HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Monterey

$153+ 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 8/7. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MRY
Aug 8 — Aug 151
Sat 8/8
Sat 8/15
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Chicago to Monterey with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 July 9, 2026.

This Trip.com deal was found by Cheapflights users on 7/4. 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.
Tue 8/186:20 am
ORD
-
MRY
1 stop10h 08m
Alaska Airlines
Tue 8/252:43 pm
MRY
-
ORD
1 stop7h 14m
Alaska Airlines
Deal found 7/4$333
This United Airlines deal was found by Cheapflights users on 7/8. 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 8/158:57 am
ORD
-
MRY
Nonstop4h 46m
United Airlines
Sat 8/223:36 pm
MRY
-
ORD
1 stop7h 23m
United Airlines
Deal found 7/8$339
This United Airlines deal was found by Cheapflights users on 7/6. 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 9/191:00 pm
ORD
-
MRY
1 stop6h 58m
United Airlines
Wed 9/231:51 pm
MRY
-
ORD
1 stop7h 14m
United Airlines
Deal found 7/6$349
This American Airlines deal was found by Cheapflights users on 7/8. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/191:46 pm
ORD
-
MRY
2 stops10h 35m
American Airlines
Wed 9/2312:37 pm
MRY
-
ORD
1 stop8h 53m
American Airlines
Deal found 7/8$354
This American Airlines deal was found by Cheapflights users on 7/4. 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 8/155:00 am
ORD
-
MRY
2 stops9h 10m
American Airlines
Sat 8/2212:40 pm
MRY
-
ORD
1 stop8h 50m
American Airlines
Deal found 7/4$355
This Alaska Airlines deal was found by Cheapflights users on 7/8. 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 9/91:03 pm
ORD
-
MRY
2 stops12h 56m
Alaska Airlines
Tue 9/156:01 am
MRY
-
ORD
2 stops15h 58m
Alaska Airlines
Deal found 7/8$359
This United Airlines deal was found by Cheapflights users on 7/4. 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 8/110:00 am
ORD
-
MRY
Nonstop4h 49m
United Airlines
Tue 8/41:54 pm
MRY
-
ORD
1 stop9h 21m
United Airlines
Deal found 7/4$371
This United Airlines deal was found by Cheapflights users on 7/6. 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 7/2510:00 am
ORD
-
MRY
Nonstop4h 49m
United Airlines
Mon 7/273:30 pm
MRY
-
ORD
1 stop7h 29m
United Airlines
Deal found 7/6$374
This Alaska Airlines deal was found by Cheapflights users on 7/7. 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.
Sat 10/37:20 am
ORD
-
MRY
1 stop8h 47m
Alaska Airlines
Tue 10/62:44 pm
MRY
-
ORD
1 stop7h 15m
Alaska Airlines
Deal found 7/7$383
This United Airlines deal was found by Cheapflights users on 7/6. 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.
Fri 7/243:47 pm
ORD
-
MRY
1 stop6h 49m
United Airlines
Mon 7/273:30 pm
MRY
-
ORD
1 stop7h 29m
United Airlines
Deal found 7/6$384
This Alaska Airlines deal was found by Cheapflights users on 7/7. 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 8/178:20 pm
ORD
-
MRY
2 stops20h 08m
Alaska Airlines
Thu 8/206:01 am
MRY
-
ORD
1 stop11h 20m
Alaska Airlines
Deal found 7/7$388
This Alaska Airlines deal was found by Cheapflights users on 7/7. 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.
Sat 9/196:00 am
ORD
-
MRY
2 stops19h 59m
Alaska Airlines
Wed 9/232:43 pm
MRY
-
ORD
2 stops13h 37m
Alaska Airlines
Deal found 7/7$393

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 July 9, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$333
(Trip.com)

One-way from

$153
(Kiwi.com)

Popular in

December

Cheapest in

July

Average price

$348
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, 4% potential price rise
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($20 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 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 July 9, 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

