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Cheap flights from Chicago to San Francisco from $157

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to San Francisco departing on 6/19. 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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Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
7:15 am - 9:10 pm
ORD
-
MRY
15h 55m
1 stop
Multiple Airlines Logo
10:04 pm - 5:28 am
MRY
-
ORD
29h 24m
1 stop
$280Multiple Airlines
Fri, Jul 31 - Mon, Aug 10
Multiple Airlines Logo
7:15 am - 9:14 pm
ORD
-
MRY
15h 59m
1 stop
Multiple Airlines Logo
10:04 pm - 5:28 am
MRY
-
ORD
29h 24m
1 stop
$288Multiple Airlines
Fri, Aug 7 - Mon, Aug 10
Multiple Airlines Logo
7:15 am - 9:10 pm
ORD
-
MRY
15h 55m
1 stop
Multiple Airlines Logo
10:04 pm - 5:28 am
MRY
-
ORD
29h 24m
1 stop
$296Multiple Airlines
Mon, Aug 3 - Mon, Aug 10
Alaska Airlines Logo
9:00 am - 2:18 pm
ORD
-
MRY
7h 18m
1 stop
Alaska Airlines Logo
2:55 pm - 11:55 pm
MRY
-
ORD
7h 00m
1 stop
$313Alaska Airlines
Sat, May 23 - Sat, Jun 6
Multiple Airlines Logo
5:46 pm - 9:14 pm
ORD
-
MRY
29h 28m
2 stops
Multiple Airlines Logo
10:04 pm - 5:28 am
MRY
-
ORD
29h 24m
1 stop
$317Multiple Airlines
Thu, Aug 6 - Mon, Aug 10
United Airlines Logo
9:05 am - 11:54 am
ORD
-
MRY
4h 49mnonstop
United Airlines Logo
2:05 pm - 8:39 pm
MRY
-
ORD
4h 34mnonstop
$329United Airlines
Sat, Jun 27 - Sat, Jul 11
Alaska Airlines Logo
2:10 pm - 11:31 pm
ORD
-
MRY
11h 21m
1 stop
Alaska Airlines Logo
2:55 pm - 1:14 pm
MRY
-
ORD
20h 19m
1 stop
$331Alaska Airlines
Thu, May 28 - Tue, Jun 2
United Airlines Logo
1:00 pm - 8:36 pm
ORD
-
MRY
9h 36m
1 stop
United Airlines Logo
2:05 pm - 8:39 pm
MRY
-
ORD
4h 34mnonstop
$335United Airlines
Wed, Jul 15 - Sat, Jul 18
Alaska Airlines Logo
7:40 am - 11:31 pm
ORD
-
MRY
17h 51m
2 stops
Alaska Airlines Logo
2:55 pm - 1:14 pm
MRY
-
ORD
20h 19m
1 stop
$336Alaska Airlines
Thu, May 28 - Tue, Jun 2
United Airlines Logo
9:05 am - 11:54 am
ORD
-
MRY
4h 49mnonstop
United Airlines Logo
1:54 pm - 1:15 am
MRY
-
ORD
9h 21m
1 stop
$339United Airlines
Sat, Jun 27 - Tue, Jun 30

Alaska Airlines flights from Chicago to Monterey

Our best Alaska Airlines deals on Chicago to Monterey flight tickets
Alaska Airlines
May 23
ORD9:00 amChicago O'Hare Intl
7h 18m
1 stop
MRY2:18 pmMonterey Regional
May 30
MRY2:55 pmMonterey Regional
7h 00m
1 stop
ORD11:55 pmChicago O'Hare Intl
$313
Alaska Airlines
May 28
ORD2:10 pmChicago O'Hare Intl
11h 21m
1 stop
MRY11:31 pmMonterey Regional
Jun 2
MRY2:55 pmMonterey Regional
20h 19m
1 stop
ORD1:14 pmChicago O'Hare Intl
$331
Alaska Airlines
May 28
ORD7:40 amChicago O'Hare Intl
17h 51m
2 stops
MRY11:31 pmMonterey Regional
Jun 2
MRY2:55 pmMonterey Regional
20h 19m
1 stop
ORD1:14 pmChicago O'Hare Intl
$336

United Airlines flights from Chicago to Monterey

Our best United Airlines deals on Chicago to Monterey flight tickets
United Airlines
Jul 15
ORD1:00 pmChicago O'Hare Intl
9h 36m
1 stop
MRY8:36 pmMonterey Regional
Jul 18
MRY2:05 pmMonterey Regional
4h 34m
ORD8:39 pmChicago O'Hare Intl
$335
United Airlines
May 27
ORD3:47 pmChicago O'Hare Intl
6h 49m
1 stop
MRY8:36 pmMonterey Regional
May 30
MRY2:06 pmMonterey Regional
4h 34m
ORD8:40 pmChicago O'Hare Intl
$339
United Airlines
Jun 8
ORD3:47 pmChicago O'Hare Intl
6h 22m
1 stop
MRY8:09 pmMonterey Regional
Jun 13
MRY2:06 pmMonterey Regional
4h 34m
ORD8:40 pmChicago O'Hare Intl
$368

momondo Fare Finder

 
Customize your flight search to find flights from Chicago to Monterey 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 May 4, 2026.
Use the filters below to find and compare flights from Chicago to Monterey that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoMonterey

