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Cheap flights from Monterey to Chicago from $149

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 1/17. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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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
10:06 pm - 12:13 amMRY-ORD
48h 07m2 stops
Multiple Airlines Logo
3:27 pm - 5:12 pmORD-MRY
27h 45m1 stop
$240Multiple Airlines
Find Deal
Fri, Dec 12 - Thu, Dec 18
Alaska Airlines Logo
6:00 am - 2:09 pmMRY-ORD
6h 09m1 stop
Alaska Airlines Logo
3:05 pm - 11:29 pmORD-MRY
10h 24m1 stop
$288Alaska Airlines
Find Deal
Wed, Dec 3 - Tue, Dec 9
Multiple Airlines Logo
10:06 pm - 6:05 amMRY-ORD
29h 59m2 stops
Multiple Airlines Logo
12:59 pm - 9:16 pmORD-MRY
10h 17m1 stop
$293Multiple Airlines
Find Deal
Fri, Dec 12 - Mon, Dec 15
Alaska Airlines Logo
6:00 am - 2:09 pmMRY-ORD
6h 09m1 stop
Alaska Airlines Logo
8:55 am - 11:29 pmORD-MRY
16h 34m1 stop
$298Alaska Airlines
Find Deal
Wed, Dec 3 - Tue, Dec 9
Alaska Airlines Logo
6:00 am - 2:09 pmMRY-ORD
6h 09m1 stop
Alaska Airlines Logo
8:00 am - 11:29 pmORD-MRY
17h 29m2 stops
$304Alaska Airlines
Find Deal
Wed, Dec 3 - Tue, Dec 9
Alaska Airlines Logo
6:00 am - 2:09 pmMRY-ORD
6h 09m1 stop
Alaska Airlines Logo
3:05 pm - 11:29 pmORD-MRY
10h 24m1 stop
$308Alaska Airlines
Find Deal
Tue, Dec 9 - Tue, Dec 16
American Airlines Logo
12:45 pm - 11:35 pmMRY-ORD
8h 50m2 stops
American Airlines Logo
10:24 am - 6:41 pmORD-MRY
10h 17m2 stops
$309American Airlines
Find Deal
Wed, Dec 3 - Tue, Dec 9
United Airlines Logo
7:00 am - 4:55 pmMRY-ORD
7h 55m1 stop
United Airlines Logo
12:55 pm - 5:57 pmORD-MRY
7h 02m1 stop
$334United Airlines
Find Deal
Wed, Mar 11 - Tue, Mar 24
American Airlines Logo
12:45 pm - 11:35 pmMRY-ORD
8h 50m2 stops
American Airlines Logo
8:11 am - 3:52 pmORD-MRY
9h 41m2 stops
$344American Airlines
Find Deal
Wed, Dec 3 - Tue, Dec 9
United Airlines Logo
10:27 am - 7:30 pmMRY-ORD
7h 03m1 stop
United Airlines Logo
3:46 pm - 9:36 pmORD-MRY
7h 50m1 stop
$424United Airlines
Find Deal
Thu, Nov 27 - Wed, Dec 3

Alaska Airlines flights from Monterey to Chicago

Our best Alaska Airlines deals on Monterey to Chicago flight tickets
Alaska Airlines
Dec 3
MRY6:00 amMonterey Regional
6h 09m
1 stop
ORD2:09 pmChicago O'Hare Intl
Dec 9
ORD3:05 pmChicago O'Hare Intl
10h 24m
1 stop
MRY11:29 pmMonterey Regional
$288
Find similar
Alaska Airlines
Dec 3
MRY6:00 amMonterey Regional
6h 09m
1 stop
ORD2:09 pmChicago O'Hare Intl
Dec 9
ORD8:55 amChicago O'Hare Intl
16h 34m
1 stop
MRY11:29 pmMonterey Regional
$298
Find similar
Alaska Airlines
Dec 3
MRY6:00 amMonterey Regional
6h 09m
1 stop
ORD2:09 pmChicago O'Hare Intl
Dec 9
ORD8:00 amChicago O'Hare Intl
17h 29m
2 stops
MRY11:29 pmMonterey Regional
$304
Find similar

