In terms of precipitation, rainfall in Chicago Midway Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 1.7 in.

If weather is an important factor for your trip to Chicago Midway Airport, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

What is the cheapest time of day to fly from MRY to MDW?

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Monterey to Chicago Midway Airport as you normally would.

What airport do you fly from for flights from Monterey to Chicago Midway?

Located just 3.2 mi from the city center, Monterey Regional is the airport most travelers will use when flying to Chicago Midway from Monterey. Booking flights from Monterey Regional (MRY) to Chicago Midway should be relatively easy as there are 0 daily outbound flights to Chicago Midway from 0 different airlines.

Can I find deals for flights from Monterey to Midway that include hotel bookings?

Yes. In addition to deals on Monterey to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

How can I find direct flights from Monterey to Midway?

After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Monterey to Midway.

Can I find deals for business class flights from Monterey to Midway?

Yes. Cheapflights offers flight deals from Monterey to Midway by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

$383+ Cheap Flights from Monterey to Chicago Midway Airport

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Cheap flight deals from Monterey to Midway

One-way

One-way flights from Monterey to Midway
Search for one-way flight options from Monterey to Midway. Find affordable one-way fares based on user searches. Data last updated September 8, 2026.

Fri 10/24:10 pm -

2 stops17h 49m

Wed 12/3112:00 am -

Nonstop0h 00m

Deal found 9/6

$383

Sun 11/293:59 pm -

2 stops43h 00m

Wed 12/3112:00 am -

Nonstop0h 00m

Deal found 9/4

$446

Tue 9/296:23 pm -

3 stops51h 21m

Wed 12/3112:00 am -

Nonstop0h 00m

Deal found 9/6

$550

Wed 9/306:23 pm -

3 stops36h 44m

Wed 12/3112:00 am -

Nonstop0h 00m

Deal found 9/6

$853

Thu 10/16:23 pm -

3 stops36h 44m

Wed 12/3112:00 am -

Nonstop0h 00m

Deal found 9/6

$911

Find flight deals from Monterey to Midway

Most accurate provider	FlightHub 3 stars
Most trusted provider	FlightHub 3 stars
Popular in	July
Cheapest in	February
Average price	$371

Provider with most accurate pricing for San Francisco-Chicago (CHI) flight deals.

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Highest demand for flights based on searches. 7% potential increase in price ($35 potential increase over avg. RT price).

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Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).

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Average for round-trip flights in September 2026

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Cheapflights Fare Finder

Use the filters below to find and compare flights from Monterey to Chicago Midway Airport that are best for you.

Fly from

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Route

Depart

Return

Price

Cheapest round-trip

Quickest round-trip

MontereyChicago

MRY Monterey Regional - MDW Chicago Midway

MRYMDW

Monterey Regional

Fri 10/2

4:10 pm-5:51 pm

2 stops23h 41m

Chicago Midway

Wed 12/31

12:00 am-10:00 pm

Nonstop0h 00m

$384

MontereyChicago

MRY Monterey Regional - MDW Chicago Midway

MRYMDW

Monterey Regional

Sun 11/29

3:59 pm-12:59 pm

2 stops43h 00m

Chicago Midway

Wed 12/31

12:00 am-10:00 pm

Nonstop0h 00m

$446

MontereyChicago

MRY Monterey Regional - MDW Chicago Midway

MRYMDW

Monterey Regional

Tue 9/29

6:23 pm-11:44 pm

3 stops51h 21m

Chicago Midway

Wed 12/31

12:00 am-10:00 pm

Nonstop0h 00m

$550

MontereyChicago

MRY Monterey Regional - MDW Chicago Midway

MRYMDW

Monterey Regional

Wed 9/30

6:23 pm-9:07 am

3 stops36h 44m

Chicago Midway

Wed 12/31

12:00 am-10:00 pm

Nonstop0h 00m

$853

MontereyChicago

MRY Monterey Regional - MDW Chicago Midway

MRYMDW

Monterey Regional

Sun 10/4

5:28 pm-10:33 pm

3 stops51h 05m

Chicago Midway

Wed 12/31

12:00 am-10:00 pm

Nonstop0h 00m

$1,169

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/7

Sorted by cheapest first

Best time to book a flight from Monterey to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Monterey with our price prediction graph.

MRY-MDW

Estimated round-trip price

Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Related info for your journey

What airport do you fly from for flights from Monterey to Chicago Midway?
Located just 3.2 mi from the city center, Monterey Regional is the airport most travelers will use when flying to Chicago Midway from Monterey. Booking flights from Monterey Regional (MRY) to Chicago Midway should be relatively easy as there are 0 daily outbound flights to Chicago Midway from 0 different airlines.
Can I find deals for flights from Monterey to Midway that include hotel bookings?
Yes. In addition to deals on Monterey to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.
How can I find direct flights from Monterey to Midway?
After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Monterey to Midway.
Can I find deals for business class flights from Monterey to Midway?
Yes. Cheapflights offers flight deals from Monterey to Midway by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

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$383+ Cheap flights from Monterey (MRY) to Midway (MDW)

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/2. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Monterey to Midway with Cheapflights

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

Cheap flight deals from Monterey to Midway

One-way flights from Monterey to MidwaySearch for one-way flight options from Monterey to Midway. Find affordable one-way fares based on user searches. Data last updated September 8, 2026.

Search for one-way flight options from Monterey to Midway. Find affordable one-way fares based on user searches. Data last updated September 8, 2026.

Find flight deals from Monterey to Midway

Most accurate provider

Most trusted provider

Popular in

Cheapest in

Average price

Cheapflights Fare Finder

Use the filters below to find and compare flights from Monterey to Chicago Midway Airport that are best for you.

Best time to book a flight from Monterey to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Monterey with our price prediction graph.

Related info for your journey

What airport do you fly from for flights from Monterey to Chicago Midway?

Can I find deals for flights from Monterey to Midway that include hotel bookings?

How can I find direct flights from Monterey to Midway?

Can I find deals for business class flights from Monterey to Midway?

Traveling to a place near Chicago Midway Airport?

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Monterey to Midway

See prices for flight routes from nearby airports that may be better suited for you.

Complete your trip

Complete your trip to Midway by adding a car rental and/or hotel reservation to your travel itinerary.

Search flights from Monterey to Midway by cabin class

Find flights from Monterey to Midway, based on your preferred cabin class, be it economy, premium economy, business, or first class.

Other flights to Midway

Explore flights to Midway departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on September 8, 2026.

Monterey and Midway flights

Browse other Monterey and Midway flight options. Last updated on September 8, 2026.

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Browse through other flights departing from Monterey. Flights are based on user searches made on Cheapflights and were last updated on September 8, 2026.

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One-way flights from Monterey to Midway
Search for one-way flight options from Monterey to Midway. Find affordable one-way fares based on user searches. Data last updated September 8, 2026.