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Do I have enough time???

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I'm flying outbound from Chicago to Washington Dulles to Johannesburg to Cape Town.

My main concern is the changing of flights. I am planning on sending my luggage all the way from Chicago to Cape Town. I have a 1 hour 40 mins layover in Washington Dulles and I wanted to know is anyone knows if this is enough time to change planes?

My layover in Johannesburg is 2 hours - should this be enough time? Customs should be a breeze because South Africa is my home country and I have a SA Passport.

But I have never been to Washington Dulles airport and I need to know if I will have enough time with the 1 hour 40 mins to climb off the plane and catch the different one?

Thanks.

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