Chicago Travel Podcasts

28 podcast episodes about Chicago

Destination Eat Drink on Radio Misfits

Destination Eat Drink – Pizza in Naples, New York, Chicago, and Campania

Released: Duration: 32:18

Pizza is one of the most popular dishes in the world! We sample the pizza from Naples and find out why pizza had to get popular in the United States before it could take over Italy. Then, we try the real Chicago-style pizza (hint: it’s not deep dish!) and take the pizza bus all over New York. And, t… more

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D

We Took a Day Trip from Chicago to the Grand Canyon | Drop a Pin Ep. 71

Released: Duration: 01:33:44

This week on Drop A Pin we are recapping our trip featured in our new series Daytripping. We break down our trip to the American Southwest and then talk about what Chap's learned about the Grand Canyon during his time in seminary and how prostitution helped shape the American West!

Find out why Nut…
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Zero To Travel Podcast

Queer Travel in the United States: Unexpected Small Towns and the Importance of Inclusive Spaces with Chase Vondran

Released: Duration: 59:21

What does queer travel in the US look like beyond the big cities? And what can all travelers learn from the LGBTQ+ travel experience? 

Chase Vondran is a full-time travel creator and writer based in Chicago who helps transgender and gender-diverse travelers explore safely while advocating for great…
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Destination Eat Drink on Radio Misfits

Destination Eat Drink – Whiskeys and Liqueurs from Ireland, Chicago, Malta, and Estonia

Released: Duration: 22:41

We’re toasting 2026 with whiskeys and liqueurs around the world. There’s a new favorite Irish whiskey, a liqueur that causes you to make a sour face, a drink made from cacti, and the signature drink of Estonia. [Ep 370]

Show Notes:

Destination Eat Drink foodie travel guides

Destination Eat Drink …
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Travel with Kids

Chicago at Christmas with Kids

Released: Duration: 37:02

Chicago is one of the most festive cities in the USA to visit at Christmas time with kids, so in today's episode I'm sharing all of the fun things to do with kids in Chicago at Christmas.

I'll share the hotel we stayed at, top things to do from the Christmas Markets to epic ice skating spots, where…
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Travel with Kids

Milwaukee with Kids - an Unexpected Family Travel Destination

Released: Duration: 25:04

Have you ever considered traveling to Milwaukee with Kids?

I know it might not be at the top of everyone's travel bucket list, but you might be surprised at how much there is to do here, especially in the summertime! Plus you could easily combine Milwaukee with a trip to Chicago, Wisconsin Dells, o…
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Stacking Adventures: Every Traveler Has a Story

YOUR Adventure Tales from Greece, Paris, Disney, Chicago, and more!

Released: Duration: 55:53

Why settle for one vacation story when you can get a whole passport's worth in a single episode? Crystal Hammond and Joe Saul-Sehy are joined by fellow wanderlusters from the Stacking Adventures community to swap tales that stretch from Main Street U.S.A. to the shores of Zakynthos. Think budget-fri… more

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Traveling with AAA

Foodie Finds in Chicago with Kit Bernardi

Released: Duration: 0:09:30

If food is your favorite travel companion, Chicago may be your ultimate destination in the U.S. Beyond its iconic hot dogs and deep-dish pizza, the Windy City is bursting with flavors that tell stories of immigrant traditions, culinary innovation, and neighborhood pride. Every corner offers somethin… more

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Destination Eat Drink on Radio Misfits

Destination Eat Drink – Transplanted cuisine in Sicily, Chicago, and Kuala Lumpur

Released: Duration: 24:59

Food doesn’t recognize borders, so Brent explores some of the best Transplanted Cuisine from around the world. There’s a famous dish from Sicily that got its start in northern Africa, a dish that came to Chicago via Hawaii, and so much great food from Indonesia in Malaysia. [Ep 353]

Show Notes:

De…
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Traveling with AAA

What’s New and Exciting in Chicago with Kit Bernardi

Released: Duration: 0:24:27

Dreaming of a city escape that blends world-famous architecture, lakefront beauty, rich history, and dynamic culture? Chicago has it all. From iconic skyscrapers to hidden neighborhood gems, this episode will change the way you see the Windy City.

