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Cheap flights from Chicago to San Francisco from $135

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 9/22. 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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Find the cheapest flights from Chicago to San Francisco (CHI-MRY)

Cheap round-trip flights

Hawaiian Airlines Logo
3:50 pm - 11:37 pmORD-MRY
9h 47m1 stop
Hawaiian Airlines Logo
6:00 am - 2:50 pmMRY-ORD
6h 50m1 stop
$259Hawaiian Airlines
Find Deal
lun., oct. 6 - mar., oct. 14
American Airlines Logo
1:28 pm - 6:41 pmORD-MRY
7h 13m1 stop
American Airlines Logo
12:31 pm - 10:20 pmMRY-ORD
7h 49m1 stop
$269American Airlines
Find Deal
mar., nov. 11 - sáb., nov. 15
American Airlines Logo
10:25 am - 6:41 pmORD-MRY
10h 16m2 stops
American Airlines Logo
4:23 pm - 12:31 amMRY-ORD
6h 08m1 stop
$274American Airlines
Find Deal
mar., nov. 11 - mié., dic. 3
Hawaiian Airlines Logo
9:00 am - 1:56 pmORD-MRY
6h 56m1 stop
Hawaiian Airlines Logo
2:40 pm - 11:10 pmMRY-ORD
6h 30m1 stop
$276Hawaiian Airlines
Find Deal
mié., ene. 21 - lun., ene. 26
Logo
6:15 am - 8:35 pmORD-MRY
16h 20m1 stop
Logo
9:54 pm - 9:32 pmMRY-ORD
21h 38m1 stop
$292
Find Deal
lun., sep. 15 - vie., sep. 19
Alaska Airlines Logo
2:54 pm - 11:32 pmORD-MRY
10h 38m1 stop
Alaska Airlines Logo
6:00 am - 2:09 pmMRY-ORD
6h 09m1 stop
$295Alaska Airlines
Find Deal
mar., nov. 11 - jue., dic. 4
Logo
6:15 am - 8:35 pmORD-MRY
16h 20m1 stop
Logo
9:54 pm - 9:28 pmMRY-ORD
21h 34m2 stops
$300
Find Deal
lun., sep. 15 - vie., sep. 19
Alaska Airlines Logo
2:05 pm - 11:25 pmORD-MRY
11h 20m2 stops
Alaska Airlines Logo
6:00 am - 1:59 pmMRY-ORD
5h 59m1 stop
$303Alaska Airlines
Find Deal
mié., ene. 21 - lun., ene. 26
United Airlines Logo
2:30 pm - 9:37 pmORD-MRY
9h 07m1 stop
United Airlines Logo
2:33 pm - 11:10 pmMRY-ORD
6h 37m1 stop
$310United Airlines
Find Deal
mié., nov. 12 - mar., dic. 2
United Airlines Logo
1:05 pm - 5:43 pmORD-MRY
6h 38m1 stop
United Airlines Logo
2:19 pm - 12:54 amMRY-ORD
8h 35m1 stop
$359United Airlines
Find Deal
mié., sep. 24 - dom., sep. 28

Alaska Airlines flights from Chicago to Monterey

Our best Alaska Airlines deals on Chicago to Monterey flight tickets
Alaska Airlines
Nov 11
ORD2:54 pmChicago O'Hare Intl
10h 38m
1 stop
MRY11:32 pmMonterey Regional
Dec 4
MRY6:00 amMonterey Regional
6h 09m
1 stop
ORD2:09 pmChicago O'Hare Intl
$295
Find similar
Alaska Airlines
Jan 21
ORD2:05 pmChicago O'Hare Intl
11h 20m
2 stops
MRY11:25 pmMonterey Regional
Jan 26
MRY6:00 amMonterey Regional
5h 59m
1 stop
ORD1:59 pmChicago O'Hare Intl
$303
Find similar
Alaska Airlines
Dec 5
ORD3:05 pmChicago O'Hare Intl
10h 29m
1 stop
MRY11:34 pmMonterey Regional
Dec 12
MRY2:55 pmMonterey Regional
20h 14m
2 stops
ORD1:09 pmChicago O'Hare Intl
$348
Find similar

