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$112+ 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 2/25. Fares are subject to change and may not be available on all flights or dates of travel.
MRY — CHI
Mar 6 — Mar 131
Fri 3/6
Fri 3/13
1 adult, Economy
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Cheap flight deals from Monterey to Chicago

Cheapest flights from Monterey to Chicago
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 February 4, 2026.

This Alaska Airlines deal was found by Cheapflights users on 2/3. 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.
Tue 3/106:00 am
MRY
-
ORD
1 stop6h 58m
Alaska Airlines
Tue 3/177:40 am
ORD
-
MRY
1 stop18h 03m
Alaska Airlines
Deal found 2/3$270
This Trip.com deal was found by Cheapflights users on 2/2. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/192:34 pm
MRY
-
ORD
1 stop7h 25m
Alaska Airlines
Thu 3/264:10 pm
ORD
-
MRY
1 stop9h 38m
Alaska Airlines
Deal found 2/2$283
This Alaska Airlines deal was found by Cheapflights users on 2/3. 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 10/286:46 pm
MRY
-
ORD
1 stop10h 14m
Alaska Airlines
Sat 10/318:00 am
ORD
-
MRY
1 stop12h 09m
Alaska Airlines
Deal found 2/3$289
This Alaska Airlines deal was found by Cheapflights users on 2/2. 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.
Fri 5/157:19 pm
MRY
-
ORD
1 stop9h 21m
Alaska Airlines
Tue 5/193:43 pm
ORD
-
MRY
1 stop9h 54m
Alaska Airlines
Deal found 2/2$290
This Alaska Airlines deal was found by Cheapflights users on 2/2. 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.
Thu 5/146:00 am
MRY
-
ORD
1 stop15h 41m
Alaska Airlines
Tue 5/193:43 pm
ORD
-
MRY
1 stop9h 54m
Alaska Airlines
Deal found 2/2$293
This Alaska Airlines deal was found by Cheapflights users on 2/2. 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.
Fri 5/16:02 am
MRY
-
ORD
2 stops15h 57m
Alaska Airlines
Wed 5/63:52 pm
ORD
-
MRY
1 stop10h 07m
Alaska Airlines
Deal found 2/2$295
This Alaska Airlines deal was found by Cheapflights users on 2/3. 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.
Tue 10/273:06 pm
MRY
-
ORD
1 stop6h 53m
Alaska Airlines
Sat 10/319:20 am
ORD
-
MRY
1 stop7h 13m
Alaska Airlines
Deal found 2/3$323
This United Airlines deal was found by Cheapflights users on 2/3. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/196:40 am
MRY
-
ORD
1 stop8h 22m
United Airlines
Tue 2/244:20 pm
ORD
-
MRY
1 stop8h 09m
United Airlines
Deal found 2/3$324
This Expedia deal was found by Cheapflights users on 2/3. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/196:00 am
MRY
-
ORD
1 stop6h 58m
Alaska Airlines
Tue 2/242:07 pm
ORD
-
MRY
2 stops11h 36m
Alaska Airlines
Deal found 2/3$326
This Alaska Airlines deal was found by Cheapflights users on 2/2. 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.
Sun 5/176:00 am
MRY
-
ORD
1 stop6h 47m
Alaska Airlines
Tue 5/193:43 pm
ORD
-
MRY
1 stop9h 54m
Alaska Airlines
Deal found 2/2$335

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 February 4, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$270
(Alaska Airlines)

One-way from

$112
(Alaska Airlines)

Popular in

December

Cheapest in

March

Average price

$297
Provider with most accurate pricing for Monterey Regional-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Monterey Regional-Chicago (CHI) flights.
Search Deals
From Monterey Regional to Chicago (CHI)
Search Deals
One-way flight from Monterey Regional to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 20% potential increase in price ($116 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($23 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
Search Deals

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 February 4, 2026.
Use the filters below to find and compare flights from Monterey to Chicago that are best for you.

