Travel like a local.

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Deep Dish Pizza, Baseball and The Bean in Chicago, Illinois

Best things to do in Chicago Illinois Bethany Bayless Cloud Gateway The Bean

Bethany at the Cloud Gateway aka The Bean

I’m really excited to interview Bethany Bayless of The Money Millhouse Podcast about Chicago, Illinois. Bethany’s tips for the best things to do in Chicago are awesome because she lived in Chicago during college and, although she moved away a few years ago, she visits as often as she can.

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Best things to do in Chicago Illinois - Bethany Bayless - Chicago skyline by Pedro Lastra on Unsplash

The Chicago skyline. Photo by Pedro Lastra 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 convention and 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 - Bethany Bayless - Architectural Boat Tour by Dimitry Anikin on Unsplash

Architectural Boat Tour. Photo by Dimitry Anikin on Unsplash.

Getting around Chicago

You have two airport options when flying into Chicago. And which one you choose is largely based on which airline you’re flying. If you’re flying Southwest, you’ll most likely be arriving at Chicago Midway International Airport (MDW), which is about a twenty-minute drive to downtown. For the major airlines like American Airlines, you’ll fly into Chicago O’Hare International Airport (ORD), which is about 30 minutes outside of downtown. Use our Expedia tool below to find flight, hotel, and rental car options.

Bethany says that, if you’re staying downtown, there’s no need to rent a car. Uber and Lyft are excellent ways to get around. The Chicago bus, rail, and subway lines make it easy to get around. And I’ve personally found the downtown area very walkable.

If you decide to rent a car, click here for the best offers from Avis, Budget, or Hertz.

And 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 Bethany Bayless Portillos hot dog Ben Komenkul

You need to visit Portillo’s and order a Chicago-style dog. Photo courtesy of Ben Komenkul.

Places we talked about on the podcast

Here is a map of all of the places we talked about on the podcast episode with Bethany Bayless 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 Bethany Bayless?

Bethany Bayless is the wife of Travis, mother of Caden (baby boy) and London (Goldendoodle puppy), and Director of Communications for Heroes at Home. She holds a Bachelor of Arts in Communications from Moody Bible Institute, Chicago, IL, and has been a social media coordinator for several organizations including two international groups.

She is a self-professed geek, aspiring home-cook, and globe-trotter (not the basketball kind). In her spare time, Bethany draws and hand letters, throws tennis balls for her puppy, London, and quotes movie lines with her family near and far. Bethany is the co-host of The Money Millhouse Podcast and you can find her blog at

Best things to do in Chicago Illinois Bethany Bayless headshot

Here are a few of her podcast episodes to listen to:

You can connect with Bethany on her website and on Facebook and Instagram.


Click here to download our one-page guide of Bethany’s tips for Chicago.


And… from our conversation, here is the Married With Children intro that shows the Buckingham Fountain in the center of Grant Park.

Big thanks to today’s affiliate partner – AwardWallet

This episode is brought to you, in part, by AwardWallet. Using airline miles and hotel points makes travel affordable, but keeping track of all of those loyalty programs can be a challenge.

That’s why I use AwardWallet to track my miles and points balances, reservations, and special goodies like free hotel night certifications and airline companion passes.

Having everything in one easy-to-use dashboard helps ensure I don’t let any rewards expire and makes logging into my accounts super easy. Go to to start your free account.

Best things to do in Chicago Illinois - Bethany Bayless - Giordanos Pizza by Matt Antonioli on Unsplash

My favorite deep-dish pizza in Chicago is at Giordano’s. Photo by Matt Antonioli on Unsplash.

Stay tuned for our next episode

a man with long hair and mustacheListen to the next episode when Steve Mangano of CurEat shares the best things to do in Raleigh, North Carolina. 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!

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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.:


  1. Fun stuff. I love Giordano’s but a lot of locals consider it tourist pizza. I disagree. Another airport option for Chicago is Milwaukee. While it’s about a 2 hour train ride from the airport to downtown Chicago you can drive it in light traffic in about an hour, of course having a car downtown isn’t awesome but not the worse city for downtown driving, it’s more the parking costs.

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