Best of Chicago Tour: Small Group Sightseeing with Architecture Cruise, Skyline Views & Iconic Landmarks

What you'll do:

Explore the Windy City with See Sight Tours, Chicago’s best small group tours (max. 6 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.

Why we love it for your party:

• VIP vibes with private hotel pick-up, a personal guide, and no long lines — just maximum fun!

• Snap Insta-worthy pics of Chicago’s epic skyline from the best city viewpoints

• Cruise down the Chicago River and see over 40 iconic landmarks on a narrated architecture tour

• Strike a pose at famous spots like Buckingham Fountain and the legendary Chicago Bean

• Small group size (max 6 guests) means a more personal, unforgettable Windy City adventure!

About this experience partner:

Ready for an unforgettable adventure? With See Sight Tours, experience the world through smaller, more intimate lenses. Our small-group tours are designed to give you a deeper connection to each destination, letting you explore like a local while avoiding the typical tourist crowds.

Whether you're uncovering hidden gems or immersing yourself in a city's unique culture, our tours offer an authentic, personalized experience that brings out the best in both the place and you. Book a tour today and discover how meaningful travel can change the way you see the world—one unforgettable moment at a time.