ORD - MRY

ORDMRY

Chicago O'Hare Intl

Fri 7/31

7:15 am-9:10 pm

1 stop15h 55m

Monterey Regional

Mon 8/10

10:04 pm-5:28 am

1 stop29h 24m

$280

ChicagoMonterey

ORD - MRY

ORDMRY

Chicago O'Hare Intl

Fri 8/7

7:15 am-9:14 pm

1 stop15h 59m

Monterey Regional

Mon 8/10

10:04 pm-5:28 am

1 stop29h 24m

$288

ChicagoMonterey

ORD - MRY

ORDMRY

Chicago O'Hare Intl

Mon 8/3

7:15 am-9:10 pm

1 stop15h 55m

Monterey Regional

Mon 8/10

10:04 pm-5:28 am

1 stop29h 24m

$296

ChicagoMonterey

ORD - MRY

ORDMRY

Chicago O'Hare Intl

Sat 5/23

9:00 am-2:18 pm

1 stop7h 18m

Monterey Regional

Sat 6/6

2:55 pm-11:55 pm

1 stop7h 00m

$313

ChicagoMonterey

ORD - MRY

ORDMRY

Chicago O'Hare Intl

Thu 8/6

5:46 pm-9:14 pm

2 stops29h 28m

Monterey Regional

Mon 8/10

10:04 pm-5:28 am

1 stop29h 24m

$317
Quickest round-trip

ChicagoMonterey

ORD - MRY

ORDMRY

Chicago O'Hare Intl

Sat 6/27

9:05 am-11:54 am

Nonstop4h 49m

Monterey Regional

Sat 7/11

2:05 pm-8:39 pm

Nonstop4h 34m

$329

ChicagoMonterey

ORD - MRY

ORDMRY

Chicago O'Hare Intl

Thu 5/28

2:10 pm-11:31 pm

1 stop11h 21m

Monterey Regional

Tue 6/2

2:55 pm-1:14 pm

1 stop20h 19m

$331

ChicagoMonterey

ORD - MRY

ORDMRY

Chicago O'Hare Intl

Wed 7/15

1:00 pm-8:36 pm

1 stop9h 36m

Monterey Regional

Sat 7/18

2:05 pm-8:39 pm

Nonstop4h 34m

$335

ChicagoMonterey

ORD - MRY

ORDMRY

Chicago O'Hare Intl

Thu 5/28

7:40 am-11:31 pm

2 stops17h 51m

Monterey Regional

Tue 6/2

2:55 pm-1:14 pm

1 stop20h 19m

$336

ChicagoMonterey

ORD - MRY

ORDMRY

Chicago O'Hare Intl

Sat 6/27

9:05 am-11:54 am

Nonstop4h 49m

Monterey Regional

Tue 6/30

1:54 pm-1:15 am

1 stop9h 21m

$339

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 San Francisco from

How to get the cheapest flight ticket from Chicago to Monterey

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 Chicago and Monterey?

What is the cheapest month to fly to Monterey?

The month of January is, on average, the cheapest month to fly to Monterey from Chicago, with most prices found around $260. If you’re not able to fly to Monterey in January, then October is your next best option. Flight prices from Chicago to Monterey during October average around $268.

What is the cheapest Chicago to Monterey Regional flight route?

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

How have Chicago to Monterey flight prices changed over time?

When to book flights from Chicago to Monterey

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

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

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

Fastest flight time

4h 49m

Direct flights

Sun

Airports in Monterey

1 airport
The fastest flight from Chicago to Monterey takes 4h 49m
Direct flights go from Chicago to Monterey on Sunday. There are no airlines offering direct flights.
There is 1 airport in Monterey. From Chicago there are direct flights to Monterey Regional (MRY).
Search flight deals

Frequently asked questions about flying from Chicago to Monterey

  • How far is Chicago to Monterey Regional by plane?

    Monterey Regional is 1855.5 mi away from Chicago. A reasonable flight in good conditions will take 4h 49m.

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

    Prices for flights from Chicago to Monterey Regional Airport are refreshed on a daily basis.

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

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

    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 Chicago to Monterey Regional Airport.

  • What documentation or ID do you need to fly to Monterey Regional Airport?

    The required travel and health documents for your Monterey Regional Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Monterey Regional Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

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

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

Best airlines flying from Chicago to Monterey

Compare and see reviews for airlines that fly from Chicago to Monterey with momondo
Airline
Rating
Free Cancellation
Price
American AirlinesPriceFrom $268Free CancellationRating
7.1
11,668 reviews
Search American Airlines flights
United AirlinesPriceFrom $289Free CancellationRating
7.4
9,683 reviews
Search United Airlines flights
Alaska AirlinesPriceFrom $352Free CancellationRating
7.9
12,329 reviews
Search Alaska Airlines flights

Why use momondo?

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

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Chicago to Monterey. Millions of users trust and use momondo every year so you are in good hands.

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

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

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

momondo helps you find the best flight between Chicago and Monterey by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

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

Price alerts on flights to Monterey from Chicago are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

An easier way to manage your Monterey trip

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