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$138+ 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 2/8. Fares are subject to change and may not be available on all flights or dates of travel.
MRY — CHI
oct. 16 — oct. 231
jue. 10/16
jue. 10/23
1 adult, Economy
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Cheap 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 septiembre 16, 2025.

Round-trip from

$276
(Hawaiian Airlines)

One-way from

$138
(Hawaiian Airlines)

Popular in

January

Cheapest in

August

Average price

$445
From Monterey Regional to Chicago (CHI)
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One-way flight from Monterey Regional to Chicago (CHI)
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Highest demand for flights based on searches. 16% potential increase in price ($110 potential increase over avg. RT price).
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Cheapest flight prices on average. 6% potential price decrease ($32 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find 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 septiembre 16, 2025.

This Alaska Airlines deal was found by Cheapflights users on 9/15. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/106:00 amMRY - ORD
1 stop6h 09mAlaska Airlines
dom. 12/147:59 pmORD - MRY
1 stop20h 19mAlaska Airlines
Deal found 9/15$277
This Alaska Airlines deal was found by Cheapflights users on 9/14. 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.
vie. 11/146:00 amMRY - ORD
2 stops13h 40mAlaska Airlines
lun. 11/246:00 amORD - MRY
2 stops19h 33mAlaska Airlines
Deal found 9/14$287
This American Airlines deal was found by Cheapflights users on 9/14. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 10/304:07 pmMRY - ORD
1 stop6h 23mAmerican Airlines
dom. 11/25:18 amORD - MRY
1 stop8h 23mAmerican Airlines
Deal found 9/14$322
This Alaska Airlines deal was found by Cheapflights users on 9/14. 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.
jue. 10/236:00 amMRY - ORD
1 stop6h 50mAlaska Airlines
lun. 10/272:54 pmORD - MRY
1 stop10h 38mAlaska Airlines
Deal found 9/14$330
This Alaska Airlines deal was found by Cheapflights users on 9/15. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 10/156:00 amMRY - ORD
2 stops21h 01mAlaska Airlines
mié. 10/226:00 amORD - MRY
2 stops18h 51mAlaska Airlines
Deal found 9/15$356
This Alaska Airlines deal was found by Cheapflights users on 9/14. 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.
mar. 12/236:00 amMRY - ORD
1 stop6h 37mAlaska Airlines
mié. 12/243:37 pmORD - MRY
1 stop10h 10mAlaska Airlines
Deal found 9/14$359
This United Airlines deal was found by Cheapflights users on 9/16. 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.
sáb. 10/412:35 pmMRY - ORD
1 stop6h 55mUnited Airlines
sáb. 10/116:15 amORD - MRY
1 stop6h 16mUnited Airlines
Deal found 9/16$364
This United Airlines deal was found by Cheapflights users on 9/14. 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.
mar. 10/142:19 pmMRY - ORD
1 stop8h 35mUnited Airlines
dom. 10/196:15 amORD - MRY
1 stop6h 18mUnited Airlines
Deal found 9/14$367
This Alaska Airlines deal was found by Cheapflights users on 9/15. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 10/306:00 amMRY - ORD
2 stops21h 01mAlaska Airlines
dom. 11/28:59 pmORD - MRY
1 stop19h 29mAlaska Airlines
Deal found 9/15$371
This Alaska Airlines deal was found by Cheapflights users on 9/14. 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.
sáb. 11/227:46 pmMRY - ORD
1 stop8h 42mAlaska Airlines
mié. 11/263:51 pmORD - MRY
1 stop9h 42mAlaska Airlines
Deal found 9/14$372
This Alaska Airlines deal was found by Cheapflights users on 9/14. 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.
sáb. 11/227:46 pmMRY - ORD
1 stop8h 42mAlaska Airlines
vie. 11/286:00 amORD - MRY
1 stop15h 09mAlaska Airlines
Deal found 9/14$390

