DreamTrips Podcast

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Experience Chicago

October 6, 2017

Experience the sights, sports, culture and cuisine of Chicago through the eyes of a local in our latest Destination Focus.

We’ve added a new Destination Focus series to our podcast lineup that will fall between the 6th and 10th of each month. Last month we highlighted Rome, and this month we call on the expertise of longtime DreamTrips Member and Chicago native John Heerhold to guide us through the Windy City.


A proud fan of both the Chicago White Sox and Chicago Bears, John highlights the best things for sports enthusiasts to do and see in the city. But the fun doesn’t end there! You’ll also learn about the gastronomic delicacies that Chi-Town has to offer, and hear a list of the sights you shouldn’t miss.

We turned this episode over to John — leaving out the Social Beat and “More Than a Travel Tip … Tip” — so we could focus on the city spotlight. We hope you enjoy your chance to experience Chicago through the eyes of a local!


  • [01:02]   The introduction of another Destination Focus episode of the DreamTrips Podcast.
  • [01:14]   Find out what you can expect from Chicago native John Heerhold.

Today’s Feature

  • [01:47]   Destination Focus: Chicago, Illinois, United States.
  • [02:32]   John touches on his love for his city.
  • [02:50]   The Polish connection.
  • [03:43]   The must-see sights of Chicago.
  • [03:57]   A little Chicago folklore.
  • [04:32]   Baseball is a big part of this city.
  • [06:25]   Watering holes near Wrigley Field.
  • [07:10]   A new name, but it’s certainly a tall tale.
  • [07:36]   Iconic stadiums of Chicago.
  • [09:42]   The straight-forward attitude.
  • [10:30]   Lake Michigan and beach fun with DreamTrips Members.
  • [12:00]   DreamTrips Local and incredible Chicago food.
  • [15:43]   Theatre, improv and the blues.
  • [18:04]   Getting around the city.
  • [18:45]   They don’t call it the Windy City for nothing!
  • [19:56]   A shiny, reflective photo opportunity and more.
  • [21:27]   John explains why he thinks the DreamTrips community is so great.


  • [23:40]   Thanks to longtime DreamTrips Member and Chicago expert John Heerhold.
  • [23:47]   Contact the DreamTrips Podcast on social media with #DTpodcast.
  • [24:21]   The podcast airs every month on the 1st and 15th, and again between the 6th and 10th. Our next episode is about Halloween trips, so get ready for some spooky entertainment!

Addresses, websites and phone #s mentioned in this episode: