$247 Cheap Flights from Massena (MSS) to Chicago (ORD)

View $247 flight on Sat, Nov 22, 2025Opens in a new window

Popular airlines from Massena, NY (MSS-Massena Intl.) to Chicago O'Hare Intl. Airport (ORD)

Cheap Flights from Massena to Chicago (MSS-ORD)

Prices were available within the past 7 days and start at $247 for one-way flights and $336 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Boutique Air
Wed, Dec 24 - Wed, Dec 31
MSS
Massena
ORD
Chicago
$336 Roundtrip, found 3 days ago
$336
Roundtrip
found 3 days ago
Select Boutique Air flight, departing Wed, Dec 24 from Massena to Chicago, returning Wed, Dec 31, priced at $336 found 3 days ago
Boutique Air
Sun, Dec 21 - Wed, Dec 31
MSS
Massena
ORD
Chicago
$338 Roundtrip, found 3 days ago
$338
Roundtrip
found 3 days ago
Select Boutique Air flight, departing Sun, Dec 21 from Massena to Chicago, returning Wed, Dec 31, priced at $338 found 3 days ago
Boutique Air
Tue, Dec 30 - Tue, Jan 13
MSS
Massena
ORD
Chicago
$339 Roundtrip, found 5 days ago
$339
Roundtrip
found 5 days ago
Select Boutique Air flight, departing Tue, Dec 30 from Massena to Chicago, returning Tue, Jan 13, priced at $339 found 5 days ago
Boutique Air
Wed, Dec 3 - Thu, Dec 18
MSS
Massena
ORD
Chicago
$341 Roundtrip, found 5 days ago
$341
Roundtrip
found 5 days ago
Select Boutique Air flight, departing Wed, Dec 3 from Massena to Chicago, returning Thu, Dec 18, priced at $341 found 5 days ago
Boutique Air
Wed, Dec 3 - Mon, Dec 15
MSS
Massena
ORD
Chicago
$342 Roundtrip, found 5 days ago
$342
Roundtrip
found 5 days ago
Select Boutique Air flight, departing Wed, Dec 3 from Massena to Chicago, returning Mon, Dec 15, priced at $342 found 5 days ago
Boutique Air
Wed, Dec 24 - Sat, Dec 27
MSS
Massena
ORD
Chicago
$345 Roundtrip, found 3 days ago
$345
Roundtrip
found 3 days ago
Select Boutique Air flight, departing Wed, Dec 24 from Massena to Chicago, returning Sat, Dec 27, priced at $345 found 3 days ago
Boutique Air
Tue, Nov 11 - Fri, Nov 14
MSS
Massena
ORD
Chicago
$346 Roundtrip, found 5 days ago
$346
Roundtrip
found 5 days ago
Select Boutique Air flight, departing Tue, Nov 11 from Massena to Chicago, returning Fri, Nov 14, priced at $346 found 5 days ago
Boutique Air
Sun, Dec 21 - Sat, Dec 27
MSS
Massena
ORD
Chicago
$347 Roundtrip, found 3 days ago
$347
Roundtrip
found 3 days ago
Select Boutique Air flight, departing Sun, Dec 21 from Massena to Chicago, returning Sat, Dec 27, priced at $347 found 3 days ago
Boutique Air
Mon, Dec 15 - Sat, Dec 27
MSS
Massena
ORD
Chicago
$348 Roundtrip, found 3 days ago
$348
Roundtrip
found 3 days ago
Select Boutique Air flight, departing Mon, Dec 15 from Massena to Chicago, returning Sat, Dec 27, priced at $348 found 3 days ago
Boutique Air
Sat, Nov 8 - Fri, Nov 14
MSS
Massena
ORD
Chicago
$351 Roundtrip, found 5 days ago
$351
Roundtrip
found 5 days ago
Select Boutique Air flight, departing Sat, Nov 8 from Massena to Chicago, returning Fri, Nov 14, priced at $351 found 5 days ago
Boutique Air
Sat, Nov 8 - Thu, Nov 27
MSS
Massena
ORD
Chicago
$352 Roundtrip, found 5 days ago
$352
Roundtrip
found 5 days ago
Select Boutique Air flight, departing Sat, Nov 8 from Massena to Chicago, returning Thu, Nov 27, priced at $352 found 5 days ago

