Page 2 - Best Romance & Special Occasions in Chicago

Local Recommendations from our My Guide Chicago team

Book Top Experiences and Tours in Chicago:

If youʻre booking your trip to Chicago last minute, we have you covered. Below are some of the top tours and experiences!

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Chicago: Private Yacht Charter

Discover the magic of Chicago's waterways with a private yacht charter. Blend the thrill of the open lake with the iconic skyline of the city as a backdrop.

$1,820.00

~~From $2,275.00~~

Chicago: Luxury Private Flying Dress Photoshoot 2 Locations

1 Reviews

Chicago: Luxury Private Flying Dress Photoshoot 2 Locations

Make your time in Chicago into a piece of art with this private photoshoot that includes the rental of a stunning flying dress. Share your glamorous moment with ease with 25 digital photos.

$315.00

~~From $350.00~~

Chicago: 360 Chicago Observation Deck Sip and View Ticket

172 Reviews

Chicago: 360 Chicago Observation Deck Sip and View Ticket

Take your cocktail hour to a new level at CloudBar, 1,000 ft above the Magnificent Mile, with a full 360-degree view of Chicago.

$43.50

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Chicago: 360 Chicago Observation Deck General Admission

1842 Reviews

Chicago: 360 Chicago Observation Deck General Admission

Skip the ticket purchase desk to enjoy the best panoramic views of Chicago, 94 stories above the Windy City. Enjoy stunning lake views and close-up vistas of Chicago’s amazing skyscrapers.

$30.00

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