American Airlines flights from Monterey to Chicago

Our best American Airlines deals on Monterey to Chicago flight tickets
American Airlines
Dec 3
MRY12:45 pmMonterey Regional
8h 50m
2 stops
ORD11:35 pmChicago O'Hare Intl
Dec 9
ORD10:24 amChicago O'Hare Intl
10h 17m
2 stops
MRY6:41 pmMonterey Regional
$309
Find similar
American Airlines
Dec 3
MRY12:45 pmMonterey Regional
8h 50m
2 stops
ORD11:35 pmChicago O'Hare Intl
Dec 9
ORD8:11 amChicago O'Hare Intl
9h 41m
2 stops
MRY3:52 pmMonterey Regional
$344
Find similar
American Airlines
Dec 3
MRY12:45 pmMonterey Regional
8h 50m
2 stops
ORD11:35 pmChicago O'Hare Intl
Dec 8
ORD5:00 amChicago O'Hare Intl
9h 15m
1 stop
MRY12:15 pmMonterey Regional
$382
Find similar

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 November 3, 2025.
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

MontereyChicago

MRY - ORD

MRYORD

Monterey Regional

Fri 12/12

10:06 pm-12:13 am

2 stops48h 07m

Chicago O'Hare Intl

Thu 12/18

3:27 pm-5:12 pm

1 stop27h 45m

$240

MontereyChicago

MRY - ORD

MRYORD

Monterey Regional

Wed 12/3

6:00 am-2:09 pm

1 stop6h 09m

Chicago O'Hare Intl

Tue 12/9

3:05 pm-11:29 pm

1 stop10h 24m

$288

MontereyChicago

MRY - ORD

MRYORD

Monterey Regional

Fri 12/12

10:06 pm-6:05 am

2 stops29h 59m

Chicago O'Hare Intl

Mon 12/15

12:59 pm-9:16 pm

1 stop10h 17m

$293

MontereyChicago

MRY - ORD

MRYORD

Monterey Regional

Wed 12/3

6:00 am-2:09 pm

1 stop6h 09m

Chicago O'Hare Intl

Tue 12/9

8:55 am-11:29 pm

1 stop16h 34m

$298

MontereyChicago

MRY - ORD

MRYORD

Monterey Regional

Wed 12/3

6:00 am-2:09 pm

1 stop6h 09m

Chicago O'Hare Intl

Tue 12/9

8:00 am-11:29 pm

2 stops17h 29m

$304

MontereyChicago

MRY - ORD

MRYORD

Monterey Regional

Tue 12/9

6:00 am-2:09 pm

1 stop6h 09m

Chicago O'Hare Intl

Tue 12/16

3:05 pm-11:29 pm

1 stop10h 24m

$308

MontereyChicago

MRY - ORD

MRYORD

Monterey Regional

Wed 12/3

12:45 pm-11:35 pm

2 stops8h 50m

Chicago O'Hare Intl

Tue 12/9

10:24 am-6:41 pm

2 stops10h 17m

$309

MontereyChicago

MRY - ORD

MRYORD

Monterey Regional

Wed 3/11

7:00 am-4:55 pm

1 stop7h 55m

Chicago O'Hare Intl

Tue 3/24

12:55 pm-5:57 pm

1 stop7h 02m

$334

MontereyChicago

MRY - ORD

MRYORD

Monterey Regional

Wed 12/3

12:45 pm-11:35 pm

2 stops8h 50m

Chicago O'Hare Intl

Tue 12/9

8:11 am-3:52 pm

2 stops9h 41m

$344

MontereyChicago

MRY - ORD

MRYORD

Monterey Regional

Thu 11/27

10:27 am-7:30 pm

1 stop7h 03m

Chicago O'Hare Intl

Wed 12/3

3:46 pm-9:36 pm

1 stop7h 50m

$424

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 August is, on average, the cheapest month to fly to Chicago from Monterey, with most prices found around $326. If you’re not able to fly to Chicago in August, then February is your next best option. Flight prices from Monterey to Chicago during February average around $328.

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 $405. 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 $506.

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 afternoon. Flights from Monterey to Chicago during this time can be as low as $412. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $467.

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

Direct flights

None
There are no direct flights from Monterey to Chicago. There are no popular flight routes from Monterey to Chicago.
Search flight deals

  • How far is Monterey Regional to Chicago by plane?

    Chicago is 1855.5 mi away from Monterey Regional. 5h 59m 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 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 $268Free CancellationRating
7.2
11,038 reviews
Search American Airlines flights
United AirlinesPriceFrom $443Free CancellationRating
7.4
8,997 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
Benton Harbor
Saint Joseph
Portage
Lansing
Schererville
Valparaiso
Crown Point
Munster
Chesterton
Monticello
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