U.S. Road Trip Re-Cap: Weeks Nine, Ten, Eleven & Twelve (Chicago & Oshkosh)

North to South U.S. road trip recap weeks nine, ten, eleven and twelve

Two months of nearly non-stop road-tripping exhausted us, so we decided to take a break.

We wanted some time to relax, regroup, and work on our blogs, and to do that, we needed to stay still. Luckily, we were traveling around the midwest at the time, and my twin brother had a room available for rent in his Chicago apartment. So we settled down for a full month and used the time to explore Chicago more, set new goals for our projects, dabble in some artistic hobbies, and even launch a new business. See what else we accomplished during our month-long road trip break in Chicago below!

Note: I’m still catching up on our weekly road trip re-caps! This one covers July 5 – August 1. 

Diana Southern at North Avenue Beach, Chicago
awesome views of the Chicago skyline over Lake Michigan from North Avenue Beach

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You can get an overview of our trip each week here on the blog, but we’re posting more frequent updates of our cross-country U.S. road trip on Facebook and Instagram.

Mimosa time with the twin! #Chicago #NTSroadtrip2015

A photo posted by North To South • Diana + Ian (@dianasouth) on

Oshkosh fly-in air show 2015
We did take one mini road trip this month — to the Oshkosh fly-in in Wisconsin.
pepperoni deep dish pizza at Giordano's Chicago
We decided our favorite deep dish pizza in Chicago is Giordano’s!

States Visited These Weeks

  • Illinois
  • Wisconsin

(no new states visited these weeks)

States Visited in Previous Weeks


I’ve been meaning to post this one for awhile! Isn’t it beautiful? #shrimpstagram #chicago #NTSroadtrip2015


A photo posted by North To South • Diana + Ian (@dianasouth) on

Diana and Ian at the beach in Chicago
Hello from the beach in Chicago!

Total States Visited So Far: 19

California, Nevada, Arizona, New Mexico, Texas, Louisiana, Mississippi, Tennessee, Arkansas, Missouri, Illinois, Wisconsin, Iowa, Nebraska, South Dakota, Wyoming, Idaho, Montana, North Dakota

Seabee Warbird at the Oshkosh fly-in convention in Wisconsin
We did take one mini road trip this month — to the Oshkosh fly-in in Wisconsin.
Diana Southern and the Chicago skyline
Diana on the North Avenue Beach Pier in Chicago


  • Chicago, Illinois
  • EAA AirVenture Oshkosh fly-in convention (Oshkosh, WI)
Seabee Warbird at the annual Oshkosh fly-in convention in Wisconsin
At the Oshkosh fly-in, we visited Ian’s parents and their plane, the Seabee Warbird (in the background).
Oshkosh fly-in air show 2015
Planes fly in formation overhead at the Oshkosh fly-in in Wisconsin


  • playing Whirlyball for the first time in Chicago
  • visiting Ian’s parents and the Seabee Warbird at the Oshkosh fly-in convention in Wisconsin
  • homemade beer brewing, video game nights playing DOTA 2, and repeated delicious barbecue nights with my twin brother in Chicago
  • oodles of deep dish pizza
  • getting artsy-craftsy with jewelry and camera strap making
  • testing out the GoPro HERO4 Session
  • rock climbing
  • rainy days
  • meeting up with some fellow freelancers and entrepreneurs
  • launching Boost Marketing by Diana

moonrise over Lake Michigan, Chicago

Notes and Insights

  • Playing the game of Whirlyball requires a great deal of hand-eye coordination.
  • Playing the game of Whirlyball while also wielding a selfie stick requires a great deal MORE hand-eye coordination.
  • Barbecuing with butter is definitely the most delicious way to prepare shrimp.

Planning your own trip to Chicago? Check out Airbnb’s list of things to do in the Windy City.

playing Whirlyball in Chicago
Winning at Whirlyball in Chicago with my twin
Chicago skyline long exposure photo by Ian Norman
one more shot of that awesome Chicago skyline

Home brew bottling before we leave Chicago. Making room in the bottles for the new batch. Time to drink up! #NTSroadtrip2015 #chicago A photo posted by North To South • Diana + Ian (@dianasouth) on

Photo Gallery

Seabee Warbird at Oshkosh 2015 Flying contraption at Oshkosh fly-in 2015 rock climbing in Chicago entrepreneur's meetup in Chicago plane flying overhead at Oshkosh fly-in 2015 Seabee Warbird at the Oshkosh fly-in convention in Wisconsin Diana at North Avenue Beach Chicago plane at Oshkosh 2015 Diana jumping in front of Chicago skyline Thai food night with friends in Chicago Diana Southern Chicago skyline Seabee Warbird at Oshkosh 2015

All photos were taken by Ian and Diana with the Sony a7 II (Ian’s camera), Sony RX100 III (Diana’s camera — review here) and our smartphones.

Week 13 Preview

  • Ann Arbor, Michigan and a visit to Dynamic Perception, makers of the slider we used in the making of our On Photographing the Milky Way video
  • Pittsburgh, Pennsylvania (Ian’s college town)

I hope you enjoyed this U.S. road trip re-cap! In case you missed them, check out our other weekly recaps from our road trip. Have you road-tripped to any of these U.S. locations? Tell us about your trips in the comments.

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