Chicago

Why I Love Chicago

Imagine strolling along the stunning Lake Michigan waterfront, the breeze carrying the distant tunes of a saxophonist playing in the park. That’s Chicago for you. The first time I experienced Chicago’s skyline was from the top of the Willis Tower, and it’s not just the height that took my breath away — it's the vibrant pulse of the city below. The blend of striking architecture, deep-rooted jazz culture, and the smell of deep-dish pizza wafting through the streets makes Chicago feel like an old friend. There's something magical about this city that draws you in, leaving you eager to explore every corner.

Quick Facts

• Best time to visit: Late Spring (May-June) and early Fall (September)
• Currency: US Dollar (USD)
• Language: English
• Time zone: Central Time Zone (CT)
• Getting around: Public transit (CTA), walking, biking
• Daily budget (budget traveler): $60-$100
• Daily budget (mid-range): $150-$250

Getting There

Chicago is served by two major airports: O’Hare International Airport (ORD) and Midway International Airport (MDW). O’Hare is one of the busiest in the world, making it a hub for international and domestic flights. If you’re flying from London, the direct flight takes about 8 hours; from New York, it’s around 2 hours; and from Dubai, roughly 14 hours. Airlines like American, United, and Emirates often offer competitive fares. Don’t forget to check the visa-waiver program if you're eligible as it streamlines entry for many travelers.

Where to Stay

Budget (under $80/night)

Check out Chicago Getaway Hostel in Lincoln Park. It's youthful, vibrant, and ideal for solo travelers and backpackers. You’ll love its proximity to Lincoln Park and the free weekend pancake breakfast. Check availability on Expedia

Mid-Range ($80-200/night)

Try The Robey in Wicker Park. This place effortlessly combines historic charm with modern elegance. It's perfect if you’re into quirky neighborhoods, great food, and vibrant nightlife. Plus, the rooftop bar offers spectacular views. Check availability on Expedia

Luxury ($200+/night)

If luxury is your style, The Langham, located along the Chicago River, offers everything from stunning views to top-notch service. Ideal for romantic getaways or treating yourself to something special. Check availability on Expedia

>My Favourite Things To Do

Explore Millennium Park

One of my favorite things to do here is to wander through Millennium Park. You’ve got to see the Cloud Gate sculpture (a.k.a. "The Bean") and don’t miss a concert at the Jay Pritzker Pavilion. It’s where art, architecture, and nature come together beautifully. Book with Viator

Architectural River Cruise

The river cruise is a must. You float along the Chicago River while guides narrate the city’s architectural wonders. It’s relaxing and informative — plus, those skyline views are unbeatable. Book with GetYourGuide

Visit the Art Institute of Chicago

Spend an afternoon at the Art Institute of Chicago. It’s filled with masterpieces like Grant Wood’s "American Gothic" and Sunday afternoons here are a quiet escape into a world of creativity. Book with Viator

>Where to Eat

You have to try Giordano’s for deep-dish pizza. It’s the classic, gooey cheese you crave, and it’s family-friendly, too. For a different bite, head to Portillo’s for a Chicago-style hot dog — don't skimp on the relish! And make sure to hit up Girl & the Goat in the West Loop for small plates bursting with flavor; the atmosphere is electric, and the wood-fired oysters are a must.

>Honest Local Tips

• Public Transit is Your Friend: The CTA is efficient and cheap. Get a Ventra pass for unlimited rides if you’re staying a while.
• Lakefront Trail Perks: Rent a bike and explore the Lakefront Trail; it's scenic and a great way to see the city.
• Chicago Weather Lied to Me: Pack layers — Chicago’s weather is famously unpredictable, and wind off the lake can be surprising.
• Skip Navy Pier on Weekends: It can be overwhelmingly crowded; weekdays are much more enjoyable.
• Street Parking is Tricky: Use apps like SpotHero to find parking beforehand and save some headaches.
• Chicago Greeter: Take advantage of the free Chicago Greeter program for personalized city tours led by locals.
• Try Not to Mispronounce: Locals don’t say "Chi-cah-go" — it’s "Chi-ca-go" with a short ‘i’. Trust me, they’ll appreciate it!

>Getting Around

Download the Transit app for smooth navigation through CTA's buses and trains. Rideshares like Uber and Lyft are convenient if you prefer door-to-door service. Renting a bike is also popular, with Divvy bike-share stations located conveniently around the city. Be cautious with taxis: ensure the meter is running or agree on a fare upfront to avoid scams.

>Is Chicago Worth It?

Absolutely! Chicago is a treasure trove of culture, food, and Midwestern charm sans the typical fast-paced grind of other major cities. It’s perfect for travelers who love a mix of artsy adventures, culinary escapades, and rich history. If crowded urban environments aren’t your vibe, some parts may feel overwhelming. But would I go back? In a heartbeat — there’s always more to uncover in Chicago!