This is built up as one of the most important things you will literally ever do. Not to downplay it, but the partner you show up as everyday and the life you are building together is way more important. That being said, this is the moment to think through every detail, utterly personal and truly special.

After years of photographing these kinds of celebrations, I've seen the same questions and frustrations come up over and over again, so I put together this guide based on the most meaningful proposals I have seen.

Because… this shit is supposed to be fun.

PART I - What are we doing

Where to start

Depending on your relationship, you already have the ring you know they are going to love and know exactly what to do or you have literally no clue. If you have literally no idea please talk to their friends and family I promise they will have some insight if you don’t know where to start.

Things to think about

  • Does your partner want a public proposal or would they rather die?

  • Do they want family there?

  • Would they want photos?

  • Is there somewhere meaningful to you?

  • Should it be a surprise, or just the timing be a surprise?

PART II - Where are we going

Where do you love

First decide if you want to go somewhere together and propose, or if you want them to be brought by friends or family to your proposal spot.

Would your person want an iconic Chicago spot, or somewhere more personal and unique.

If you are looking for iconic Chicago locations, see the list to the right for free spots with incredible views.

Classic Chicago spots to propose

  • North Pond

  • Olive Park

  • Alfred Caldwell Lily Pool

  • Montrose Harbor

  • The Art Institute

  • Garfield Park Conservatory

  • Ping Tom Park

  • The Chicago Riverwalk

  • Navy Pier

Underrated alternatives

  • Where you met

  • Your favorite bar/ restaurant

  • At home

  • Your favorite walking path

  • Where you became official

  • Dog park

  • Weekend cabin

  • Summer camp

  • Favorite bookstore

PART III - What are we doing after

Keep the momentum going

This can be an easy thing to forget about, but it just as important.

Thank about

  • what time of day is it

  • who would they want to celebrate with

  • where do they want to go

  • what do they want to be wearing

Options

  • Dinner reservations (see to the right)

  • Surprise party

  • Weekended getaway

  • Cubs game

  • Staycation

  • Movie night set up waiting at home

Romantic restaurant

  • Trivoli Tavern

  • Obélix

  • Bavette's

  • Rose Mary

  • Armitage Alehouse

  • Alla Vita

  • Le Bouchon

  • Monteverde

  • The Loyalist

PART IV - Proposal Myths

Bigger isn't better.

Nobody needs a drone.

The perfect speech doesn't exist.

The ring doesn't have to be a surprise.

If they cry, you're doing great.

This shit is supposed to be fun.

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You got this! Obviously, I would love to hear from you if you are interested in photo coverage. Please do not hesitate to reach out if you are looking for more advice or other vendor recommendations!