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Cheap flights from Monterey to Chicago from $136

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 10/17. 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

Alaska Airlines Logo
2:40 pm - 11:10 pmMRY-ORD
6h 30m1 stop
Alaska Airlines Logo
7:45 am - 1:35 pmORD-MRY
7h 50m1 stop
$259Alaska Airlines
Find Deal
Thu, Jan 22 - Mon, Jan 26
Alaska Airlines Logo
6:00 am - 2:50 pmMRY-ORD
6h 50m1 stop
Alaska Airlines Logo
3:50 pm - 11:37 pmORD-MRY
9h 47m1 stop
$277Alaska Airlines
Find Deal
Tue, Oct 14 - Fri, Oct 17
Alaska Airlines Logo
6:00 am - 5:01 amMRY-ORD
21h 01m2 stops
Alaska Airlines Logo
3:50 pm - 10:51 pmORD-MRY
9h 01m1 stop
$282Alaska Airlines
Find Deal
Wed, Oct 15 - Wed, Oct 22
Alaska Airlines Logo
6:00 am - 10:30 pmMRY-ORD
14h 30m2 stops
Alaska Airlines Logo
6:00 am - 11:34 pmORD-MRY
19h 34m2 stops
$287Alaska Airlines
Find Deal
Wed, Dec 10 - Sun, Dec 14
American Airlines Logo
12:30 pm - 11:53 pmMRY-ORD
9h 23m1 stop
American Airlines Logo
5:18 am - 11:41 amORD-MRY
8h 23m1 stop
$322American Airlines
Find Deal
Thu, Oct 30 - Sun, Nov 2
Alaska Airlines Logo
11:14 am - 9:40 pmMRY-ORD
8h 26m1 stop
Alaska Airlines Logo
8:59 pm - 11:32 pmORD-MRY
28h 33m1 stop
$330Alaska Airlines
Find Deal
Fri, Oct 31 - Sun, Nov 2
United Airlines Logo
12:35 pm - 9:30 pmMRY-ORD
6h 55m1 stop
United Airlines Logo
6:15 am - 10:31 amORD-MRY
6h 16m1 stop
$364United Airlines
Find Deal
Sat, Oct 4 - Sat, Oct 11
United Airlines Logo
5:10 am - 1:12 pmMRY-ORD
6h 02m1 stop
United Airlines Logo
6:15 am - 10:33 amORD-MRY
6h 18m1 stop
$367United Airlines
Find Deal
Sat, Oct 18 - Sun, Oct 19
Hawaiian Airlines Logo
7:56 pm - 7:03 amMRY-ORD
9h 07m1 stop
Hawaiian Airlines Logo
3:50 pm - 10:51 pmORD-MRY
9h 01m1 stop
$450Hawaiian Airlines
Find Deal
Tue, Sep 30 - Sat, Oct 4
American Airlines Logo
12:46 pm - 11:59 pmMRY-ORD
9h 13m2 stops
American Airlines Logo
7:34 am - 12:16 pmORD-MRY
6h 42m1 stop
$456American Airlines
Find Deal
Tue, Sep 30 - Sat, Oct 4

American Airlines flights from Monterey to Chicago

Our best American Airlines deals on Monterey to Chicago flight tickets
American Airlines
Oct 30
MRY12:30 pmMonterey Regional
9h 23m
1 stop
ORD11:53 pmChicago O'Hare Intl
Nov 2
ORD5:18 amChicago O'Hare Intl
8h 23m
1 stop
MRY11:41 amMonterey Regional
$322
Find similar
American Airlines
Sep 30
MRY12:46 pmMonterey Regional
9h 13m
2 stops
ORD11:59 pmChicago O'Hare Intl
Oct 4
ORD7:34 amChicago O'Hare Intl
6h 42m
1 stop
MRY12:16 pmMonterey Regional
$456
Find similar
American Airlines
Oct 10
MRY4:07 pmMonterey Regional
6h 23m
1 stop
ORD12:30 amChicago O'Hare Intl
Oct 12
ORD3:22 pmChicago O'Hare Intl
9h 07m
1 stop
MRY10:29 pmMonterey Regional
$457
Find similar

