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$177+ 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 5/9. Fares are subject to change and may not be available on all flights or dates of travel.
MRY — CHI
May 4 — May 111
Sun 5/4
Sun 5/11
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 April 29, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
2 stars

Round-trip from

$349
(Kiwi.com)

One-way from

$177
(Mytrip)

Popular in

January

Cheapest in

February

Average price

$520
Provider with most accurate pricing for Monterey Regional-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Monterey Regional-Chicago (CHI) flights.
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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. 11% potential increase in price ($75 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($30 potential savings vs. average RT price).
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Average for round-trip flights in April 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 April 29, 2025.

This Kiwi.com deal was found by Cheapflights users on 4/29. 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.
Sat 5/246:43 pmMRY - ORD
1 stop8h 57mHawaiian Airlines
Fri 5/3010:00 amORD - MRY
1 stop10h 03mHawaiian Airlines
Deal found 4/29$349
This American Airlines deal was found by Cheapflights users on 4/29. 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 8/166:05 amMRY - ORD
1 stop7h 49mAmerican Airlines
Wed 8/206:00 amORD - MRY
1 stop7h 29mAmerican Airlines
Deal found 4/29$369
This Alaska Airlines deal was found by Cheapflights users on 4/29. 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 5/246:43 pmMRY - ORD
1 stop8h 57mAlaska Airlines
Fri 5/302:09 pmORD - MRY
2 stops11h 22mAlaska Airlines
Deal found 4/29$370
This United Airlines deal was found by Cheapflights users on 4/29. 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 5/135:00 amMRY - ORD
1 stop7h 55mUnited Airlines
Fri 5/163:55 pmORD - MRY
1 stop6h 45mUnited Airlines
Deal found 4/29$459

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 April 29, 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

Sat 5/24

6:43 pm-5:40 am

1 stop8h 57m

Chicago O'Hare Intl

Fri 5/30

10:00 am-6:03 pm

1 stop10h 03m

$349

MontereyChicago

MRY - ORD

MRYORD

Monterey Regional

Sat 8/16

6:05 am-3:54 pm

1 stop7h 49m

Chicago O'Hare Intl

Wed 8/20

6:00 am-11:29 am

1 stop7h 29m

$369

MontereyChicago

MRY - ORD

MRYORD

Monterey Regional

Sat 5/24

6:43 pm-5:40 am

1 stop8h 57m

Chicago O'Hare Intl

Fri 5/30

2:09 pm-11:31 pm

2 stops11h 22m

$370

MontereyChicago

MRY - ORD

MRYORD

Monterey Regional

Tue 5/13

5:00 am-2:55 pm

1 stop7h 55m

Chicago O'Hare Intl

Fri 5/16

3:55 pm-8:40 pm

1 stop6h 45m

$459

MontereyChicago

MRY - ORD

MRYORD

Monterey Regional

Fri 5/9

10:08 pm-8:55 am

2 stops32h 47m

$177

MontereyChicago

MRY - ORD

MRYORD

Monterey Regional

Sat 5/24

6:43 pm-5:40 am

1 stop8h 57m

$178

MontereyChicago

MRY - ORD

MRYORD

Monterey Regional

Thu 7/3

7:06 pm-6:03 am

1 stop8h 57m

$188

MontereyChicago

MRY - ORD

MRYORD

Monterey Regional

Thu 5/22

10:28 am-8:25 pm

1 stop7h 57m

$252

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

  • 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, 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 April 29, 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.

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 April 29, 2025.
Read reviews from past customers who have flown Alaska Airlines, Hawaiian Airlines and United Airlines from Monterey to Chicago. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
9,968 reviews

Entertainment

7.1

Boarding

8.2

Overall

8.0

Crew

8.5

Food

7.1

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very good
9,968 reviews
Alaska Airlines
8.0
Very good
9,968 reviews

Entertainment

7.1

Boarding

8.2

Overall

8.0

Crew

8.5

Food

7.1

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Hawaiian Airlines
7.9
Good
2,406 reviews
Alaska Airlines
8.0
Very good
9,968 reviews

Entertainment

7.1

Boarding

8.2

Overall

8.0

Crew

8.5

Food

7.1

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
United Airlines
7.4
Good
8,696 reviews
Alaska Airlines
8.0
Very good
9,968 reviews

Entertainment

7.1

Boarding

8.2

Overall

8.0

Crew

8.5

Food

7.1

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
9,968 reviews

Entertainment

7.1

Boarding

8.2

Overall

8.0

Crew

8.5

Food

7.1

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

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.

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

    Our cheapest airline available from Monterey to Chicago is Hawaiian Airlines. Our recent data shows that you can find tickets from as low as $349 on this airline. Additional options worth looking into are American Airlines and Alaska Airlines, starting at $369 and $370 round-trip. Hawaiian Airlines is currently priced 41% below the average price you’ll pay for this route.

  • What are the cheapest airlines to fly from Monterey to Chicago one-way?

    To fly one-way, consider booking your trip with Alaska Airlines, which is currently one of the cheapest options available, starting at $178. American Airlines flights start at $188 while deals on United Airlines start at $252 one-way.

  • 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 Monterey?

Book flights to Monterey if you plan to visit one of these locations
Merrillville
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
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 April 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$388Average$676FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$401Average$486FlexibilityNo cancel feeOn-time71%

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