Alternative airports near Chicago

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city center is 23 minutes. Flights from $483
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $483
Flights from Massena (MSS) to Chicago (ORD)
Origin airport
Massena Intl.
Destination airport
O'Hare Intl.
Roundtrip price
$336
Distance
685 mi

Massena to Chicago Flights

The cheapest times to fly from Massena to Chicago

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 Massena to Chicago are during the month of December. You can find some of the cheapest flights from Massena to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Massena to Chicago

Sunday is one of the best days to book for cheap flights from Massena to Chicago: 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 Massena to Chicago

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 Massena to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $247 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 Massena to Chicago 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 Massena to Chicago 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.

 

Frequently asked questions

How much does a flight from Massena Intl. Airport (MSS) to O'Hare Intl. Airport (ORD) cost?
Lock in a cheap one-way flight from $247 or cheap return flight from $336 from Massena Intl. Airport (MSS) to O'Hare Intl. Airport (ORD) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight offers on this route.
What is the cheapest month to fly from Massena Intl. Airport (MSS) to O'Hare Intl. Airport (ORD)?
The cheapest month to fly from MSS to ORD is December, when there's less demand. Off-peak season is generally when you'll find cheap fares for travel between these airports.
Which airlines fly direct from Massena Intl. Airport (MSS) to O'Hare Intl. Airport (ORD)?
You can't fly nonstop to O'Hare Intl. Airport (ORD) from Massena, NY (MSS-Massena Intl.). However, you can seamlessly travel to Chicago without any layovers by taking off from Macdonald-Cartier Intl. Airport (YOW).
What is the cheapest airline that flies from Massena Intl. Airport (MSS) to O'Hare Intl. Airport (ORD)?
Expedia's filter tool lets you easily compare different airlines, flight durations and fares all in one place. Select your preferences, then sort by "Price (lowest to highest)" to see which carrier offers the cheapest MSS to ORD flight.
How many flights per day from Massena Intl. Airport (MSS) to O'Hare Intl. Airport (ORD)?
You'll need to hop on a flight with a layover when traveling from Massena Intl. Airport (MSS) to O'Hare Intl. Airport (ORD). Direct flights don't operate daily on this route. However, just filter your search to include one or two stops to find the best option for your trip.
What day of the week has the most flights from MSS to ORD?
You'll usually find Tuesday the quietest day for flights, while Fridays are often the busiest.* However this can change from season to season and during public holidays or peak travel times.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Massena Intl. Airport (MSS) to O'Hare Intl. Airport (ORD)?
Opt for a flight from Massena Intl. Airport (MSS) to O'Hare Intl. Airport (ORD) that takes off before 3 PM to reduce the risk of cancellations. Departures after this hour are on average 22% more likely to be canceled.**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 Massena Intl. Airport (MSS) to O'Hare Intl. Airport (ORD) last-minute?
Holding off until just before your departure to book a flight from MSS to ORD often results in higher prices. While it's possible to find some last-minute deals, they aren't always guaranteed. Keep your travel schedule open to maximize your chances of snagging a bargain.
Is it cheaper to book a MSS to ORD flight and hotel package?
Booking a MSS to ORD flight and hotel package is usually cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your trip all in one place. Pick from our extensive range of hotels and then add car rentals, flights and activities to your booking. Bundle it all together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Massena Intl. Airport (MSS) to O'Hare Intl. Airport (ORD)?
Usually, it's possible to reschedule or cancel your MSS to ORD flight. However, for bookings made more than 24 hours ago, additional charges may apply. Refer to 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.

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*Available to One Key members.