How to Propose in Chicago

Featured Chicago Proposal Tips
  • Choose a special location to pop the question in Chicago
  • Practice getting down on one knee beforehand
  • Think about what you will say
  • Make reservations so you have a reason to dress up
  • Hire a proposal photographer to plan and capture the moment

Since 2013, Flytographer has captured thousands of surprise proposal photos all around the globe. Explore romantic proposal ideas and tips from real couples, including their top proposal ideas and tips, and the best ways and the best places to propose in Chicago. Explore our customers’ heartwarming Chicago proposal stories below.

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Christopher & Kelsey's Proposal Story in Chicago

How did you meet?

School

What is your love story?

We met in college and after being friends for a couple of years, we both ended up single at the right time! The rest is history. She's my best friend and I knew she was the one when I couldn't envision an exciting future without her around.

What made you choose this proposal destination?

The first gift I ever gave her was a vinyl copy of Wilco's "Yankee Hotel Foxtrot" which features the Marina towers on the cover. When we planned a Memorial Day getaway to Chicago, I knew wanted to make it memorable!

What is your proposal story?

We spent the day on a architecture boat tour and had reservations for dinner on the River Walk. I casually mentioned that we should get some good photos together before dinner with the city in the background, all the while I knew I'd be popping the question with the help of my photographer in the area.

Best tip for proposing in Chicago

Prepare for weather!

Proposed in Chicago in May

Photo Shoot Location: Chicago Riverwalk

Joe in Chicago for Flytographer


Aaron & Sarah's Proposal Story in Chicago

How did you meet?

School

Proposed in Chicago in August

Photo Shoot Location: Custom Route

Lukas in Chicago for Flytographer


Taylor & Becca's Proposal Story in Chicago

How did you meet?

Hinge

What is your love story?

We connected on Hinge just before New Years Eve, and I decided that my buddy and I were going to crash her NYE plans. What was the worst that could happen... Unlimited food and drink? Best case scenario - we hit it off. Lucky for me, I got both! The following weekend was my birthday, and I knew she was the one when she celebrated me at midnight with 27 candles stuck into a Hawaiian role (all she could find on short notice) haha.

What made you choose this proposal destination?

We have spent a ton of time wandering Lincoln Park with our dog, Teddy, and have always loved the view of the skyline that you get from Fullerton Beach; so I knew that would be the perfect spot for this moment.

What is your proposal story?

I got two of her best girl friends (the ones that were there the night we first met) to take her out for drinks at Theater on the Lake in Lincoln Park - a short distance from where I was secretly setting up with my best friend (and our dog, Teddy). On the girls' "way to dinner", they decided to walk through the park so that they could get a quick shot of the three of them with the skyline in the background. When Becca finally looked up ahead, she saw me and Teddy standing there with a set up of rose petals and champagne. She stopped in her tracks, realized this was all for her, and immediately started crying (happy tears, of course) :). Our photographer, Lukas, was there to capture her reaction and the moment she finally made it to us, where I shared some words (that neither of us remember) about how I knew she was the one before getting down one one knee and asking her to marry me.

Best tip for proposing in Chicago

Scout out your spot ahead of time, try to choose a space that's not overly crowded, and be sure your partner's friends are able to stick to a timeline if they're helping you with the surprise ;).

Proposed in Chicago in August

Photo Shoot Location: Custom Route

Lukas in Chicago for Flytographer


Zach & Michael's Proposal Story in Chicago

How did you meet?

Hinge

Proposed in Chicago in July

Photo Shoot Location: Custom Route

Danielle in Chicago for Flytographer


John & Kim's Proposal Story in Chicago

How did you meet?

Social Media

What is your love story?

We met through Bumble and unlike most girls, Kim made me call her before we went out. I liked that. We had an amazing connection right away. After our first date, I texted my best friend and said, "I knew in 5 mins that she will be the future Mrs. Hamby. Quote me." Now after that, things were really up and down. We both moved away from AZ for work. Me to San Francisco. Kim to four different states for a clinical rotation for anesthesia. We had broken up, dated other ppl, but were always on each others' mind. Eventually, we started meeting up in different states and put the pieces back together and she agreed to move back to AZ again after I did. After that, we moved in a bit later, combined our forces (ie: 3 dogs), and want to ride off into the sunset! Ps. The day we got back from Chicago, officially engaged, we found out we are expecting! We are super pumped!

What made you choose this proposal destination?

I used to live in Chicago and Kim often quotes it as her "favorite food city." We had never been together, so we made it a point to go this year.

