$488 Cheap Flights from Chicago (ORD) to Reggio di Calabria (REG)

View $488 flight on Wed, Jan 21, 2026Opens in a new window

Popular airlines from Chicago O'Hare Intl. Airport (ORD) to Strait of Messina Airport (REG)

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Cheap Flights from Chicago to Reggio di Calabria (ORD-REG)

Prices were available within the past 7 days and start at $488 for one-way flights and $639 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

TAP Portugal
Wed, Feb 18 - Thu, Feb 26
ORD
Chicago
REG
Metropolitan City of Reggio Calabria
$639 Roundtrip, found 2 days ago
$639
Roundtrip
found 2 days ago
Select TAP Portugal flight, departing Wed, Feb 18 from Chicago to Metropolitan City of Reggio Calabria, returning Thu, Feb 26, priced at $639 found 2 days ago
TAP Portugal
Wed, Feb 18 - Thu, Feb 26
ORD
Chicago
REG
Metropolitan City of Reggio Calabria
$639 Roundtrip, found 2 days ago
$639
Roundtrip
found 2 days ago
Select TAP Portugal flight, departing Wed, Feb 18 from Chicago to Metropolitan City of Reggio Calabria, returning Thu, Feb 26, priced at $639 found 2 days ago
TAP Portugal
Wed, Apr 8 - Wed, Apr 15
ORD
Chicago
REG
Metropolitan City of Reggio Calabria
$647 Roundtrip, found 3 days ago
$647
Roundtrip
found 3 days ago
Select TAP Portugal flight, departing Wed, Apr 8 from Chicago to Metropolitan City of Reggio Calabria, returning Wed, Apr 15, priced at $647 found 3 days ago
TAP Portugal
Sun, Feb 1 - Sat, Feb 7
ORD
Chicago
REG
Metropolitan City of Reggio Calabria
$659 Roundtrip, found 1 hour ago
$659
Roundtrip
found 1 hour ago
Select TAP Portugal flight, departing Sun, Feb 1 from Chicago to Metropolitan City of Reggio Calabria, returning Sat, Feb 7, priced at $659 found 1 hour ago
ITA Airways
Tue, Mar 10 - Tue, Mar 24
ORD
Chicago
REG
Metropolitan City of Reggio Calabria
$660 Roundtrip, found 4 days ago
$660
Roundtrip
found 4 days ago
Select ITA Airways flight, departing Tue, Mar 10 from Chicago to Metropolitan City of Reggio Calabria, returning Tue, Mar 24, priced at $660 found 4 days ago
TAP Portugal
Sun, Feb 1 - Sat, Feb 7
ORD
Chicago
REG
Metropolitan City of Reggio Calabria
$689 Roundtrip, found 1 hour ago
$689
Roundtrip
found 1 hour ago
Select TAP Portugal flight, departing Sun, Feb 1 from Chicago to Metropolitan City of Reggio Calabria, returning Sat, Feb 7, priced at $689 found 1 hour ago
TAP Portugal
Fri, Feb 20 - Wed, Feb 25
ORD
Chicago
REG
Metropolitan City of Reggio Calabria
$696 Roundtrip, found 4 hours ago
$696
Roundtrip
found 4 hours ago
Select TAP Portugal flight, departing Fri, Feb 20 from Chicago to Metropolitan City of Reggio Calabria, returning Wed, Feb 25, priced at $696 found 4 hours ago
Delta
Wed, Jan 21 - Sun, Jan 25
ORD
Chicago
REG
Metropolitan City of Reggio Calabria
$710 Roundtrip, found 18 hours ago
$710
Roundtrip
found 18 hours ago
Select Delta flight, departing Wed, Jan 21 from Chicago to Metropolitan City of Reggio Calabria, returning Sun, Jan 25, priced at $710 found 18 hours ago
KLM
Mon, Nov 24 - Tue, Dec 9
ORD
Chicago
REG
Metropolitan City of Reggio Calabria
$711 Roundtrip, found 4 days ago
$711
Roundtrip
found 4 days ago
Select KLM flight, departing Mon, Nov 24 from Chicago to Metropolitan City of Reggio Calabria, returning Tue, Dec 9, priced at $711 found 4 days ago
United
Mon, Mar 9 - Sun, Mar 15
ORD
Chicago
REG
Metropolitan City of Reggio Calabria
$722 Roundtrip, found 18 hours ago
$722
Roundtrip
found 18 hours ago
Select United flight, departing Mon, Mar 9 from Chicago to Metropolitan City of Reggio Calabria, returning Sun, Mar 15, priced at $722 found 18 hours ago

