Chicago Travel Guide is part of the Round The Atlantic Trip Report. It was originally published on 6/30/2020. It has been updated since my trip Punxsutawney TPOL Trip Report in October 2021.
TPOL’s Guns & Butter Travel Guide is the best way to see as much as you can in as little time as possible. Here’s how it works – A trip is composed of two factors: Labor And Lazy. The opportunity cost (what is given up) for relaxing and being Lazy is gained by being adventurous in the form of Labor and vice versa. The guide includes inefficient activities i.e., tourist traps that should be avoided and aspirational activities that are worth doing but may be impossible to see given the constraints of time and resources.
“Chicago! Chicago!” Not my favorite Sinatra song, but it is a city worth singing about. Here’s what I did in Chicago. As usual, the Travel Guide is a good start but far from comprehensive.
Arrive in Style
Iberia has consistent availability from Madrid to Chicago (see Iberia Business Madrid Chicago: Solid Sweetness).
Stay
From the best hotel to questionable service the second time around, the Waldorf Astoria is worth a look. 
The Tremont is no longer a Marriott but benefits from its location and affordable nightly rate.
Another option is the Radisson Blu Aqua.
A central option is the Hyatt Regency (see Hyatt Regency Chicago: Bedtime).
If you have an early flight out of O’Hare stay at the Hyatt Regency (see Hyatt Regency O’Hare: The Best Airport Hotel).
Sports
Chicago is a great sports town. I’m not a baseball fan but I enjoyed going to U.S. Cellular for Memorial Day. Catch any game from any sport.
Food
New Orleans is the best city in the US for food (see Guns & Butter: New Orleans Travel Guide (Binge Edition)). Chicago is also a premier food destination.
Be sure to have a few hot dogs (see Chicago Style: Hot Dogs! Hot Dogs! Beer Anyone?).
The reason to go to Chicago is for the pizza. I’ve evaluated plenty of locations and stand by my original assessment that Lou Malnati’s is the best (see The World’s Best Pizza: Chicago Deep Dish Edition). 
2021 TPOL Update: Lou’s wasn’t as good this time (see Post Lockdown Dream Fulfilled? Deep Dish Pizza in Chicago).
Others may recommend Giordano’s, but it’s not for me (see Giordano’s Pizza Chicago: Trust Your Taste Buds, Not Your Friends). 
For all my pho lovers, Chicago is one of the best places in the world for pho. It has an entire street just for pho sampling (see Pho Paradise Found: Asia on Argyle, Chicago). 
Drinks
Traveling means drinking. If you’ve been Scottsdale you’ll recognize two bars: El Hefe and Bottled Blond (see Scottsdale To Chicago, El Hefe Sunday Funday). I preferred the Chicago Bottled Blond location to my former home course.
Billy Goat
I don’t know if it’s world-famous or a tourist trap, but I enjoyed stopping at Billy Goat.
Tourism Must Do
- Walk down the Magnificent Mile.
- Go to the 96th floor of the John Hancock Building.
Willis Tower on the right - Go to the beach
- Go to Navy Pier via Lakeshore Drive.
- Act like Ferris Bueller.
Tourism You Can Skip After Your First Time
- See the stupid Bean.
Always Skip
Chicago in the winter. It doesn’t look like this:
Overall
I love Chicago in the summer and will go back for more baseball, hot dogs, pizza, beer, and pho.
Chicago Travel Guide is part of the Round The Atlantic Trip Report.