What is your proposal story?

I had been planning on proposing on this trip for quite a while now and have been trying to get her off the scent so much that it came between us a little. We got in a bit of a fight a month back because she didn't think I wanted to marry her. haha. I didn't want to spoil the upcoming plans so it was a tough conversation but I just assured her it would happen (ps. I already had the ring.) Once I booked Flytographer, JOE WAS GREAT, and planned everything, I felt great about it. We got to our Lincoln Park spot on time, I spotted Joe as we walked past him, and he trailed us as we went to find the spot. The only thing was...the spot I wanted to propose was BLOCKED OFF! The park was under complete construction. Nooooo! So, I had to improvise a little bit. I found a beautiful tree with some color and did it there. She was in pure shock. She cried, which is unusual for her and claims she didn't hear a word I said. I believe her because she actually said "yes" before I even asked her. hahaha. Joe was amazing because he took a terrible "construction fence" background and made it look magical. We love our photos.

Proposed in Chicago in April

Photo Shoot Location: Custom Route

Joe in Chicago for Flytographer


Chris's Proposal Story in Chicago

What is your love story?

The moment I told Simona I loved her for the first time, I knew that I wanted to spend the rest of my life with her.

What made you choose this proposal destination?

Simona, my fiancee, has always loved Chicago and was so excited when we booked the trip to go together. If I could get everything in order in time, I thought Chicago would be the perfect location. It would make Chicago a special place for both of us and one that we could re-visit in the future. After some planning (thank Flytographer!), it looked like I'd be able to get everything in order for our trip, so Chicago became option number one on where to propose.

What is your proposal story?

Proposal went as smooth as I could have imagined. First, the weather. We visited Chicago over New Years, and I was constantly checking the weather to see if we would get some sun on the day of the proposal. The day we arrived--snow. The three days in Chicago after the proposal--clouds, wind, rain or all three. The day of the proposal--perfectly sunny day with fresh snow in Millennium Park. Then came the location. I found a great location in Millennium Park that overlooks the city skyline, so I began organizing the proposal in a way that would get us to the park. After talking with Joe, our Flytographer photographer, we agreed noon would be the perfect time. I told my fiancee that we had brunch, but thought it would be nice to walk through the park on our way--as our hotel was walking distance to both the park and our brunch location. Luckily, it was sunny and wasn't raining, so a walk through the park didn't seem like such a strange idea. We got to the park about 10 minutes before the proposal time and eventually made our way to the location I had picked out. We snapped a couple pictures ourselves on my phone (my cue to our photographer that I was ready), and then our photographer (a stranger to my fiancee, but my co-conspirator) offered to take a few pictures for us on my phone. He positioned us for the soon-to-be proposal, took a few pictures on my phone, we said thanks and he (unbeknownst to my fiancee) got into position. We started to walk away when I told my fiancee how much I loved her, she smiled and reciprocated the feeling to me thinking it was me just being affectionate, and then I laughed and said, "No no no, this is different - I am about to say A LOT more." I told my fiancee I want to spend the rest of my life with her and eventually got down on one knee, pulled the ring out of my pocket and asked her to marry me. My fiancee was absolutely stunned and through her amazing smile she shouted "a million times yes!" We were both completely overjoyed and could not stop smiling as we took some post-proposal photos and celebrated the rest of the day. Greatest day of our lives.

Proposed in Chicago in December

Photo Shoot Location: Custom Route

Joe in Chicago for Flytographer


Conrad's Proposal Story in Chicago

What is your love story?

Growing up in the South, I never would have thought I'd end up marrying a girl from Chicago. Steph and I met through Twitter, but originally planned to stay friends. God, however, had other plans. We fell in love and quickly began making visits back and forth. It didn't take long at all for me to know I wanted to marry her.

What made you choose this proposal destination?

Steph has lived in a suburb of Chicago her entire life. On one of my trips to visit her, we went downtown and I instantly fell in love with the city. It was then that I decided one day I would come back downtown and ask her to marry me.

What is your proposal story?

I had originally planned to propose on Friday, but weather forced us to move it back to Sunday afternoon. Rain threatened all day, but we managed to find an hour-long clear window. I had told Steph that we were meeting a friend who was a photographer for some couple pictures (we had recently celebrated our second dating anniversary), and somehow she believed me. We met the photographer down on the lakefront. He took a few casual pictures and then asked Steph to pose looking out over the water. I then got down on one knee and told her to turn around. The look of pure joy and total shock on her face is one I will remember for the rest of my life - and I'm so glad Michael was there to capture it forever!

