Looking to book a hotel in Downtown Chicago with Amex points this march…is the best bang for my buck the Amex rewards site or is there something I’m missing?

- I’ll be staying for 5 nights

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Amex doesn't transfer very well to hotels. You'd be looking at Marriott at 1:1 or Hilton at 1:2 which both aren't great.

I would book with cash and save the points. Don't use the portal. Amex points are best used on international business class flights, like to Europe or Asia.

If you have Chase points, Park Hyatt Chicago is an option.

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If you have the platinum card, you get $200 for a FHR booking. Points are 1cpp - not great redemption, but can be helpful.

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Also I know the travel portal isn’t great but I don’t have any plans/time for overseas travel for a while

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Ended up transferring 1-1 at Marriott and booked the ritz for 5 nights at 201K not the best but woulda been 253K on the Amex travel portal

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Oof

Depends which hotel you are staying at. Sometimes it can be much easier to buy free night certs or points for that hotel and then book

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