Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Monterey to Chicago from $145

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 6/16. 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

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Find the cheapest flights from Monterey to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Alaska Airlines Logo
6:00 am - 2:58 pm
MRY
-
ORD
6h 58m
1 stop
Alaska Airlines Logo
3:07 pm - 11:43 pm
ORD
-
MRY
10h 36m
1 stop
$223Alaska Airlines
Thu, Mar 5 - Thu, Mar 12
Alaska Airlines Logo
6:00 am - 2:58 pm
MRY
-
ORD
6h 58m
1 stop
Alaska Airlines Logo
3:07 pm - 11:43 pm
ORD
-
MRY
10h 36m
1 stop
$283Alaska Airlines
Mon, Mar 9 - Wed, Mar 11
United Airlines Logo
7:00 pm - 5:07 am
MRY
-
ORD
8h 07m
1 stop
United Airlines Logo
12:54 pm - 6:01 pm
ORD
-
MRY
7h 07m
1 stop
$289United Airlines
Thu, Mar 5 - Thu, Mar 12
Alaska Airlines Logo
6:00 am - 2:58 pm
MRY
-
ORD
6h 58m
1 stop
Alaska Airlines Logo
3:07 pm - 11:43 pm
ORD
-
MRY
10h 36m
1 stop
$293Alaska Airlines
Mon, Mar 9 - Thu, Mar 12
Alaska Airlines Logo
6:00 am - 2:58 pm
MRY
-
ORD
6h 58m
1 stop
Alaska Airlines Logo
8:20 am - 2:06 pm
ORD
-
MRY
7h 46m
1 stop
$303Alaska Airlines
Sat, Mar 7 - Tue, Mar 10
Alaska Airlines Logo
6:00 am - 2:58 pm
MRY
-
ORD
6h 58m
1 stop
Alaska Airlines Logo
7:40 am - 11:43 pm
ORD
-
MRY
18h 03m
1 stop
$313Alaska Airlines
Mon, Mar 9 - Fri, Mar 13
American Airlines Logo
7:22 pm - 5:21 am
MRY
-
ORD
7h 59m
1 stop
American Airlines Logo
5:00 am - 12:12 pm
ORD
-
MRY
9h 12m
1 stop
$323American Airlines
Fri, May 1 - Wed, May 6
United Airlines Logo
6:03 pm - 5:12 am
MRY
-
ORD
9h 09m
1 stop
United Airlines Logo
2:33 pm - 9:30 pm
ORD
-
MRY
8h 57m
1 stop
$324United Airlines
Fri, Feb 20 - Fri, Feb 27
Alaska Airlines Logo
6:00 am - 2:58 pm
MRY
-
ORD
6h 58m
1 stop
Alaska Airlines Logo
8:20 am - 11:43 pm
ORD
-
MRY
17h 23m
1 stop
$333Alaska Airlines
Wed, Feb 25 - Sun, Mar 8
Alaska Airlines Logo
6:00 am - 2:58 pm
MRY
-
ORD
6h 58m
1 stop
Alaska Airlines Logo
3:07 pm - 11:43 pm
ORD
-
MRY
10h 36m
1 stop
$335Alaska Airlines
Wed, Feb 18 - Wed, Feb 25

American Airlines flights from Monterey to Chicago

Our best American Airlines deals on Monterey to Chicago flight tickets
American Airlines
May 1
MRY7:22 pmMonterey Regional
7h 59m
1 stop
ORD5:21 amChicago O'Hare Intl
May 6
ORD5:00 amChicago O'Hare Intl
9h 12m
1 stop
MRY12:12 pmMonterey Regional
$323
American Airlines
Jun 27
MRY7:12 pmMonterey Regional
8h 57m
1 stop
ORD6:09 amChicago O'Hare Intl
Jul 2
ORD2:21 pmChicago O'Hare Intl
6h 10m
1 stop
MRY6:31 pmMonterey Regional
$357
American Airlines
Jun 28
MRY7:12 pmMonterey Regional
8h 57m
1 stop
ORD6:09 amChicago O'Hare Intl
Jul 3
ORD2:21 pmChicago O'Hare Intl
6h 10m
1 stop
MRY6:31 pmMonterey Regional
$418