Sat 8/15

5:59 pm-11:58 pm

1 stop7h 59m

Monterey Regional

Sat 8/22

6:01 am-7:21 pm

1 stop11h 20m

$349

ChicagoMonterey

ORD - MRY

ORDMRY

Chicago O'Hare Intl

Sat 8/15

3:56 pm-9:10 pm

1 stop7h 14m

Monterey Regional

Sat 8/22

1:51 pm-11:05 pm

1 stop7h 14m

$349

ChicagoMonterey

ORD - MRY

ORDMRY

Chicago O'Hare Intl

Sat 8/15

5:00 am-12:10 pm

2 stops9h 10m

Monterey Regional

Sat 8/22

12:40 pm-11:30 pm

1 stop8h 50m

$355

ChicagoMonterey

ORD - MRY

ORDMRY

Chicago O'Hare Intl

Sun 10/18

7:16 pm-6:03 pm

1 stop24h 47m

Monterey Regional

Wed 10/21

2:44 pm-11:59 pm

1 stop7h 15m

$383

ChicagoMonterey

ORD - MRY

ORDMRY

Chicago O'Hare Intl

Sat 10/3

7:20 am-2:07 pm

1 stop8h 47m

Monterey Regional

Tue 10/6

2:44 pm-11:59 pm

1 stop7h 15m

$383
Quickest round-trip

ChicagoMonterey

ORD - MRY

ORDMRY

Chicago O'Hare Intl

Sat 7/25

4:12 pm-9:10 pm

1 stop6h 58m

Monterey Regional

Mon 7/27

3:30 pm-12:59 am

1 stop7h 29m

$384

ChicagoMonterey

ORD - MRY

ORDMRY

Chicago O'Hare Intl

Mon 8/17

8:20 pm-2:28 pm

2 stops20h 08m

Monterey Regional

Thu 8/20

6:01 am-7:21 pm

1 stop11h 20m

$388

ChicagoMonterey

ORD - MRY

ORDMRY

Chicago O'Hare Intl

Sat 9/19

6:00 am-11:59 pm

2 stops19h 59m

Monterey Regional

Wed 9/23

2:43 pm-6:20 am

2 stops13h 37m

$393

ChicagoMonterey

ORD - MRY

ORDMRY

Chicago O'Hare Intl

Sat 10/3

2:21 pm-10:52 pm

1 stop10h 31m

Monterey Regional

Fri 10/9

6:03 am-11:59 pm

2 stops15h 56m

$418

ChicagoMonterey

ORD - MRY

ORDMRY

Chicago O'Hare Intl

Sun 9/13

6:00 am-11:59 pm

2 stops19h 59m

Monterey Regional

Fri 9/18

6:01 am-7:21 pm

1 stop11h 20m

$418

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/9

Showing 1-10 of 19 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 July.
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.

What is the cheapest time of day to fly from CHI to MRY?

Find hourly flight availability from Chicago to Monterey. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 9, 2026.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago to Monterey as you normally would.

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 July 9, 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
9,955 reviews

Entertainment

7.1

Overall

7.4

Boarding

7.7

Food

6.7

Comfort

7.3

Crew

8.1

Reviews

1 / 20
10.0
Excellent

Tim,May 2023

ORD - DLH

Didn’t have to wait long for the plane and was in the lounge through that time could relax there made it nice.
United Airlines
7.4
Good
9,955 reviews
United Airlines
7.4
Good
9,955 reviews

Entertainment

7.1

Overall

7.4

Boarding

7.7

Food

6.7

Comfort

7.3

Crew

8.1

Reviews

1 / 20
10.0
Excellent

Tim,May 2023

ORD - DLH

Didn’t have to wait long for the plane and was in the lounge through that time could relax there made it nice.
American Airlines
7.1
Good
11,789 reviews
United Airlines
7.4
Good
9,955 reviews

Entertainment

7.1

Overall

7.4

Boarding

7.7

Food

6.7

Comfort

7.3

Crew

8.1

Reviews

1 / 20
10.0
Excellent

Tim,May 2023

ORD - DLH

Didn’t have to wait long for the plane and was in the lounge through that time could relax there made it nice.

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, United Airlines, and American Airlines fly from Chicago to Monterey in about 4h 46m. The time it takes to get you to your destination can typically vary by up to 5h 49m. 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 49% 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

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Chicago to Monterey

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Las Vegas flights
O'Hare Intl to Los Angeles flights
O'Hare Intl to San Francisco flights
O'Hare Intl to San Diego flights
O'Hare Intl to Ontario flights
Midway to Las Vegas flights
St. Louis to Las Vegas flights
O'Hare Intl to Santa Ana flights
Midway to San Francisco flights
Midway to Los Angeles flights
O'Hare Intl to San Jose flights
Midway to San Diego flights
O'Hare Intl to Burbank flights
O'Hare Intl to Reno flights
Rockford to Las Vegas flights
O'Hare Intl to Palm Springs flights
St. Louis to Los Angeles flights
O'Hare Intl to Sacramento flights
O'Hare Intl to Oakland flights
St. Louis to San Francisco flights
O'Hare Intl to Fresno flights
St. Louis to San Diego flights
O'Hare Intl to Santa Barbara flights
O'Hare Intl to Long Beach flights
Midway to Palm Springs flights
St. Louis to Sacramento flights
Midway to Reno flights
Midway to Oakland flights
Midway to San Jose flights
St. Louis to Ontario flights
Moline to Las Vegas flights
Midway to Ontario flights
St. Louis to Burbank flights
Midway to Sacramento flights
St. Louis to Santa Ana flights
Peoria to Las Vegas flights
Peoria to San Diego flights
St. Louis to San Jose flights
Bloomington to Las Vegas flights
Midway to Long Beach flights
Moline to San Francisco flights
St. Louis to Oakland flights
Peoria to Los Angeles flights
O'Hare Intl to Monterey flights
St. Louis to Reno flights
Moline to Los Angeles flights
Midway to Fresno flights

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 July 9, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$268Average$509FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$289Average$459FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$352Average$458FlexibilityNo cancel feeOn-time75%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.