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Cheap flights from Monterey to Chicago from $127

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 6/15. 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

Enter your travel dates to find the best prices.
Multiple Airlines Logo
10:04 pm - 12:49 am
MRY
-
ORD
24h 45m
2 stops
Multiple Airlines Logo
7:15 am - 9:14 pm
ORD
-
MRY
15h 59m
1 stop
$290Multiple Airlines
Mon, Aug 10 - Fri, Aug 14
Multiple Airlines Logo
10:04 pm - 12:49 am
MRY
-
ORD
24h 45m
2 stops
Multiple Airlines Logo
7:15 am - 9:14 pm
ORD
-
MRY
15h 59m
1 stop
$295Multiple Airlines
Mon, Aug 10 - Mon, Aug 17
Multiple Airlines Logo
10:04 pm - 5:28 am
MRY
-
ORD
29h 24m
1 stop
Multiple Airlines Logo
7:15 am - 9:14 pm
ORD
-
MRY
15h 59m
1 stop
$299Multiple Airlines
Mon, Aug 10 - Fri, Aug 14
Multiple Airlines Logo
10:04 pm - 5:28 am
MRY
-
ORD
29h 24m
1 stop
Multiple Airlines Logo
7:15 am - 9:14 pm
ORD
-
MRY
15h 59m
1 stop
$304Multiple Airlines
Mon, Aug 10 - Mon, Aug 17
Alaska Airlines Logo
2:55 pm - 11:55 pm
MRY
-
ORD
7h 00m
1 stop
Alaska Airlines Logo
9:00 am - 2:18 pm
ORD
-
MRY
7h 18m
1 stop
$313Alaska Airlines
Sat, May 30 - Tue, Jun 2
Alaska Airlines Logo
2:55 pm - 11:55 pm
MRY
-
ORD
7h 00m
1 stop
Alaska Airlines Logo
5:59 pm - 11:58 pm
ORD
-
MRY
7h 59m
1 stop
$331Alaska Airlines
Sat, Jun 6 - Sat, Jun 13
Alaska Airlines Logo
6:00 am - 6:50 pm
MRY
-
ORD
10h 50m
1 stop
Alaska Airlines Logo
2:20 pm - 11:58 pm
ORD
-
MRY
11h 38m
1 stop
$336Alaska Airlines
Sat, Jun 6 - Fri, Jun 12
United Airlines Logo
2:06 pm - 8:40 pm
MRY
-
ORD
4h 34mnonstop
United Airlines Logo
2:30 pm - 8:36 pm
ORD
-
MRY
8h 06m
1 stop
$339United Airlines
Sat, Jun 6 - Fri, Jun 12
Alaska Airlines Logo
6:40 pm - 6:20 am
MRY
-
ORD
9h 40m
1 stop
Alaska Airlines Logo
7:20 am - 2:07 pm
ORD
-
MRY
8h 47m
1 stop
$349Alaska Airlines
Wed, Oct 28 - Sat, Oct 31
Alaska Airlines Logo
6:03 am - 11:59 pm
MRY
-
ORD
15h 56m
2 stops
Alaska Airlines Logo
2:21 pm - 10:52 pm
ORD
-
MRY
10h 31m
1 stop
$354Alaska Airlines
Wed, Oct 28 - Sat, Oct 31

United Airlines flights from Monterey to Chicago

Our best United Airlines deals on Monterey to Chicago flight tickets
United Airlines
Jun 6
MRY2:06 pmMonterey Regional
4h 34m
ORD8:40 pmChicago O'Hare Intl
Jun 12
ORD2:30 pmChicago O'Hare Intl
8h 06m
1 stop
MRY8:36 pmMonterey Regional
$339
United Airlines
May 23
MRY2:06 pmMonterey Regional
4h 34m
ORD8:40 pmChicago O'Hare Intl
May 27
ORD7:40 amChicago O'Hare Intl
9h 15m
1 stop
MRY2:55 pmMonterey Regional
$409
United Airlines
Jun 5
MRY3:30 pmMonterey Regional
7h 29m
1 stop
ORD12:59 amChicago O'Hare Intl
Jun 13
ORD9:17 amChicago O'Hare Intl
4h 49m
MRY12:06 pmMonterey Regional
$418

