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$127+ 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 6/15. Fares are subject to change and may not be available on all flights or dates of travel.
MRY — CHI
Jun 9 — Jun 161
Tue 6/9
Tue 6/16
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 May 10, 2026.

This Kiwi.com deal was found by Cheapflights users on 5/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/1010:04 pm
MRY
-
ORD
2 stops24h 45m
Multiple Airlines
Fri 8/147:15 am
ORD
-
MRY
1 stop15h 59m
Multiple Airlines
Deal found 5/8$290
This Kiwi.com deal was found by Cheapflights users on 5/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/1010:04 pm
MRY
-
ORD
2 stops24h 45m
Multiple Airlines
Mon 8/177:15 am
ORD
-
MRY
1 stop15h 59m
Multiple Airlines
Deal found 5/8$295
This Alaska Airlines deal was found by Cheapflights users on 5/5. 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.
Sat 5/302:55 pm
MRY
-
ORD
1 stop7h 00m
Alaska Airlines
Tue 6/29:00 am
ORD
-
MRY
1 stop7h 18m
Alaska Airlines
Deal found 5/5$313
This Alaska Airlines deal was found by Cheapflights users on 5/9. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/62:55 pm
MRY
-
ORD
1 stop7h 00m
Alaska Airlines
Sat 6/135:59 pm
ORD
-
MRY
1 stop7h 59m
Alaska Airlines
Deal found 5/9$331
This Alaska Airlines deal was found by Cheapflights users on 5/8. 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 6/66:00 am
MRY
-
ORD
1 stop10h 50m
Alaska Airlines
Fri 6/122:20 pm
ORD
-
MRY
1 stop11h 38m
Alaska Airlines
Deal found 5/8$336
This United Airlines deal was found by Cheapflights users on 5/8. 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 6/62:06 pm
MRY
-
ORD
Nonstop4h 34m
United Airlines
Fri 6/122:30 pm
ORD
-
MRY
1 stop8h 06m
United Airlines
Deal found 5/8$339
This Alaska Airlines deal was found by Cheapflights users on 5/8. 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 10/286:40 pm
MRY
-
ORD
1 stop9h 40m
Alaska Airlines
Sat 10/317:20 am
ORD
-
MRY
1 stop8h 47m
Alaska Airlines
Deal found 5/8$349
This Kiwi.com deal was found by Cheapflights users on 5/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/1510:01 pm
MRY
-
ORD
1 stop29h 06m
Multiple Airlines
Fri 6/197:20 am
ORD
-
MRY
1 stop15h 51m
Multiple Airlines
Deal found 5/7$358
This Alaska Airlines deal was found by Cheapflights users on 5/8. 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 8/53:05 pm
MRY
-
ORD
1 stop6h 31m
Alaska Airlines
Sat 8/156:20 am
ORD
-
MRY
1 stop10h 08m
Alaska Airlines
Deal found 5/8$359

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 May 10, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$290
(Kiwi.com)

One-way from

$127
(Kiwi.com)

Popular in

December

Cheapest in

March

Average price

$487

Good round-trip deal

$339 or less
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. 21% potential increase in price ($120 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($24 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
Search Deals
Price to beat on a round-trip flight from Monterey Regional to Chicago (CHI).
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 May 10, 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

