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!

Filter Romance & Special Occasions in Chicago

Chicago: 360 Chicago Observation Deck Sip and View Ticket

170 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: Fireworks Cruise with Lake or River Viewing Options

248 Reviews

Chicago: Fireworks Cruise with Lake or River Viewing Options

Get up-close and personal to the epic Navy Pier fireworks display every Wednesday & Saturday during the Summer. Choose between viewing from either the Chicago River or Lake Michigan.

$28.00

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Chicago: 1.5-Hour Lake and River Architecture Cruise

1380 Reviews

Chicago: 1.5-Hour Lake and River Architecture Cruise

Skip the ticket line for Chicago’s only architecture cruise on both Lake Michigan and the Chicago River. Learn about Chicago's internationally-known architecture from expert local guides as you discover the city from riverfront to shoreline.

$44.00

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Romantic Date Private Art Experience

Present your loved one with an unforgettable date! What could be more romantic than creating together?

$463.05

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Chicago: Summer Fireworks Cruise with 3D Glasses and Music

29 Reviews

Chicago: Summer Fireworks Cruise with 3D Glasses and Music

Enjoy unbeatable views of the Navy Pier fireworks enhanced with commentary 3D glasses, a musical accompaniment, and lively narration on this cruise. Capture photos in front of the Chicago skyline.

$49.00

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Chicago: Wine & Cheese or Beer & BBQ Thursday Evening Cruise

11 Reviews

Chicago: Wine & Cheese or Beer & BBQ Thursday Evening Cruise

Enjoy a relaxing cruise on the Chicago River and Lake Michigan. Take in the skyline while enjoying a wine and cheese or a beer and BBQ tasting supplied by local purveyors.

$65.00

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Chicago: Christmas Eve Gourmet Dinner Cruise Lake Michigan

4 Reviews

Chicago: Christmas Eve Gourmet Dinner Cruise Lake Michigan

Celebrate Christmas Eve on a cruise on Lake Michigan aboard the Odyssey. Savor a delicious holiday 3-course plated meal served at your private table with a live onboard DJ.

$184.13

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Chicago: Private Catamaran Sailing for up to 12 people

This exclusive sailing experience includes breathtaking views of the Chicago skyline, refreshing swims, and the luxury of private yachting including Chicago’s largest chartered Catamaran.

$1,500.00

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Chicago: 1.5-Hour Scenic Sunset Lake Cruise

527 Reviews

Chicago: 1.5-Hour Scenic Sunset Lake Cruise

Watch the sun slowly set behind the city from the tranquil waters of Lake Michigan on this serene and romantic cruise. Toast the end of the day with a glass of wine, ice-cold beer or hand-crafted cocktail.

$44.00

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A Romantic Journey Through Milwaukee

This tour combines the romance of scenic views and historic landmarks with the excitement of live music and outdoor activities.

$315.90

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Best Seller

Chicago: 360 Chicago Observation Deck General Admission

1834 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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Chicago: Seadog Speedboat Fireworks Cruise on Lake Michigan

72 Reviews

Chicago: Seadog Speedboat Fireworks Cruise on Lake Michigan

Watch the fireworks dance over Chicago's skyline on this popular 60-minute speedboat tour. Enjoy panoramic views of a magnificent fireworks display from the waters of Lake Michigan. Perfect for a romantic evening or a memorable night out with friends.

$59.44

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