United Airlines flights from Chicago to Monterey

Our best United Airlines deals on Chicago to Monterey flight tickets
United Airlines
Nov 12
ORD2:30 pmChicago O'Hare Intl
9h 07m
1 stop
MRY9:37 pmMonterey Regional
Dec 2
MRY2:33 pmMonterey Regional
6h 37m
1 stop
ORD11:10 pmChicago O'Hare Intl
$310
Find similar
United Airlines
Sep 24
ORD1:05 pmChicago O'Hare Intl
6h 38m
1 stop
MRY5:43 pmMonterey Regional
Sep 28
MRY2:19 pmMonterey Regional
8h 35m
1 stop
ORD12:54 amChicago O'Hare Intl
$359
Find similar
United Airlines
Oct 2
ORD1:05 pmChicago O'Hare Intl
6h 38m
1 stop
MRY5:43 pmMonterey Regional
Oct 9
MRY8:01 amMonterey Regional
8h 51m
1 stop
ORD6:52 pmChicago O'Hare Intl
$377
Find similar

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 septiembre 3, 2025.
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

ChicagoMonterey

ORD - MRY

ORDMRY

Chicago O'Hare Intl

lun. 10/6

3:50 pm-11:37 pm

1 stop9h 47m

Monterey Regional

mar. 10/14

6:00 am-2:50 pm

1 stop6h 50m

$259

ChicagoMonterey

ORD - MRY

ORDMRY

Chicago O'Hare Intl

mar. 11/11

1:28 pm-6:41 pm

1 stop7h 13m

Monterey Regional

sáb. 11/15

12:31 pm-10:20 pm

1 stop7h 49m

$269

ChicagoMonterey

ORD - MRY

ORDMRY

Chicago O'Hare Intl

mar. 11/11

10:25 am-6:41 pm

2 stops10h 16m

Monterey Regional

mié. 12/3

4:23 pm-12:31 am

1 stop6h 08m

$274

ChicagoMonterey

ORD - MRY

ORDMRY

Chicago O'Hare Intl

mié. 1/21

9:00 am-1:56 pm

1 stop6h 56m

Monterey Regional

lun. 1/26

2:40 pm-11:10 pm

1 stop6h 30m

$276

ChicagoMonterey

ORD - MRY

ORDMRY

Chicago O'Hare Intl

lun. 9/15

6:15 am-8:35 pm

1 stop16h 20m

Monterey Regional

vie. 9/19

9:54 pm-9:32 pm

1 stop21h 38m

$292

ChicagoMonterey

ORD - MRY

ORDMRY

Chicago O'Hare Intl

mar. 11/11

2:54 pm-11:32 pm

1 stop10h 38m

Monterey Regional

jue. 12/4

6:00 am-2:09 pm

1 stop6h 09m

$295

ChicagoMonterey

ORD - MRY

ORDMRY

Chicago O'Hare Intl

lun. 9/15

6:15 am-8:35 pm

1 stop16h 20m

Monterey Regional

vie. 9/19

9:54 pm-9:28 pm

2 stops21h 34m

$300

ChicagoMonterey

ORD - MRY

ORDMRY

Chicago O'Hare Intl

mié. 1/21

2:05 pm-11:25 pm

2 stops11h 20m

Monterey Regional

lun. 1/26

6:00 am-1:59 pm

1 stop5h 59m

$303

ChicagoMonterey

ORD - MRY

ORDMRY

Chicago O'Hare Intl

mié. 11/12

2:30 pm-9:37 pm

1 stop9h 07m

Monterey Regional

mar. 12/2

2:33 pm-11:10 pm

1 stop6h 37m

$310

ChicagoMonterey

ORD - MRY

ORDMRY

Chicago O'Hare Intl

mié. 9/24

1:05 pm-5:43 pm

1 stop6h 38m

Monterey Regional

dom. 9/28

2:19 pm-12:54 am

1 stop8h 35m

$359

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 cheapest month to fly to Monterey?

The month of October is, on average, the cheapest month to fly to Monterey from Chicago, with most prices found around $463. If you’re not able to fly to Monterey in October, then May is your next best option. Flight prices from Chicago to Monterey during May average around $464.

What is the cheapest day to depart on your flight to Monterey?

The cheapest day to depart from Chicago to Monterey is on a Tuesday. Travelers who choose to depart for Monterey on a Tuesday will often find tickets for as low as $432. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Chicago to Monterey for around $695.

What is the cheapest time of day to depart on your flight to Monterey?

According to our data, the cheapest time of day to fly to Monterey is in the afternoon. momondo users have found flights departing from Chicago to Monterey in the afternoon for as low as $445. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. Flights in the morning are often more expensive with an average ticket price of $551.

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

Direct flights

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

  • 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 6h 16m.

  • 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 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
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $358Free CancellationRating
7.4
8,937 reviews
Search United 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.

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lun. 9/8
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