$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 8 — Sep 151
Round-trip
1 adult, Economy
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Find cheap flights from Monterey to Chicago 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 Monterey to Chicago
Cheapest
Best
Last-minute
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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 9, 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 9, 2026.
This United Airlines deal was found by Cheapflights users on 8/8. 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 9/212:15 pm -
1 stop6h 25m
Sun 9/67:00 am -
1 stop6h 48m
Deal found 8/8![United Airlines logo]()
$359
This Alaska Airlines deal was found by Cheapflights users on 8/7. 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
Tue 9/86:00 am -
2 stops19h 59m
Deal found 8/7![Alaska Airlines logo]()
$364
This American Airlines deal was found by Cheapflights users on 8/7. 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.
Tue 9/112:40 pm -
2 stops9h 38m
Sat 9/512:10 pm -
2 stops8h 30m
Deal found 8/7![American Airlines logo]()
$369
This Orbitz deal was found by Cheapflights users on 8/8. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/166:01 am -
2 stops15h 58m
Wed 9/236:00 am -
2 stops19h 59m
Deal found 8/8![Alaska Airlines logo]()
$370
This United Airlines deal was found by Cheapflights users on 8/8. 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 8/8![United Airlines logo]()
$378
This Alaska Airlines deal was found by Cheapflights users on 8/7. 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 8/262:43 pm -
1 stop20h 39m
Fri 8/288:17 pm -
1 stop19h 49m
Deal found 8/7![Alaska Airlines logo]()
$394
This American Airlines deal was found by Cheapflights users on 8/7. 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 8/2612:40 pm -
2 stops9h 38m
Sun 8/306:00 am -
1 stop7h 42m
Deal found 8/7![American Airlines logo]()
$399
This American Airlines deal was found by Cheapflights users on 8/8. 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 8/2212:40 pm -
2 stops9h 38m
Sat 8/2912:10 pm -
2 stops8h 30m
Deal found 8/8![American Airlines logo]()
$404
This Alaska Airlines deal was found by Cheapflights users on 8/8. 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 10/105:28 pm -
1 stop10h 12m
Wed 10/149:00 am -
1 stop9h 51m
Deal found 8/8![Alaska Airlines logo]()
$429
This Orbitz deal was found by Cheapflights users on 8/6. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/226:00 am -
2 stops15h 59m
Sun 10/256:00 am -
1 stop12h 51m
Deal found 8/6![Alaska Airlines logo]()
$444
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 9, 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 9, 2026.
This United Airlines deal was found by Cheapflights users on 8/8. 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 8/8![United Airlines logo]()
$378
This Alaska Airlines deal was found by Cheapflights users on 8/6. 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 8/246:01 am -
1 stop11h 20m
Fri 8/282:18 pm -
1 stop11h 41m
Deal found 8/6![Alaska Airlines logo]()
$394
This American Airlines deal was found by Cheapflights users on 8/6. 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 11/2012:49 pm -
1 stop8h 45m
Mon 11/235:00 am -
1 stop9h 25m
Deal found 8/6![American Airlines logo]()
$474
This United Airlines deal was found by Cheapflights users on 8/8. 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 8/228:00 am -
1 stop7h 05m
Sat 8/296:03 am -
1 stop7h 45m
Deal found 8/8![United Airlines logo]()
$394
This Alaska Airlines deal was found by Cheapflights users on 8/7. 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 9/266:01 am -
1 stop11h 20m
Sun 10/46:00 am -
2 stops18h 57m
Deal found 8/7![Alaska Airlines logo]()
$399
This United Airlines deal was found by Cheapflights users on 8/7. 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 8/278:00 am -
1 stop7h 05m
Thu 9/34:25 pm -
1 stop7h 34m
Deal found 8/7![United Airlines logo]()
$394
This Alaska Airlines deal was found by Cheapflights users on 8/8. 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 10/105:28 pm -
1 stop10h 12m
Wed 10/149:00 am -
1 stop9h 51m
Deal found 8/8![Alaska Airlines logo]()
$429
This United Airlines deal was found by Cheapflights users on 8/8. 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 8/275:00 am -
1 stop6h 29m
Wed 9/24:25 pm -
1 stop7h 34m
Deal found 8/8![United Airlines logo]()
$394
This Alaska Airlines deal was found by Cheapflights users on 8/6. 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 9/16:23 pm -
1 stop9h 57m
Mon 9/76:01 am -
1 stop19h 58m
Deal found 8/6![Alaska Airlines logo]()
$462
This United Airlines deal was found by Cheapflights users on 8/7. 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 9/56:45 pm -
1 stop8h 16m
Sun 9/68:40 am -
1 stop8h 21m
Deal found 8/7![United Airlines logo]()
$453
This United Airlines deal was found by Cheapflights users on 8/5. 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 9/115:00 am -
1 stop8h 00m
Sun 9/135:00 am -
1 stop7h 15m
Deal found 8/5![United Airlines logo]()
$459
Last-minute flights from Monterey to ChicagoDiscover last-minute flight deals from Monterey to Chicago. Data last updated August 9, 2026 and is based on user searches.
