Our Top 10 Insider's Picks in Chicago

Chicago Architecture River Cruise

5 star rating: Highly Recommended 437 Reviews

Experience one of the world’s most beautiful cities on a 75-minute cruise on the historic Chicago River. On this architecture cruise, head down the main branch ...  Read more

Location: Chicago, Illinois
Duration: 75 minutes

From USD $31.75
$34.61 Save $2.86

Chicago City Hop-on Hop-off Tour

4.5 star rating: Recommended 497 Reviews

See all the sights of Chicago at your own pace! On a Chicago City Hop-on Hop-off Tour you can get off the bus at any scheduled stop to visit Chicago's most ...  Read more

Location: Chicago, Illinois
Duration: Flexible

From USD $35.00

Viator VIP: Willis Tower Skydeck Early Access, Trolley City Tour and Chicago River Cruise

See classic Chicago sights with this Viator VIP package that includes early entry to the Skydeck in Willis (formerly Sears) Tower where you'll be greeted and ...  Read more

Location: Chicago, Illinois
Duration: 6 hours

From USD $124.99

Chicago Segway Tour

5 star rating: Highly Recommended 104 Reviews

Hop on the most innovative tour to hit Chicago in years! Gliding around the Windy City on your very own Segway, you'll see all the famous sights - Buckingham ...  Read more

Location: Chicago, Illinois
Duration: 2 or 3 hours

From USD $60.00

Chicago Grand Half-Day Tour

4 star rating: Recommended 141 Reviews

This comprehensive half-day tour of Chicago is the perfect introduction to the Windy City! Discover the highlights of Chicago’s North Side and South Side and ...  Read more

Location: Chicago, Illinois
Duration: 4 hours

From USD $45.00

Blue Man Group at the Briar Street Theater in Chicago

5 star rating: Highly Recommended 50 Reviews

See the Blue Man Group, one of Chicago's longest running shows, at the Briar Street Theater in downtown Chicago. The phenomenon that has visited cities around ...  Read more

Location: Chicago, Illinois
Duration: 105 minutes

From USD $69.00

Chicago by Night Helicopter Tour

5 star rating: Highly Recommended 9 Reviews

Watch the Chicago skyline sparkle from the air on this thrilling nighttime helicopter tour! Aboard a heated, state-of-the-art helicopter, soak in amazing views ...  Read more

Location: Chicago, Illinois
Duration: 30 minutes

From USD $198.99

Skydeck Chicago Admission

4.5 star rating: Recommended 175 Reviews

Gaze upon the city sights from the pinnacle of Chicago, the Skydeck. Located on the 103rd floor of Willis Tower, formerly Sears Tower -- the third-tallest ...  Read more

Location: Chicago, Illinois
Duration: Flexible

From USD $18.00

Chicago Sunset Dinner Cruise with Buffet

4.5 star rating: Recommended 22 Reviews

Celebrate a night out in Chicago with dinner, dancing and sightseeing aboard a three-hour luxury cruise on Lake Michigan. Glimpse top Chicago attractions like ...  Read more

Location: Chicago, Illinois
Duration: 3 hours

From USD $99.14

Behind-the-Scenes Chicago Pizza Tour by Coach

4.5 star rating: Recommended 26 Reviews

Get an exclusive view inside four famous Chicago pizzerias on this 3.5-hour tour and enjoy delicious slices at each! With your small group by mini-coach, go ...  Read more

Location: Chicago, Illinois
Duration: 3 hours 30 minutes

From USD $60.00

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