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Chicago Uncovered: The Ultimate Windy City Travel Guide You Can’t Miss

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Picture this: a city where gleaming skyscrapers kiss the sky, jazz music spills out from cozy bars, and the aroma of deep-dish pizza fills the air. Welcome to Chicago — a city that’s as vibrant and eclectic as your Spotify playlist. But planning a trip here can sometimes feel like trying to decide between a Chicago-style hot dog or Italian beef sandwich (spoiler: why not both?). Fear not! We’ve crafted the ultimate, detailed, and wallet-friendly guide to make your Chicago escapade unforgettable — with zero fuss and all the fun.

Why Chicago? Why Now?

Chicago isn’t just the third-largest city in the U.S.; it’s a cultural powerhouse where every corner has a story. From iconic architecture by Frank Lloyd Wright and Mies van der Rohe to world-class museums, sprawling parks, and music scenes that would make even Louis Armstrong proud — Chicago delivers it all.

And don’t forget Lake Michigan, a sparkling freshwater lake that offers everything from relaxing beach vibes to picturesque riverwalks. Whether you’re a history buff, foodie, art lover, or just someone who wants to stroll through photogenic streets, Chicago welcomes you with open arms and (usually) a gentle breeze.

When to Visit Chicago?

Chicago’s weather is like your unpredictable friend — it can surprise you! The best times are:

  • Spring (April-June): Flowers bloom, outdoor festivals pop up, and the weather is pleasantly cool.

  • Fall (September-November): Crisp air, vibrant fall colors, and fewer tourists make exploring a dream.

Winter? Unless you’re a snow-lover or planning to ski, brace yourself for biting cold winds and snowstorms. Summer is lively but expect crowds and some sticky heat.

Budget Breakdown: How Much Will It Cost?

Traveling to Chicago doesn’t have to drain your wallet. Here’s a realistic estimate for a 5-day trip:

Category Cost Estimate (USD) Notes
Round-trip Flight $250 – $400 From major US cities; book early for deals
Accommodation $100 – $180 per night Mid-range hotels downtown or nearby
Food $30 – $50 per day Mix of street food and casual dining
Transportation $15/day (Ventra card) Buses, ‘L’ trains, taxis
Attractions & Tours $40 – $70 Museums, Skydeck, boat tours
Miscellaneous $50 Shopping, souvenirs, extra snacks
Total (5 days) Approx. $900 – $1200 All-inclusive, comfortable budget

Where to Stay? Top Hotel Picks for Every Style

Finding the perfect place to rest your head after a day of exploring can make or break your trip. Here are some handpicked hotels that balance comfort, location, and price.

The Palmer House Hilton

A historic gem in the heart of downtown Chicago. Think grand ballrooms, plush rooms, and a lobby that screams luxury without the insane price tag. Walking distance from Millennium Park and the Art Institute.
Price: Around $150 per night.

Hyatt Place Chicago/Downtown – The Loop

Modern, clean, and super convenient. Great for those who want quick access to public transport and restaurants. The complimentary breakfast is a lifesaver on busy mornings.
Price: Around $130 per night.

Freehand Chicago

A cool hybrid of hostel and hotel with vibrant decor and a buzzing bar. Ideal for solo travelers and groups who want to mix socializing with budget savings. Located close to the River North district.
Price: Around $100 per night.

How to Get Around?

Public transit is your best friend! Chicago’s Ventra Card works on buses and the famous “L” elevated trains. It’s cheap, easy to use, and helps avoid traffic snarls. Taxis and rideshares (Uber/Lyft) are widely available, but can get pricey during rush hours.

Tip: Download apps like Transit or Citymapper to plan your routes efficiently.

The Chicago Bucket List: Must-See Places & Experiences

Millennium Park & The Bean (Cloud Gate)

The quintessential Chicago landmark. This shiny, reflective “bean” is perfect for selfies and watching street performers. Don’t miss the nearby Crown Fountain — a quirky display of digital faces that splash water!
Cost: Free.

The Art Institute of Chicago

Prepare to be wowed by masterpieces from Monet, Picasso, and Grant Wood’s iconic American Gothic. The museum is massive — plan at least 3 hours.
Entry: $25 (free certain days for Illinois residents).

Navy Pier

A lakeside playground with rides, shops, restaurants, and even a mini Ferris wheel with stunning skyline views. Ideal for families or romantic sunsets.
Entry: Free, rides and activities extra.

Skydeck Chicago at Willis Tower

For the brave-hearted, step onto the glass “Ledge” 1,353 feet above the city streets. The views? Breathtaking. The experience? Heart-stopping.
Ticket: Around $30.