Discover last-minute flight deals from Monterey to Chicago. Data last updated August 9, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 8/8. 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 8/145:00 am -
1 stop6h 30m
Mon 8/243:56 pm -
1 stop7h 14m
Deal found 8/8![United Airlines logo]()
$609
This United Airlines deal was found by Cheapflights users on 8/9. 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 8/152:05 pm -
Nonstop4h 22m
Sun 8/237:00 am -
1 stop6h 48m
Deal found 8/9![United Airlines logo]()
$599
This United Airlines deal was found by Cheapflights users on 8/9. 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 8/163:36 pm -
1 stop7h 23m
Sun 8/235:55 am -
1 stop7h 53m
Deal found 8/9![United Airlines logo]()
$730
This American Airlines deal was found by Cheapflights users on 8/6. 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 8/167:01 pm -
1 stop8h 58m
Mon 8/179:40 am -
2 stops11h 00m
Deal found 8/6![American Airlines logo]()
$832
This American Airlines deal was found by Cheapflights users on 8/6. 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 8/167:01 pm -
1 stop8h 58m
Tue 8/188:20 am -
2 stops12h 20m
Deal found 8/6![American Airlines logo]()
$837
This KAYAK deal was found by Cheapflights users on 8/8. 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.
Sun 8/166:00 am -
1 stop15h 36m
Wed 8/199:00 am -
1 stop10h 46m
Deal found 8/8![Alaska Airlines logo]()
$961
This United Airlines deal was found by Cheapflights users on 8/6. 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 8/168:00 am -
2 stops18h 43m
Wed 8/1910:27 am -
1 stop9h 31m
Deal found 8/6![United Airlines logo]()
$992
This deal was found by Cheapflights users on 8/7. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/186:45 pm -
1 stop8h 16m
Tue 8/252:42 pm -
1 stop8h 28m
Deal found 8/7![United Airlines logo]()
$574
This Alaska Airlines deal was found by Cheapflights users on 8/8. 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 8/196:23 pm -
1 stop9h 57m
Tue 8/256:01 am -
1 stop10h 05m
Deal found 8/8![Alaska Airlines logo]()
$474
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 9, 2026.
Search for one-way flight options from Monterey to Chicago. Find affordable one-way fares based on user searches. Data last updated August 9, 2026.
This Alaska Airlines deal was found by Cheapflights users on 8/6. 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 8/6![Alaska Airlines logo]()
$180
This Expedia deal was found by Cheapflights users on 8/5. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/276:01 am -
1 stop11h 20m
Deal found 8/5![Alaska Airlines logo]()
$185
This Alaska Airlines deal was found by Cheapflights users on 8/8. 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 10/285:28 pm -
1 stop10h 12m
Deal found 8/8![Alaska Airlines logo]()
$215
This Travelocity deal was found by Cheapflights users on 8/6. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/222:43 pm -
1 stop20h 39m
Deal found 8/6![Alaska Airlines logo]()
$220
This Kiwi.com deal was found by Cheapflights users on 8/5. 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.
Fri 8/1410:04 pm -
1 stop29h 33m
Deal found 8/5![Multiple Airlines logo]()
$237
This Alaska Airlines deal was found by Cheapflights users on 8/8. 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 8/153:05 pm -
1 stop20h 16m
Deal found 8/8![Alaska Airlines logo]()
$265
This Expedia deal was found by Cheapflights users on 8/6. 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 9/162:43 pm -
2 stops13h 37m
Deal found 8/6![Alaska Airlines logo]()
$271
This Alaska Airlines deal was found by Cheapflights users on 8/5. 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.
