Jeff’s Interview – Chicago

Jeff and I grew up in the same small, rural town of Storm Lake, Iowa. We were friends in high school and have reconnected the past few years over social media and our shared passion for travel! After graduating from college Jeff spent two years with the Peace Corps in Poland. He's currently visiting friends there and making new travel memories (follow his adventures on instagram). Being an avid traveler; his adventures the past few years have included Croatia, Turkey, Poland, Australia and Mexico. His travels also include exploring the US, with recent visits to Colorado, California, Florida, and Arizona. He's also a doting uncle with frequent visits to Colorado and Iowa to spend time with family. Jeff resides on the north side of Chicago and lives the urban life. In our interview he shares his insider tips about visiting the Windy City - enjoy!

What area of Chicago do you suggest visitors stay?

If I were visiting Chicago for the first time, I would target River North/Gold Cost as a central place to stay in the city.  From here, you have easy access to the shopping, restaurants, nightlife, museums and public transportation both to the north and south of the downtown area.

Underrated neighborhood worth exploring?

Chicago is full of such fantastic neighborhoods it really depends on what you are looking for - food, different culture, bars, etc.  I'm partial to the northside as its where I live, easily walkable and lots of activities for everyone.

Insider tip one won't find in a guide book?

If you enjoy street festivals, Chicago is the epicenter - do some research before you come and perhaps decide which area of the city you are interested in as we have 2-3 fests every weekend all over the city.  Food, music, drinks - all outside and fun!

Favorite Chicago restaurant?

So I'm a big BBQ fan and highly recommend Smoque.  It's a fun spot, great food and everyone from all over the city is lined up waiting patiently.

Favorite season?

Fall in Chicago is fantastic.

Where would you live if not the Windy City?

I'd like to think that if I could live anywhere possible it would be in Europe but the most realistic alternative to Chicago would be San Fran.

Beach or mountains?


Do you prefer trains, planes or automobiles?

Trains for sure.

Best thing about growing up in Iowa?

The best thing about growing up in Iowa is all of the close friends I still have, a great education and that "small town" wonder of the greater world outside that still makes me explore.

Favorite travel app?

United and SPG apps are my most important.

Window or aisle?

Window and, if at all possible, seat 10F.

Best advice to business travelers?

For me, I take the first plane out when traveling - it almost always flies despite the weather and you don't have the hassle of the normal inexperienced travelers.  I also recommend keeping your loyalty to one airline as they will fail at one point in time so having the perks of priority or access to the clubs makes the difference between them wanting to help or leaving you standing in a long line with everyone else.

Your must haves on a plane?

Economy plus towards the front - I like the leg room and the ability to get off the plane earlier.

Would you use airline travel reward points for an upgrade or free ticket?

I am careful about using my reward miles but weigh the cost of the trip or upgrade against using points - occasionally points win.  However, I largely accumulate points for a big trip that might otherwise not be feasible were it not for the ticket being essentially free.

Packing tip?

I roll all of my things, allow only one pair of shoes in the luggage and everything else needs to layer and work like garanimals.  Flexibility to weather and social settings is important.

Favorite hotel or brand?

Starwood all the way.

Best travel memory or destination?

All of my trips I would say are very memorable as my goal is to collect these experiences vs. things.  That said, Turkey has been my favorite trip.

Favorite travel quote?

"Perhaps travel cannot prevent bigotry, but by demonstrating that all peoples cry, laugh, eat, worry, and die, it can introduce the idea that if we try and understand each other, we may even become friends."  Maya Angelou.

"If something good happens, travel to celebrate. If something bad happens, travel to forget. If nothing happens, travel to make something happen."

Bucket list trip?

Bucket list must is South Africa - safari, wine country and seeing the great whites.

Where to next?

I traveled 105K miles in 2015 so I'm on a travel lock down for a while.  My first break will be off to Denver to see my nieces and nephew in March.  (by the way you may want to check in with me later as I've had offers from friends to travel to Singapore or the Florida Keys........very tempting)

  • The friends won, as Jeff did travel to the Keys in late February and is currently in Poland. Follow his adventures on instagram

Until the next adventure - bon voyage!



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