Best of Chicago Tour

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Highlights

  • Skydeck Chicago - Observatory and The Ledge

  • Chicago Bean

  • Architectural Sightseeing Cruise

  • Chicago Adler view point

  • Chicago Buckingham Fountain

Summary

Explore the best of Chicago on our small-group tour! See iconic attractions like the Chicago Skydeck, Adler viewpoint, and the famous Bean. Enjoy a scenic boat tour and a narrated drive past the Aqua Tower and Buckingham Fountain. Experience the Windy City's highlights in one unforgettable adventure! 

Tour info

Duration
4 hours
Group Size
6
Pricing (From)
Adult: (13-99 years)
$199.00
Child: (5-12 years)
$129.00
Infant: (0-4 years)
$20.00
Commentary
Meeting Point
Dropoff location

Why take this tour?

Explore the Windy City with See Sight Tours, Chicago’s best small group tours (max. 7 guests). 

Immerse yourself in Chicago’s distinct skyline with bold skyscrapers and incredible views of Lake Michigan. Enjoy the efficiency of having your own local expert and personal guide to share unique and fascinating stories about the surrounding area including exclusive local insights, historic highlights and personalized recommendations. 

The tour includes complimentary pick-up and drop-off, all attraction admission fees, and skip the ticket line entry - helping you avoid long wait lines and wait times and freeing up more valuable time to enjoy your vacation.

Begin your 4 hour small-group Scenic Night Tour of Chicago with complimentary downtown Chicago hotel pick up in the comfort and style of one of our complimentary vehicles where you will be escorted to your very first stop - Willis Tower. 

No trip to Chicago is complete without a visit to the top of the tallest building in the Western Hemisphere - Skydeck Chicago (formerly Sears Tower). Taking the elevator all the way up to the 103rd floor where you will enjoy a spectacular 360-degree view spanning 50 miles and 4 states. The most spectacular view - 1,353 feet down "Dare to Stand Out" on The Ledge - special glass balconies extending 4.3 feet outside the building which provides a thrilling, once-in-a-lifetime experience. 

Next, once your feet are back on solid ground your guide will take you to the Adler Planetarium Pier, a must-stop while in the Windy City. As the mecca for American architects, Chicago’s skyline is one of the greatest and this viewpoint is the best place to marvel at the skyline Lake Michigan. 

Your guide will then take you to see the beauty of Chicago's architecture by seeing world-famous skyscrapers from the Chicago River. Aboard the Shoreline Architecture Cruise you will enjoy a narrated boat tour where you will see the breathtaking views of over 40 Chicago iconic landmarks, from hidden architectural features to the Windy City's most famous monuments. 

To finish your tour, you will get to visit two iconic Chicago landmarks - the Buckingham Fountain, one the largest fountains in the world and the Chicago Bean (Cloud Gate) - British artist Anish Kapoor's first public outdoor work installed in the United States - both great locations to take great pictures. 

At the end of your tour your guide will take you back to your downtown Chicago hotel. 

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What’s included?

  • Intimate, guided tour to explore Chicago (groups are limited to 6 people)

  • Complimentary hotel pick up and drop off in downtown Chicago

  • Small-group tour (max 6 guests)

  • Skip the ticket line entry

  • Take in the very best views at the Adler Planetarium Skyline Walk

  • Visit iconic landmarks - Chicago Bean (Cloud Gate) and Buckingham Fountain

  • Shoreline Sightseeing Architecture Cruise

  • All attraction admission fees included

  • Navy Pier, and millenium park

  • Food and Drinks

  • Gratuities (optional)

Things to know

Before you book

  • The exact length of time for tour may vary slightly based on traffic and seasonality (e.g. during off-peak times, tours tend to be a little shorter due to less traffic)

  • From June 18th to August 13th we cannot guarantee the stops Buckingham Fountain and Adler viewpoint. If we cannot visit those stops, we will substitute with a luxurious drive up Chicago's famed Magnificient Mile; including hop-out stops at The Chicago Theatre, the electric and unnamed Chicago Picasso sculpture in Daley Plaza, and the Chicago Watertower (sole survivor of the Chicago Fire).

Before you go

  • Operates in all weather conditions, please dress appropriately

  • A moderate amount of walking is involved

  • Pick up time will be confirmed 1-3 days prior to the tour date via email or phone. If you do not have access to these, please be ready 30 minutes prior to tour start time in the hotel lobby.

Cancellation Policy

    Full refunds will be offered for cancellations made at least 24 hours prior to departure time. For cancellations made with less than 24 hours to departure time, a $50 cancellation fee per guest will apply.
Operator Website

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About operator:

Tripshepherd specializes in offering intimate small-group tours across popular destinations in North America. Our commitment to small-group dynamics ensures a more personal connection, greater flexibility, and an escape from the hassle of crowded buses and the need for microphones. At the heart of our tours are local experiences; we proudly hire local guides to support community growth, create jobs, and provide our guests with an authentic glimpse into each destination. Our friendly guides are dedicated to connecting personally with each guest, ensuring a caring and memorable experience. With Tripshepherd, every journey is not just a tour, but a unique story woven into the fabric of local life, guaranteeing an authentic, personal, and local adventure.

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