Frequently asked questions

How much does a flight from O'Hare Intl. Airport (ORD) to Strait of Messina Airport (REG) cost?
Get a cheap one-way flight from $488 or cheap return flight from $639 from O'Hare Intl. Airport (ORD) to Strait of Messina Airport (REG) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight offers on this route.
What is the cheapest month to fly from O'Hare Intl. Airport (ORD) to Strait of Messina Airport (REG)?
Traveling in February can help you save, as it's the cheapest month for flights between ORD and REG. You'll usually find the lowest fares during the off-season.
What is the cheapest airline that flies from O'Hare Intl. Airport (ORD) to Strait of Messina Airport (REG)?
Expedia's filter tool lets you easily compare airlines, flight times and baggage options all in one place. Choose your preferences, then sort by "Price (lowest to highest)" to find the carrier with the cheapest ORD to REG flight.
How many flights per day from O'Hare Intl. Airport (ORD) to Strait of Messina Airport (REG)?
There are no daily direct flights from O'Hare Intl. Airport (ORD) to Strait of Messina Airport (REG). But you can opt for flights with layovers. Filter your search results on Expedia to include one or two stops, and you'll be cruising above the clouds before you know it.
What day of the week has the most flights from ORD to REG?
You'll usually find Tuesday the quietest day for flights, while Fridays tend to be the busiest.* However this can change 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 O'Hare Intl. Airport (ORD) to Strait of Messina Airport (REG)?
To avoid potential delays on the O'Hare Intl. Airport (ORD) to Strait of Messina Airport (REG) route, aim to fly before 3 PM. Flights after this time are 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 O'Hare Intl. Airport (ORD) to Strait of Messina Airport (REG) last-minute?
Booking your plane ticket from ORD to REG shortly before your getaway is usually more expensive. However, if you're flexible with your departure times and dates, you could bag a cheap last-minute fare.
Is it cheaper to book an ORD to REG flight and hotel package?
You'll typically save money by securing an ORD to REG flight and hotel package compared to booking separately. In fact, you could save hundreds of dollars by bundling with Expedia. And it's easy to manage it all in one place. After selecting your ideal accommodations and flights, you can add extras such as tours, car rentals and activities.
Can I cancel or change the date of my flight from O'Hare Intl. Airport (ORD) to Strait of Messina Airport (REG)?
If you booked your ORD to REG flight in the last 24 hours, you may be able to modify or cancel it without fees. Depending on the airline and the type of fare you purchased, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, go to our Customer Service portal for more information.

Travel information

Origin airport
O'Hare Intl.
Destination airport
Strait of Messina
Airlines serving
Austrian Airlines, Brussels Airlines, Emirates, ITA Airways, KLM, Lufthansa, Swiss International Air Lines, TAP Portugal, United
Roundtrip price
$639
Distance
5114 mi

Book with confidence

Chicago to Reggio di Calabria Flights

The cheapest times to fly from Chicago to Reggio di Calabria

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

 

The best time to book a flight from Chicago to Reggio di Calabria

Sunday is one of the best days to book for cheap flights from Chicago to Reggio di Calabria: 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 Reggio di Calabria

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 Reggio di Calabria in 2025. You can also book with separate airlines for your outbound and return journeys, from $488 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 Reggio di Calabria 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 Reggio di Calabria 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 Reggio di Calabria Flights

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