Museum of Science and Industry

One of the largest science museums in the world — explore a WWII submarine, a coal mine, and a futuristic Smart Home. Perfect for curious minds of all ages.
Entry: $21.95.

Chicago Riverwalk & Architecture Tours

Stroll along the scenic Riverwalk or hop on a boat tour to admire Chicago’s legendary skyline and learn about its history. Boat tours cost around $40 and are worth every penny.

Wrigley Field

Sports fans, rejoice! Catch a Cubs game or tour this historic ballpark. Even if you’re not a baseball fanatic, the atmosphere here is electric during game days.

Magnificent Mile

Shop till you drop (or window shop to your heart’s content) along this famous stretch filled with flagship stores, cafes, and high-end restaurants.

Foodie Highlights: Eat Like a Chicagoan

Chicago’s culinary scene is as diverse as its neighborhoods. Here are some iconic eats you can’t skip:

  • Deep-Dish Pizza: The thick, cheesy, tomato-packed pies from Lou Malnati’s or Giordano’s are legendary.

  • Chicago-Style Hot Dog: All-beef hot dogs loaded with mustard, onions, relish, tomato, pickle, and sport peppers — but no ketchup! Try Portillo’s for the real deal.

  • Italian Beef Sandwich: Thinly sliced beef dripping with gravy, served on a fresh roll, often dipped in au jus. Al’s Beef is the go-to.

  • Craft Breweries & Bars: Chicago boasts a booming craft beer scene. Don’t miss Revolution Brewing or Goose Island.

Sample 5-Day Itinerary: See It All, Eat It All

Day 1:

  • Arrive, check into your hotel downtown.

  • Afternoon visit to Millennium Park and snap your Bean selfie.

  • Dinner at Giordano’s for that iconic deep-dish pizza experience.

Day 2:

  • Morning at the Art Institute of Chicago.

  • Lunch in Grant Park.

  • Afternoon thrill at Skydeck Willis Tower.

  • Evening stroll and drinks along the Chicago Riverwalk.

Day 3:

  • Explore the Museum of Science and Industry (half or full day).

  • Head to Navy Pier for sunset, ride the Ferris wheel, and enjoy lakeside snacks.

Day 4:

  • Shop or window shop along Magnificent Mile.

  • Catch a Cubs game at Wrigley Field or enjoy live jazz at a local club.

Day 5:

  • Breakfast at a local café — try Intelligentsia Coffee in Logan Square.

  • Last-minute visit to Lincoln Park Zoo (free and adorable).

  • Head back to the airport with memories and a full camera roll.

Insider Tips You’ll Thank Me For

  • Weather: Chicago’s wind earns it the nickname “Windy City” for a reason — pack a windbreaker even if the forecast looks clear.

  • Ventra Card: Buy it at airports or local stores for unlimited bus and train rides.

  • Reservations: Book popular attractions online to skip lines, especially Skydeck and museum entries.

  • Free Fun: Lincoln Park Zoo, Garfield Park Conservatory, and many museums offer free or donation-based entry on specific days.

Final Thought

Chicago is a city of contrasts — historic yet modern, bustling yet relaxed, and always delicious. This plan gives you a mix of must-see landmarks, local secrets, and a taste of Chicago’s heart and soul — all without blowing your budget. Pack your bags, bring your curiosity, and get ready to make memories that last longer than your pizza cravings.

Chicago is more than just a city — it’s an experience waiting to happen. From iconic landmarks and world-class museums to mouthwatering food and vibrant neighborhoods, the Windy City offers something for every traveler. With this carefully crafted plan, you can explore the best of Chicago without breaking the bank or missing out on any must-see spots. So get ready to dive into a whirlwind of culture, history, and fun — Chicago is calling, and you don’t want to keep it waiting!

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Pride Fizzles, Glenwood Bar Shuts in Liquor License Storm

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The Glenwood Bar’s sudden closure has cast a shadow over Rogers Park’s festive spirit, following a surprise liquor license lapse and the abrupt cancellation of the beloved Pride North festival. On Saturday night, police shut the bar after discovering its expired state license, just a day after city permits for the annual street celebration were officially denied. As confusion stirred and updates lagged, both the bar and the festival lost their summer spotlight—leaving residents with unanswered questions and a once-vibrant event dimmed by administrative stumbles.

