a citizen’s guide to Chicago

Imagine a giant, sparkling blue lake, then imagine a bustling city right next to it. That's Chicago, right on the edge of Lake Michigan, in the state of Illinois, USA. It's the third biggest city in the US, but don't let that intimidate you – it's as friendly as a warm slice of its famous dish. And guess what? It's actually closer to Canada than you might think. If you fancy a road trip, you can even reach the Canadian border in a day's drive.

The best time to visit Chicago is from May through to September. High season is between June and August, with temperatures reaching X degrees. Craving a slice of the Windy City all to yourself? Drop by during the shoulder season – that's April, May, and September. Yes, the weather could throw a curveball or two, but hey, isn’t life more exciting when dancing with the unexpected? Plus, you get to dodge the bustling crowds and bask in the city's attractions in your own sweet time. Whether it's a sun-drenched day or a little on the chilly side, Chicago always has a jazz tune playing somewhere for every mood.

Yes, citizens, the weather in the Windy City is a thing. Chicago has a bit of a reputation for having a bone-chilling winter. Come summer, the city comes alive with festivals, outdoor concerts and throngs of sunbathers on the beaches of Lake Michigan.

Don’t mind a bit of the cold? Low season from November to March can be great fun. And trust us, there are plenty of fun things to do in Chicago with bad weather too.

Navigating through Chicago is as easy as (pizza) pie. Whether you're riding the ‘L’ trains, jumping on a bus or doing the old pedal-and-go on a bicycle, this city is just waiting for you to explore it. If you're feeling lazy, you've got taxis and ride shares at your fingertips. Prefer a bit of fresh air? Chicago is very walk-friendly too.

Train and bus

So what exactly are the ‘L trains’ in Chicago? The ‘L’ (short for elevated) trains are the lifeline of the city, weaving their web through the suburbs to the underground and overground tracks.

Citizens insider tip: Score a CTA visitor pass from the Chicago Transit Authority and enjoy the freedom of unlimited rides on the iconic 'L' train and bus system. Valid for as long as you need, it's the savvy and wallet-friendly way to see the city.

Taxis

While Chicago's weather may keep you guessing, the abundance of taxis won't. Looking for a less pricey option? Pop onto Lyft or Uber – Chicago's best alternative driver apps.

Bikes

In the mood to stretch those legs? Rent a bike in Chicago from Bike and Roll, with convenient locations at Navy Pier and Millennium Park. You're free to choose between a full-day or half-day hire.

Get ready to rock Chicago's playground of awesomeness! With lakeside adventures, underground art or belly-aching comedy clubs, this city has it all. Let’s dive into the 13 must-do’s when visiting Chicago. 

1. Visit Navy Pier
This iconic lakefront spot boasts an unbeatable combo of rides, food stalls, beer gardens and free fireworks. Catch a Lake Michigan boat tour or rent a bike to peddle yourself to the nearest beaches. 

2. Stroll through Millennium Park
If an art-meets-nature fiesta sounds appealing, don't miss this Chicago must-see. The Cloud Gate – also known as ‘The Bean’ – is perfect for an obligatory selfie moment.

3. Visit the Art Institute of Chicago
Filled with the creative genius of legends like Monet, Picasso and Grant Wood, this is the perfect spot to take a colourful detour into the realm of imagination.

4. Dine deep-dish style
A slice of Chicago’s deep-dish pizza is like a love letter from the city’s culinary scene, best read at joints like Giordano's or Lou Malnati's. Buckle up for a cheese fest!

5. Shop til you drop at the Magnificent Mile
If your idea of a good time is some retail therapy, you're going to love this upscale section of Michigan Avenue.

6. Navigate The Labyrinth at The Chicago Cultural Center
The world's largest Tiffany glass dome at the heart of the city? It's an aesthetic journey you'd not want to miss!

7. Visit The Skydeck
Elevate your perspective (literally) with a breathtaking view from Willis Tower. Trust us, it’s one of the best skyline views of Chicago. It's like living on top of the world!