Fly from

Monterey

Fly to

Chicago

Route

Depart

Return

Price

MontereyChicago

MRY - ORD

MRYORD

Monterey Regional

Tue 3/10

6:00 am-2:58 pm

1 stop6h 58m

Chicago O'Hare Intl

Tue 3/17

7:40 am-11:43 pm

1 stop18h 03m

$270

MontereyChicago

MRY - ORD

MRYORD

Monterey Regional

Sat 5/16

6:00 am-11:41 pm

1 stop15h 41m

Chicago O'Hare Intl

Tue 5/19

3:43 pm-11:37 pm

1 stop9h 54m

$283

MontereyChicago

MRY - ORD

MRYORD

Monterey Regional

Fri 5/1

6:02 am-1:13 pm

1 stop29h 11m

Chicago O'Hare Intl

Wed 5/6

8:50 am-2:14 pm

1 stop7h 24m

$283

MontereyChicago

MRY - ORD

MRYORD

Monterey Regional

Wed 6/3

6:00 am-2:47 pm

1 stop6h 47m

Chicago O'Hare Intl

Tue 6/9

3:43 pm-11:37 pm

1 stop9h 54m

$289

MontereyChicago

MRY - ORD

MRYORD

Monterey Regional

Thu 5/14

6:00 am-11:41 pm

1 stop15h 41m

Chicago O'Hare Intl

Tue 5/19

3:43 pm-11:37 pm

1 stop9h 54m

$293

MontereyChicago

MRY - ORD

MRYORD

Monterey Regional

Wed 6/3

6:00 am-2:47 pm

1 stop6h 47m

Chicago O'Hare Intl

Mon 6/8

3:43 pm-11:37 pm

1 stop9h 54m

$323

MontereyChicago

MRY - ORD

MRYORD

Monterey Regional

Thu 2/19

6:40 am-5:02 pm

1 stop8h 22m

Chicago O'Hare Intl

Tue 2/24

4:20 pm-10:29 pm

1 stop8h 09m

$324

MontereyChicago

MRY - ORD

MRYORD

Monterey Regional

Fri 5/15

7:19 pm-6:40 am

1 stop9h 21m

Chicago O'Hare Intl

Wed 5/20

3:43 pm-11:37 pm

1 stop9h 54m

$350

MontereyChicago

MRY - ORD

MRYORD

Monterey Regional

Sat 6/27

7:12 pm-6:09 am

1 stop8h 57m

Chicago O'Hare Intl

Thu 7/2

2:21 pm-6:31 pm

1 stop6h 10m

$357

MontereyChicago

MRY - ORD

MRYORD

Monterey Regional

Wed 2/25

2:43 pm-11:59 pm

1 stop7h 16m

$112

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/3

Showing 1-10 of 19 results
1
2
  • 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.
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

What is the cheapest month to book a flight from Monterey to Chicago?

Currently, October is the cheapest month in which you can book a flight from Monterey to Chicago (average of $125). Flying from Monterey to Chicago in December is currently the most expensive (average of $233). 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.

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 February 4, 2026.
Read through reviews of airlines operating flights from Monterey to Chicago, such as Alaska Airlines, United Airlines, and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
11,839 reviews

Comfort

7.8

Entertainment

7.0

Crew

8.5

Food

7.1

Overall

8.0

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading
Alaska Airlines
8.0
Very good
11,839 reviews
Alaska Airlines
8.0
Very good
11,839 reviews

Comfort

7.8

Entertainment

7.0

Crew

8.5

Food

7.1

Overall

8.0

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading
United Airlines
7.4
Good
9,236 reviews
Alaska Airlines
8.0
Very good
11,839 reviews

Comfort

7.8

Entertainment

7.0

Crew

8.5

Food

7.1

Overall

8.0

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading
American Airlines
7.2
Good
11,222 reviews
Alaska Airlines
8.0
Very good
11,839 reviews

Comfort

7.8

Entertainment

7.0

Crew

8.5

Food

7.1

Overall

8.0

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading

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.

  • What airport do you fly from for flights from Monterey to Chicago?

    Most people fly from Monterey Regional (MRY) if they book a flight from Monterey to Chicago. On average, Monterey Regional has 0 outbound flights to Chicago per day from 2 airlines. Monterey Regional is conveniently located just 3.2 mi from Monterey’s city center.

  • How long is the flight from Monterey to Chicago?

    Departing from Monterey to Chicago will take you 6h 58m. The distance from Monterey to Chicago is about 1839 mi.

  • What are the cheapest airlines flying from Monterey to Chicago round-trip?

    Our cheapest airline available from Monterey to Chicago is American Airlines. Our recent data shows that you can find tickets from as low as $268 on this airline. An additional option worth looking into is United Airlines, starting at $276. American Airlines is currently priced 41% below the average price you’ll pay for this route.

  • Can I find deals for flights from Monterey to Chicago that include hotel bookings?

    Yes. In addition to deals on Monterey to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Monterey to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Monterey to Chicago.

  • Can I find deals for business class flights from Monterey to Chicago?

    Yes. Cheapflights offers flight deals from Monterey to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Monterey to Chicago?

    Currently, October is the cheapest month in which you can book a flight from Monterey to Chicago (average of $125). Flying from Monterey to Chicago in December is currently the most expensive (average of $233). 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.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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Alternative routes for Monterey to Chicago

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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 February 4, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$268Average$450FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$276Average$543FlexibilityNo cancel feeOn-time69%

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