How to get amazing photos from your destination engagement session

Chicago Photographer

Although I am not a Chicago based photographer I had a great time photographing this California couple who lives in Chicago.

This Chicago destination engagement session is one of  favorites.  The couple getting married are from California but they met in Chicago where they both currently live. Although they are having their wedding ceremony and reception in Los Angeles they could not decide where they should take their engagement pictures. I asked them a simple question “do you want something different”? With a simple reply they said “Yes”.

The next thing I know we are taking amazing photos in the Loop of downtown Chicago.

How to get amazing photos for your  destination engagement session

With a quick phone conversation the bride to be and myself (the photographer) put together a plan of action for our one day photo session in the city.

I wanted to know if there were any landmarks or points of interest in Chicago that were special to the couple. From there we drew up a map and a plan.

In the plan we allowed time for outfit changes and strategic bathroom and water breaks. Well not all sessions stay on schedule and to the original timeline. This proved to be true for our Chicago engagement session.

Number one reason the weather.

It was forecasted to rain from 2 pm to midnight and we were scheduled to begin our photo shoot at 1 pm.

So we threw out the original plan and started the session at 5 am. There was not a cloud in the sky and best of all we had the city almost completely to ourselves. We walked all around town for around five hours. At this point we took a much needed break to recharge and refuel ourselves.

We planned on continuing the e-session in the evening for some romantic night shots.

Sure enough the clouds rolled in and just like the weather forecast predicted the later part of the afternoon was full of showers.

We all agreed that some night pictures in the rain would be epic. With umbrellas in tow we made the most unforgettable engagement pictures to end the day.

Have a plan

  • Know where you will start the engagement session
  • where you will have to park (without getting a parking ticket)
  • Know how far points of interests are between each other (can the bride to be walk long distance in high heels)
  • Where will the couple change outfits
  • Arrange for hair and make up to be on time
  • Know when the sun sets or in this situation rises
  • Will you need to take a taxi from point a to point b
  • Do you have a realistic timeline

But the number one piece of advice

Be flexible

You cannot control the weather

Adapt to the obstacles as they arise

This goes for your photographer and you as the couple

If a photo opp goes off course go with it

But most importantly

Have fun

This is such a great time in your relationship

It’s exciting to be engaged and plan a wedding

Have fun, relax, and go with the flow

You will have amazing engagement pictures!

Really got to to see the city of Chicago while on this epic engagement session.

The L train station was a great place for creative engagement photos.
Couldn’t resist this one.
It rained on us but we had a great time shooting in the middle of the street.

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