Chicago Surprise Proposal | S & N

April 24, 2026 EngagementGeneralSurprise Proposal

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River Point Park Chicago Proposal | Jay & Peace

April 17, 2026 EngagementGeneralSurprise Proposal

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Pendry Chicago Surprise Proposal | Sanjit & Shivani

April 10, 2026 EngagementGeneralSurprise Proposal

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Lincoln Park Zoo Chicago Surprise Proposal | K & R

April 3, 2026 EngagementGeneralSurprise Proposal

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Lincoln Park Zoo Chicago Proposal | Ellie & Kevin

March 27, 2026 EngagementGeneralSurprise Proposal

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Montrose Harbor Chicago Surprise Proposal | B & L

March 20, 2026 EngagementSurprise Proposal

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RPM Seafood Chicago Surprise Proposal | Aiden & Abby

March 13, 2026 EngagementSurprise Proposal

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Grant Park Chicago Surprise Proposal | Jeremy & Maddie

March 6, 2026 EngagementGeneralSurprise Proposal

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Chicago Skyline Surprise Proposal Locations

February 26, 2026 GeneralSurprise Proposal

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a couple holds umbrellas and share a kiss in front of the chicago skyline after getting engaged

Freddy & Shauna’s Chicago Olive Park Proposal

August 12, 2025 GeneralSurprise Proposal

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a couple celebrates their Surprise engagement holding hands in front of the chicago skyline at the adler planetarium

Adler Planetarium Surprise Proposal | Matt & Myriam

July 7, 2025 EngagementGeneralSurprise Proposal

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A man gets down on one knee to propose to his fiance in front of the chicago skyline

T & K Chicago Surprise Proposal

June 26, 2025 GeneralSurprise Proposal

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