The cheapest order to fly Johannesburg, Cape Town and Nairobi from Chicago
There are 6 ways to fly these cities, and 2 of them can be priced from fares we have seen. They do not cost the same. The cheapest works out at about $1,706 a person and the most expensive at $1,716, a difference of $10 for visiting exactly the same places.
Fly them in this order
Chicago → Johannesburg → Cape Town → Nairobi → Chicago
About $1,706 per person in flights, based on fares recently seen on these routes, and the cheapest of the 2 ways round we could price.
The 2 we can price
- Chicago → Johannesburg → Cape Town → Nairobi → Chicago$1,706cheapest order
- Chicago → Cape Town → Johannesburg → Nairobi → Chicago$1,716$10 more per person
The cheapest order, leg by leg
- Chicago to Johannesburg$673
- Johannesburg to Cape Town$94
- Cape Town to Nairobi$355
- Nairobi to Chicago$584
- Out of Chicago, the cheapest first flight goes to Nairobi at about $559, but the cheapest order starts in Johannesburg at $673 because the rest of the route is cheaper that way.
- Cape Town to Nairobi is about $355, but the other way round is $372. Same two cities, $17 apart on direction alone.
- The dearest order pays $802 for Chicago to Cape Town, a flight the cheapest order never takes.
Between the cities
- Johannesburg to Cape Town: about 1,260 km (780 miles) as the crow flies. No train or bus we would suggest instead of flying.
- Cape Town to Nairobi: about 4,100 km (2550 miles) as the crow flies. No train or bus we would suggest instead of flying.
Entry rules on a US passport
- US passport: visa-free in South Africa for up to 90 days. Official source
- US passport: an Electronic Travel Authorisation (eTA) is required for Kenya. Official source
Rules change; check the official source for your passport and dates before you book.
What these numbers are
Cached one-way fares, 10 of 12 legs priced from real observations, put together on October 29, 2026, from fares departing October 30, 2026 onwards. Right for comparing one order with another, not a quote for your dates.
A plan prices your own dates and weighs hours as well as fares, so it can pick a different order from this page.
Put dates on it
Same cities on real dates, plus what one search cannot show: layovers long enough to count as a free city, two tickets that beat one, and cheaper days either side. No account and no card.
One press starts it on January 2, 2027 to January 16, 2027, 14 days, for 2 travelers. Our dates, not yours, and about two minutes.
Plan Johannesburg, Cape Town and Nairobi from Chicago nowOpen the form instead and pick your own datesSigned out, 3 plans a day per address, priced from cached fares and the free sources, so some legs may be estimates and the plan says which. Signed in, legs are checked live, with 2 free trips you can change afterwards.