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Monterey

$739+ Cheap flights from Midway (MDW) to Monterey (MRY)

MDW — MRY
Nov 27 — Dec 41
Fri 11/27
Fri 12/4
1 adult, Economy
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Cheap flight deals from Midway to Monterey

Best flights from Midway to Monterey

Sat 4/179:30 am -
2 stops8h 45m
Thu 4/227:40 am -
2 stops12h 30m
Deal found 10/25$739
Sat 3/209:55 am -
2 stops8h 20m
Thu 3/254:55 pm -
2 stops13h 50m
Deal found 10/25$749
Thu 2/412:30 pm -
2 stops10h 25m
Sun 2/77:40 am -
2 stops12h 30m
Deal found 10/23$1,022
Sat 3/276:00 am -
2 stops12h 15m
Fri 4/24:55 pm -
2 stops13h 50m
Deal found 10/27$1,893

Find flight deals from Midway to Monterey

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$739
(Delta)

Popular in

June

Cheapest in

September

Average price

$376
Provider with most accurate pricing for Chicago Midway-Monterey Regional flight deals.
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Provider most trusted by Cheapflights users for Chicago Midway-Monterey Regional flights.
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From Chicago Midway to Monterey Regional
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Highest demand for flights based on searches. 6% potential increase in price ($25 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($7 potential savings vs. average RT price).
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Average for round-trip flights in October 2026
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Cheapflights Fare Finder

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

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

ChicagoMonterey

MDW Chicago Midway - MRY Monterey Regional

MDWMRY

Chicago Midway

Sat 4/17

9:30 am-4:15 pm

2 stops8h 45m

Monterey Regional

Thu 4/22

7:40 am-10:10 pm

2 stops12h 30m

$739

ChicagoMonterey

MDW Chicago Midway - MRY Monterey Regional

MDWMRY

Chicago Midway

Sat 3/20

9:55 am-4:15 pm

2 stops8h 20m

Monterey Regional

Thu 3/25

4:55 pm-8:45 am

2 stops13h 50m

$749

ChicagoMonterey

MDW Chicago Midway - MRY Monterey Regional

MDWMRY

Chicago Midway

Wed 11/25

6:17 pm-5:29 pm

3 stops25h 12m

Monterey Regional

Wed 12/31

12:00 am-2:00 am

Nonstop0h 00m

$768

ChicagoMonterey

MDW Chicago Midway - MRY Monterey Regional

MDWMRY

Chicago Midway

Thu 2/4

12:30 pm-8:55 pm

2 stops10h 25m

Monterey Regional

Sun 2/7

7:40 am-10:10 pm

2 stops12h 30m

$1,022

ChicagoMonterey

MDW Chicago Midway - MRY Monterey Regional

MDWMRY

Chicago Midway

Sat 3/27

6:00 am-4:15 pm

2 stops12h 15m

Monterey Regional

Fri 4/2

4:55 pm-8:45 am

2 stops13h 50m

$1,893

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/25

Sorted by cheapest first

Compare providers for flights from Midway to Monterey

Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Midway to Monterey in October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy2 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago Midway Airport-Monterey flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago Midway Airport-Monterey flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-Monterey flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago Midway Airport-Monterey flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago Midway Airport-Monterey flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Midway to Monterey

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

Related info for your journey

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

    Monterey Regional (MRY) is the airport you will fly into if you book a flight from Chicago Midway to Monterey. You should not have trouble finding flights to Monterey Regional from Chicago Midway; the airport handles an average of 0 inbound flights from Chicago Midway per day. You should also have plenty of airline options to choose from since 0 airlines have flights to the Monterey airport from Chicago Midway. It is only a 3.2 mi journey from Monterey Regional (MRY) to Monterey’s city center.

  • How long is the flight from Chicago Midway Airport to Monterey?

    For as low as $739, Delta can have you in Monterey from Chicago Midway Airport in 8h 45m. Airlines will cover a distance of 1847 mi.

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

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

  • How can I find direct flights from Midway to Monterey?

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

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

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

See more FAQs

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