United Airlines flights from Monterey to Chicago

Our best United Airlines deals on Monterey to Chicago flight tickets
United Airlines
Mar 5
MRY7:00 pmMonterey Regional
8h 07m
1 stop
ORD5:07 amChicago O'Hare Intl
Mar 12
ORD12:54 pmChicago O'Hare Intl
7h 07m
1 stop
MRY6:01 pmMonterey Regional
$289
United Airlines
Feb 20
MRY6:03 pmMonterey Regional
9h 09m
1 stop
ORD5:12 amChicago O'Hare Intl
Feb 27
ORD2:33 pmChicago O'Hare Intl
8h 57m
1 stop
MRY9:30 pmMonterey Regional
$324
United Airlines
Feb 19
MRY6:40 amMonterey Regional
6h 05m
1 stop
ORD2:45 pmChicago O'Hare Intl
Feb 23
ORD4:00 pmChicago O'Hare Intl
7h 30m
1 stop
MRY9:30 pmMonterey Regional
$359

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 February 7, 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

MontereyChicago

MRY - ORD

MRYORD

Monterey Regional

Thu 3/5

6:00 am-2:58 pm

1 stop6h 58m

Chicago O'Hare Intl

Thu 3/12

3:07 pm-11:43 pm

1 stop10h 36m

$223

MontereyChicago

MRY - ORD

MRYORD

Monterey Regional

Mon 3/9

6:00 am-2:58 pm

1 stop6h 58m

Chicago O'Hare Intl

Wed 3/11

3:07 pm-11:43 pm

1 stop10h 36m

$283

MontereyChicago

MRY - ORD

MRYORD

Monterey Regional

Thu 3/5

7:00 pm-5:07 am

1 stop8h 07m

Chicago O'Hare Intl

Thu 3/12

12:54 pm-6:01 pm

1 stop7h 07m

$289

MontereyChicago

MRY - ORD

MRYORD

Monterey Regional

Mon 3/9

6:00 am-2:58 pm

1 stop6h 58m

Chicago O'Hare Intl

Thu 3/12

3:07 pm-11:43 pm

1 stop10h 36m

$293

MontereyChicago

MRY - ORD

MRYORD

Monterey Regional

Sat 3/7

6:00 am-2:58 pm

1 stop6h 58m

Chicago O'Hare Intl

Tue 3/10

8:20 am-2:06 pm

1 stop7h 46m

$303

MontereyChicago

MRY - ORD

MRYORD

Monterey Regional

Mon 3/9

6:00 am-2:58 pm

1 stop6h 58m

Chicago O'Hare Intl

Fri 3/13

7:40 am-11:43 pm

1 stop18h 03m

$313

MontereyChicago

MRY - ORD

MRYORD

Monterey Regional

Fri 5/1

7:22 pm-5:21 am

1 stop7h 59m

Chicago O'Hare Intl

Wed 5/6

5:00 am-12:12 pm

1 stop9h 12m

$323

MontereyChicago

MRY - ORD

MRYORD

Monterey Regional

Fri 2/20

6:03 pm-5:12 am

1 stop9h 09m

Chicago O'Hare Intl

Fri 2/27

2:33 pm-9:30 pm

1 stop8h 57m

$324

MontereyChicago

MRY - ORD

MRYORD

Monterey Regional

Wed 2/25

6:00 am-2:58 pm

1 stop6h 58m

Chicago O'Hare Intl

Sun 3/8

8:20 am-11:43 pm

1 stop17h 23m

$333

MontereyChicago

MRY - ORD

MRYORD

Monterey Regional

Wed 2/18

6:00 am-2:58 pm

1 stop6h 58m

Chicago O'Hare Intl

Wed 2/25

3:07 pm-11:43 pm

1 stop10h 36m

$335

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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 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 $406. 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 $494.

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 $409. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $457.

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

Sun

Airports in Chicago

3 airports
The fastest flight from Monterey to Chicago takes 4h 50m
Direct flights go from Monterey to Chicago on Sunday. There are no airlines offering direct flights.
There are 3 airports in Chicago. From Monterey there are direct flights to Chicago O'Hare Intl (ORD).
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
11,247 reviews
Search American Airlines flights
United AirlinesPriceFrom $276Free CancellationRating
7.4
9,245 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
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.

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Mon 3/9
Mon 3/16
By creating a price alert you accept our terms of use and privacy policy.

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