Explore the Windy City with Tripshepherd, 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 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 - 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.