This past weekend, I enjoyed a somewhat spontaneous escape to Chicago, where I stayed at the luxurious Park Hyatt Chicago. It was quite an indulgent trip, but one that perfectly showcased the power of points and miles.
The main reason for my visit? A Saturday night dinner at Oriole with some friends who have a stake in the spectacular fine dining restaurant. The meal was an unforgettable experience, featuring creative dishes and impeccable service that made the journey completely worth it.

I booked a two-night stay in a king bed room at the Park Hyatt, which would have cost $1,100 if paid in cash. Instead, I used just 21,000 Hyatt points per night, as this property is categorized as a Category 6 under Hyatt’s award chart. The value I received from my points was incredible, reaffirming why I prioritize earning and saving points that can score me these Hyatt stays.
When I got to the hotel, I was upgraded to a suite that would have been $1,592 for the stay. I got this incredible upgrade because of my Globalist status. What made it even better was that I actually called the hotel on my way to the airport, instead of waiting to check in, and that proactive step paid off. Calling in advance made all the difference, and I’m so glad I took the time to do it.
The complimentary breakfast, a generous $60 per person, was great and a very nice way to start each morning. But we had to be careful, the menu items were pretty high so we did almost go over our allotment.
Chicago is an amazing city, and the Park Hyatt’s location makes it ideal for exploring everything the city has to offer. From indulging in some delicious meals, enjoying a bit of shopping, and getting a pre-breakfast donut at Stan’s Donuts across the street, made all the better by the ease of my points redemption.
If you’re planning a trip and looking to maximize your travel budget, the Park Hyatt Chicago is a gem to consider. Just don’t forget to book early to snag those award nights!


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