Price

Cheapest round-trip

MontereyChicago

MRY - ORD

MRYORD

Monterey Regional

Sat 5/30

2:55 pm-11:55 pm

1 stop7h 00m

Chicago O'Hare Intl

Tue 6/2

9:00 am-2:18 pm

1 stop7h 18m

$313

MontereyChicago

MRY - ORD

MRYORD

Monterey Regional

Sat 7/18

2:05 pm-8:39 pm

Nonstop4h 34m

Chicago O'Hare Intl

Tue 7/21

2:30 pm-8:36 pm

1 stop8h 06m

$339

MontereyChicago

MRY - ORD

MRYORD

Monterey Regional

Sat 8/22

1:51 pm-11:10 pm

1 stop7h 19m

Chicago O'Hare Intl

Sat 8/29

3:55 pm-9:09 pm

1 stop7h 14m

$349

MontereyChicago

MRY - ORD

MRYORD

Monterey Regional

Wed 10/28

6:03 am-6:53 pm

1 stop10h 50m

Chicago O'Hare Intl

Sat 10/31

7:20 am-2:07 pm

1 stop8h 47m

$349

MontereyChicago

MRY - ORD

MRYORD

Monterey Regional

Fri 6/5

6:00 am-6:50 pm

1 stop10h 50m

Chicago O'Hare Intl

Fri 6/12

2:20 pm-11:58 pm

1 stop11h 38m

$359

MontereyChicago

MRY - ORD

MRYORD

Monterey Regional

Wed 6/10

3:05 pm-11:36 pm

1 stop6h 31m

Chicago O'Hare Intl

Sat 6/13

5:59 pm-11:58 pm

1 stop7h 59m

$359

MontereyChicago

MRY - ORD

MRYORD

Monterey Regional

Tue 10/6

2:44 pm-11:59 pm

1 stop7h 15m

Chicago O'Hare Intl

Thu 10/15

7:20 am-2:07 pm

1 stop8h 47m

$389

MontereyChicago

MRY - ORD

MRYORD

Monterey Regional

Tue 8/18

3:05 pm-11:36 pm

1 stop6h 31m

Chicago O'Hare Intl

Thu 8/20

6:01 am-2:06 pm

1 stop10h 05m

$428

MontereyChicago

MRY - ORD

MRYORD

Monterey Regional

Sat 8/22

2:01 pm-8:35 pm

Nonstop4h 34m

Chicago O'Hare Intl

Sun 8/23

7:40 am-3:01 pm

1 stop9h 21m

$439
Quickest round-trip

MontereyChicago

MRY - ORD

MRYORD

Monterey Regional

Sat 5/30

2:06 pm-8:40 pm

Nonstop4h 34m

Chicago O'Hare Intl

Tue 6/2

6:00 am-11:41 am

1 stop7h 41m

$439

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/7

Showing 1-10 of 21 resultsSorted by cheapest first
1
2
3
  • 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 $179). Flying from Monterey to Chicago in April is currently the most expensive (average of $409). 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.

How much does it cost to fly round-trip from Monterey to Chicago?

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 May 10, 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.
Alaska Airlines
7.9
Good
12,348 reviews

Boarding

8.1

Entertainment

7.0

Crew

8.5

Food

7.0

Comfort

7.8

Overall

7.9

Reviews

1 / 20
10.0
Excellent

Franzi,Mar 2026

SFO - PDX

I love flying with Alaska. I think they sre the best airline.
Alaska Airlines
7.9
Good
12,348 reviews
Alaska Airlines
7.9
Good
12,348 reviews

Boarding

8.1

Entertainment

7.0

Crew

8.5

Food

7.0

Comfort

7.8

Overall

7.9

Reviews

1 / 20
10.0
Excellent

Franzi,Mar 2026

SFO - PDX

I love flying with Alaska. I think they sre the best airline.
United Airlines
7.4
Good
9,694 reviews
Alaska Airlines
7.9
Good
12,348 reviews

Boarding

8.1

Entertainment

7.0

Crew

8.5

Food

7.0

Comfort

7.8

Overall

7.9

Reviews

1 / 20
10.0
Excellent

Franzi,Mar 2026

SFO - PDX

I love flying with Alaska. I think they sre the best airline.
American Airlines
7.1
Good
11,667 reviews
Alaska Airlines
7.9
Good
12,348 reviews

Boarding

8.1

Entertainment

7.0

Crew

8.5

Food

7.0

Comfort

7.8

Overall

7.9

Reviews

1 / 20
10.0
Excellent

Franzi,Mar 2026

SFO - PDX

I love flying with Alaska. I think they sre the best airline.

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 4h 34m. 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 $258 on this airline. An additional option worth looking into is United Airlines, starting at $276. American Airlines is currently priced 42% below the average price you’ll pay for this route.

  • What are the cheapest flights from Monterey to Chicago?

    Looking at all options, your cheapest flight can be booked for $339. While the most popular route (Monterey Regional - Chicago O'Hare Intl) can be booked for $339 on average, our data indicates $413 when flying from Monterey to Chicago.

  • 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 $179). Flying from Monterey to Chicago in April is currently the most expensive (average of $409). 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
Benton Harbor
Lansing
Merrillville
Hammond
Porter

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Alternative routes for Monterey to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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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 May 10, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$258Average$456FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$276Average$498FlexibilityNo cancel feeOn-time69%

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