Thu 10/296:00 am -
1 stop29h 25m
Deal found 8/5![Alaska Airlines logo]()
$287
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 9, 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 2,558,603 searches. Data last updated August 9, 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
$378
MontereyChicago
MRY Monterey Regional - ORD Chicago O'Hare Intl
MRYORD
Monterey Regional
Mon 8/24
6:01 am-7:21 pm
1 stop11h 20m
Chicago O'Hare Intl
Fri 8/28
2:18 pm-11:59 pm
1 stop11h 41m
$394
MontereyChicago
MRY Monterey Regional - ORD Chicago O'Hare Intl
MRYORD
Monterey Regional
Sat 8/22
8:00 am-5:05 pm
1 stop7h 05m
Chicago O'Hare Intl
Sat 8/29
6:03 am-11:48 am
1 stop7h 45m
$394
MontereyChicago
MRY Monterey Regional - ORD Chicago O'Hare Intl
MRYORD
Monterey Regional
Thu 8/27
8:00 am-5:05 pm
1 stop7h 05m
Chicago O'Hare Intl
Thu 9/3
4:25 pm-9:59 pm
1 stop7h 34m
$394
Quickest round-trip
MontereyChicago
MRY Monterey Regional - ORD Chicago O'Hare Intl
MRYORD
Monterey Regional
Thu 8/27
5:00 am-1:29 pm
1 stop6h 29m
Chicago O'Hare Intl
Wed 9/2
4:25 pm-9:59 pm
1 stop7h 34m
$394
MontereyChicago
MRY Monterey Regional - ORD Chicago O'Hare Intl
MRYORD
Monterey Regional
Sat 9/26
6:01 am-7:21 pm
1 stop11h 20m
Chicago O'Hare Intl
Sun 10/4
6:00 am-10:57 pm
2 stops18h 57m
$399
MontereyChicago
MRY Monterey Regional - ORD Chicago O'Hare Intl
MRYORD
Monterey Regional
Sat 10/10
5:28 pm-5:40 am
1 stop10h 12m
Chicago O'Hare Intl
Wed 10/14
9:00 am-4:51 pm
1 stop9h 51m
$429
MontereyChicago
MRY Monterey Regional - ORD Chicago O'Hare Intl
MRYORD
Monterey Regional
Sat 9/5
6:45 pm-5:01 am
1 stop8h 16m
Chicago O'Hare Intl
Sun 9/6
8:40 am-3:01 pm
1 stop8h 21m
$453
MontereyChicago
MRY Monterey Regional - ORD Chicago O'Hare Intl
MRYORD
Monterey Regional
Fri 9/11
5:00 am-3:00 pm
1 stop8h 00m
Chicago O'Hare Intl
Sun 9/13
5:00 am-10:15 am
1 stop7h 15m
$459
MontereyChicago
MRY Monterey Regional - ORD Chicago O'Hare Intl
MRYORD
Monterey Regional
Tue 9/1
6:23 pm-6:20 am
1 stop9h 57m
Chicago O'Hare Intl
Mon 9/7
6:01 am-11:59 pm
1 stop19h 58m
$462
Showing 1-10 of 20 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 $561). 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 9, 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 9, 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.
Entertainment
7.0
Overall
7.9
Crew
8.5
Comfort
7.8
Boarding
8.1
Food
7.0
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
Entertainment
7.0
Overall
7.9
Crew
8.5
Comfort
7.8
Boarding
8.1
Food
7.0
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
Entertainment
7.0
Overall
7.9
Crew
8.5
Comfort
7.8
Boarding
8.1
Food
7.0
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
Entertainment
7.0
Overall
7.9
Crew
8.5
Comfort
7.8
Boarding
8.1
Food
7.0
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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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 9, 2026.
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Monterey and Chicago flights
Browse other Monterey and Chicago flight options. Last updated on August 9, 2026.
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Browse through other flights departing from Monterey. Flights are based on user searches made on Cheapflights and were last updated on August 9, 2026.
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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 2,558,603 searches. Data last updated August 9, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$258 | Average$488 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$289 | Average$479 | FlexibilityNo cancel fee | On-time69% |