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Monterey

$175+ Cheap flights from Chicago (CHI) to Monterey (MRY)

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 6/13. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MRY
Jun 10 — Jun 171
Wed 6/10
Wed 6/17
1 adult, Economy
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Cheap flight deals from Chicago to Monterey

Cheapest flights from Chicago to Monterey
Explore the most affordable flight options available from Chicago to Monterey. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 11, 2026.

This Kiwi.com deal was found by Cheapflights users on 5/10. 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 7/37:20 am
ORD
-
MRY
1 stop15h 50m
Multiple Airlines
Mon 7/610:00 pm
MRY
-
ORD
1 stop29h 28m
Multiple Airlines
Deal found 5/10$303
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/279:05 am
ORD
-
MRY
Nonstop4h 49m
United Airlines
Sat 7/112:05 pm
MRY
-
ORD
Nonstop4h 34m
United Airlines
Deal found 5/7$329
This Expedia deal was found by Cheapflights users on 5/10. 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.
Tue 6/92:10 pm
ORD
-
MRY
1 stop11h 23m
Alaska Airlines
Tue 6/163:05 pm
MRY
-
ORD
1 stop6h 31m
Alaska Airlines
Deal found 5/10$331
This Alaska Airlines 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/282:10 pm
ORD
-
MRY
1 stop11h 21m
Alaska Airlines
Tue 6/26:00 am
MRY
-
ORD
1 stop10h 50m
Alaska Airlines
Deal found 5/7$336
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.
Thu 6/42:10 pm
ORD
-
MRY
1 stop11h 21m
Alaska Airlines
Mon 6/86:57 pm
MRY
-
ORD
1 stop9h 23m
Alaska Airlines
Deal found 5/8$349
This American Airlines deal was found by Cheapflights users on 5/10. 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 6/911:43 am
ORD
-
MRY
2 stops9h 00m
American Airlines
Sat 6/137:03 pm
MRY
-
ORD
1 stop9h 16m
American Airlines
Deal found 5/10$354
This Alaska Airlines 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/177:59 pm
ORD
-
MRY
1 stop20h 29m
Alaska Airlines
Thu 8/202:43 pm
MRY
-
ORD
1 stop7h 14m
Alaska Airlines
Deal found 5/7$359
This Alaska Airlines deal was found by Cheapflights users on 5/10. 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 6/92:10 pm
ORD
-
MRY
1 stop11h 23m
Alaska Airlines
Sat 6/136:00 am
MRY
-
ORD
1 stop11h 37m
Alaska Airlines
Deal found 5/10$365

Find flight deals from Chicago to Monterey

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Monterey (MRY). 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 11, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$303
(Kiwi.com)

One-way from

$175
(Expedia)

Popular in

December

Cheapest in

November

Average price

$657
Provider with most accurate pricing for Chicago (CHI)-Monterey Regional flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Monterey Regional flights.
Search Deals
From Chicago (CHI) to Monterey Regional
Search Deals
One-way flight from Chicago (CHI) to Monterey Regional
Search Deals
High demand for flights, 7% potential price rise
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($15 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Monterey 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 11, 2026.
Use the filters below to find and compare flights from Chicago to Monterey that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoMonterey

