Stopover
Plan a trip

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 $1,808 a person and the most expensive at $2,031, a difference of $223 for visiting exactly the same places.

Fly them in this order

Chicago → Johannesburg → Cape Town → Nairobi → Chicago

About $1,808 per person in flights, based on fares recently seen on these routes, and the cheapest of the 2 ways round we could price.

One press plans it on January 16, 2027 to January 30, 2027 for 2 travelers.

Plan this trip on real dates

The 2 we can price

  1. Chicago → Johannesburg → Cape Town → Nairobi → Chicago$1,808
    cheapest order
  2. Chicago → Cape Town → Johannesburg → Nairobi → Chicago$2,031
    $223 more per person

Why Johannesburg first

  1. Chicago to Johannesburg$741
  2. Johannesburg to Cape Town$96
  3. Cape Town to Nairobi$357
  4. Nairobi to Chicago$614
  • Out of Chicago, Johannesburg is the cheapest first stop at about $741. Cape Town would be $1,091.
  • Cape Town to Nairobi is about $357, but the other way round is $374. Same two cities, $17 apart on direction alone.
  • The dearest order pays $1,091 for Chicago to Cape Town, a flight the cheapest order never takes.
  • Chicago to Johannesburg is 41% of what the cheapest order spends on flights, so it is the leg to watch.

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 November 13, 2026, from fares departing November 13, 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.

Other trips priced this way

From Chicago

Trips through the same cities

Put dates on it

One press starts it on January 16, 2027 to January 30, 2027, 14 days, for 2 travelers. Our dates, not yours, and about two minutes.

Plan Johannesburg, Cape Town and Nairobi from ChicagoOpen the form instead and pick your own dates
What a plan adds, and the limits

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.

Without an account, 2 trips 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, your first trip also searches Google Flights live, and you can change your trips afterwards.