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Cheap flights from Monterey to Chicago from $180

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Monterey to Chicago departing on 10/1. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Find the cheapest flights from Monterey to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
2:33 pm - 10:01 amMRY  Monterey Regional-ORD Chicago O'Hare Intl
17h 28m2 stops Las Vegas Harry Reid Intl Denver Intl
Multiple Airlines Logo
7:00 am - 1:43 pmORD  Chicago O'Hare Intl-MRY Monterey Regional
8h 43m1 stop Las Vegas Harry Reid Intl
$309Multiple Airlines
Fri, Nov 6 - Fri, Nov 13
American Airlines Logo
4:12 pm - 12:35 amMRY  Monterey Regional-ORD Chicago O'Hare Intl
6h 23m1 stop Phoenix Sky Harbor Intl
American Airlines Logo
6:00 am - 11:54 amORD  Chicago O'Hare Intl-MRY Monterey Regional
7h 54m1 stop Dallas/Fort Worth
$359American Airlines
Thu, Oct 8 - Sun, Oct 11
United Airlines Logo
2:00 pm - 10:59 pmMRY  Monterey Regional-ORD Chicago O'Hare Intl
6h 59m1 stop Los Angeles
United Airlines Logo
2:30 pm - 7:19 pmORD  Chicago O'Hare Intl-MRY Monterey Regional
6h 49m1 stop San Francisco
$359United Airlines
Fri, Nov 6 - Fri, Nov 13
United Airlines Logo
10:20 am - 6:56 pmMRY  Monterey Regional-ORD Chicago O'Hare Intl
6h 36m1 stop Los Angeles
United Airlines Logo
7:00 am - 11:52 amORD  Chicago O'Hare Intl-MRY Monterey Regional
6h 52m1 stop Los Angeles
$359United Airlines
Fri, Nov 13 - Wed, Nov 18
Alaska Airlines Logo
6:01 am - 7:21 pmMRY  Monterey Regional-ORD Chicago O'Hare Intl
11h 20m1 stop San Diego
Alaska Airlines Logo
2:18 pm - 11:59 pmORD  Chicago O'Hare Intl-MRY Monterey Regional
11h 41m1 stop San Diego
$359Alaska Airlines
Tue, Sep 15 - Thu, Sep 17
Alaska Airlines Logo
6:00 am - 6:59 pmMRY  Monterey Regional-ORD Chicago O'Hare Intl
10h 59m1 stop San Diego
Alaska Airlines Logo
7:00 am - 4:06 pmORD  Chicago O'Hare Intl-MRY Monterey Regional
11h 06m1 stop Seattle/Tacoma Intl
$359Alaska Airlines
Thu, Nov 12 - Wed, Nov 18
American Airlines Logo
7:01 pm - 5:24 amMRY  Monterey Regional-ORD Chicago O'Hare Intl
8h 23m1 stop Phoenix Sky Harbor Intl
American Airlines Logo
5:00 am - 11:47 amORD  Chicago O'Hare Intl-MRY Monterey Regional
8h 47m1 stop Dallas/Fort Worth
$359American Airlines
Sun, Sep 6 - Sun, Sep 13
American Airlines Logo
12:40 pm - 11:30 pmMRY  Monterey Regional-ORD Chicago O'Hare Intl
8h 50m1 stop Phoenix Sky Harbor Intl
American Airlines Logo
5:00 am - 12:10 pmORD  Chicago O'Hare Intl-MRY Monterey Regional
9h 10m1 stop Phoenix Sky Harbor Intl
$359American Airlines
Wed, Sep 2 - Tue, Sep 8
United Airlines Logo
7:55 pm - 5:04 amMRY  Monterey Regional-ORD Chicago O'Hare Intl
7h 09m1 stop San Francisco
United Airlines Logo
4:20 pm - 9:12 pmORD  Chicago O'Hare Intl-MRY Monterey Regional
6h 52m1 stop Denver Intl
$359United Airlines
Fri, Nov 6 - Sat, Nov 14
Alaska Airlines Logo
6:00 am - 6:59 pmMRY  Monterey Regional-ORD Chicago O'Hare Intl
10h 59m1 stop San Diego
Alaska Airlines Logo
7:00 am - 10:31 pmORD  Chicago O'Hare Intl-MRY Monterey Regional
17h 31m2 stops Seattle/Tacoma Intl San Diego
$364Alaska Airlines
Thu, Nov 12 - Wed, Nov 18