Proposed in Chicago in September

Photo Shoot Location: North Avenue Beach

Michael in Chicago for Flytographer


Armando's Proposal Story in Chicago

What is your love story?

A colombian girl moved to Mexico and met a neighbour that help her to open a door and then he made her feel in love of his country and his heart. Now they are engaged!!!

What made you choose this proposal destination?

Chicago has everything we wished for: an amazing marathon, interesting places to go, delicious food and love in the air!!!

What is your proposal story?

It was perfect!!! We feel very connect and our engage day is the best begging of this journey that we are starting and what can be better to keep all our memories in this amazing photo shot.

Proposed in Chicago in October

Photo Shoot Location: North Avenue Beach

Lukas in Chicago for Flytographer


Brian's Proposal Story in Chicago

What is your love story?

We met in college. We actually lived about 3 rooms away from one another in our dorm hall. However we didn't talk or really know each other for the entire year! It wasn't until a mutual friend of ours invited Paula over to my apartment for a party where we started our love story.

What made you choose this proposal destination?

We both love Chicago. I'm originally from the area and it's Paula's favorite big city. She also loves the water so I made sure to choose a proposal spot around the water, this shoot by the river which was our photographer's (Francisco) idea. Great decision and the photos turned out amazing!

What is your proposal story?

It went really well! At first when showing up to the proposal shot, I was nervous due to the large crowds around and even standing in the spot I was suppose to meet Francisco for the moment! But after a few minutes, everyone in the planned proposal shot moved out of the way just in time for Francisco to arrive and capture the big moment. The timing of it all couldn't have been better!

Proposed in Chicago in August

Photo Shoot Location: Custom Route

Francisco in Chicago for Flytographer


Philip's Proposal Story in Chicago

What is your love story?

Katie and I met through Match.com while she was touring with a North American Broadway show. I sent her a message to see if she wanted to go to the Cubs vs Cardinals season opener that evening. She, being a Cubs fan, said she was already going but could use a "body guard." I agreed and picked her up after her show. We ended up not being able to get tickets, but wandered around until we found ourselves in BallPark Village to try and catch the last few innings. Before long, we were lost in conversation and forgot about the game completely. (It even started to rain!) The date went great and I asked if I could see her again. She sent me the rest of her touring schedule and I decided I couldn't wait to see her and I scheduled a flight out to Boston for the very next weekend. After some terrible travel luck and flight into the wrong city, I rented a car and drove into Boston. We celebrated all weekend and decided to make our relationship official. After dating long distance and seeing each other as often as we could, I asked Katie if she'd like to move to Saint Louis. She was planning on going back to school to become a Physician Assistant after tour. By August, we drove all of her things down from Manhattan and she was officially a STL resident. Month after month the relationship grew. We joked about making it official, but between her crazy full time student and full time job and my Marine Corps schedule, we never had a day off together. I knew that my buddy's wedding weekend in Chicago had to be it. I contacted Flytographer and was put in contact with Francisco.

What made you choose this proposal destination?

It was the only weekend Katie and I would have to ourselves. She hadn't had a day off in six months and I had a very busy schedule as well. Katie also lived in Chicago for a couple of years and loves the city.

What is your proposal story?

Francisco was perfectly perched on the steps of the Riverwalk. I had convinced Katie that I wanted to see the "touristy" parts of Chicago and she was excited to walk the Riverwalk with me prior to a nice dinner reservation I had set up for us. Little did she know that halfway through the walk, I had planned a sneaky surprise proposal. Just before the Clark St bridge, I stopped her and told her that I had lied about the reservation. Shocked, she didn't really know what to think. I got down on one knee, told her I loved her and asked her to marry me. She said yes! Relief was an understatement, but there was still one more step. Katie wears her mother's Tiffany sterling silver ring on that finger. I jokingly told her it was "probably time to take the old ring off." She laughed and removed the ring... Only to have it slip from her fingers, bounce three times, and fall into Lake Michigan. We were both shocked. You can clearly see it in the photos! We laughed it off and considered it a sacrifice to the wedding gods. Overall, it went extremely well. It wouldn't really be "us" without a crazy story to tell. We're both extremely excited to begin our wedding planning adventures and we couldn't be happier that Francisco and flytographers captured the whole thing.

Proposed in Chicago in June

Photo Shoot Location: Chicago Riverwalk

Francisco in Chicago for Flytographer


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