📌 STORY HIGHLIGHTS

  • Glenwood Bar shut down by police after state liquor license expired

  • Annual Pride North street festival canceled due to city permit issues

  • Bar’s city liquor license remains active, but state license lapsed

  • Confusion among residents as no formal cancellation was announced

  • Ald. Hadden says her office tried to assist in the permit process

  • Similar permit issues have occurred in past years, Hadden noted

  • Owner Treacy silent, festival organizers issue vague online post

It was around 11:30 p.m. on Saturday when officers from the Chicago Police Department conducted a “premises check” at The Glenwood, located at 6962 N. Glenwood Ave. That visit ended with more than just a routine walkthrough. Officers issued a citation after discovering the state liquor license was no longer valid, and ordered the premises to close immediately.

The Illinois Liquor Control Commission later confirmed that the Glenwood does not hold an active state license at this time. However, officials offered no comment on whether the bar’s management had initiated a renewal process.

The business remained closed through Tuesday, even during its usual operating hours. Multiple efforts to reach owner Colm Treacy went unanswered.

What Happened to Pride North?

The Glenwood’s closure may have been a late-night surprise, but trouble was already brewing before the lights went out. Pride North, an annual street celebration of LGBTQ+ pride held outside the bar, was expected to kick off Friday and run through the weekend. That, too, fell apart — but in a far less visible fashion.

The festival was advertised on social media as proceeding as planned. Streets were marked, posts shared, and anticipation built — but behind the scenes, city permits never materialized.

On Friday afternoon — the very day the festival was set to begin — Ald. Maria Hadden (49th) posted a public message confirming what organizers hadn’t: the event would not take place.

“The city denied the permits on June 23,” Hadden explained. “We worked with Mr. Treacy to correct issues in the application, but those corrections were never submitted. My office can guide and provide sample forms, but the applicant must take the final step.”

Lack of Communication Fuels Confusion

What followed was a weekend of mixed messages and mounting confusion. Neighbors questioned whether the festival was happening, and if not, why no one had said so. Hadden followed up with a second statement Saturday, clarifying both the permit denial and her office’s involvement — or lack thereof — in the matter.

She noted that problems with the Pride North application were not new this year. “These weren’t isolated issues,” she said. “We’ve seen similar complications in the past.”

Despite the lack of outdoor festivities, Pride North organizers made a brief statement via Facebook on Saturday, writing:
“Pride is on. Inside Glenwood Bar we will survive.”
The cryptic message only deepened frustration, with many commenters accusing the bar and organizers of poor communication.

Liquor License Not to Blame for Permit Denial — Officially

While speculation swirled about whether the expired liquor license was linked to the permit denial, Ald. Hadden clarified that this was not the case. She confirmed the bar’s city liquor license remains active, and the permit decision was based solely on the incomplete application.

The city’s Business Affairs and Consumer Protection department also confirmed it had no role in closing the Glenwood. That action was taken independently by police based on the expired state license.

A Familiar Face Behind the Scene

Colm Treacy, owner of The Glenwood, is no stranger to Chicago’s bar scene. Before launching The Glenwood in 2008, he operated T’s Bar in Uptown, as well as Sidecar (now Rogers Park Social) and the short-lived MorseL.

Earlier this year, he opened GW Martini Bar, located next door to The Glenwood at 6958 N. Glenwood Ave. Its status remains unclear in light of recent developments.

A Troubled History With Permits

This isn’t the first time Pride North has drawn scrutiny. In 2021, Block Club Chicago reported that attendees were charged a $20 cover to enter the street festival — a move deemed illegal under city law, which prohibits charging for access to public streets.

These past missteps now raise further questions about oversight and event organization, particularly as the neighborhood seeks clarity on what went wrong this year.

Looking Ahead — But With Uncertainty

Whether The Glenwood will reopen or Pride North will return in 2026 remains to be seen. For now, the Rogers Park community is left without one of its staple summer events and with the doors of a longtime neighborhood bar closed — at least temporarily.

“It’s unfortunate,” Hadden said. “This is a cherished community event that people in Rogers Park — and even beyond — look forward to each year.”

While the summer carries on, The Glenwood’s future — like the festival it once hosted — hangs in limbo.

The abrupt closure of The Glenwood Bar and the cancellation of the Pride North festival reflect a broader breakdown in planning, communication, and compliance. What was meant to be a vibrant celebration of community turned into a weekend of confusion and disappointment. As questions linger over licensing, permits, and leadership, residents are left hoping that the iconic event — and the neighborhood bar that once anchored it — can return next year with renewed clarity, responsibility, and the same spirit that once brought Rogers Park together.

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