ORD - MRY

ORDMRY

Chicago O'Hare Intl

Thu 5/28

7:40 am-11:31 pm

2 stops17h 51m

Monterey Regional

Tue 6/2

6:00 am-6:50 pm

1 stop10h 50m

$336

ChicagoMonterey

ORD - MRY

ORDMRY

Chicago O'Hare Intl

Wed 9/9

6:01 am-2:06 pm

1 stop10h 05m

Monterey Regional

Tue 9/15

6:26 pm-6:22 am

1 stop9h 56m

$349

ChicagoMonterey

ORD - MRY

ORDMRY

Chicago O'Hare Intl

Mon 8/17

2:20 pm-11:58 pm

1 stop11h 38m

Monterey Regional

Thu 8/20

6:01 am-7:03 pm

1 stop11h 02m

$349
Quickest round-trip

ChicagoMonterey

ORD - MRY

ORDMRY

Chicago O'Hare Intl

Wed 9/2

6:01 am-2:06 pm

1 stop10h 05m

Monterey Regional

Thu 9/10

2:43 pm-11:57 pm

1 stop7h 14m

$349

ChicagoMonterey

ORD - MRY

ORDMRY

Chicago O'Hare Intl

Sat 10/3

9:00 am-6:03 pm

1 stop11h 03m

Monterey Regional

Fri 10/9

6:03 am-6:53 pm

1 stop10h 50m

$383

ChicagoMonterey

ORD - MRY

ORDMRY

Chicago O'Hare Intl

Tue 8/11

7:20 am-11:58 pm

2 stops18h 38m

Monterey Regional

Sun 8/16

6:00 am-6:57 pm

1 stop10h 57m

$388

ChicagoMonterey

ORD - MRY

ORDMRY

Chicago O'Hare Intl

Sun 10/18

2:21 pm-10:52 pm

1 stop10h 31m

Monterey Regional

Wed 10/21

6:03 am-11:59 pm

2 stops15h 56m

$388
Cheapest one-way

ChicagoMonterey

ORD - MRY

ORDMRY

Chicago O'Hare Intl

Thu 6/4

2:10 pm-11:31 pm

1 stop11h 21m

$180

ChicagoMonterey

ORD - MRY

ORDMRY

Chicago O'Hare Intl

Sat 6/27

5:59 am-11:54 am

1 stop7h 55m

$209

ChicagoMonterey

ORD - MRY

ORDMRY

Chicago O'Hare Intl

Tue 7/14

6:20 am-2:28 pm

1 stop10h 08m

$209

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/9

Showing 1-10 of 13 resultsSorted by cheapest first
1
2

Compare providers for flights from Chicago to Monterey

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to Monterey in May.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago-Monterey flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Monterey flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Monterey flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-Monterey 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 Chicago-Monterey 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 Chicago to Monterey

Have a flexible travel schedule? Discover the best time to fly to Monterey from Chicago 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 Chicago to Monterey

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

Currently, January is the cheapest month in which you can book a flight from Chicago to Monterey (average of $260). Flying from Chicago to Monterey in June is currently the most expensive (average of $448). 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 Chicago to Monterey?

Reviews of airlines servicing Monterey

Get insights into the airlines that provide service to Monterey. 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 Monterey. Reviews last updated May 11, 2026.
See what other customers who have flown with United Airlines and American Airlines from Chicago to Monterey have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
9,699 reviews

Overall

7.4

Food

6.6

Crew

8.1

Entertainment

7.1

Comfort

7.3

Boarding

7.7

Reviews

1 / 20
8.0
Excellent

Ruth,Dec 2024

ORD - AMS

United Airlines flights seem to always use a bus to/from the boarding gate to the plane. Can they not get their own gate? This time there was no lift when leaving the plane and people in wheelchairs somehow had to climb down the steps to the ground to get to the bus. I udon’t know how some managed that!
United Airlines
7.4
Good
9,699 reviews
United Airlines
7.4
Good
9,699 reviews

Overall

7.4

Food

6.6

Crew

8.1

Entertainment

7.1

Comfort

7.3

Boarding

7.7

Reviews

1 / 20
8.0
Excellent

Ruth,Dec 2024

ORD - AMS

United Airlines flights seem to always use a bus to/from the boarding gate to the plane. Can they not get their own gate? This time there was no lift when leaving the plane and people in wheelchairs somehow had to climb down the steps to the ground to get to the bus. I udon’t know how some managed that!
American Airlines
7.1
Good
11,667 reviews
United Airlines
7.4
Good
9,699 reviews

Overall

7.4

Food

6.6

Crew

8.1

Entertainment

7.1

Comfort

7.3

Boarding

7.7

Reviews

1 / 20
8.0
Excellent

Ruth,Dec 2024

ORD - AMS

United Airlines flights seem to always use a bus to/from the boarding gate to the plane. Can they not get their own gate? This time there was no lift when leaving the plane and people in wheelchairs somehow had to climb down the steps to the ground to get to the bus. I udon’t know how some managed that!

Related info for your journey

Find useful and relevant information for your journey from Chicago to Monterey. 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 into for flights to Monterey from Chicago?

    Monterey Regional (MRY), located 3.2 mi from the city center, is the airport you fly into when you book flights from Chicago to Monterey. 3 airlines have flights to Monterey Regional from Chicago on a regular basis. Booking flights from Chicago to Monterey Regional should not be difficult; the airport handles an average of 0 inbound flights from Chicago per day.

  • How long is the flight from Chicago to Monterey?

    Airlines like Alaska Airlines and United Airlines fly from Chicago to Monterey in about 7h 39m. The time it takes to get you to your destination can typically vary by up to 10h 12m. Chicago and Monterey are separated by a distance of 1839 mi. This flight may include one or multiple stops.

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

    Flying on American Airlines is currently your cheapest option to Monterey, with prices starting at $268. Additional round-trip tickets that might be worth considering are offered by United Airlines and Alaska Airlines, with the lowest prices starting at $289 and $352, respectively. American Airlines is 48% cheaper than the average price of flights available within the next 90 days to this destination.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Chicago to Monterey 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 Chicago to Monterey?

    Currently, January is the cheapest month in which you can book a flight from Chicago to Monterey (average of $260). Flying from Chicago to Monterey in June is currently the most expensive (average of $448). 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

Browse thousands of different options on Cheapflights for your next trip

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Top 3 airlines flying from Chicago to Monterey

Discover the top 3 airlines that operate flights from Chicago to Monterey. 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 11, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$268Average$509FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$289Average$488FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$352Average$458FlexibilityNo cancel feeOn-time75%

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