HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$123+ 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 9/8. Fares are subject to change and may not be available on all flights or dates of travel.
MRY — CHI
Aug 5 — Aug 121
Tue 8/5
Tue 8/12
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Monterey to Chicago 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 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 July 31, 2025.

Round-trip from

$268
(American Airlines)

One-way from

$135
(Alaska Airlines)

Popular in

January

Cheapest in

February

Average price

$409
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 ($141 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 7% potential price decrease ($35 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2025
Search Deals

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 July 31, 2025.

This American Airlines deal was found by Cheapflights users on 7/31. 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.
Fri 9/512:46 pmMRY - ORD
1 stop7h 38mAmerican Airlines
Sat 9/136:00 amORD - MRY
1 stop7h 39mAmerican Airlines
Deal found 7/31$268
This Alaska Airlines deal was found by Cheapflights users on 7/30. 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.
Fri 10/36:00 amMRY - ORD
2 stops14h 07mAlaska Airlines
Sun 10/57:59 pmORD - MRY
1 stop20h 14mAlaska Airlines
Deal found 7/30$319
This Mytrip deal was found by Cheapflights users on 7/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/129:54 pmMRY - ORD
2 stops19h 56mMultiple Airlines
Fri 9/199:00 amORD - MRY
1 stop14h 04mMultiple Airlines
Deal found 7/30$330
This United Airlines deal was found by Cheapflights users on 7/31. 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.
Thu 9/47:45 amMRY - ORD
1 stop9h 08mUnited Airlines
Tue 9/910:55 amORD - MRY
1 stop8h 48mUnited Airlines
Deal found 7/31$359

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 July 31, 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

Wed 10/8

6:00 am-2:50 pm

1 stop6h 50m

Chicago O'Hare Intl

Tue 10/14

8:20 am-2:13 pm

1 stop7h 53m

$244

MontereyChicago

MRY - ORD

MRYORD

Monterey Regional

Fri 9/5

12:46 pm-10:24 pm

1 stop7h 38m

Chicago O'Hare Intl

Sat 9/13

6:00 am-11:39 am

1 stop7h 39m

$268

MontereyChicago

MRY - ORD

MRYORD

Monterey Regional

Wed 10/8

6:00 am-5:01 am

2 stops21h 01m

Chicago O'Hare Intl

Tue 10/14

3:50 pm-10:51 pm

1 stop9h 01m

$299

MontereyChicago

MRY - ORD

MRYORD

Monterey Regional

Fri 9/12

9:54 pm-7:50 pm

2 stops19h 56m

Chicago O'Hare Intl

Fri 9/19

9:00 am-9:04 pm

1 stop14h 04m

$330

MontereyChicago

MRY - ORD

MRYORD

Monterey Regional

Sat 8/23

5:15 am-1:15 pm

1 stop6h 00m

Chicago O'Hare Intl

Tue 8/26

2:35 pm-8:18 pm

1 stop7h 43m

$359

MontereyChicago

MRY - ORD

MRYORD

Monterey Regional

Mon 9/8

8:39 pm-4:49 am

1 stop6h 10m

$123

MontereyChicago

MRY - ORD

MRYORD

Monterey Regional

Fri 9/5

7:56 pm-7:03 am

1 stop9h 07m

$135

MontereyChicago

MRY - ORD

MRYORD

Monterey Regional

Wed 8/20

12:19 pm-11:43 pm

1 stop9h 24m

$160

MontereyChicago

MRY - ORD

MRYORD

Monterey Regional

Wed 8/27

6:01 am-2:35 pm

1 stop6h 34m

$219

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/28

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 July 31, 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 July 31, 2025.
Read through reviews of airlines operating flights from Monterey to Chicago, such as Alaska Airlines, United Airlines, and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Overall

8.0

Boarding

8.1

Crew

8.5

Entertainment

7.1

Food

7.1

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
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Overall

8.0

Boarding

8.1

Crew

8.5

Entertainment

7.1

Food

7.1

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
8,900 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Overall

8.0

Boarding

8.1

Crew

8.5

Entertainment

7.1

Food

7.1

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
10,000 reviews

Comfort

7.8

Overall

8.0

Boarding

8.1

Crew

8.5

Entertainment

7.1

Food

7.1

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 American Airlines. Our recent data shows that you can find tickets from as low as $268 on this airline. Additional options worth looking into are Alaska Airlines and United Airlines, starting at $319 and $359 round-trip. American Airlines is currently priced 49% 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 $135. American Airlines flights start at $180 while deals on United Airlines start at $239 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 Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Valparaiso
Chesterton

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 Monterey to Chicago

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

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 July 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$352Average$450FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$388Average$664FlexibilityNo cancel feeOn-time69%

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.