Our Top 15 Insider's Picks in Chicago

Skydeck Chicago Admission

4.5 star rating: Recommended 518 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 $22.00

Chicago City Hop-on Hop-off Tour

4.5 star rating: Recommended 858 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 $33.00

Chicago Crime and Mob Tour

4.5 star rating: Recommended 266 Reviews

Some of the world’s most notorious criminals, mobsters and gangsters bamboozled their way through Chicago. On this Chicago crime tour, escape into the city’s ...  Read more

Location: Chicago, Illinois
Duration: 90 minutes

From USD $35.95
$39.95 Save $4.00

360 Chicago Observation Deck (formerly John Hancock Observatory) Admission

4.5 star rating: Recommended 68 Reviews

The best views of Chicago can be yours at 360 Chicago (John Hancock Observatory)! Perched 94 stories above the Windy City, the 360 Chicago provides commanding ...  Read more

Location: Chicago, Illinois
Duration: Flexible

From USD $20.00

Chicago Grand Half-Day Tour

4 star rating: Recommended 289 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 ...  Read more

Location: Chicago, Illinois
Duration: 4 hours

From USD $48.00

Famous Tastes of Chicago Food Tour

5 star rating: Highly Recommended 28 Reviews

What should a visitor see and do while in Chicago? It goes without saying that the Windy City has it all; from food, history, architecture, culture and beyond ...  Read more

Location: Chicago, Illinois
Duration: 3 hours

From USD $49.95

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

4.5 star rating: Recommended 76 Reviews

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 $124.00

Blue Man Group at the Briar Street Theater in Chicago

5 star rating: Highly Recommended 94 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

Field Museum of Natural History Admission

Explore 26 million artifacts, including SUE, the world’s largest T. rex!  Discover 23 mummies, our dazzling Gem Hall or journey to the powerful Aztec empire!

Location: Chicago, Illinois
Duration: Varies

From USD $23.25

Big Bus Chicago Hop-On Hop-Off Tour

4 star rating: Recommended 48 Reviews

The lakeside metropolis of Chicago is famous for its striking skyscrapers, world-class museums and colorful political history. Explore the Windy City at your ...  Read more

Location: Chicago, Illinois
Duration: 24, 48 or 72 hours

From USD $40.00

Chicago Prohibition Tour

5 star rating: Highly Recommended 53 Reviews

Discover the underground world of the Prohibition-era speakeasy on an entertaining adults-only tour that takes you to four historic Chicago bars. Learn why the ...  Read more

Location: Chicago, Illinois
Duration: 3 hours 30 minutes

From USD $44.99

Chicago Segway Tour

5 star rating: Highly Recommended 194 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 $70.85

Behind-the-Scenes Chicago Pizza Tour by Coach

5 star rating: Highly Recommended 74 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 $59.99

Chicago Walking Tour: Interior Architecture of the Loop and Pedway Tour

5 star rating: Highly Recommended 54 Reviews

Get an in-depth look at Chicago Loop architecture on a walking tour that takes you inside landmark buildings in the design-rich city. Appreciate the interiors ...  Read more

Location: Chicago, Illinois
Duration: 2 hours

From USD $26.00

Chicago Explorer Pass

4.5 star rating: Recommended 138 Reviews

Create your own sightseeing itinerary with the Chicago Explorer Pass, saving up to 42% on ticket prices. This multi-attraction pass, valid for 30 days after ...  Read more

Location: Chicago, Illinois
Duration: Flexible

From USD $71.99

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