8. Laugh it up at Second City
This comedy club in Chicago is the birthplace of improv comedy, where famous funny people like Tina Fey got their start. If laughter is the best medicine, consider this your health hub.

9. Take the Chicago Riverwalk
Cityscape, water and a walk – a poetic mélange of city life at its best. Expect tall buildings, cocktail bars, kayaking, gelato and waterfront dining: the Chicago Riverwalk is the real thing, citizens. Don't forget your camera!

10. Delve into Chicago's underground art scene
Chicago’s neighbourhoods are bursting with street art, galleries and edgy performances. It's like stumbling into a living, breathing canvas.

11. Get lost in Chicago’s best art museums
Bad weather? Try some of Chicago’s best art museums. The National Museum of Mexican Art, Museum of Contemporary Art and Smart Museum of Art Chicago won’t let you down. 

12. See a show at the Chicago Theatre
Ladies and gents, behold the mesmerising extravaganza at the one and only Chicago Theatre! Get ready to be dazzled by glitter, glam and oh-my-goosebumps performances! This stunning landmark will treat you to the crème de la crème of shows.

13. Jazz it up at Green Mill
Step back in time at this Prohibition-era jazz bar. It’s music, cocktails and classy vibes with a side of history.

So, there you go! We’ve just handed you your ready-to-rock guide to the Windy City. Go forth and discover Chicago – one cool experience at a time.

Chicago’s best jazz clubs for a balmy night out

• The Green Mill
  Steeped in Prohibition-era allure, The Green Mill has been serving up jazz since Al Capone was making headlines. Rumor has it, Capone had his own booth here. Feel the history come alive in its Art Deco interiors while you enjoy top-tier jazz performances.

• Jazz Showcase
  The oldest historic jazz club in Chicago, founded in 1947. This is the place to witness both local legends and international jazz maestros strut their stuff.

• Andy's Jazz Club
  Kick back and let the music take you away at Andy's, where there's live jazz seven nights a week. A local favorite since the '70s, this spot is as much about the warm, welcoming vibe as it is about the fantastic tunes.

• Constellation
  For a modern twist on Chicago's jazz scene, the Constellation offers an experimental blend of jazz and contemporary classical performances. Expect the unexpected!

So, there you have it, jazzy citizens. The best jazz spots in Chicago are all yours. Don your best flapper dress or slick zoot suit, let the city lights guide you, and immerse yourself in the rhythm of this magnificent musical city. Oh, and don't forget to tip the musicians!

Ever been so starstruck by a high rise you got a bit light-headed? Buckle up, skyscraper enthusiasts, because we're about to amp up that feeling to 11. Join us as we dive headfirst into the dizzying heights of Chicago's skyline superheroes.

1. Willis Tower
Formerly known as the Sears Tower, this 1,450 feet wonder was once the tallest building in the world. A ride in its speedy elevators takes you to the Skydeck, where you'll be rewarded with jaw-dropping views of the city.

2. Trump International Hotel and Tower
With its dazzling design reaching 1,388 feet, this mixed-use tower is all about luxury living, upscale dining, and breathtaking views.

3. Aon Center
This monolithic marvel stands tall at 1,136 feet. The Aon Center may be mostly offices, but its gleaming exterior makes it a true icon of the city skyline.

4. 875 North Michigan Avenue (formerly John Hancock Center)
This 1,128 feet multi-use building offers residences, offices, shops, and a 360-degree observation deck. It’s more than just a tall building; it's a vertical city!

5. St. Regis Chicago (formerly Vista Tower)
As the third-tallest skyscraper in Chicago, it stretches up to 1,191 feet, housing a hotel and luxury apartments. Its cascading design gives it a distinct look, making it stand out in the city skyline.

6. Two Prudential Plaza
This 995-foot giant has an iconic chevron-shaped top that lights up beautifully at night. It's an elegant addition to Chicago's architectural portfolio.

Get ready to look up, way up, as you explore these cloud-tickling giants of Chicago's skyline. Happy skyscraper-spotting, urban explorers!