HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Windhoek

$797+ Cheap flights from Chicago (CHI) to Windhoek

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 5/16. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — ERS
Mar 8 — Mar 151
Sun 3/8
Sun 3/15
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Chicago to Windhoek with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Chicago to Windhoek

Cheapest flights from Chicago to Windhoek
Explore the most affordable flight options available from Chicago to Windhoek. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 6, 2026.

This oojo deal was found by Cheapflights users on 2/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/2610:15 am
ORD
-
WDH
1 stop20h 05m
Ethiopian Air
Sun 4/52:30 pm
WDH
-
ORD
2 stops24h 45m
Ethiopian Air
Deal found 2/5$1,246
This Ovago deal was found by Cheapflights users on 2/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Ovago is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/2610:15 am
ORD
-
WDH
2 stops26h 30m
Multiple Airlines
Sun 4/52:30 pm
WDH
-
ORD
2 stops24h 45m
Multiple Airlines
Deal found 2/5$1,308
This FlightHub deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/171:10 pm
ORD
-
WDH
2 stops40h 10m
Etihad Airways
Tue 3/32:30 pm
WDH
-
ORD
2 stops49h 05m
Etihad Airways
Deal found 2/2$1,451
This KAYAK deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/161:10 pm
ORD
-
WDH
2 stops64h 10m
Etihad Airways
Wed 3/42:30 pm
WDH
-
ORD
2 stops49h 05m
Etihad Airways
Deal found 2/2$1,470
This Etihad Airways deal was found by Cheapflights users on 2/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Etihad Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/41:10 pm
ORD
-
WDH
2 stops40h 10m
Etihad Airways
Sun 3/82:30 pm
WDH
-
ORD
2 stops49h 05m
Etihad Airways
Deal found 2/5$1,509
This KAYAK deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/181:02 pm
ORD
-
WDH
2 stops40h 18m
Ethiopian Air
Sun 3/12:30 pm
WDH
-
ORD
2 stops25h 10m
Ethiopian Air
Deal found 2/2$1,530
This KAYAK deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/161:10 pm
ORD
-
WDH
2 stops64h 10m
Etihad Airways
Thu 3/52:30 pm
WDH
-
ORD
2 stops49h 05m
Etihad Airways
Deal found 2/2$1,556

Find flight deals from Chicago to Windhoek

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Windhoek (NA1). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated February 6, 2026.

Round-trip from

$1,246
(oojo)

One-way from

$797
(Kiwi.com)
From Chicago (CHI) to Windhoek
Search Deals
One-way flight from Chicago (CHI) to Windhoek
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Windhoek that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated February 6, 2026.
Use the filters below to find and compare flights from Chicago to Windhoek that are best for you.

Fly from

Chicago

Fly to

Windhoek

Route

Depart

Return

Price

ChicagoWindhoek

ORD - WDH

ORDWDH

Chicago O'Hare Intl

Thu 3/26

10:15 am-7:45 pm

2 stops26h 30m

Windhoek Hosea Kutako Intl

Sun 4/5

2:30 pm-8:15 am

2 stops24h 45m

$1,308

ChicagoWindhoek

ORD - WDH

ORDWDH

Chicago O'Hare Intl

Mon 2/16

1:10 pm-1:20 pm

2 stops64h 10m

Windhoek Hosea Kutako Intl

Wed 3/4

2:30 pm-7:35 am

2 stops49h 05m

$1,470

ChicagoWindhoek

ORD - WDH

ORDWDH

Chicago O'Hare Intl

Wed 3/4

1:10 pm-1:20 pm

2 stops40h 10m

Windhoek Hosea Kutako Intl

Sun 3/8

2:30 pm-8:35 am

2 stops49h 05m

$1,509

ChicagoWindhoek

ORD - WDH

ORDWDH

Chicago O'Hare Intl

Wed 2/18

1:02 pm-1:20 pm

2 stops40h 18m

Windhoek Hosea Kutako Intl

Tue 3/3

2:30 pm-7:40 am

2 stops25h 10m

$1,530

ChicagoWindhoek

ORD - WDH

ORDWDH

Chicago O'Hare Intl

Tue 2/17

1:10 pm-1:20 pm

2 stops40h 10m

Windhoek Hosea Kutako Intl

Sun 3/1

2:30 pm-7:35 am

2 stops49h 05m

$1,596

ChicagoWindhoek

ORD - WDH

ORDWDH

Chicago O'Hare Intl

Sat 3/7

1:10 pm-1:20 pm

2 stops40h 10m

Windhoek Hosea Kutako Intl

Sat 3/14

2:30 pm-8:35 am

2 stops49h 05m

$1,636

ChicagoWindhoek

ORD - WDH

ORDWDH

Chicago O'Hare Intl

Fri 3/27

2:10 pm-1:20 pm

2 stops40h 10m

Windhoek Hosea Kutako Intl

Sun 4/5

2:30 pm-8:35 am

2 stops49h 05m

$1,640

ChicagoWindhoek

ORD - WDH

ORDWDH

Chicago O'Hare Intl

Mon 2/16

1:02 pm-1:20 pm

2 stops40h 18m

Windhoek Hosea Kutako Intl

Fri 3/6

2:30 pm-7:40 am

2 stops25h 10m

$1,673

ChicagoWindhoek

ORD - WDH

ORDWDH

Chicago O'Hare Intl

Sat 5/16

4:47 pm-9:10 am

3 stops57h 23m

$797

ChicagoWindhoek

ORD - WDH

ORDWDH

Chicago O'Hare Intl

Mon 5/18

10:25 pm-1:20 pm

3 stops55h 55m

$810

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/6

Showing 1-10 of 17 results
1
2

Best time to book a flight from Chicago to Windhoek

Have a flexible travel schedule? Discover the best time to fly to Windhoek from Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago to Windhoek
No data available for this route at this time. Please check back soon.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Windhoek. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Chicago to Windhoek?

    Etihad Airways can get you from Chicago to Windhoek in just under 64h 10m. Your travel time can differ by up to . The distance between Chicago and Windhoek is about 8007 mi.

  • Can I find deals for flights from Chicago to Windhoek that include hotel bookings?

    Yes. In addition to deals on Chicago to Windhoek flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Windhoek?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Windhoek.

  • Can I find deals for business class flights from Chicago to Windhoek?

    Yes. Cheapflights offers flight deals from Chicago to Windhoek by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Chicago to Windhoek

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Hosea Kutako Intl flights
St. Louis to Hosea Kutako Intl flights

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.