RareNonstop · 5h
CHI to SJUPuerto Rico
San Juan
$162
usually $340
−52%
Most monthly lows $287–$340. Cheaper than every other month on record (3).
Flights · CHI → CPT
Chicago to Cape Town
Best fare, round trip
$1,696
Too little price history on this route to compare — the fare is shown as found.
Found
- Depart
- Sun 22 Nov
- Return
- Fri 27 Nov
- Stay
- 5 nights
- Flight
- 1 stop · 22h
- Airline
Turkish Airlines
Cached fare — the booking search re-prices live before you pay.
South AfricaCape TownTable Mountain, two oceans and winelands 40 minutes out — the long-haul that overdelivers.Best windowNov–MarAirportsCape Town (CPT)Every route into Cape TownFare seasonality
When this route gets cheap.
The cheapest itinerary we are tracking makes one stop and takes about 22 hours outbound, on a 5-night trip — ticketed under Turkish Airlines, which on a connecting fare need not operate every leg. At $1,696 for 13,668 km each way, that works out to about $62 per 1,000 km flown. That is above the $42 per 1,000 km typical of ultra-long-haul fares here. Across the 20 departure cities we track at a similar distance from Cape Town, this fare ranks 17th — 3.3× the $516 we hold from Toronto. For context, the middle fare among the 30 routes of similar length we watch out of Chicago is $995. We have 1 month of cached prices for this route so far — not enough to call a fare cheap or expensive, so we publish the price without a percentage. Fare history here is still too short to name a cheap season. The best time to be in Cape Town: Nov–Mar.
The one day we hold a cached fare for
Press a date to compare its fares
The median cached fare across this calendar is 26% higher than when tracking began on 13 Sep — $1,344 then versus $1,696 now, across 3 recorded snapshots. This is a calendar-level trend, so an individual deal above can be lower. The lowest single day we have seen here is $1,295, on 11 Nov.
These are the only days we have a cached price for on this route so far — not the only days it flies. The search above covers any date.
Cached fares · checked 13 Oct 2026
We are still collecting this route's months — 1 month of cached prices so far, too few to chart.
Route facts
- Airports
- O’Hare (ORD) · Midway (MDW) ↔ Cape Town (CPT)
- Flight time
- ≈22 hours outbound
- Distance
- ≈13,668 km each way
- Airlines on the board
- Turkish Airlines
- Itineraries
- Connections on current fares
- Best months to visit
- Nov–Mar
Good to know
CHI → CPT, answered.
How far in advance should I book CHI → Cape Town?
We do not publish a number for this, because we cannot measure it yet. Answering it honestly means watching the same departure date on this route over many weeks as it approaches, and that archive is still filling up — so any "book N days ahead" figure here would be borrowed from somewhere else rather than measured. Our guide Why flight prices change covers the levers we can measure.
Are there nonstop flights from Chicago to Cape Town?
The current cheapest fares involve a connection, ticketed under Turkish Airlines. We hold no nonstop fare on this route right now, which does not mean none flies — search your exact dates to see what does.
Are these prices guaranteed?
No — these are cached fares found on real searches (this one on 15 October). Airlines reprice constantly, so the booking search re-checks the live price before you pay. Fresher finds are far more likely to still be available.
Next step
Sleeping in Cape Town?
Lock the flight first — then compare stays for 22–27 Nov · 5 nights.
Browse hotelsMissed it?
Cached fares expire. This route has a feed of its own — follow it and the next CHI → CPT drop reaches you as soon as we find it.
Follow this route’s feedKeep browsing
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