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Chicago, couple trip, Things to Do
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Best Things to Do in Chicago, couple trip

Photo of 360 CHICAGO

360 CHICAGO

92%Couple-Friendly

360 CHICAGO is 92% Couple-Friendly

Couples get sweeping sunset views, sip cocktails at CloudBar, snap romantic photos, and share the TILT thrill, so the deck delivers an easy, memorable date with few logistical hassles.

Recommended visit duration: 1–2 hours

👉 See FULL guide to 360 CHICAGO (couple trip)
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✨Sip cocktails 1000ft up with your loved one

Average price

US$ 27
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Millennium Park

92%Couple-Friendly

Millennium Park is 92% Couple-Friendly

Couples can picnic on the Great Lawn, stroll Lurie Garden, and enjoy free evening concerts under city lights. Limited privacy and occasional event closures are the only real downsides.

Recommended visit duration: 1-3 hours

👉 See FULL guide to Millennium Park (couple trip)
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✨Reflect love beneath the iconic Bean at sunset

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Skydeck Chicago

92%Couple-Friendly

Skydeck Chicago is 92% Couple-Friendly

Couples enjoy sunset champagne, VIP dinners, and dazzling skyline views from The Ledge for memorable photos; timed tickets and crowds curb spontaneity but the romance factor is very high.

Recommended visit duration: 1-2 hours

👉 See FULL guide to Skydeck Chicago (couple trip)
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✨Sip champagne at sunset 1,353 ft above Chicago

Average price

US$ 42.3
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Shoreline Sightseeing

92%Couple-Friendly

Shoreline Sightseeing is 92% Couple-Friendly

Sunset, fireworks, or wine cruises create romantic ambiance; bars, music, and 45–75 min durations fit date-night plans, so couples get memorable skyline moments without demanding logistics.

Recommended visit duration: 1-3 hours

👉 See FULL guide to Shoreline Sightseeing (couple trip)
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✨Romantic Chicago skyline cruises by boat

Average price

US$ 48.82
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The Art Institute of Chicago

91%Couple-Friendly

The Art Institute of Chicago is 91% Couple-Friendly

Pairs can share audio guides, linger on the terrace, dine at Terzo Piano, and visit on calmer Thursday nights; only heavy weekend crowds slightly reduce the romantic feel.

Recommended visit duration: 3-5 hours

👉 See FULL guide to The Art Institute of Chicago (couple trip)
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✨Artful couple’s escape with skyline dining

Average price

US$ 44.16
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Field Museum

90%Couple-Friendly

Field Museum is 90% Couple-Friendly

Couples enjoy ‘After 5’ date nights, indoor garden seating, shared 3D films, and iconic SUE photos; cafés and calm corners enhance bonding, though crowds can trim spontaneity at peak times.

Recommended visit duration: 3-5 hours

👉 See FULL guide to Field Museum (couple trip)
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✨Early-morning T. rex & serene garden date

Average price

US$ 27.58
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Photo of Grant Park

Grant Park

89%Couple-Friendly

Grant Park is 89% Couple-Friendly

Sunset picnics by Buckingham Fountain, nightly light shows, and lawn concerts give couples romantic, low-cost experiences without tight schedules or entry fees.

Recommended visit duration: 3–5 hours

👉 See FULL guide to Grant Park (couple trip)
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✨Picnic by a dancing fountain under city lights

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Photo of Museum Of Contemporary Art Chicago

Museum Of Contemporary Art Chicago

88%Couple-Friendly

Museum Of Contemporary Art Chicago is 88% Couple-Friendly

Changing exhibits, sculpture terrace, and Marisol restaurant give couples a cultured half-day date with art, views, and dining; limited interactive spots slightly reduce the romantic variety.

Recommended visit duration: 2–4 hours

👉 See FULL guide to Museum Of Contemporary Art Chicago (couple trip)
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✨Savor terrace views and cutting-edge art

Average price

US$ 19.83
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Photo of Willis Tower

Willis Tower

86%Couple-Friendly

Willis Tower is 86% Couple-Friendly

Couples get sunset or dinner packages, champagne add-ons, and photo-ready glass balconies for shared memories, but heavy crowds around dusk lower privacy slightly.

Recommended visit duration: 1–2 hours

👉 See FULL guide to Willis Tower (couple trip)
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✨Sip Champagne at Chicago’s Highest Sunset

Average price

US$ 42.3
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Photo of Navy Pier

Navy Pier

86%Couple-Friendly

Navy Pier is 86% Couple-Friendly

Couples can ride the Centennial Wheel’s enclosed gondola at sunset, share lake-view cocktails at RIVA or Offshore, and watch summer fireworks, offering an easy, romantic half-day with minimal planning.

Recommended visit duration: 3-5 hours

👉 See FULL guide to Navy Pier (couple trip)
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✨Sunset Ferris Wheel & Lakeside Romance

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