
Deal found 8/19![Alaska Airlines logo]()
$215
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 9/56:23 pm -
1 stop9h 57m
Deal found 8/20![Alaska Airlines logo]()
$260
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.
Mon 8/316:01 am -
1 stop11h 20m
Deal found 8/20![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.
Sun 10/116:03 am -
1 stop29h 22m
Deal found 8/18![Alaska Airlines logo]()
$297
This KAYAK 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2712:40 pm -
1 stop8h 50m
Deal found 8/19![American Airlines logo]()
$308
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 8/286:23 pm -
1 stop9h 57m
Deal found 8/20![Alaska Airlines logo]()
$310
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 August 23, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $359 (United Airlines) |
One-way from | $180 (Alaska Airlines) |
Popular in | December |
Cheapest in | March |
Average price | $429 |
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 August 23, 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
Fri 9/18
3:36 pm-12:59 am
1 stop7h 23m
Chicago O'Hare Intl
Mon 9/21
5:00 am-10:15 am
1 stop7h 15m
$359
MontereyChicago
MRY Monterey Regional - ORD Chicago O'Hare Intl
MRYORD
Monterey Regional
Sat 9/19
5:00 am-1:21 pm
1 stop6h 21m
Chicago O'Hare Intl
Tue 9/22
12:58 pm-5:58 pm
1 stop7h 00m
$359
Quickest round-trip
MontereyChicago
MRY Monterey Regional - ORD Chicago O'Hare Intl
MRYORD
Monterey Regional
Fri 12/11
6:00 am-1:54 pm
1 stop5h 54m
Chicago O'Hare Intl
Mon 12/14
9:20 am-2:33 pm
1 stop7h 13m
$394
MontereyChicago
MRY Monterey Regional - ORD Chicago O'Hare Intl
MRYORD
Monterey Regional
Fri 2/12
6:00 am-1:54 pm
1 stop5h 54m
Chicago O'Hare Intl
Fri 2/19
2:54 pm-11:28 pm
1 stop10h 34m
$394
MontereyChicago
MRY Monterey Regional - ORD Chicago O'Hare Intl
MRYORD
Monterey Regional
Sat 9/5
2:43 pm-1:26 pm
2 stops20h 43m
Chicago O'Hare Intl
Fri 9/11
3:52 pm-2:06 pm
2 stops24h 14m
$429
MontereyChicago
MRY Monterey Regional - ORD Chicago O'Hare Intl
MRYORD
Monterey Regional
Thu 10/22
5:28 pm-5:40 am
1 stop10h 12m
Chicago O'Hare Intl
Sat 10/24
7:20 am-2:07 pm
1 stop8h 47m
$429
MontereyChicago
MRY Monterey Regional - ORD Chicago O'Hare Intl
MRYORD
Monterey Regional
Sat 10/10
6:03 am-5:40 am
2 stops21h 37m
Chicago O'Hare Intl
Mon 10/12
7:49 pm-2:07 pm
1 stop20h 18m
$434
MontereyChicago
MRY Monterey Regional - ORD Chicago O'Hare Intl
MRYORD
Monterey Regional
Sat 9/19
6:23 pm-6:20 am
1 stop9h 57m
Chicago O'Hare Intl
Wed 9/23
7:20 am-11:59 pm
1 stop18h 39m
$446
MontereyChicago
MRY Monterey Regional - ORD Chicago O'Hare Intl
MRYORD
Monterey Regional
Fri 9/4
12:15 pm-9:34 pm
1 stop7h 19m
Chicago O'Hare Intl
Tue 9/8
12:58 pm-5:58 pm
1 stop7h 00m
$453
Cheapest one-way
Quickest one-way
MontereyChicago
MRY Monterey Regional - ORD Chicago O'Hare Intl
MRYORD
Monterey Regional
Thu 10/1
2:43 pm-11:59 pm
1 stop7h 16m
$180
Showing 1-10 of 14 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 November is currently the most expensive (average of $535). 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 MRY to CHI?
Find hourly flight availability from Monterey to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 23, 2026.
When flying from Monterey to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
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 August 23, 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.
Boarding
8.1
Food
7.0
Comfort
7.8
Crew
8.5
Entertainment
7.0
Overall
7.9
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
Boarding
8.1
Food
7.0
Comfort
7.8
Crew
8.5
Entertainment
7.0
Overall
7.9
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
Boarding
8.1
Food
7.0
Comfort
7.8
Crew
8.5
Entertainment
7.0
Overall
7.9
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
Boarding
8.1
Food
7.0
Comfort
7.8
Crew
8.5
Entertainment
7.0
Overall
7.9
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
Lansing
Merrillville
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 August 23, 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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Monterey and Chicago flights
Browse other Monterey and Chicago flight options. Last updated on August 23, 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 August 23, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 2 airlines flying from Monterey to Chicago
Discover the top 2 airlines 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 August 23, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$258 | Average$556 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$289 | Average$453 | FlexibilityNo cancel fee | On-time69% |