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Windhoek

$1,012+ 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 9/15. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — ERS
Jun 6 — Jun 131
Sat 6/6
Sat 6/13
1 adult, Economy
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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 May 7, 2026.

This Turkish Airlines deal was found by Cheapflights users on 5/4. 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 Turkish Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/128:10 pm
ORD
-
WDH
2 stops38h 30m
Turkish Airlines
Wed 11/181:45 pm
WDH
-
ORD
2 stops36h 40m
Turkish Airlines
Deal found 5/4$1,620
This Ovago deal was found by Cheapflights users on 5/4. 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.
Sat 9/1210:15 am
ORD
-
WDH
2 stops24h 25m
Multiple Airlines
Wed 11/189:20 am
WDH
-
ORD
3 stops30h 20m
Multiple Airlines
Deal found 5/4$1,767
This oojo deal was found by Cheapflights users on 5/2. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/266:30 am
ORD
-
WDH
2 stops23h 50m
Ethiopian Air
Tue 6/22:30 pm
WDH
-
ORD
2 stops24h 45m
Ethiopian Air
Deal found 5/2$1,856
This oojo deal was found by Cheapflights users on 5/6. 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.
Sun 5/249:55 pm
ORD
-
WDH
2 stops32h 25m
Ethiopian Air
Thu 7/92:30 pm
WDH
-
ORD
2 stops24h 45m
Ethiopian Air
Deal found 5/6$1,884
This oojo deal was found by Cheapflights users on 5/5. 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.
Fri 6/56:30 am
ORD
-
WDH
2 stops23h 50m
Ethiopian Air
Fri 7/32:30 pm
WDH
-
ORD
2 stops24h 45m
Ethiopian Air
Deal found 5/5$1,941

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 May 7, 2026.

Round-trip from

$1,620
(Turkish Airlines)

One-way from

$1,012
(oojo)
From Chicago (CHI) to Windhoek
Search Deals
One-way flight from Chicago (CHI) to Windhoek
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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 May 7, 2026.
Use the filters below to find and compare flights from Chicago to Windhoek that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoWindhoek

ORD - WDH

ORDWDH

Chicago O'Hare Intl

Sat 9/12

8:10 pm-5:40 pm

2 stops38h 30m

Windhoek Hosea Kutako Intl

Wed 11/18

1:45 pm-6:25 pm

2 stops36h 40m

$1,620
Quickest round-trip

ChicagoWindhoek

ORD - WDH

ORDWDH

Chicago O'Hare Intl

Tue 6/2

6:30 am-1:20 pm

2 stops23h 50m

Windhoek Hosea Kutako Intl

Tue 6/9

2:30 pm-8:15 am

2 stops24h 45m

$1,856

ChicagoWindhoek

ORD - WDH

ORDWDH

Chicago O'Hare Intl

Tue 5/26

6:30 am-1:20 pm

2 stops23h 50m

Windhoek Hosea Kutako Intl

Tue 6/2

2:30 pm-8:15 am

2 stops24h 45m

$1,887

ChicagoWindhoek

ORD - WDH

ORDWDH

Chicago O'Hare Intl

Fri 6/5

6:30 am-1:20 pm

2 stops23h 50m

Windhoek Hosea Kutako Intl

Fri 7/3

2:30 pm-8:15 am

2 stops24h 45m

$1,941

ChicagoWindhoek

ORD - WDH

ORDWDH

Chicago O'Hare Intl

Sat 9/12

10:15 am-1:20 pm

1 stop20h 05m

Windhoek Hosea Kutako Intl

Wed 11/18

2:30 pm-6:25 pm

2 stops59h 55m

$1,977

ChicagoWindhoek

ORD - WDH

ORDWDH

Chicago O'Hare Intl

Sun 5/24

9:55 pm-1:20 pm

2 stops32h 25m

Windhoek Hosea Kutako Intl

Thu 7/9

2:30 pm-2:29 pm

3 stops30h 59m

$2,020
Cheapest one-way

ChicagoWindhoek

ORD - WDH

ORDWDH

Chicago O'Hare Intl

Tue 9/15

8:10 pm-1:20 pm

2 stops34h 10m

$1,012

ChicagoWindhoek

ORD - WDH

ORDWDH

Chicago O'Hare Intl

Fri 5/15

9:35 pm-1:20 pm

2 stops32h 45m

$1,310

ChicagoWindhoek

ORD - WDH

ORDWDH

Chicago O'Hare Intl

Fri 5/15

6:15 pm-8:10 am

1 stop30h 55m

$1,354
Quickest one-way

ChicagoWindhoek

ORD - WDH

ORDWDH

Chicago O'Hare Intl

Sat 5/30

10:15 am-1:20 pm

1 stop20h 05m

$3,826

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/5

Showing 1-10 of 11 resultsSorted by cheapest first
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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?

    Turkish Airlines and Ethiopian Air can get you from Chicago to Windhoek in just under 23h 50m. Your travel time can differ by up to 14h 40m. The distance between Chicago and Windhoek is about 8007 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • 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

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Alternative routes for Chicago to Windhoek

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