$205+ 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 12/25. Fares are subject to change and may not be available on all flights or dates of travel.
MRY — MDW
Nov 24 — Dec 11
Round-trip
1 adult, Economy
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1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Monterey to Midway
Cheapest
Best
One-way
Cheapest flights from Monterey to MidwayExplore the most affordable flight options available from Monterey to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 25, 2026.
Explore the most affordable flight options available from Monterey to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 25, 2026.
This Delta deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/314:51 pm -
2 stops14h 22m
Sun 1/39:30 am -
2 stops8h 41m
Deal found 10/23![Delta logo]()
$679
This Delta deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/234:51 pm -
2 stops14h 22m
Fri 1/19:30 am -
2 stops8h 41m
Deal found 10/22![Delta logo]()
$709
Best flights from Monterey to MidwayDiscover carefully curated flight deals from Monterey to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 25, 2026.
Discover carefully curated flight deals from Monterey to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 25, 2026.
This Delta deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/314:51 pm -
2 stops14h 22m
Sun 1/39:30 am -
2 stops8h 41m
Deal found 10/23![Delta logo]()
$679
This Delta deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/127:40 am -
2 stops12h 30m
Fri 2/199:30 am -
2 stops8h 45m
Deal found 10/25![Delta logo]()
$779
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 October 25, 2026.
Search for one-way flight options from Monterey to Midway. Find affordable one-way fares based on user searches. Data last updated October 25, 2026.
This Delta deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/257:05 am -
2 stops8h 39m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![Delta logo]()
$205
This Kiwi.com deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/24:31 pm -
2 stops16h 51m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/24![Multiple Airlines logo]()
$242
This Kiwi.com deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/303:41 pm -
2 stops24h 06m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/24![Multiple Airlines logo]()
$362
This Delta deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/247:05 am -
2 stops8h 39m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![Delta logo]()
$405
This Delta deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/37:05 am -
2 stops31h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![Delta logo]()
$533
This Delta deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/24:51 pm -
2 stops14h 22m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![Delta logo]()
$565
This Kiwi.com deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/56:00 am -
3 stops32h 47m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![Multiple Airlines logo]()
$571
This Delta deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/14:51 pm -
2 stops14h 22m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![Delta logo]()
$655
This Kiwi.com deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/26:09 pm -
3 stops43h 58m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![Multiple Airlines logo]()
$666
Find flight deals from Monterey to Midway
Discover tips and strategies to find the most affordable flight options for your journey from Monterey (MRY) to Midway (MDW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated October 25, 2026.
Most accurate provider | eDreams 2 stars |
|---|---|
Most trusted provider | eDreams 3 stars |
Round-trip from | $679 (Delta) |
One-way from | $205 (Delta) |
Popular in | September |
Cheapest in | March |
Average price | $513 |
Cheapflights Fare Finder
Customize your flight search to find flights from Monterey to Midway 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, Cheapflights users made 7,457,451 searches. Data last updated October 25, 2026.
Use the filters below to find and compare flights from Monterey to Chicago Midway Airport that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Quickest round-trip
MontereyChicago
MRY Monterey Regional - MDW Chicago Midway
MRYMDW
Monterey Regional
Fri 12/25
7:05 am-5:44 pm
2 stops8h 39m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$205
MontereyChicago
MRY Monterey Regional - MDW Chicago Midway
MRYMDW
Monterey Regional
Mon 11/2
4:31 pm-11:47 pm
3 stops29h 16m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$305
MontereyChicago
MRY Monterey Regional - MDW Chicago Midway
MRYMDW
Monterey Regional
Thu 12/24
7:05 am-5:44 pm
2 stops8h 39m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$405
MontereyChicago
MRY Monterey Regional - MDW Chicago Midway
MRYMDW
Monterey Regional
Sun 1/3
7:05 am-4:50 pm
2 stops31h 45m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$533
MontereyChicago
MRY Monterey Regional - MDW Chicago Midway
MRYMDW
Monterey Regional
Sat 1/2
4:51 pm-9:13 am
2 stops14h 22m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$565
MontereyChicago
MRY Monterey Regional - MDW Chicago Midway
MRYMDW
Monterey Regional
Fri 1/1
4:51 pm-9:13 am
2 stops14h 22m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$655
MontereyChicago
MRY Monterey Regional - MDW Chicago Midway
MRYMDW
Monterey Regional
Wed 12/2
6:09 pm-4:07 pm
3 stops43h 58m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$666
MontereyChicago
MRY Monterey Regional - MDW Chicago Midway
MRYMDW
Monterey Regional
Thu 12/31
4:51 pm-9:13 am
2 stops14h 22m
Chicago Midway
Sun 1/3
9:30 am-4:11 pm
2 stops8h 41m
$679
MontereyChicago
MRY Monterey Regional - MDW Chicago Midway
MRYMDW
Monterey Regional
Fri 2/12
7:40 am-10:10 pm
2 stops12h 30m
Chicago Midway
Fri 2/19
9:30 am-4:15 pm
2 stops8h 45m
$779
MontereyChicago
MRY Monterey Regional - MDW Chicago Midway
MRYMDW
Monterey Regional
Sun 1/17
7:20 am-10:16 pm
2 stops12h 56m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$905
Showing 1-10 of 12 resultsSorted by cheapest first
- Most accurate provider: When it comes to deals on Monterey-Chicago Midway Airport flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Monterey-Chicago Midway Airport flight deals on Cheapflights vs. eDreams 90-95% of the time. Price accuracy is based on data collected from Monterey-Chicago Midway Airport flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Monterey-Chicago Midway Airport flights, Cheapflights users trust eDreams the most. eDreams 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 Monterey-Chicago Midway Airport 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 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
Find useful and relevant information for your journey from Monterey to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago Midway Airport?
Book flights to Chicago Midway Airport if you plan to visit one of these locationsBenton Harbor
Merrillville
Lansing
Valparaiso
Hammond
Saint Joseph
Porter
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