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 septiembre 16, 2025.
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

sáb. 1/17

6:00 am-1:59 pm

1 stop5h 59m

Chicago O'Hare Intl

sáb. 1/31

9:00 am-1:56 pm

1 stop6h 56m

$276

MontereyChicago

MRY - ORD

MRYORD

Monterey Regional

mié. 12/10

10:25 am-8:25 pm

1 stop8h 00m

Chicago O'Hare Intl

sáb. 12/13

4:10 pm-9:59 pm

1 stop7h 49m

$277

MontereyChicago

MRY - ORD

MRYORD

Monterey Regional

mar. 10/14

6:00 am-2:50 pm

1 stop6h 50m

Chicago O'Hare Intl

vie. 10/17

3:50 pm-11:37 pm

1 stop9h 47m

$277

MontereyChicago

MRY - ORD

MRYORD

Monterey Regional

mié. 12/10

6:00 am-2:09 pm

1 stop6h 09m

Chicago O'Hare Intl

dom. 12/14

7:59 pm-2:18 pm

1 stop20h 19m

$277

MontereyChicago

MRY - ORD

MRYORD

Monterey Regional

mié. 10/15

6:00 am-2:50 pm

1 stop6h 50m

Chicago O'Hare Intl

mié. 10/22

3:50 pm-10:51 pm

1 stop9h 01m

$277

MontereyChicago

MRY - ORD

MRYORD

Monterey Regional

mié. 12/10

6:00 am-2:09 pm

1 stop6h 09m

Chicago O'Hare Intl

sáb. 12/13

8:00 am-11:34 pm

2 stops17h 34m

$282

MontereyChicago

MRY - ORD

MRYORD

Monterey Regional

sáb. 1/17

6:00 am-1:59 pm

1 stop5h 59m

Chicago O'Hare Intl

sáb. 1/31

7:45 am-11:25 pm

2 stops17h 40m

$282

MontereyChicago

MRY - ORD

MRYORD

Monterey Regional

jue. 10/30

12:30 pm-11:53 pm

1 stop9h 23m

Chicago O'Hare Intl

dom. 11/2

5:18 am-11:41 am

1 stop8h 23m

$322

MontereyChicago

MRY - ORD

MRYORD

Monterey Regional

jue. 10/23

6:00 am-2:50 pm

1 stop6h 50m

Chicago O'Hare Intl

lun. 10/27

2:54 pm-11:32 pm

1 stop10h 38m

$330

MontereyChicago

MRY - ORD

MRYORD

Monterey Regional

sáb. 11/8

11:14 am-9:40 pm

1 stop8h 26m

$138

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Showing 1-10 of 20 results
1
2

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, August is the cheapest month in which you can book a flight from Monterey to Chicago (average of $245). Flying from Monterey to Chicago in March is currently the most expensive (average of $321). 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 septiembre 16, 2025.

A simple way to save on the total cost of your ticket is to fly from Monterey to Chicago in the evening. If you’re flexible enough to do this you can expect to save up to 38% on your trip compared to booking a flight at noon.

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 septiembre 16, 2025.
Read through reviews of airlines operating flights from Monterey to Chicago, such as United Airlines and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
8,929 reviews

Overall

7.4

Food

6.6

Comfort

7.3

Boarding

7.7

Entertainment

7.1

Crew

8.1

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!
United Airlines
7.4
Good
8,929 reviews
United Airlines
7.4
Good
8,929 reviews

Overall

7.4

Food

6.6

Comfort

7.3

Boarding

7.7

Entertainment

7.1

Crew

8.1

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!
American Airlines
7.2
Good
10,000 reviews
United Airlines
7.4
Good
8,929 reviews

Overall

7.4

Food

6.6

Comfort

7.3

Boarding

7.7

Entertainment

7.1

Crew

8.1

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!

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 5h 59m. The distance from Monterey to Chicago is about 1839 mi. This flight may include one or multiple stops.

  • 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 $542. American Airlines is currently priced 52% 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, August is the cheapest month in which you can book a flight from Monterey to Chicago (average of $245). Flying from Monterey to Chicago in March is currently the most expensive (average of $321). 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
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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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 septiembre 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$268Average$449FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$542Average$777FlexibilityNo cancel feeOn-time69%

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