Cheap flight tickets from Chicago to Windhoek

Compare Chicago to Windhoek flight deals

Find the cheapest month or even day of the year to fly to Windhoek

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Flight deals from Chicago to Windhoek

Looking for a cheap last-minute deal or the best return flight from Chicago to Windhoek? If you want to travel next month, return fares start from RM7,245. Find the lowest prices on one-way and return tickets right here.

Find the cheapest month to fly from Chicago to Windhoek

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Chicago to Windhoek flights are currently cheapest in April.

Alternative Chicago to Windhoek routes

Looking for the cheapest, fastest or easiest route from Chicago to Windhoek? You could fly into the following airports instead.

Chicago to Windhoek: Flight information

The things to know before you go.
Cheapest flight foundRM4,426
Cheapest month to flyApril

Finding cheap flights from Chicago to Windhoek: Frequently asked questions

There are 2 airports in Windhoek: Windhoek Eros and Windhoek Hosea Kutako.
The best price we found for a return flight from Chicago to Windhoek is RM6,250. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
Currently, there are no airlines that fly direct from Chicago to Windhoek. But we found flights with one or more stops from RM6,250.
As of April 2026, there are no flights flying from Chicago to Windhoek.
The cheapest month to fly from Chicago to Windhoek is usually March.
If you're flying from Chicago, the cheapest airport near Windhoek is Windhoek Hosea Kutako – which is 40.1 km away from the centre of Windhoek. We've found flights into this airport from RM6,250.
After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Chicago to Windhoek on Wednesday, 10 March 2027.
No airlines currently offer direct flights between Chicago and Windhoek. Most routes have one or more stops.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Windhoek but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.
We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Windhoek is around 40 days in advance, so don’t leave your flight to the last minute.
In April, the average temperature is usually around 20°C. January is typically the warmest month in Windhoek, when it usually averages around 32°C. You can expect the least rain in June. The coldest month is July, with temperatures averaging 5°C. The rainiest month is February.
The cheapest airline that flies to Windhoek is Qatar Airways .

Travelling from Chicago to Windhoek: what you need to know

  • Get your holiday planning started by considering where you'll catch your flight from Chicago to Windhoek. O'Hare International Airport (ORD) and Chicago Midway International Airport (MDW) are Chicago's main airports.

  • Hosea Kutako International Airport (WDH) is where your flight will arrive in Windhoek.

  • The timezone in Windhoek is UTC+2, which is seven hours ahead of Chicago.

  • To ensure you catch your Chicago to Windhoek flight, leave plenty of time to navigate the airport and find your gate. Turning up two hours before international departures and one hour before domestic flights is a good rule of thumb.

  • Travelling during a popular month such as August? Major public holidays and other popular seasons can lead to longer queues and delays at security. Play things extra safe and get there up to four hours before an international flight and two hours before a domestic departure.

How to find the cheapest flights from Chicago to Windhoek

  • Don't leave everything to the last minute. You're more likely to find cheap Chicago to Windhoek flights if you book ahead. Airlines often have some fantastic early bird deals.

  • The 'Whole month' search tool will show you the cheapest plane tickets from Chicago to Windhoek across the entire month. It's a good way to find a bargain if your plans aren't set in stone.

  • Save time searching for cheap flights from Chicago to Windhoek by creating a Price Alert. We'll send you an email or notification on the app when a lower fare becomes available.

  • Tailor your flights using filters. Choose your departure and arrival times, airlines and total journey duration. You can also sort your results by 'Cheapest,' 'Best' or 'Fastest' Chicago to Windhoek flights.

Flying from Chicago

O'Hare International Airport (ORD)

  • Whether you're eager to visit a new place on the way or just have a break, we make it a cinch to find a flight with a stopover. To see your options leaving from O'Hare International Airport, deselect 'Direct flights only.' Addis Ababa Bole International Airport (ADD) is a stop you can make on your Chicago to Windhoek flight.

  • Located around 26 kilometres from the centre of Chicago, ORD can be reached in about 35 minutes by car (depending on traffic). The journey on public transport takes roughly 55 minutes.

  • Booked an early flight from Chicago to Windhoek? Avoid rushing to the airport (and catch some extra z's) by choosing one of these stays close to O'Hare International Airport:

  • 74.85% of flights departing from O'Hare International Airport touch down at their destination on schedule.

  • ORD's address is 10000 West O'Hare.

Chicago Midway International Airport (MDW)

  • MDW is around 14 kilometres from central Chicago. It takes 20 minutes or so to get to the airport in a car from the city centre. Public transport takes roughly 45 minutes.

  • You're off on holiday, so why not extend it with an additional night away? Think about kicking back in one of these accommodation options near Chicago Midway International Airport the day before your flight from Chicago to Windhoek:

  • As far as flight punctuality goes, Chicago Midway International Airport has an on-time arrival rate of 78%.

  • MDW is located at 5700 South Cicero.

Arriving in Windhoek

Hosea Kutako International Airport (WDH)

  • Hosea Kutako International Airport (WDH) to central Windhoek takes around 40 minutes to reach by car. The centre is roughly 40 kilometres away.

  • After your flight from Chicago to Windhoek has touched down, kick back and relax at a nearby hotel. Etango Ranch Guest Farm is a good option that's a quick drive from WDH.

  • Grab a Hosea Kutako International Airport rental car and discover Windhoek and beyond with your own set of wheels. Hertz, Europcar and Budget are top outlets to choose from here.

  • Booking your ride from Hosea Kutako International Airport around one week ahead can help you get the lowest rate.

Best time to go to Windhoek

  • July is the busiest month for flights from Chicago to Windhoek. To travel when it's less crowded, head to Windhoek in February.

  • Book a Chicago to Windhoek ticket departing in November if you want to visit the city during its warmest month. You can expect temperatures in Windhoek to range from 14ºC (57ºF) to 32ºC (90ºF).

  • Look for cheap flights from Chicago to Windhoek in July if you want to travel in cooler conditions. Temperatures are at their lowest then, ranging between 3ºC (37ºF) and 22ºC (72ºF) on average.

More about Windhoek

  • After booking your flight from Chicago to Windhoek, find a hotel that offers the right mix of comfort and location. Make one of these accommodation options your base for exploring Windhoek:

  • There are so many things to explore in this city it can be tricky to work out where to begin. Christuskirche, National Museum of Namibia and National Botanic Garden of Namibia are popular attractions which should feature on any good Windhoek itinerary.

Explore more of Namibia

  • You've seen Windhoek, now it's time to discover other parts of Namibia. Travel around 274 kilometres west to Walvis Bay to check off its leading sights. From Walvis Bay Waterfront to PELICAN POINT and Walvis Bay Lagoon, you'll have a packed itinerary ahead.

  • Around 257 kilometres west of Windhoek, Swakopmund is another essential stop in Namibia. No visit is complete without checking out National Marine Aquarium, Swakopmund Museum and Hohenzollernhaus.

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.