Get views of Chicago’s most famous buildings, as well as insider info from an expert guide, on this architecture-focused cruise. See all the most important buildings on one tour, a hard-to-accomplish task on foot....read more
1–2 hours
Best Seller
from $50.36
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2–3 hours
from $150.78
If your feet need a break from the city streets, a short skyline cruise is the perfect way to see the best of Chicago without breaking a sweat. Offered regularly throughout the day, it’s easy to fit this tour into...read more
40 minutes
from $34.93
Stroll around the Loop with a guide, discovering Chicago's lively food scene, on this small-group walking tour. Learn about the city's history and culinary heritage from your guide as you stop at favorite local...read more
3 hours
from $87.87
Check many Chicago landmarks off your must-see list on this small-group sightseeing tour aboard a...read more
2 hours
LIKELY TO SELL OUT*
from $46.95
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2 hours
from $46.95
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3 hours
from $184.38
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1–2 hours
from $75.00
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2 hours
from $483.96
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2 hours
LIKELY TO SELL OUT*
from $483.96
RHJpbmslMjBpbiUyMGElMjBvbmUtb2YtYS1raW5kJTIwcGVyc3BlY3RpdmUlMjBvbiUyMHRoZSUyMFdpbmR5JTIwQ2l0eSUyMHdoZW4lMjB5b3UlMjBnbyUyMGZvciUyMGFuJTIwZXZlbmluZyUyMGNydWlzZSUyQyUyMHBlcmZlY3RseS4uLg==read more
1–2 hours
Best Seller
from $42.00
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2 hours
from $542.82
Enjoy a private two and a half hour sailing experience for up to four people along Chicago’s beautiful lakefront. Kick back, relax, and let the US Coast Guard licensed captain treat you to stunning views of...read more
2 hours
from $433.82
VHJhdmVsJTIwdGhyb3VnaCUyMHRoZSUyMFdpbmR5JTIwQ2l0eSUyMGluJTIwc3R5bGUlRTIlODAlOTRhbmQlMjBwbGFuJTIweW91ciUyMG93biUyMGRheSUyMG91dCUyMG9yJTIwc2lnaHRzZWVpbmclMjBpdGluZXJhcnklRTIlODAlOTR3aXRoJTIwdGhpcyUyMHByaXZhdGUlMkMlMjBmdWxseSUyMGN1c3RvbWl6YWJsZSUyMHN0cmV0Y2glMjBsaW1vJTIwY2hhcnRlci4lMjBNZWV0JTIweW91ciUyMGRyaXZlciUyMGF0JTIwYSUyMHN0YXJ0aW5nJTIwdGltZSUyMGFuZCUyMHBsYWNlJTIwdGhhdCUyMHdvcmslMjBiZXN0JTIwZm9yLi4uread more
Taking safety measures 2 hours
from $650.00
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2 hours
from $75.00
The educational sail aboard Chicago's Official Flagship Windy departs at 11am Thursday thru Monday...read more
1–2 hours
LIKELY TO SELL OUT*
from $39.00
The famous Tall Ship Windy sunset sail is truly famous. Used in many world-renown photos, backdrops for special events, weddings, or just an evening out, the sunset sail aboard one of the only four-mast Schooners...read more
1–2 hours
from $59.00
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Taking safety measures 20 minutes
from $8.00
Explore the surprising beauty and history of the Windy City with this combo tour of Chicago’s Millennium Park and Riverwalk! Snap a picture by the famous Cloud Gate sculpture and get away from the hustle and bustle...read more
Taking safety measures 1 hour
from $16.99
Our flagship vessel boasts a Tiki Chic vibe, two climate controlled decks, two bars, two bathrooms, premium sound system, outdoor and indoor viewing areas. Our upscale "Admirals Lounge" features top-shelf alcohol,...read more
Taking safety measures 1–2 hours
from $35.00
Join us for a 2-hour concert sail from 7pm-9pm every Monday this Summer! Chase your Monday BLUES away aboard the 148 foot Tall Ship Windy as you enjoy the breathtaking views of Chicago from the waters of Lake...read more
Taking safety measures 2 hours
from $99.00
Delve into Chicago’s one-of-a-kind cuisine and learn something that you would never expect on this small-group Secret Food Tour. Eat your way through the most prominent neighborhoods of the city and immerse yourself...read more
3 hours
from $145.00
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Taking safety measures 3 hours
from $400.00
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2 hours
from $433.82
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Frequently Asked Questions about Chicago Skyline Tours and Tickets
- If you're short on time, these are the best half-day Chicago Skyline tickets and tours:
- Chicago Architecture River Cruise (From US$50.36)
- Chicago Premier Dinner Cruise on Lake Michigan (From US$160.20)
- Lake Michigan Skyline Cruise in Chicago (From US$34.93)
- Chicago Walking Food Tour With Secret Food Tours (From US$87.87)
- Chicago Small-Group City Tour with Optional Architecture River Cruise (From US$46.95)
