LondonHouse Chicago, Curio Collection by Hilton

The tri-level rooftop at LondonHouse delivers that rare Chicago experience where the view actually lives up to the hype. Perched 22 floors up, you'll find yourself eye-to-eye with architectural icons while the Chicago River snakes below—it's the kind of perspective that makes locals remember why they endure winter. The cocktail program matches the elevation with creative concoctions worth their hefty price tags, though you're partially paying for that Instagram-worthy backdrop. Fair warning: securing a spot requires planning (reservations are your friend) and patience (the elevator wait can test it). While the crowd skews touristy and the service occasionally feels rushed, there's something undeniably magical about sipping a well-crafted Old Fashioned as the sunset paints the skyline gold. Come for the panorama, stay for the people-watching, and accept that sometimes paying for the view is absolutely worth it.