Ask ChicagoNow: What is the best Chicago tour?

Ask ChicagoNow: What is the best Chicago tour?

ChicagoNow is a group of bloggers from all sorts of different backgrounds.

With so much collective experience, we’ve decided to put that knowledge to use by posing some of the oldest and most popular questions to the group.

What is the best Chicago tour?

“Chicago Greeter Tours are awesome.” — Carole Kuhrt Brewer, Show Me Chicago

“We did [Chicago’s Original Gangster Tour] one for my friend’s 30th birthday and it was fantastic! The guys running the show were absolutely hysterical and incredibly informed. 10/10 totally recommend!” — Michelle Cahill, Mindful Chicago

“For architectural river tours, skip Wendella and go straight to the expert – Chicago Architecture Foundation. In general, CAF is the best for tours related to architecture and its intersection with history. Plus, they host Open House Chicago, a weekend in October when you can tour close to 200 places in Chicago, some well-known and others obscure and/or private. And it’s all free. For a tour of the Pedway, Chicago Elevated can’t be beat. Margaret, the owner and tour guide, is a wealth of knowledge, and highly entertaining.” — Jessica Gardner, Little Merry Sunshine

“Disclosure: I have not been on this walking tour, but it sounds fabulous for all fans of comedy and Chicago history. Led by Second City alum Margaret Hicks, author of Chicago Comedy: A Fairly Serious History. Includes behind-the-scenes stories of Old Town and ‘Second City alumni haunts.’ Late May-October.” — Teme Ring, Comedians Defying Gravity

“Chicago Greeter! They put you in touch with a local who will show you a part of the city, many times off the beaten path. And it is free!” — Ana Martin Sagredo, Foreign Affairs: Children Edition

“Whenever we have out-of-town guests we take them on our own Sullivan tour. We tailor it to our guests’ interests. It’s often a combination of skyline vistas, gangster landmarks, sports arenas, architecture, historic locations (Chicago Fire, first nuclear reaction, Fort Dearborn etc.), Obama’s house, hot dogs, Italian beefs, Chess Records, sometimes Oak Park childhood locations (along with Frank Lloyd Wright and gangsters), and even best terra cotta buildings. Or anything else that comes to mind!” — Floyd Sullivan, Waiting4Cubs

“Leentje, originally from Belgium, is the best! She takes you on walk or bike tours through Chicago. She speaks English, French and Dutch. She is very knowledgeable about Chicago and a very pleasant person too.” — Annemarie Verweij, Dutch Alien Lands in the U.S.

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Lead image via Stacey Wescott/Chicago Tribune

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