Last August 2024, I attended my first points & miles meetup in Seattle. It was with the Award Travel group and I made connections and learned a lot. During that meetup, they announced the next one was going to be in Chicago. I purchased my ticket, my flight and my hotel right away. I didn’t know who would go with me or if I would go alone, but either way would be OK!
The Seattle 2024 meetup is where Lisa & I learned about the casino status merry-go-round that I have spoken about in previous posts. That is what led us to a free room at Atlantis (only paid taxes, fees & gratuities), a free room in St. Thomas at Margaritaville (used the points that were earned from opening the Wyndham Business Earners credit card) and the free room at Wynn Resort in Las Vegas (only paid for an upgrade to a top floor room).
As time got nearer, I talked to my friend Roni (a local to the Chicago area) about meeting up with me so that I could visit the Indiana Dunes National Park while I was in the area. And then as time got even nearer, we talked our friend Diana into joining us as well!
Flights:
I had originally booked an American Airlines flight out of XNA (Northwest Arkansas National Airport) paying cash one way and 9,000 AA points for the return flight. I watched the rates and searched with Delta and United Airlines as well. At one point, there was a Delta flight for near the same cash amount and I had a credit with Delta which would make the flight much cheaper (almost free). I earned this credit by using my Delta Amex credit card. But then, I kept watching for even cheaper fares. I finally found a flight for 4,500 points using Alaska Airline points (there’s a hack there, too – I’ll share later). So I switched it again. I also searched on Alaska’s website to see if I could purchase the trip home for 4,500 points as well. They did not have main cabin seats, but they did have first class seats for the same rate that I had booked with AA points. So 9,000 Alaska points for first class or 9,000 AA points for main cabin…hmmmm, let me see. Yes, I changed that flight too!
Hotels:
My flight was scheduled to arrive late Thursday night. The conference started Friday evening in downtown Chicago. The Hyatt Regency O’Hare was 12,000 points, the Hyatt Regency Chicago (downtown) was 18,000 points. So I booked Thursday night near O’Hare, then Friday and Saturday night in downtown. If you know anything at all, you know that people who do points & miles LOVE Hyatt! First, the points for Hyatt hotels are so much less than points for other hotels, such as Hilton or Marriott. And when you book a room with points (an award room), you also get the resort fees waived. And, if you have Globalist Status, you also get a free breakfast and free parking. To become a globalist, you have to stay 60 nights at a Hyatt hotel. There are other ways to obtain this status by doing challenges or using your credit card. I have not reached this status yet, but Diana has. I originally booked the room with my points, in my name. By switching the downtown reservation to Diana’s name with her globalist status, we received those benefits. Parking in downtown Chicago was $87 per night – Roni drove so that was quite a savings. Breakfast buffet was $28 per person plus tip if we had to pay for this but because of the globalist status, the breakfast was free INCLUDING the tip! So 18,000 points gave us a room in downtown Chicago, $87 parking each day, $28×3 breakfasts each day, access to the Club which is only available to globalists and had snacks and drinks throughout the day. Thank you, Diana, for sharing your globalist status with us! 🙂
Getting around:
From the airport, I took the hotel shuttle. The shuttle ran a continuous loop from the airport to the hotel. I walked out the airport door and the shuttle was just pulling up. That was about as easy as it gets! Roni planned to pick me up Friday morning from the airport hotel and drive into the city. There was another couple with our group that was landing about the same time, so I reached out to them and had them take the hotel shuttle to the hotel to avoid us having to fight the airport traffic. I think that worked out perfectly.
Once at the hotel, we parked the car and walked. We walked over 18,000 steps Friday! We left the hotel and walked to Millennium Park where the “Bean” sculpture is and took all the pictures! Then we walked to LondonHouse Rooftop Bar for lunch. Then we walked to Lake Michigan along the riverwalk. Then we walked back to the hotel. Then we walked to our evening event near Navy Pier. And after a fun evening catching up with old friends and making new ones, we walked back to the hotel!
Saturday morning bright and early (5am!), we drove to the airport to pick Diana up. Once back at the hotel, the car got parked again. And we walked! We walked to our classes that were about 1/2 mile away from the hotel. Then after the morning session was over, we walked to Chicago Pizza and Oven Grinder (over 3 miles away) for their famous pot pie pizza – it is cooked upside down with the cheese on the bottom and the pizza crust on top – then flipped over when it’s served. We took a Lyft ride back to the hotel. My Chase Sapphire Reserve comes with the Lyft Pink membership and $10 credit per month. This saved us more than half the fare and we were able to get across town for $11 plus tip. Our evening event was at the iO Theater for improv night. Again, this was back across town. We chose to take the Red Line subway/elevated train “The L”. It was a short walk to the station in downtown and a $2.50 fare to get within a few blocks of the theater. Our ride home was with Lyft again – Diana used her $10 credit and we made it back across town for around $5!
Sunday the meetup was over. We had the wonderful buffet breakfast and then walked back over to Millennium Park so Diana could see the bean, too. More pictures were taken! Then back to the hotel to stock up on snacks from The Club. Then off to the National Park.
We had reached out to another friend, Kristen, that lived south of the city and had her meet us there. We checked in at the Visitor Center so we could all get our stamps in our NP passport book. And then scouted out a couple of hikes. The first was the Dune Ridge Trail that was a .70 mile trail that hiked up a forested dune to an overlook of the marshlands. Then we went a little further to Dunbar Beach where we crossed a sand dune to the lake shore and could see the Chicago skyline in the distance. Next was the West Beach and the Dune Succession Trail that was a nice .90 mile loop trail over the dunes and through the pine forest. It was mostly a boardwalk and had over 270 stairs! It also ended on the beach with a great view of the Chicago skyline. After a fun-filled day exploring, it was back to the airport to head home.
Lounges:
Northwest Arkansas National Airport (XNA) has just opened it’s first lounge! It’s called the Escape Lounges. You can access the lounge if you have American Express Platinum or Delta Reserve or a Priority Pass card (I have mine through Chase Sapphire Reserve and Capital One VentureX) or you can pay $29.95. The lounge is located just after security before the walkway to the American/Delta/United gates. It was very clean and had a variety of sandwiches, soups, salads and sweets. They also have a full selection of complimentary drinks. I arrived to the airport early because I was hoping to fly standby on an earlier flight since storms were expected to move into Chicago later in the evening.
Chicago O’Hare International Airport (ORD) did not have any lounges that I had access to. So Diana & I sat at a pub and visited a little longer before my flight took off.
Here is a summary of the points and miles used on this trip:
