
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.

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 💻]

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?

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
- 🏎️ Speed & Sound Fest | DuSable Black History Museum | Hyde Park
- 🎤 World's Largest Karaoke | Salt Shed | Goose Island
- 📚 Guided Exhibition Tour: "Winging It" | Newberry Library | River North
- 🍗 The River's Ribapalooza | The River Kitchen and Bar | Lakeview
- 🎆 Taste of Oak Brook | Village Sports Core Fields | Oak Brook
- 🖼️ Danger AKA Dan Wininger: Ancient Future | International Museum of Surgical Science | Streeterville
- 🎭 The Roys of Succession Do Something Normal: An Improvised Show! | iO Theater | Lincoln Park
- 🎸 Kicking It Curbside | Tack Room | Pilsen
- 🍺 Brews and Bad Movies | The Lincoln Lodge | Logan Square
- 🎤 The Powerful Hourful | Bughouse Theater | North Center
Friday, July 4
- 🇺🇸 Hyde Park 4th on 53rd Parade | 55th Street to 53rd Street | Hyde Park
- 🎉 Post-Parade Festival | Nichols Park | Hyde Park
- 🍻 4th of July 2025 Summer Bash | Offshore Rooftop | Navy Pier
- 🥂 4th of July at Broken Shaker Chicago | Freehand Chicago | Streeterville
- 🎇 Fireworks | Evanston Lakefront | Evanston
- 🎆 Fireworks | Richards High School | Oak Lawn
- 🎉 Skokie Fireworks Festival & Parade | Downtown Skokie and Niles West High School | Skokie
- 🌭 Chicago Dogs 4th of July Happy Friday | Impact Field | Rosemont
- 🍔 All-You-Can-Eat Grill Out Bash | Aura on the Beach | Edgewater
- 🍺 Red, White & Brew Party | Howl at the Moon Chicago | Streeterville
- 🇺🇸 Fourth of July at Celeste Garden Rooftop | Celeste | River North
- 🎶 The Friday Night Cruise - R&B Vibes | Island Party Hut | Riverwalk
Saturday, July 5
- 🏎️ NASCAR Chicago Street Race | Loop
- 🎆 Fireworks | Navy Pier
- 🎥 “A Story of Floating Weeds” | Music Box Theatre | Lakeview
- 🏳️🌈 Chicago Black Pride 2025: The BLOQ Day Party | The Promontory | Hyde Park
- 🖼️ Connie Noyes: “Dispatched” opening reception | Compound Yellow | Oak Park
- 🎨 “A Swamp Beneath the Concrete” opening reception | Roman Susan | Rogers Park
- 🏳️🌈 Sapphic Factory: queer joy party | Empty Bottle | Ukrainian Village
- 🖼️ Alan Emerson Hicks: Artist Talk | SoNa Chicago Art Gallery | Wicker Park
- 🎨 Workshop: Ukiyo-e with Mami Takahashi | International Museum of Surgical Science | Streeterville
- 🎭 Love, Chaos, and Dinner | Teatro ZinZanni | Loop
Sunday, July 6
- 🌳 Humboldt Park Arboreal Society (DJs) | Humboldt Park
- 🏎️ NASCAR Chicago Street Race | Loop
- 🎶 Under the Bridge | Ping Tom Memorial Park | Chinatown
- 🎵 First Sundays | South Shore Social Beach Club | South Shore
- 🎤 Live on the Lawn | Epiphany Center for the Arts | West Loop
- 🎷 An Evening of Jazz and R&B | DuSable Black History Museum | Hyde Park
- 👽 “War of the Worlds” | Lifeline Theater | Rogers Park
- 🎭 "The Curious Circumstances of Louis Le Prince" | The Factory Theater | Rogers Park
- 🎤 “That's What Friends Are For” | Black Ensemble Theater | Uptown
🌭 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?
Free · Daily

