Travel to Chicago on Points


How to get there

Southwest Airlines is always my initial choice for domestic travel. My initial flight from BNA to MDW was about $198 round trip when I booked the flight in late July. Besides Southwest generous baggage policy which I don’t need because I’m #teamcarryononly, my favorite perk of Southwest is the No Change Fee policy. Three weeks before departure, Southwest lowered the round trip cost to $95. Yes, $95. Because of Southwest no change fee policy, I logged into my account online and rebooked my same flight and received a $103 credit to be used for a future flight. I could have used Southwest Rapid Rewards miles for this trip, but since it was so cheap, I didn’t want to waste my points.

Remember, Southwest Rapid Reward program is a 1:1 transfer partner of Chase Ultimate Rewards.


Where to Stay

Chicago is home to Hyatt headquarters, so there’s no secret there are plenty of Hyatt hotels to choose from including:

  • Park Hyatt
  • Hyatt Chicago Magnficient Mile
  • Hyatt Regency Chicago
  • Hyatt Regency McCormick Place
  • Hyatt Place

Other options include the Omni and Four Seasons.

Personally, on my recent trip I stay at the Park Hyatt and Hyatt Regency Chicago.

In case you missed my previous posts, check out my Nerd Report on the Park Hyatt and Hyatt Regency Chicago:

Nerd Report: Park Hyatt

Nerd Report: Hyatt Regency Chicago


Where to Eat


After finally checking into the lovely Park Hyatt Chicago, I was starving so I asked the bell man at the Park Hyatt for any suggestions on lunch. He then mention Giordano’s.
Giordano’s and Gino’s East are two of the more famous Chicago style deep dish pizza locations.


Giordano’s was literally 100 yards from the Park Hyatt. After a quick walk and snapping a few pictures of the store front, I stepped inside. The place was packed for lunch. I was eating solo, but still had a 20 minute wait. I decided to go for the smallest 6″ personal pizza. The small pizza still required a 30-40 minute cook time. The cook time is standard, so keep that in mind if you are super hungry. When the pizza came to my table it was piping hot with the signature sauce on top presentation. Let me tell you, this was the best pizza I’ve had in my life. The cheese was plenty, pepperoni was tender, and beef wasn’t dry. It was simply perfect.




The Gage

While walking along South Michigan Ave and visiting Millennium Park, I decided to step into The Gage. The Gage serves American fare with a slight spin on classics. Since this day 2 for me in Chicago and again during lunch time, the restaurant was booming. Luckily, I found the last seat at the open seating bar. The bartender recommended I try a dish called “The Gage Venison Burger”. Now I’m not a fan of venison because of the “gamey” taste it can have at times. However, this burger was different. They use fresh venison, infused with beef fat, smoked gouda, fried jalapenos, woodland mushrooms, pickled onions, and a mustard aioli. Just crazy. And let me tell you, when you time into the burger, it was like butter.

The Gage Burger

Things to Do

360 Chicago

Travel 1,000 feet up to the 94th floor of the historic John Hancock building to get a 360 view of Chicago. 360 Chicago experience will cost you $20. If you are feeling extra adventurous you can pay an extra $7 for the “Tilt” experience. More details can be found atĀ

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Millennium Park

If you looking to get out of your hotel room, Millennium Park is the perfect destination. The park is known for one of the most visited attractions in the city, Cloud Gate. The park also has plenty of sculptures and green areas for picnics or taking in the Chicago air.

Jay Pritzker Pavilion


Cloud Gate





Art Institute of Chicago

One of the old and largest Art museums in the world resides in Chicago. As someone who loves art and design, I couldn’t pass up the opportunity to visit the Art Institute of Chicago. There are over 11 curatorial departments such as Modern and Contemporary Art, Photography, Print/Drawings, European Decorative Arts, Asian Art, American Art, and African Art and others.

I spent a couple of hour at the Art Institute, and took way to many pictures. I won’t overwhelm you with a million pictures, but I found the picture titled “Brilliant Yellow #9” by Jo Baer rather interesting. Stare at the picture and tell me if you see anything.




African Art



Chicago was fun. The Cubs had won the World Series my 1st night there. The city was alive, the food was great and so was the weather. There is never enough time to do all that you want, but I will be back. Credit card points help me save a ton on hotel stays this trip, and guess what you can do it to.

Remember, click the links below to read the latest Nerd Reports:

Nerd Report: Park Hyatt

Nerd Report: Hyatt Regency Chicago

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