Travel like a local.


Pequod’s Pizza, Ricobene’s Carpet & Taste of Chicago in Chicago, Illinois

Best things to do in Chicago Illinois - Michael Sparrow - Cloud Gate in Millenium Park aka The Bean by Christopher Alvarenga on Unsplash

Cloud Gate in Millenium Park aka The Bean. Photo by Christopher Alvarenga on Unsplash.

I’m really excited to interview Michael Sparrow of Team FRWRD about Chicago, Illinois. Michael’s tips for the best things to do in Chicago are awesome because he was born and raised in Chicago, and his family has been here for more than 100 years, which means they’ve seen it all when it comes to the best that Chicago has to offer.

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Best things to do in Chicago Illinois - Michael Sparrow - View of the shore from the Hancok Tower by Gautam Krishnan on Unsplash

View of the shore from the Hancock Tower. Photo by Gautam Krishnan on Unsplash.

Chicago, Illinois

We share a lot of resources and local suggestions in today’s podcast, but you should also check out Choose Chicago, the local visitor’s bureau. They are a wealth of information and can help you plan an itinerary based on your time, budget, and interests.


If you’d like to learn how to travel for free using airline miles and hotel points, check out my free 7-day email course.

Best things to do in Chicago Illinois - Michael Sparrow - The Chicago Theatre by Sawyer Bengtson on Unsplash

The Chicago Theatre. Photo by Sawyer Bengtson on Unsplash.

Getting around Chicago

The local airport is O’Hare International Airport (ORD), which is about a 30-minute drive to downtown. Chicago Midway International Airport (MDW) is another option, depending on where you’re traveling from. Use our Expedia tool below to find flight, hotel, and rental car options.


Michael says that there’s no need to rent a car when visiting Chicago. The light rail trains are easy to use and very budget-friendly. However, if you plan on visiting areas outside the city, you should rent a car. For the best rental car offers, visit Avis, Budget, or Hertz.

Uber and Lyft are excellent ways to get around. Chicago’s public transportation is also a great way to get around the city.

When you only need a car for a couple of hours, you can rent by the hour with Zipcar. Join now to get $25 loaded into your account.

Best things to do in Chicago Illinois - Michael Sparrow - Chicago River dyed green for St Patricks Day by Brigitte Werner on Pixabay

Chicago River dyed green for St Patricks Day. Photo by Brigitte Werner on Pixabay.

Places we talked about on the podcast

Here is a map of all of the places we talked about on the podcast episode with Michael Sparrow about Chicago, Illinois. You can zoom into the map and click on each dot to explore the city.

  • Red dots = best places to eat in Chicago, Illinois
  • Green dots = best things to do in Chicago, Illinois
  • Yellow dots = best places to stay in Chicago, Illinois

Who is Michael Sparrow?

Michael Sparrow is a Certified Financial Educator as well as a licensed advisor working in the financial industry. He has over ten years of experience working in various leadership and advisory roles. His practice focuses on advisory services and behavioral finance. In addition to his work with clients, he also has a passion for politics. He splits his time between growing his financial practice and working with a close group of friends advocating for ethical financial legislation. Michael runs his own podcast called “Cafe on Main Street” which focuses on the history of money and behavioral finance.

As a Chicago native living on the north side, he has a great road map of the city and plenty of suggestions for people making their way over. He sees himself as the “go-to guy” for insider knowledge on things to do both inside the city and in the suburbs. In his spare time, Michael enjoys playing music, exercising, traveling, reading, and spending time with his family.

Best things to do in Chicago Illinois - Michael Sparrow

Here are a few of his podcast episodes:

You can connect with Michael on his website and on Twitter, Facebook, and Instagram.

Big thanks to today’s affiliate partner – Acorns

With Acorns, you can invest spare change automatically on every purchase that you make. With your registered cards, purchases are rounded up to the next dollar and added to your investment account. When you shop at participating retailers, you can also earn bonus dollars called “Found Money.” Acorns is a great way to build up your travel fund automatically.

I’ve been using Acorns for years, and I love how easy it is to use. For a limited time, when you sign up at, we’ll both earn $5.

Best things to do in Chicago Illinois - Michael Sparrow - Dinosaur exhibit at the Field Museum by Katie Rose on Pixabay

Dinosaur exhibit at the Field Museum. Photo by Katie Rose on Pixabay.

Stay tuned for our next episode

Listen to the next episode when Michael Belmont of The Park Prodigy shares how to save money at theme parks. In this episode, Michael and I talk about the best ways to save money on theme park travel, when’s the best time of year to visit, and how to figure out if it makes sense to upgrade your hotel and theme park tickets. We hope you’ll join us when We Travel There.

What’s your favorite part of Chicago? Send us a Tweet, let us know in the comment section below, or continue the discussion in our Facebook group!

Please take a moment to follow the podcast on your favorite podcast apps, like Apple Podcasts or Stitcher, so you don’t miss the next episode! While you’re at it, give us a rating and Tweet the podcast to your friends.

To see which cities we’ve interviewed and scheduled, please visit If you’d like to be a guest on the show, please submit an application at

Related episodes

To learn more about the Midwest, listen to our other episodes from this region of the U.S.:

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