Today host Angie Orth welcomes Kit Bernardi, a Chic…
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Stacking Adventures: Every Traveler Has a Story

The Ultimate Chicago Experience: What to See and Do

Released: Duration: 01:02:08

Planning your first visit to Chicago? Don't just snap a selfie at The Bean and call it a day—let Stacking Adventures hosts Crystal Hammond and Joe Saul-Sehy be your insider guides to one of America's most vibrant, layered, and delicious cities.

In this jam-packed episode, Crystal and Joe serve up t…
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The Frommer's Travel Show

Chicago, Its Awesome Art Institute, and How To Improve Your Time in Any Museum. Plus How to Better Your Chances of Surviving a Plane Crash

Released: Duration: 37:53

Joe Cunniff, DePaul University instructor and tour guide extraordinaire, led us on a virtual tour of Chicago and its world class art museum. Then former NTSB inspector and aviation safety consultant Jeff Guzzetti gave some straight talk about what passengers need to research, and do, before and duri… more

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The Informed Traveler

On Location in Chicago

Released: Duration: 20:13

Send us Fan Mail We spent 5 fantastic days in Chicago last week attending the US Travel Association and Brand USA's annual IPW travel conference. While there I met up with Lisa Nucci, Chief Marketing Officer with Choose Chicago to discuss the sites we experienced and some of the other things Chicago… more

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Award Travel 101

A Magnificent Meet Up

Released: Duration: 48:10

In Episode 121 of the Award Travel 101 podcast, Angie Sparks and Mike Zaccheo recap a packed week of travel news, personal updates, and a deep dive into the recent "Magnificent Miles Meetup" in Chicago. They highlight a popular Facebook post comparing Andaz Maui and HR Maui, with opinions divided ba… more

Zero To Travel Podcast

Shred America: 950 Miles from Chicago to NYC by Skateboard with Mike Kosciesza

Released: Duration: 50:20

Would you skateboard nearly 1,000 miles across the U.S. with no real plan, just to see what would happen? 

Mike Kosciesza did just that with three friends and a dream to make a documentary out of it. Back in 2008, these four 20-year-olds set off from Chicago with their skateboards pointed toward Ne…
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Destination Eat Drink on Radio Misfits

Destination Eat Drink – Tacos in Texas, Chicago & Seattle

Released: Duration: 27:07

To celebrate Cinco de Mayo we’re sampling some of the best tacos in Texas including West Indian tacos in San Antonio, Baja tacos in Fort Worth, and puffy tacos. Plus, donuts with tacos and Taco Bell almost breaking up a marriage. [Ep 335]

Show Notes:

Destination Eat Drink foodie travel guide ebook…
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MTM Travel - The Fun Side of Points & Travel!

Hyatt's Chicago Problem, Destroying Southwest's Brand, Reevaluating Lounge Certs & Bahamas Preview!

Released: Duration: 39:08

Episode Description

On this episode of MTM Travel Shawn and Mark dive into some of the changes Southwest announced after our previous show. It's far worse than anyone imagined including cuts in benefits, no free bags, basic economy and more. Are they destroying the brand or will it grow from this b…
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Destination Eat Drink on Radio Misfits

Destination Eat Drink – Santa Fe, Detroit & Chicago with Darley Newman

Released: Duration: 33:10

Darley Newman joins Brent to talk about the new season (her 12th!) of Travels with Darley and all the great things she ate & drank along the way. From mole and cocktails infused with local honey in Santa Fe to pizza made in car parts trays in Detroit and more pizza in Chicago, Darley’s tried it all.… more

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Award Travel 101

2024 Year End Wrap Up

Released: Duration: 42:43

Mike and Angie recap an exciting year in the world of award travel. This milestone episode kicks off with a look at the lively community debate over a 47-hour Amtrak ride from Chicago to Miami—a no-go for most but sparking dreams of scenic sleeper-car journeys through the mountains. The hosts also d… more

MTM Travel - The Fun Side of Points & Travel!

Airline Bag Fee Commissions, Dueling Road Trips, Chicago Holidays Done Right & Thompson Disappoints!

Released: Duration: 40:30

Get an easy $200 from Melio for making your first payment! (Affiliate link. Terms below) https://affiliates.meliopayments.com/travelonpointsteam

Episode Description

On this episode of MTM Travel Shawn & Mark discuss their dueling weekend road trips. Shawn headed down to Long Beach for an MTM Diamo…
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