A person in a suit kneels and proposes on the rooftop terrace of LondonHouse Chicago to someone in a green dress, surrounded by scattered rose petals at night.

N&Ks LondonHouse Proposal

April 11, 2025 GeneralSurprise Proposal

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engaged couple poses for a photo at milton lee olive park chicago

How to plan a Surprise Proposal in Chicago

March 11, 2025 GeneralSurprise Proposal

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a man on a ice rink is down on one knee asking his girlfriend to marry him as she screams with excitement

Clay & Alex’s Surprise Proposal

January 10, 2025 Surprise Proposal

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a man is down on one knee asking his girlfriend to marry him in front of a christmas tree at night at the chicago pumping station

Carolyn & Matt’s Chicago Surprise Proposal

January 10, 2025 Surprise Proposal

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Maggie & Wes’s Olive Park Surprise Proposal

March 5, 2024 GeneralSurprise Proposal

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Colin & Erin’s Chicago Surprise Proposal

December 1, 2020 GeneralSurprise Proposal

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Connor & Josie’s Surprise Proposal

February 28, 2020 GeneralSurprise Proposal

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Anna & Alex’s Surprise Proposal

December 16, 2019 GeneralSurprise Proposal

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Christian & Shelby’s Surprise Proposal

December 1, 2019 GeneralSurprise Proposal

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Josh & Brittany’s The LondonHouse Proposal

September 13, 2018 GeneralSurprise Proposal

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Omar & Lauren’s LondonHouse Proposal

December 10, 2017 GeneralSurprise Proposal

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