Cheap Flights from Waterford (WAT) to Chicago (MDW)

Popular airlines from Waterford (WAT) to Chicago Midway Airport (MDW)

  • notification illustration

    Be in the know

    Get alerts if flight prices drop or rise*
  • deals illustration

    Book smarter

    Save up to 30% on select hotels after you book a flight*
  • trophy illustration

    Earn twice

    Earn your airline miles on top of our OneKeyCash
    Learn about One Key

Frequently asked questions

How much does a flight from Waterford (WAT) to Midway Intl. Airport (MDW) cost?
Get a cheap one-way flight or cheap return flight from Waterford (WAT) to Midway Intl. Airport (MDW) 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 Waterford (WAT) to Midway Intl. Airport (MDW)?
is the least expensive month to fly from WAT to MDW. Timing your trip outside of the busy season is often the key to finding better deals on flights.
What is the cheapest airline that flies from Waterford (WAT) to Midway Intl. Airport (MDW)?
To find the cheapest airline flying from WAT to MDW, use Expedia's filter tool. Tailor your search based on what matters most to you, such as preferred carriers and ideal departure window. You can then sort your results by "Price (lowest to highest)" to see the most affordable options first.
How many flights per day from Waterford (WAT) to Midway Intl. Airport (MDW)?
Direct flights from Waterford (WAT) to Midway Intl. Airport (MDW) aren't available daily, so you'll need to take a flight with a layover. Explore your options with our filter tool. Enter your travel dates and click on either "1 Stop" or "2+ Stops."
What day of the week has the most flights from WAT to MDW?
You'll generally 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 Waterford (WAT) to Midway Intl. Airport (MDW)?
To reach Midway Intl. Airport (MDW) on time, choose a flight that takes off from Waterford (WAT) 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 Waterford (WAT) to Midway Intl. Airport (MDW) last-minute?
Last-minute bookings from WAT to MDW are typically more expensive. To secure the lowest prices, start searching for flights well ahead of time. That said, if you can play around with your travel dates, it's possible to score a cheap fare right before you leave.
Is it cheaper to book a WAT to MDW flight and hotel package?
You'll generally save money by securing a WAT to MDW flight and hotel package compared to booking separately. In fact, you could save hundreds of dollars by bundling with Expedia. And it's simple to manage it all in one convenient place. Once you've selected your ideal flights and accommodations, consider adding extras including car rentals, activities and tours.
Can I cancel or change the date of my flight from Waterford (WAT) to Midway Intl. Airport (MDW)?
If you reserved your WAT to MDW flight in the last 24 hours, you may be able to modify or cancel it at no cost. Depending on the airline and the ticket type 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 if you want more information.

Travel information

Origin airport
Waterford
Destination airport
Midway Intl.
Distance
3667 mi

Book with confidence

Waterford to Chicago Flights

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

 

The best time to book a flight from Waterford to Chicago

Sunday is one of the best days to book for cheap flights from Waterford 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 Waterford 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 Waterford to Chicago 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 Waterford 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 Waterford 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.

 

Waterford to Chicago Flights

Explore a world of travel with Expedia

*Available to One Key members.