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City Cast Chicago

City Cast Chicago

😎 Is Chicago the best summer city?

July 3, 2025 · — Emmi Mack

Hey Chicago! We’re gearing up for a long holiday weekend, so we have something a little different for your inbox today. Below, you’ll find some expert Chicago travel recs, along with a special quiz designed to help you find a summer trip that fits your vibe.

Podcast Player: "Is Chicago the Best Summer City?"

And heads up, we’re off tomorrow so we won’t be back in your inbox until Monday. Try not to miss us too much, and enjoy those fireworks! (If you’re looking for a quick anecdote to sound smart at the BBQ, check out this piece on how the Independence Day fireworks tradition began.)

What Chicago’s Talking About

How to Travel the Midwest — Without a Car

👑 Calling all passenger princesses (and princes)! The long holiday weekend leaves ample time for a day trip! But remember: There are ways to see the Midwest without a car. Check out ways to hit the Dunes, the Dells, and more, by train or bus. [Hey Chicago 💻]

A Chicago Traveler’s Guide to O’Hare and Midway

Chicago airports are busy on holiday weekends — Fourth of July included. So whether you have time to kill before takeoff or are facing unexpected delays, here’s what to do at O’Hare and Midway airports. [Hey Chicago 💻]

It's always a party when the City Cast hosts get together! (City Cast)

Is Chicago the best in the country for a summer trip?

City Cast podcast hosts from all 13 cities came together for a high-stakes showdown to answer the question that’s been burning up our company-wide Slack for weeks: Which city is the best for a summer weekend trip? From naked bike rides to ‘the country’s best farmers market,’ pickle festivals to Elvis impersonators driving pink convertibles, our hosts are bringing the best of the best of what their city has to offer. And yes, we do pick a winner.

Where Should You Plan Your Next Summer Weekend Trip?

Austin, Texas; Chicago, Illinois; and Pittsburgh, Pennsylvania.
Which City Cast city will you visit this summer? From left to right: The skylines of Austin, Texas; Chicago, Illinois; and Pittsburgh, Pennsylvania. (Brandon Bell/Getty Images; Jacoby Cochran/City Cast Chicago; Jeff Greenberg/Universal Images Group via Getty Images)

While our 13 City Cast cities (Austin, Boise, Chicago, D.C., Denver, Houston, Las Vegas, Madison, Nashville, Philly, Pittsburgh, Portland, and Salt Lake) duked it out in our most recent podcast episode, debating which of our cities is the best for a long weekend trip, we wanted to give you the chance to find the summer city that best suits your vibe, too.

Would you rather eat at a kitschy Mexican restaurant with a 30-foot waterfall and cliff divers, or explore a pickle-themed festival spread across two scenic bridges? Embark on a naked bike ride (which doubles as a protest) or kayak down a historic river? The choice is (literally) yours!

What To Do

Thursday, July 3

Friday, July 4

Saturday, July 5

Sunday, July 6

🌭 An estimated 150 million hot dogs will be eaten on the Fourth of July, according to the esteemed National Hot Dog and Sausage Council. That amount of wieners would stretch lengthwise across the country (from DC to LA) at least five times.

Take this as your sign to use hot dog lengths as your standard unit of measurement this weekend. How far is it to your neighbor’s BBQ? 57 hot dogs. Where’s the nearest ATM? 456 hot dogs.

Anyway, have a great Fourth of July! 😎 See you at the beach perhaps?

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