History & Architecture Tour

Come explore the River and inside the Loop!

Our Chicago History & Architectural Tour is exactly as the name implies; the finest of everything that Chicago has to offer all combined into one tour. On this highly unique tour our guests will; hear captivating stories about the city’s rich history, view and learn about some of Chicago’s most iconic architecture and artwork, stroll the “Loop” while listening to heartrending stories of some of the city’s worse disasters and experience the newly expanded Chicago River Walk – all for the price of one!

Come explore with us the newly expanded River Walk. Opening in 2017, 3 new "Rooms" (Jetty, Water Plaza and Boardwalk). All 3 rooms promise to make the River Walk an even more exciting place to have fun!

The tour lasts about 3 hours and includes a 1 and 1/2 mile walk.

The tour begins at Peet's Coffee & Tea - 400 North Michigan Avenue - Wrigley Building Plaza - across from Walgreen's at 1:00 pm every Friday afternoon.

Tour ends at Chicago's iconic "Rookery Building" - 209 South LaSalle Street. Perhaps, Chicago's oldest and best example of the nation's first modern skyscraprers!

History & Architecture Tour Highlights

  • Tour Duration: 3 hours
  • Tours are conducted along the Chicago River and inside the “Loop”
  • Tours begin May 25 and end October 26 and are offered every Thursday at 1:00 pm
  • Tour Size Minimum: 4 Guests
  • Please note that while our tours are leisurely strolls, there are numerous stairs along the tour route. Unfortunately, we do not recommend the use of wheel chairs, strollers, canes, walkers etc.
  • Tour Topics include; Tribune & Wrigley Buildings, Chicago Cultural Center, Iroquois Theater Fire, Great Chicago Fire, Chicago “Loop”, Picasso, Chagall, Marquette, Monadnock & Rookery Buildings, Wingfoot Express Disaster, Chicago River & River Walk
  • Tours begin at Peet’s Coffee & Tea - 400 North Michigan Avenue - Wrigley Building Plaza and end at the “Rookery” Building - 209 South LaSalle Street.
  • Trivia Contest, snacks and and restroom break included in all of our tours!

See the "Finest" Chicago has to offer!

Chicago is blessed with both an incredible history and inimitable architecture. It's history is the story of unimaginable Public Works Projects and one of the most determined citizenry. Its collective "I will" attitude and brazen ambition led to its ultimate reign of becoming one of this country's most admired cities and leading "Alpha" cities in the world! Come explore the wonders of the "Windy City" on this one-of-a-kind journey!




Reviewed August 1, 2016

"Five of us took the "River Walk and Loop Tour" with Dan last week-end. I had been on a few of his tours before so knew exactly what a treat the tour would be, but the other four had not. They were absolutely delighted with the experience - as was I. We learned so much and also were entertained. Dan has a wonderful talent of telling stories that are intriguing and also likes to challenge his guests with fun trivia. While it was a typical noisy Chicago day, we all heard the entire tour since we were wearing headphones and Dan was wearing a microphone. I HIGHLY recommend booking any of the tours offered through Chicago's Finest Tours.:

Harriet R.



“A great tour for visitors and Chicagoan's”

Reviewed July 23, 2014

"We took the River Walk & Loop Tour. I live here, but had family in from out of town. The tour was great, with lots of interesting facts about Chicago's history. Sharon was a very knowledgeable guide, pleasant and attentive. Each person receives a good quality headset so that you can hear the guide over the "city sounds". This tour is not physically strenuous so it is good for a variety of ages. I've worked in the "loop" for years, but learned many things I didn't know before. Very enjoyable!"

Melissa T

Evanston, IL