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Alaska Airlines flights from Monterey to Chicago

Our best Alaska Airlines deals on Monterey to Chicago flight tickets
Alaska Airlines
Nov 12
MRY6:00 amMonterey Regional
15h 59m
2 stops
ORD11:59 pmChicago O'Hare Intl
Nov 18
ORD9:30 amChicago O'Hare Intl
15h 01m
2 stops
MRY10:31 pmMonterey Regional
$370
Alaska Airlines
Sep 28
MRY6:01 amMonterey Regional
11h 20m
1 stop
ORD7:21 pmChicago O'Hare Intl
Sep 30
ORD6:00 amChicago O'Hare Intl
19h 59m
2 stops
MRY11:59 pmMonterey Regional
$399
Alaska Airlines
Sep 15
MRY6:01 amMonterey Regional
15h 58m
2 stops
ORD11:59 pmChicago O'Hare Intl
Sep 17
ORD6:00 amChicago O'Hare Intl
19h 59m
2 stops
MRY11:59 pmMonterey Regional
$404

United Airlines flights from Monterey to Chicago

Our best United Airlines deals on Monterey to Chicago flight tickets
United Airlines
Aug 26
MRY8:00 amMonterey Regional
7h 05m
1 stop
ORD5:05 pmChicago O'Hare Intl
Aug 30
ORD4:20 pmChicago O'Hare Intl
7h 39m
1 stop
MRY9:59 pmMonterey Regional
$394
United Airlines
Aug 26
MRY12:35 pmMonterey Regional
6h 54m
1 stop
ORD9:29 pmChicago O'Hare Intl
Aug 29
ORD4:20 pmChicago O'Hare Intl
7h 39m
1 stop
MRY9:59 pmMonterey Regional
$429
United Airlines
Sep 5
MRY6:45 pmMonterey Regional
8h 16m
1 stop
ORD5:01 amChicago O'Hare Intl
Sep 6
ORD7:40 amChicago O'Hare Intl
9h 21m
1 stop
MRY3:01 pmMonterey Regional
$453

momondo 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, momondo users made 832,500 searches. Data last updated August 14, 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 Monterey Regional - ORD Chicago O'Hare Intl