Alaska Airlines flights from Monterey to Chicago

Our best Alaska Airlines deals on Monterey to Chicago flight tickets
Alaska Airlines
May 30
MRY2:55 pmMonterey Regional
7h 00m
1 stop
ORD11:55 pmChicago O'Hare Intl
Jun 2
ORD9:00 amChicago O'Hare Intl
7h 18m
1 stop
MRY2:18 pmMonterey Regional
$313
Alaska Airlines
Jun 6
MRY2:55 pmMonterey Regional
7h 00m
1 stop
ORD11:55 pmChicago O'Hare Intl
Jun 13
ORD5:59 pmChicago O'Hare Intl
7h 59m
1 stop
MRY11:58 pmMonterey Regional
$331
Alaska Airlines
Jun 6
MRY6:00 amMonterey Regional
10h 50m
1 stop
ORD6:50 pmChicago O'Hare Intl
Jun 12
ORD2:20 pmChicago O'Hare Intl
11h 38m
1 stop
MRY11:58 pmMonterey Regional
$336

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 May 10, 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

Cheapest round-trip

MontereyChicago

MRY - ORD

MRYORD

Monterey Regional

Mon 8/10

10:04 pm-12:49 am

2 stops24h 45m

Chicago O'Hare Intl

Fri 8/14

7:15 am-9:14 pm

1 stop15h 59m

$290

MontereyChicago

MRY - ORD

MRYORD

Monterey Regional

Mon 8/10

10:04 pm-12:49 am

2 stops24h 45m

Chicago O'Hare Intl

Mon 8/17

7:15 am-9:14 pm

1 stop15h 59m

$295

MontereyChicago

MRY - ORD

MRYORD

Monterey Regional

Mon 8/10

10:04 pm-5:28 am

1 stop29h 24m

Chicago O'Hare Intl

Fri 8/14

7:15 am-9:14 pm

1 stop15h 59m

$299

MontereyChicago

MRY - ORD

MRYORD

Monterey Regional

Mon 8/10

10:04 pm-5:28 am

1 stop29h 24m

Chicago O'Hare Intl

Mon 8/17

7:15 am-9:14 pm

1 stop15h 59m

$304

MontereyChicago

MRY - ORD

MRYORD

Monterey Regional

Sat 5/30

2:55 pm-11:55 pm

1 stop7h 00m

Chicago O'Hare Intl

Tue 6/2

9:00 am-2:18 pm

1 stop7h 18m

$313

MontereyChicago

MRY - ORD

MRYORD

Monterey Regional

Sat 6/6

2:55 pm-11:55 pm

1 stop7h 00m

Chicago O'Hare Intl

Sat 6/13

5:59 pm-11:58 pm

1 stop7h 59m

$331

MontereyChicago

MRY - ORD

MRYORD

Monterey Regional

Sat 6/6

6:00 am-6:50 pm

1 stop10h 50m

Chicago O'Hare Intl

Fri 6/12

2:20 pm-11:58 pm

1 stop11h 38m

$336
Quickest round-trip

MontereyChicago

MRY - ORD

MRYORD

Monterey Regional

Sat 6/6

2:06 pm-8:40 pm

Nonstop4h 34m

Chicago O'Hare Intl

Fri 6/12

2:30 pm-8:36 pm

1 stop8h 06m

$339

MontereyChicago

MRY - ORD

MRYORD

Monterey Regional

Wed 10/28

6:40 pm-6:20 am

1 stop9h 40m

Chicago O'Hare Intl

Sat 10/31

7:20 am-2:07 pm

1 stop8h 47m

$349

MontereyChicago

MRY - ORD

MRYORD

Monterey Regional

Wed 10/28

6:03 am-11:59 pm

2 stops15h 56m

Chicago O'Hare Intl

Sat 10/31

2:21 pm-10:52 pm

1 stop10h 31m

$354

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 October is, on average, the cheapest month to fly to Chicago from Monterey, with most prices found around $179. If you’re not able to fly to Chicago in October, then December is your next best option. Flight prices from Monterey to Chicago during December average around $258.

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 $424. 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 $538.

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 $430. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $469.

What is the cheapest Monterey Regional to Chicago flight route?

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

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

Best Price Found

$339

Fastest flight time

4h 34m

Direct flights

Sun

Airports in Chicago

3 airports
The best flight deal from Monterey to Chicago found on momondo in the last 72 hours is $339
The fastest flight from Monterey to Chicago takes 4h 34m
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

Frequently asked questions about flying from Monterey to Chicago

  • How far is Monterey Regional to Chicago by plane?

    Chicago is 1855.5 mi away from Monterey Regional. 4h 34m 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 $258Free CancellationRating
7.1
11,667 reviews
Search American Airlines flights
United AirlinesPriceFrom $276Free CancellationRating
7.4
9,694 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
Saint Joseph
Benton Harbor
Portage
Lansing
Valparaiso
Munster
Schererville
Crown Point
Monticello
Chesterton
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