Cheap Flights from Chicago (ORD) to Massawa (MSW)

Popular airlines from Chicago O'Hare Intl. Airport (ORD) to Massawa (MSW)

Frequently asked questions

How much does a flight from O'Hare Intl. Airport (ORD) to Massawa (MSW) cost?
Lock in a cheap one-way flight or cheap return flight from O'Hare Intl. Airport (ORD) to Massawa (MSW) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight deals on this route.
What is the cheapest month to fly from O'Hare Intl. Airport (ORD) to Massawa (MSW)?
is the most affordable month to fly from ORD to MSW. Traveling during quieter months is often the key to landing a great deal.
What is the cheapest airline that flies from O'Hare Intl. Airport (ORD) to Massawa (MSW)?
To find the cheapest airline that'll fly you from ORD to MSW, use Expedia's filter tool. Customize your search based on your travel needs, such as preferred carriers and number of stops. You can then sort your results by "Price (lowest to highest)" to discover the cheapest flight right away.
How many flights per day from O'Hare Intl. Airport (ORD) to Massawa (MSW)?
There aren't any daily direct flights from O'Hare Intl. Airport (ORD) to Massawa (MSW). But you can opt for flights with layovers. Filter your search on Expedia to include one or more stops, and you'll be soaring above the clouds before you know it.
What day of the week has the most flights from ORD to MSW?
Generally you'll find the most flight options available on a Friday. Tuesdays tend to be the quietest.* However, this can vary depending on the season, carrier and other factors.*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 Massawa (MSW)?
Select a flight from O'Hare Intl. Airport (ORD) to Massawa (MSW) that leaves before 3 PM to reduce the likelihood of delays and cancellations. Departures later than this 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 O'Hare Intl. Airport (ORD) to Massawa (MSW) last-minute?
Holding off until just before your trip to book a ticket from ORD to MSW often results in higher prices. While it's possible to find some last-minute offers, there's no guarantee. Keep your travel plans flexible to maximize your chances of getting a bargain.
Is it cheaper to book an ORD to MSW flight and hotel package?
Securing an ORD to MSW flight and hotel package is usually cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels all in one place. Select from our impressive range of accommodations 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 O'Hare Intl. Airport (ORD) to Massawa (MSW)?
In most cases, you're able to reschedule or cancel your ORD to MSW flight. However, additional fees may apply, especially if you made your booking more than 24 hours ago. Check your itinerary for the airline's rules and fees on flight changes, or if you need further details, head to our Customer Service portal.

Travel information

Travel information

Origin airport
O'Hare Intl.
Destination airport
Massawa
Distance
7229 mi

Book with confidence

Book with confidence

Chicago to Massawa Flights

The cheapest times to fly from Chicago to Massawa

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

 

The best time to book a flight from Chicago to Massawa

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

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 Massawa in 2025. 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 Massawa 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 Massawa 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 Massawa Flights
*Available to One Key members.