Cheap Flights from Windhoek (WDH) to Chicago (MDW)

Popular airlines from Windhoek (WDH-Hosea Kutako) to Chicago Midway Airport (MDW)

Frequently asked questions

How much does a flight from Hosea Kutako Airport (WDH) to Midway Intl. Airport (MDW) cost?
Lock in a cheap one-way flight or cheap return flight from Hosea Kutako Airport (WDH) to Midway Intl. Airport (MDW) 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 Hosea Kutako Airport (WDH) to Midway Intl. Airport (MDW)?
The cheapest month to fly from WDH to MDW is , when there's less demand. Off-peak months are usually when airlines offer better prices between these airports.
What is the cheapest airline that flies from Hosea Kutako Airport (WDH) to Midway Intl. Airport (MDW)?
To find the cheapest airline that'll fly you from WDH to MDW, use Expedia's filter tool. Customize your search based on what matters most to you, such as preferred carriers and flight duration. You can then sort your results by "Price (lowest to highest)" to list the most affordable options first.
How many flights per day from Hosea Kutako Airport (WDH) to Midway Intl. Airport (MDW)?
Nonstop flights from Hosea Kutako Airport (WDH) to Midway Intl. Airport (MDW) aren't available daily, so you'll have to take a flight with a layover. Explore your options with our filter tool. Enter your dates and pick either "1 Stop" or "2+ Stops."
What day of the week has the most flights from WDH to MDW?
Typically you'll have the most choice when it comes to flights on a Friday. Tuesdays tend to be the quietest.* However, this can change depending on the airline, season 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 Hosea Kutako Airport (WDH) to Midway Intl. Airport (MDW)?
Select a flight from Hosea Kutako Airport (WDH) to Midway Intl. Airport (MDW) 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 Hosea Kutako Airport (WDH) to Midway Intl. Airport (MDW) last-minute?
Waiting until just before your trip to book a ticket from WDH to MDW generally means paying more. Although you may find some last-minute discounts, they're not always guaranteed. Allow some flexibility in your schedule for a better chance of getting a bargain.
Is it cheaper to book a WDH to MDW flight and hotel package?
Compared with arranging hotels and flights separately, booking a WDH to MDW flight and hotel package with Expedia could result in significant savings. Better still, having everything in one easy place will take the stress out of planning your trip. Simply secure your flights and choose from our wide range of stays, then personalize your trip with other add-ons like car rentals and activities.
Can I cancel or change the date of my flight from Hosea Kutako Airport (WDH) to Midway Intl. Airport (MDW)?
If you reserved your WDH to MDW flight within the last 24 hours, you may be able to modify or cancel it at no cost. Depending on the airline and the type of ticket you have, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal for more information.

Travel information

Origin airport
Hosea Kutako
Destination airport
Midway Intl.
Distance
8001 mi

Book with confidence

Windhoek to Chicago Flights

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

 

The best time to book a flight from Windhoek to Chicago

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

 

Windhoek to Chicago Flights
*Available to One Key members.