Marriage Proposal + Chicago around the holidays = A definite yes…maybe!

With the Holiday season- AKA- engagement season quickly approaching, I thought it would be fun to share some ideas on how to make your proposal pop! 

Here are some won’t cost a thing but will provide awesome pictures ideas. If there aren’t pictures posted on social media, did it even really happen?

 So let’s dig in and figure out what would best suit you and your partner!

Zoo Lights at the Lincoln Park Zoo. Aside from it being free, you can also enjoy photos with Santa to show off that ring, warm spiced wine and frosty beers (in case they say no…jk) holiday snacks and so much more! 

Zoo lights

The Bean at Millenium Park- aside from ridiculously cool pictures, you can enjoy ice skating, carolers, and of course the beautifully lit- City of Chicago Christmas tree!

the bean

Christkindlemarket Chicago- Admission is always free and there is so much to be offered! This market has now become a Chicago institution offering not only typical German food and drink but also diverse holiday entertainment!

christkindle market

Once (s)he says yes, you can warm up at one of my favorite spots, Mindy’s Hot Chocolate bar… for some amazing hot chocolate along with a variety of sweet treats…fresh bling…and did I mention chocolate? Be sure to book a table ahead of time.


And if you really want to impress (or maybe scare them half to death) your partner, you can schedule a private Helicopter tour of the city with Chicago Helicopter Experience!  What better way to see the holiday lights while staying warm in the comfort of a luxury helicopter! And she or he will most likely say yes seeing as they have nowhere to go. Win/Win! 


Chicago Helicopter Experience offers many different package options, ranging in price, for more information click the link below.

If you’re looking for a romantic restaurant, Chicago has limitless possibilities. You can find one of a kind city views at Signature room at 95th, Cindy’s Rooftop located in the Chicago Athletic Association Hotel or Everest on the 40th floor.

One place that is dear to my heart is the Walnut Room located in Macy’s. The tree is unbelievable and the drinks are pretty darn good too! Whether you are looking for a sultry jazz-era vibe in Bavette’s or a warm cozy escape from the cold at Gilt Bar I have no doubt you can find exactly what you’re looking for.

So get out there and plan the perfect proposal! Best of luck. And of course, after they say yes, remember to buy my book; Weddings Unfiltered- The No Bullsh*t Wedding Planning Guide to keep your sanity once the planning process begins.


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