Chicago – The Windy City? Where to Start When Planning a Visit

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Chicagoans don’t call Chicago the “Windy City”.  How random, right?  But aren’t you curious as to why Chicago is called the Windy City?

The “Windy City” is a political term coined by a New York newspaper editor near the beginning of the 20th century.  And it’s about Chicago politicians being long-winded or a bag of wind…or something windy.

Ready for some more facts about Chicago?

Let’s get started.

Explore Chicago – An Overview

What is Chicago known for?  There are some cool things about Chicago that makes this city famous (or infamous).  Some of it you might have heard about such as Al Capone, the Chicago Bears, the White Sox or Cubs, and the Bulls (Michael Jordan…remember him?) but we have a lot of other stuff too.

Chicago tourist attractions

Chicago is a big city with tons of stuff to do!  We have museums, tall buildings, great dining options and yes, shopaholics…we have shopping.  If you want to partake of what Chicago has to offer, make the downtown area your base of operation.

For more information on where to stay, read my article “Where To Stay In Chicago”.

For my guide on downtown Chicago hotels, click here.

There are a few Chicago tourist attractions that you can not get away with not exploring during a visit to Chicago.

  • Willis Tower
  • Navy Pier
  • Buckingham Fountain
  • Millennium Park
  • Chicago Riverwalk
  • Hancock Building

A great way to get in a  lot of Chicago sightseeing at a nice discount is to purchase the Chicago Explorer Pass.  Create your itinerary by choosing 3, 4, or 5 Chicago attractions from over 25 different museums, tours, and activities.  It comes with a digital guidebook to help you choose from Chicago’s most popular attractions.

Click here to be taken to for more information on the Chicago Explorer Pass.

Chicago Museums

Chicago has museums that showcase everything from history (ancient, prehistoric and modern), the arts and science.

Most Popular Museums

  • Art Institute of Chicago
  • Field Museum of Natural History
  • Shedd Aquarium
  • Planetarium
  • Museum of Contemporary Art
  • Museum of Science and Industry

Other Museums

  • Museum of Broadcast Communication
  • DuSable Museum of African American History
  • American Writers Museum
  • National Museum of Puerto Rican Arts and Culture
  • National Museum of Mexican Arts
  • Chicago History Museum

You can gain entry into several Chicago’s most famous museums and save money when you purchase the Chicago Explorer Pass.  Click here to be taken to for more information on the Chicago Explorer Pass.

Chicago architecture and its skyline

The Chicago fire of 1871 destroyed most of the buildings in Chicago except for the Chicago Water Tower building (located north of the Chicago River on Michigan Avenue).

After the devastation, the city was tasked with rebuilding.  The city became an architectural lab, so to speak, for famous architects to test out their craft.

Chicago’s architecture reflects its history and is a tribute to the number of innovative architects that helped create the most beautiful skyline in the country.  So be ready to be amazed!

The best way to check out the history of Chicago’s architecture is a visit to the Chicago Architecture Center at 111 East Wacker.

The Chicago Architecture Center offers amazing architecture tours by trained guides that know their stuff about the city’s culture, and history.

I recommend starting with the Chicago Architecture River Cruise onboard the Chicago’s First Lady.  It’s a beautifully relaxing way to see the city by way of the Chicago River.

A lot of CAC’s walking tours are offered seasonally.  However, they do offer bus tours as well, which are a great way to tour Chicago during the winter.

For more information on CAC tours, you can click here to be taken to their website.

Tours of Chicago

A great way to get an overview of the downtown area of Chicago is by doing a Hop-On, Hop-Off Bus Tour.  My favorite is the BigBus Hop-On, Hop-off Tour – click here for information on tour prices through

Hop-On and Hop-Off at major Chicago attractions and learn a bit about Chicago’s history in the process.

The mob had a significant influence on Chicago’s history, so a trip to Chicago wouldn’t be complete without a Gangster and Ghost Tour.  Learn about Chicago’s seedy past through stories about speakeasies, mobsters and bootleggers.  For more information on tour prices through, click here.

Get to know Chicago through your stomach by taking the Chicago’s Favorites Food and Walking Tour.  What I love about this tour (besides the food) is that it makes allowances for Chicago’s changing weather.  So don’t be afraid to take this tour during the winter!  For more information on tour prices through, click here.

For information on other Chicago tours offered through Viator, click here

Free Things to do in Chicago

Exploring Chicago on a budget?  There are plenty of things to check out during your trip to Chicago that is free to visitors.


1. Lincoln Park Zoo –  This zoo is not shabby in spite of it being completely free (there is a charge for parking your car should you decide to drive).  Expect to spend a day exploring the many exhibits.  There’s always something special going on at Lincoln Park Zoo even during the winter months.

For more information, go to there website by clicking here.

2Maxwell Street Market – I can remember buying a set of tires for dirt cheap at the Maxwell Street Market back in the 90s. Back then, it was located on Maxwell Street and Halsted Street.

Man, Maxwell Street was where you found the bargains and the place to get the best polishes this side of Lake Michigan – you could smell the grilled onion from miles around…oh my God..mouth-watering.

In 1994, in the name of urban renewal, the University of Illinois at Chicago expanded and took over Maxwell Street and the surrounding area where the market was held.  It is now part of University Village.

To appease the local business whose livelihoods were affected by the UIC expansion, Maxwell Street Market was moved to its current location at 800 South Desplanes.  The Market is open on Sundays from 9 AM – 3 PM.

And as far as the polishes with the grilled onions…. check out Maxwell Street Depot (411 West 31st Street, Bridgeport), which I was told once was the original place from Maxwell Street – not sure that’s true.

3. Wednesday nights at Old Town School of Folk Music – On Wednesday nights, the Old Town School of Folk Music showcase world music and dance.  It features local talent, touring musicians and dance groups.

Most shows are sort of free – a $10 donation is suggested.

For more information, click here to be taken to the Old Town School of Folk Music.

4. Free Tuesdays at Chicago History Museum – In my opinion, no visit to Chicago is complete without a visit to the Chicago History Museum.  This museum tells the history of Chicago by way of the most fascinating of exhibits. Of all the museums in Chicago – this one is my personal favorite.


Chicago Festival and Events

Looking for things to do in Chicago?  Or perhaps you’re a self-professed foodie wanting to check out Chicago festivals such as the “Taste of Chicago” or “Ribfest” but don’t know much about either one.

In the article “17 Chicago Festivals and Events You Don’t Wanna Miss“, I discuss Chicago’s best festivals and events that you might want to fly in for.

Please note: many of Chicago festivals are free events.


Chicago is the best city ever.  Yes, I’m speaking from a very bias position. But seriously, do yourself a favor and place Chicago on your bucket list for next year (do people still make bucket lists…as a travel geek, I know I do).

Better yet; don’t wait.  Go ahead and book your trip to my city by the Lake.

Chicago! The City That Works!





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