United Airlines flights from Monterey to Chicago

Our best United Airlines deals on Monterey to Chicago flight tickets
United Airlines
Oct 4
MRY12:35 pmMonterey Regional
6h 55m
1 stop
ORD9:30 pmChicago O'Hare Intl
Oct 11
ORD6:15 amChicago O'Hare Intl
6h 16m
1 stop
MRY10:31 amMonterey Regional
$364
Find similar
United Airlines
Oct 18
MRY5:10 amMonterey Regional
6h 02m
1 stop
ORD1:12 pmChicago O'Hare Intl
Oct 19
ORD6:15 amChicago O'Hare Intl
6h 18m
1 stop
MRY10:33 amMonterey Regional
$367
Find similar
United Airlines
Oct 16
MRY5:10 amMonterey Regional
11h 15m
1 stop
ORD6:25 pmChicago O'Hare Intl
Oct 19
ORD6:15 amChicago O'Hare Intl
6h 18m
1 stop
MRY10:33 amMonterey Regional
$463
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 September 17, 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

Thu 1/22

2:40 pm-11:10 pm

1 stop6h 30m

Chicago O'Hare Intl

Mon 1/26

7:45 am-1:35 pm

1 stop7h 50m

$259

MontereyChicago

MRY - ORD

MRYORD

Monterey Regional

Tue 10/14

6:00 am-2:50 pm

1 stop6h 50m

Chicago O'Hare Intl

Fri 10/17

3:50 pm-11:37 pm

1 stop9h 47m

$277

MontereyChicago

MRY - ORD

MRYORD

Monterey Regional

Wed 10/15

6:00 am-5:01 am

2 stops21h 01m

Chicago O'Hare Intl

Wed 10/22

3:50 pm-10:51 pm

1 stop9h 01m

$282

MontereyChicago

MRY - ORD

MRYORD

Monterey Regional

Wed 12/10

6:00 am-10:30 pm

2 stops14h 30m

Chicago O'Hare Intl

Sun 12/14

6:00 am-11:34 pm

2 stops19h 34m

$287

MontereyChicago

MRY - ORD

MRYORD

Monterey Regional

Thu 10/30

12:30 pm-11:53 pm

1 stop9h 23m

Chicago O'Hare Intl

Sun 11/2

5:18 am-11:41 am

1 stop8h 23m

$322

MontereyChicago

MRY - ORD

MRYORD

Monterey Regional

Fri 10/31

11:14 am-9:40 pm

1 stop8h 26m

Chicago O'Hare Intl

Sun 11/2

8:59 pm-11:32 pm

1 stop28h 33m

$330

MontereyChicago

MRY - ORD

MRYORD

Monterey Regional

Sat 10/4

12:35 pm-9:30 pm

1 stop6h 55m

Chicago O'Hare Intl

Sat 10/11

6:15 am-10:31 am

1 stop6h 16m

$364

MontereyChicago

MRY - ORD

MRYORD

Monterey Regional

Sat 10/18

5:10 am-1:12 pm

1 stop6h 02m

Chicago O'Hare Intl

Sun 10/19

6:15 am-10:33 am

1 stop6h 18m

$367

MontereyChicago

MRY - ORD

MRYORD

Monterey Regional

Tue 9/30

7:56 pm-7:03 am

1 stop9h 07m

Chicago O'Hare Intl

Sat 10/4

3:50 pm-10:51 pm

1 stop9h 01m

$450

MontereyChicago

MRY - ORD

MRYORD

Monterey Regional

Tue 9/30

12:46 pm-11:59 pm

2 stops9h 13m

Chicago O'Hare Intl

Sat 10/4

7:34 am-12:16 pm

1 stop6h 42m

$456

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 $403. 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 $514.

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 $413. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $466.

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. 6h 02m 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
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $542Free CancellationRating
7.4
8,926 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
Lansing
Portage
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