MRYORD

Monterey Regional

Fri 11/6

2:33 pm-10:01 am

2 stops17h 28m

Chicago O'Hare Intl

Fri 11/13

7:00 am-1:43 pm

1 stop8h 43m

$309

MontereyChicago

MRY Monterey Regional - ORD Chicago O'Hare Intl

MRYORD

Monterey Regional

Thu 10/8

4:12 pm-12:35 am

1 stop6h 23m

Chicago O'Hare Intl

Sun 10/11

6:00 am-11:54 am

1 stop7h 54m

$359

MontereyChicago

MRY Monterey Regional - ORD Chicago O'Hare Intl

MRYORD

Monterey Regional

Fri 11/6

2:00 pm-10:59 pm

1 stop6h 59m

Chicago O'Hare Intl

Fri 11/13

2:30 pm-7:19 pm

1 stop6h 49m

$359
Quickest round-trip

MontereyChicago

MRY Monterey Regional - ORD Chicago O'Hare Intl

MRYORD

Monterey Regional

Fri 11/13

10:20 am-6:56 pm

1 stop6h 36m

Chicago O'Hare Intl

Wed 11/18

7:00 am-11:52 am

1 stop6h 52m

$359

MontereyChicago

MRY Monterey Regional - ORD Chicago O'Hare Intl

MRYORD

Monterey Regional

Tue 9/15

6:01 am-7:21 pm

1 stop11h 20m

Chicago O'Hare Intl

Thu 9/17

2:18 pm-11:59 pm

1 stop11h 41m

$359

MontereyChicago

MRY Monterey Regional - ORD Chicago O'Hare Intl

MRYORD

Monterey Regional

Thu 11/12

6:00 am-6:59 pm

1 stop10h 59m

Chicago O'Hare Intl

Wed 11/18

7:00 am-4:06 pm

1 stop11h 06m

$359

MontereyChicago

MRY Monterey Regional - ORD Chicago O'Hare Intl

MRYORD

Monterey Regional

Sun 9/6

7:01 pm-5:24 am

1 stop8h 23m

Chicago O'Hare Intl

Sun 9/13

5:00 am-11:47 am

1 stop8h 47m

$359

MontereyChicago

MRY Monterey Regional - ORD Chicago O'Hare Intl

MRYORD

Monterey Regional

Wed 9/2

12:40 pm-11:30 pm

1 stop8h 50m

Chicago O'Hare Intl

Tue 9/8

5:00 am-12:10 pm

1 stop9h 10m

$359

MontereyChicago

MRY Monterey Regional - ORD Chicago O'Hare Intl

MRYORD

Monterey Regional

Fri 11/6

7:55 pm-5:04 am

1 stop7h 09m

Chicago O'Hare Intl

Sat 11/14

4:20 pm-9:12 pm

1 stop6h 52m

$359

MontereyChicago

MRY Monterey Regional - ORD Chicago O'Hare Intl

MRYORD

Monterey Regional

Thu 11/12

6:00 am-6:59 pm

1 stop10h 59m

Chicago O'Hare Intl

Wed 11/18

7:00 am-10:31 pm

2 stops17h 31m

$364

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from Monterey to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Chicago?

The month of March is, on average, the cheapest month to fly to Chicago from Monterey, with most prices found around $313. If you’re not able to fly to Chicago in March, then September is your next best option. Flight prices from Monterey to Chicago during September average around $318.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Wednesday when prices can be found for as low as $443. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Monterey to Chicago for around $576.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Monterey to Chicago during this time can be as low as $470. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $510.

What is the cheapest Monterey Regional to Chicago flight route?

Fly from Monterey Regional to Chicago O'Hare Intl for the best Monterey Regional - Chicago flight prices

What cabin class options are available on Monterey to Chicago flights?

There is only 1 cabin class available to choose from on Monterey to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

When to book flights from Monterey to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from Monterey to Chicago according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Monterey to Chicago (MRY to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Monterey to Chicago

Fastest flight time

6h 11m

Direct flights

None
The fastest flight from Monterey to Chicago takes 6h 11m
There are no direct flights from Monterey to Chicago. There are no popular flight routes from Monterey to Chicago.
Search flight deals

Frequently asked questions about flying from Monterey to Chicago

  • How far is Monterey Regional to Chicago by plane?

    Chicago is 1855.5 mi away from Monterey Regional. 6h 11m is a normal flight duration for this route.

  • When did momondo last update prices for flights from Monterey Regional Airport to Chicago?

    Prices for flights from Monterey Regional Airport to Chicago are updated daily.

  • How many operators does momondo search for flights from Monterey Regional Airport to Chicago?

  • How old do you have to be to fly from Monterey Regional Airport to Chicago?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Monterey Regional Airport to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The travel and health documents you'll need for your trip to Chicago may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Monterey to Chicago?

  • What is the most popular airline from Monterey to Chicago?

Best airlines flying from Monterey to Chicago

Compare and see reviews for airlines that fly from Monterey to Chicago with momondo
Airline
Rating
Free Cancellation
Price
American AirlinesPriceFrom $258Free CancellationRating
7.1
11,929 reviews
Search American Airlines flights
United AirlinesPriceFrom $289Free CancellationRating
7.4
10,108 reviews
Search United Airlines flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Portage
Benton Harbor
Lansing
Saint Joseph
Valparaiso
Schererville
Munster
Chesterton
Monticello
Crown Point
Porter
Griffith
Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Monterey to Chicago?

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Monterey to Chicago for you.

Can I find flights from Monterey to Chicago with flexible booking policies on momondo?

momondo does allow users to show only those flights to Chicago from Monterey which offer a flexible booking policy as well as other useful filters and features.

How can momondo help me find flights from Monterey to Chicago?

Once you have performed a search for Monterey to Chicago flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

I’m not ready to book a flight from Monterey to Chicago right now. Can momondo alert me if prices change?

If you are not ready to book a flight from Monterey to Chicago now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Chicago and let you know when they change.

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport