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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 3/2. 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
0 bags

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Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
9:45 pm - 2:17 pm
MRY
-
ORD
14h 32m2 stops
Multiple Airlines Logo
9:38 pm - 8:55 pm
ORD
-
MRY
25h 17m1 stop
$239Multiple Airlines
Fri, Jan 30 - Sun, Feb 1
Alaska Airlines Logo
6:00 am - 2:58 pm
MRY
-
ORD
6h 58m1 stop
Alaska Airlines Logo
8:20 am - 2:06 pm
ORD
-
MRY
7h 46m1 stop
$279Alaska Airlines
Sat, Feb 14 - Wed, Feb 18
Alaska Airlines Logo
3:14 pm - 11:37 pm
MRY
-
ORD
6h 23m1 stop
Alaska Airlines Logo
9:00 am - 2:37 pm
ORD
-
MRY
7h 37m1 stop
$289Alaska Airlines
Sat, Jan 31 - Mon, Feb 2
Alaska Airlines Logo
3:14 pm - 11:37 pm
MRY
-
ORD
6h 23m1 stop
Alaska Airlines Logo
8:00 am - 11:26 pm
ORD
-
MRY
17h 26m2 stops
$291Alaska Airlines
Sat, Jan 31 - Sun, Feb 1
Alaska Airlines Logo
3:14 pm - 11:37 pm
MRY
-
ORD
6h 23m1 stop
Alaska Airlines Logo
9:00 am - 2:37 pm
ORD
-
MRY
7h 37m1 stop
$298Alaska Airlines
Thu, Jan 15 - Sun, Jan 18
United Airlines Logo
5:00 am - 1:24 pm
MRY
-
ORD
6h 24m1 stop
United Airlines Logo
2:40 pm - 9:18 pm
ORD
-
MRY
8h 38m1 stop
$299United Airlines
Mon, Jan 12 - Fri, Jan 16
United Airlines Logo
12:35 pm - 9:15 pm
MRY
-
ORD
6h 40m1 stop
United Airlines Logo
7:10 am - 11:52 am
ORD
-
MRY
6h 42m1 stop
$317United Airlines
Fri, Jan 30 - Sun, Feb 1
Alaska Airlines Logo
6:00 am - 2:58 pm
MRY
-
ORD
6h 58m1 stop
Alaska Airlines Logo
3:07 pm - 11:43 pm
ORD
-
MRY
10h 36m1 stop
$320Alaska Airlines
Mon, Feb 23 - Sat, Feb 28
Alaska Airlines Logo
6:00 am - 11:37 pm
MRY
-
ORD
15h 37m1 stop
Alaska Airlines Logo
9:00 am - 2:37 pm
ORD
-
MRY
7h 37m1 stop
$321Alaska Airlines
Fri, Jan 30 - Sat, Jan 31
Alaska Airlines Logo
6:00 am - 2:58 pm
MRY
-
ORD
6h 58m1 stop
Alaska Airlines Logo
8:20 am - 2:07 pm
ORD
-
MRY
7h 47m1 stop
$324Alaska Airlines
Tue, Mar 10 - Tue, Mar 24

Alaska Airlines flights from Monterey to Chicago

Our best Alaska Airlines deals on Monterey to Chicago flight tickets
Alaska Airlines
Feb 14
MRY6:00 amMonterey Regional
6h 58m
1 stop
ORD2:58 pmChicago O'Hare Intl
Feb 18
ORD8:20 amChicago O'Hare Intl
7h 46m
1 stop
MRY2:06 pmMonterey Regional
$279
Find similar
Alaska Airlines
Jan 31
MRY3:14 pmMonterey Regional
6h 23m
1 stop
ORD11:37 pmChicago O'Hare Intl
Feb 1
ORD8:00 amChicago O'Hare Intl
17h 26m
2 stops
MRY11:26 pmMonterey Regional
$291
Find similar
Alaska Airlines
Jan 15
MRY3:14 pmMonterey Regional
6h 23m
1 stop
ORD11:37 pmChicago O'Hare Intl
Jan 18
ORD3:44 pmChicago O'Hare Intl
9h 42m
1 stop
MRY11:26 pmMonterey Regional
$298
Find similar

United Airlines flights from Monterey to Chicago

Our best United Airlines deals on Monterey to Chicago flight tickets
United Airlines
Jan 31
MRY5:00 amMonterey Regional
6h 22m
1 stop
ORD1:22 pmChicago O'Hare Intl
Feb 1
ORD7:10 amChicago O'Hare Intl
6h 42m
1 stop
MRY11:52 amMonterey Regional
$289
Find similar
United Airlines
Jan 12
MRY5:00 amMonterey Regional
6h 24m
1 stop
ORD1:24 pmChicago O'Hare Intl
Jan 16
ORD2:40 pmChicago O'Hare Intl
8h 38m
1 stop
MRY9:18 pmMonterey Regional
$299
Find similar
United Airlines
Jan 30
MRY12:35 pmMonterey Regional
6h 40m
1 stop
ORD9:15 pmChicago O'Hare Intl
Feb 1
ORD7:10 amChicago O'Hare Intl
6h 42m
1 stop
MRY11:52 amMonterey Regional
$317
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 December 22, 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 1/30

9:45 pm-2:17 pm

2 stops14h 32m

Chicago O'Hare Intl

Sun 2/1

9:38 pm-8:55 pm

1 stop25h 17m

$239

MontereyChicago

MRY - ORD

MRYORD

Monterey Regional

Sat 2/14

6:00 am-2:58 pm

1 stop6h 58m

Chicago O'Hare Intl

Wed 2/18

8:20 am-2:06 pm

1 stop7h 46m

$279

MontereyChicago

MRY - ORD

MRYORD

Monterey Regional

Sat 1/31

3:14 pm-11:37 pm

1 stop6h 23m

Chicago O'Hare Intl

Mon 2/2

9:00 am-2:37 pm

1 stop7h 37m

$289

MontereyChicago

MRY - ORD

MRYORD

Monterey Regional

Sat 1/31

3:14 pm-11:37 pm

1 stop6h 23m

Chicago O'Hare Intl

Sun 2/1

8:00 am-11:26 pm

2 stops17h 26m

$291

MontereyChicago

MRY - ORD

MRYORD

Monterey Regional

Thu 1/15

3:14 pm-11:37 pm

1 stop6h 23m

Chicago O'Hare Intl

Sun 1/18

9:00 am-2:37 pm

1 stop7h 37m

$298

MontereyChicago

MRY - ORD

MRYORD

Monterey Regional

Mon 1/12

5:00 am-1:24 pm

1 stop6h 24m

Chicago O'Hare Intl

Fri 1/16

2:40 pm-9:18 pm

1 stop8h 38m

$299

MontereyChicago

MRY - ORD

MRYORD

Monterey Regional

Fri 1/30

12:35 pm-9:15 pm

1 stop6h 40m

Chicago O'Hare Intl

Sun 2/1

7:10 am-11:52 am

1 stop6h 42m

$317

MontereyChicago

MRY - ORD

MRYORD

Monterey Regional

Mon 2/23

6:00 am-2:58 pm

1 stop6h 58m

Chicago O'Hare Intl

Sat 2/28

3:07 pm-11:43 pm

1 stop10h 36m

$320

MontereyChicago

MRY - ORD

MRYORD

Monterey Regional

Fri 1/30

6:00 am-11:37 pm

1 stop15h 37m

Chicago O'Hare Intl

Sat 1/31

9:00 am-2:37 pm

1 stop7h 37m

$321

MontereyChicago

MRY - ORD

MRYORD

Monterey Regional

Tue 3/10

6:00 am-2:58 pm

1 stop6h 58m

Chicago O'Hare Intl

Tue 3/24

8:20 am-2:07 pm

1 stop7h 47m

$324

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 typical price of a round-trip flight between Monterey and Chicago?

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 August is your next best option. Flight prices from Monterey to Chicago during August average around $326.

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 $498.

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 $410. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $461.

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

4h 50m

Direct flights

None
The fastest flight from Monterey to Chicago takes 4h 50m
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. 4h 50m 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 $268Free CancellationRating
7.2
11,051 reviews
Search American Airlines flights
United AirlinesPriceFrom $276Free CancellationRating
7.4
9,102 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
Valparaiso
Schererville
Munster
Crown Point
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