1. Be thoughtful. - This story is going to be told a lot. Like over and over. So you need to make sure that it will be worth telling. It doesn’t need to be crazy wild. Just showing that you put some thought into it. It will be one of your favorite moments as a couple to tell. You will be sharing it with your children and grandchildren. Make sure you both will love to talk about it.

2. Start right with the family. - You are going to become family. Not only with your partner but with their parents and siblings as well. You will build a strong foundation by inviting them to be your new family. Even if they are not that traditional it will show that you respect them by asking their permission first. It will show that you care about their feelings too. It will start your engagement off on a good foot. 

3. Pick the Ring. - You've probably already picked up an engagement ring if you are planning on proposing to your partner. If you haven’t picked an engagement ring that your partner will love, now is the time. You are probably wondering what kind of engagement ring they would like. Try to remember if there was a time when they might have dropped a hint about the proposal idea once or twice. If you can’t recall anything, you might go for a date or a shopping trip to the local mall and by accident wander into the jewelry store. You can subtly ask “See anything you like?” If it didn’t work. I am sure that person working at the jewelry store will be able to help you pick the one that your partner will love. You can always play it safe and get a dummy ring - latest trend. It’s like a token engagement ring. Once they’ve said yes, you will go engagement ring sopping together. 

4. Choose the day. - You need to decide when will be the day you want to propose. This day will be one of the most important dates in your relationship and forever a special one. It is the day when you went from boyfriend/girlfriend to future spouse. If your partner loves tradition you can choose one of the classics like Valentine’s Day, Christmas, or New Years. During this time the romantic aura won’t let you go wrong. However, if you think that your partner would prefer something more unique proposal idea, you can go with the day you met or on the anniversary of the day you met or their birthday. If you chose a day which is completely random they’ll be less likely to see it coming!

5. Pick a location. - You need to decide when will be the day you want to propose. This day will be one of the most important dates in your relationship and forever a special one. It is the day when you went from boyfriend/girlfriend to future spouse. If your partner loves tradition you can choose one of the classics like Valentine’s Day, Christmas, or New Years. During this time the romantic aura won’t let you go wrong. However, if you think that your partner would prefer something more unique proposal idea, you can go with the day you met or on the anniversary of the day you met or their birthday. If you chose a day which is completely random they’ll be less likely to see it coming!

6. Hire a Chicago proposal photographer. - Proposing to your soon to be spouse creates an incredible emotional reaction for both of you. Whether they were expecting it or not they will be super excited. This moment will go so fast for both of you with nervousness and surprise. Your significant other will be so happy when they realize that you had a professional photographer capture it all for you. So you can look back and relive this moment for the rest of your lives together. You can also share the news with your friends and family on social media with a beautiful image. After they say yes you can start creating same day engagement session photos too!

When Hiring a Photographer: All you’ll really need is one hour session so the photographer can capture the grand moment of you proposing to your love. It might cost you approximately $400. I would recommend that you do your research and make sure that you hire a proposal photographer who is experienced and has photographed marriage proposals before. You also want to make sure that they have telephoto zoom lenses that will allow them to capture the action. Even if they are hiding across the street in the bushes.
Don’t Forget Your Permits: Cover your bases by acquiring photography and other setups permits needed. Most of the City of Chicago famous proposal places require photo permits. Try to find a location that you can actually rent.
What You’ll Need to Provide: It's a good idea to provide your proposal photographer with a your and your partner's selfie. Most likely you won’t be meeting the photographer in person before the shoot. That’s why you might want to make sure that they know who you are when they see you. Provide your Chicago proposal photographer with your phone number so you can message and keep in contact on the day of. To make sure that they’re on the spot waiting for a big moment to happen. When you have picked your Chicagoland proposal location you want to tell them the exact spot where you’ll be planting the knee. Remember you want to be positioned in a way that your proposal photographer can capture both of your faces!

7. Time of the day. - Absolutely nothing sets a romantic mood like a sunrise or a sunset. Take into the consideration what time of day you would like to propose. In order to ensure that the light is flattering for pictures. So you can grab the “Just engaged” session afterwards. With every season of the year comes different sunset times. Below I have listed the best times of day for a proposal based on my experience as a Chicago proposal photographer. You’ll want at least an hour of sunlight for your photography engagement session.

8. Make an excuse. - Why EXACTLY you need to be at this place at this time? You might want to come up with the best excuse you can. Unless you are going to propose at a location that you two are regular visitors. Keep in mind that they might be on the lookout for the signs of you proposing. I would say that women have a special sixth sense for this kind of thing. Maybe tell them that you want to check out this new fancy restaurant and that you are going on a fancy dinner date so they should dress up. Try to come up with a plan so they don't suspect anything.

9. Find the right words. - When the day approaches, take into the consideration all the sweet words you would like to say to your loved one right before you ask “Will you marry me?” Tell them how much they mean to you! What are the things that you love about them? When did you realize that they were the one? What excites you about your future life together? 

Perfect Times to Propose:

3 pm go time as sunset is around 5 pm
3.30 pm go time as sunset is around 5.30 pm 
(before time shift) 4 pm go time as sunset is around 6 pm
(after the time shift) 5 pm go time as sunset is around 7 pm
5.30 pm go time as sunset is around 7.30 pm
6 pm pm go time as sunset is around 8.00 pm
6.30 pm pm go time as sunset is around 8.30 pm
6.30 pm pm go time as sunset is around 8.30 pm
6 pm pm go time as sunset is around 8 pm
5 pm go time as sunset is around 7 pm
4 pm go time as sunset is around 6 pm
(before time shift) 3pm go time as sunset is around 5.30 pm
(after the time shift) 2.30pm go time as sunset is around
4.30pm 2 pm go time as sunset is around 4 pm

Jan:
Feb:
March:

April:
May:
June:
July:
Aug:
Sept:
Oct:
Nov:

Dec:

JANUARY:
FEBRUARY:
MARCH:

APRIL:
MAY:
JUNE:
JULY:
AUGUST:
SEPTEMBER:
OCTOPBER:
NOVEMBER:

DECEMBER: