Cheap Flights from Chicago (MDW) to Montauk (MTP)

Popular airlines from Chicago Midway Airport (MDW) to Montauk, NY (MTP)

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Frequently asked questions

How much does a flight from Midway Intl. Airport (MDW) to Montauk, NY (MTP) cost?
Secure a cheap one-way flight or cheap return flight from Midway Intl. Airport (MDW) to Montauk, NY (MTP) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight deals on this route.
What is the cheapest month to fly from Midway Intl. Airport (MDW) to Montauk, NY (MTP)?
Planning your trip for can help you save, as it's the cheapest month for flights between MDW and MTP. You'll usually find the lowest fares during the off-season.
What is the cheapest airline that flies from Midway Intl. Airport (MDW) to Montauk, NY (MTP)?
Use the filter tool on Expedia to compare airlines and find the most affordable carrier that'll take you from MDW to MTP. Then, sort your results by "Price (lowest to highest)" to score a great deal.
How many flights per day from Midway Intl. Airport (MDW) to Montauk, NY (MTP)?
You'll need to book a flight with a layover when traveling from Midway Intl. Airport (MDW) to Montauk, NY (MTP). There are no daily direct flights on this route. However, simply filter your search to include one or two stops to find an option that works for you.
What day of the week has the most flights from MDW to MTP?
You'll typically find Tuesday the quietest day for flights, while Fridays are often the busiest.* However this can vary from season to season and during peak travel times or public holidays.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Midway Intl. Airport (MDW) to Montauk, NY (MTP)?
To reach Montauk, NY (MTP) without delays, opt for a flight that leaves from Midway Intl. Airport (MDW) before 3 PM. The likelihood of cancellations is 22% higher, on average, for departures after this hour.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
Is it cheaper to buy a plane ticket from Midway Intl. Airport (MDW) to Montauk, NY (MTP) last-minute?
Waiting until right before your break to book a flight from MDW to MTP generally means paying more. While you may come across some last-minute deals, they aren't always guaranteed. Keep your travel plans flexible for a better chance of snagging a bargain.
Can I cancel or change the date of my flight from Midway Intl. Airport (MDW) to Montauk, NY (MTP)?
It's usually possible to reschedule or cancel your MDW to MTP flight. However, if the booking was made more than 24 hours ago, additional charges may apply. Check your airline's policies in your itinerary to see what changes are possible and whether any costs are involved. You'll also find more details on our Customer Service portal.

Travel information

Origin airport
Midway Intl.
Destination airport
Montauk
Distance
819 mi

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Chicago to Montauk Flights

The cheapest times to fly from Chicago to Montauk

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Chicago to Montauk are during the month of . You can find some of the cheapest flights from Chicago to Montauk with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Chicago to Montauk

Sunday is one of the best days to book for cheap flights from Chicago to Montauk: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Chicago to Montauk

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Chicago to Montauk in 2026. You can also book with separate airlines for your outbound and return journeys, from one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Chicago to Montauk flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Chicago to Montauk airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Chicago to Montauk Flights

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*Available to One Key members.