Cheap Flights from Monterey (MRY) to Chicago (MDW)

Popular airlines from Monterey Peninsula Airport (MRY) to Chicago Midway Airport (MDW)

  • Plan, book, fly with confidence

  • trending down icon
    Be in the know
    Get alerts if flight prices drop or rise*
  • bex rewards loyalty icon
    Book smarter
    Save up to 30% on select hotels after you book a flight*
  • payments icon
    Earn twice
    Earn your airline miles on top of our rewards
    Sign in

Frequently asked questions

How much is a flight from Monterey Peninsula Airport (MRY) to Midway Airport?
The lowest price advertised for a round-trip flight from Monterey Regional Airport to MDW is . But you better act quick. This figure is based on fares available within the last 7 days on Expedia for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from MRY to Chicago Airport?
When it comes to cancellation fees, each airline has different terms and conditions. If you decide to cancel your trip, head to our Customer Service Portal.
How do I find cheap flights from Monterey Peninsula Airport (MRY) to Midway Intl. Airport (MDW) that have flexible change policies?
Many airlines offer the option to reschedule your flight without a change fee. All you pay is the difference between the original flight and the new flight. When you’re searching for MRY to Midway Airport flights, you’ll see a “no change fees” filter for you to select.
How far is the flight from MRY to MDW?
The flight distance from Monterey to Chicago is 3,000 kilometres. Pack yourself a snack, a drink and a laptop filled with movies. Keep yourself entertained and the time will fly by.
Which airlines fly direct from Monterey Peninsula Airport (MRY) to MDW?
Direct flights aren’t available, so you’ll need to make at least one stop between Monterey Peninsula Airport (MRY) and Midway Intl. Airport (MDW). Use the layover time to stretch your legs and take a break.
Are MRY to MDW flight tickets cheaper when they're purchased at the last minute?
It is possible to get great last-minute deals from MRY to Midway Airport, but it can also be hit-or-miss. As many airlines advertise prices up to a year in advance, it’s worth keeping an eye on fares early and being ready to book when you spot a bargain. Expedia compares air carrier prices and updates flight deals frequently, so you can be certain you’re always getting the latest offers.
*Available to Expedia members.