The 'L' is Chicago's railway network, running to every corner of the windy city. It's speedy and reliable and the most obvious transport choice if you want to travel bigger distances across the sprawling urban jungle. There are eight rapid transit routes, based on colours, with Red and Blue operating 24 hours a day. Purchase a Chicago Card for US$5.
The CTA's bus service will be your most frequent ride around town. Buses offer over 140 routes and 12,000 stops. The 'Owl Service' operates 24 hours a day for any late-night revellers needing a safe route home. A Chicago Card works on buses and trains so your options are flexible. A tip: if you're paying cash, exact fare is required.
Chicago's taxi fleet is enormous and you'll have no trouble hailing one down whenever you need to from the sidewalk. A base rate of US$2.24 means they're generally inexpensive if you're travelling a few blocks. However, the driver will expect a 15-20 per cent tip on top of the fare, so don't forget to keep some loose change in your pocket!
When in the US, it's tempting to splash out on a Cadillac or Oldsmobile to tear around the open roads. But this isn't Route 66 and tackling the traffic might be an unnecessary stress when public transport is so good. If you want to see Chicago Ferris Bueller-style, all the major rental operators have desks in the airport and across the city.
If you're from Australia or New Zealand and you intend to travel for less than 90 days, you don't need a visa for the US as part of the Visa Waiver Program. But you will need an electronic travel authorisation (ESTA) at least 72 hours before you depart. Apply online at a cost of AU$13.55.
Travel insurance is an absolute must in America. Chicago has an excellent range of hospitals and medical centres, but they are private and treatment could cost you an arm and a leg – no pun intended. Plus, if you don't show documentation proving your cover, you could be turned away. Make sure your insurance includes medical bills and repatriation should you need it.
Chicago has a fast and sweeping wind that can attack at any time of day, month or year, even in the peak of summer – when the temperatures are so warm that most shops are equipped with air conditioning. In Winter, temperatures can drop well below zero, so layers, thick socks and boots are vital for avoiding painful extremities.
Chicago experienced a crime wave in the 1980s, which has subsided in recent years. But there are still pockets that you should avoid if you don't want to risk something unpleasant happening. Don't wander around the United Center or US Cellular Field in the dark, and remain alert on the trains and buses at night when some of the city's vagrants begin to emerge.
Get to Chicago from Sydney in around 19 hours, 30 minutes on board United, with one stop in San Francisco.
Stop in Los Angeles care of American Airlines with a journey time of just over 25 hours.
Your quickest option from Perth is on board Cathay Pacific and United, stopping over in Hong Kong.
Swing into Chicago in style, sipping bubbles in the back of a stretch limo. After a long flight and limited leg room, you deserve to stretch out a bit. Book online through A1 and a quick phone call later your luggage collector will direct you to your glamorous ride for a star quality shuttle to your accommodation's front door.
An airport shuttle bus like GO Airport Express is comfortable, convenient and won't take a big chunk out of your holiday budget. For a little extra you can choose to go private to avoid stopping at other hotels en route. Book online or at the airport Terminals 1, 2 and 3. You'll find the vans outside baggage claim, with buses leaving every 15 minutes.
A cab to Chicago city centre should cost no more than US$45 one-way and take up to an hour, depending on the traffic conditions. They operate from the lower levels at the front of each terminal on a first come, first served basis. If you're looking to lower costs, shared ride options are also available.
The Blue Line 'L' train runs a 24-hour service from O'Hare Airport and downtown Chicago. On arrival, head to the lower level concourse and follow the clear signs to CTA Trains. A one-way fare is US$2.25, the journey time is 45 minutes and trains depart every 10 minutes. A simple, speedy and super cheap transfer option.
Spend three hours speeding around Chicago's top attractions barely lifting a finger – or a foot. Roll around Museum Campus, Shedd Aquarium and the Field Museum to tick off the cultural essentials. Next, roll along the shores of famous Lake Michigan towards Buckingham Fountain. Great fun and perfect for those who like to see all the sights without the fear of sore feet.
America's second largest museum displays some of the world's most iconic pieces, ranging from glorious ancient masterpieces to the contemporary exhibits in Renzo Piano's critically acclaimed Modern Wing. Spend time with European maestros Rembrandt and Monet and soak up the culturally charged atmosphere, suitable for all ages. Open every day of the week, admission is US$18 per adult and free for under-14s.
Save your sightseeing for the evening on a magical night bike tour of Chicago – the city's skyline is spectacular lit up under the stars. Tours start at 7pm and wind though the city's most striking points of interest, including Buckingham Fountain and its famous light show. Finish at Navy Pier under the glow of the fireworks show. Prices are US$35 per adult.
Climb to the top of Chicago's most famous landmark building for a breathtaking 360° view from the 103rd floor. Next, walk out onto The Ledge, a transparent piece of glass extending out over four feet from the top floor ledge. Gaze down if you dare and see the bustling city in peace from above. Acrophobics, this isn't for you.
Cutting edge and wildly inventive cuisine crafted to perfection by Grant Achatz and his imaginative team. Achatz exploded onto the American restaurant scene from the kitchens of world famous elBulli, so a meal here is the pinnacle of fine dining. Named in the World's 50 Best restaurants in 2007, Alinea will be one of life's more memorable experiences. Try not to blanche at the prices.
Cocktails and crab claws are the stars of the show at this glitzy North River steakhouse. The vibe screams easygoing but the menu suggests otherwise. Enormous effort has gone into making Joe's a roaring success on the local food scene. Generous portions of melt-in-your-mouth seafood and steak in a glamorous but laid back setting make it the ideal Friday night destination for foodies.
Everest is one of the world's most esteemed French restaurants, serving exquisitely unique dishes and boasting an award-winning wine list. Perched on the 40th floor of the Chicago Stock Exchange, you'll struggle to divide your attention between the spectacular city views and mouthwatering plates. Start with roast lobster, followed by the guinea fowl and end with chef Taylor's Vacherin dessert.
You can't travel to the States without trying the nation's food icon: the classic hotdog. But Hot Doug's delivers dogs with a fancy, contemporary twist. Lavish fillings, an array of buns and duck fat coated French fries (believe us, it's delicious) your taste buds will scream to join the back of the queue again as soon as you get your first bite.
Boasting an impressive list of beers from all over the globe, try and sample as many as you can – without compromising your reputation – under a ceiling adorned with a blanket of world maps. This Chicago favourite has an international theme that's loved by tourists and locals alike.
Goose Island Brewpub serves no ordinary beer. This is handcrafted, pure brewed gold to rival the most upmarket wine labels and bars. Located in the heart of vibrant Lincoln Park, perch at the bar and try out some of their 20 custom drafts, accompanied by a signature Stilton burger.
Crystal chandeliers, leather and velvet give this glamorous nightclub a deliciously decadent feel. The brains behind Angels & Kings (aka AK-47) include famous names from America's music elite, so star-spotting is common. Live performances, inexpensive cocktails and inventive theme nights make this one of the city's most popular late night venues.
Immerse yourself in Chicago's famous Blues scene, at guitar legend Buddy Guy's world renowned live music lounge. Experience Blues at its best, seven days a week until late. This music is soul fuel that will have you shaking your head and clicking your fingers to big bass lines and even bigger voices.
Begin your Chicago break with a scenic stroll of the city. Wander the waterfront of enormous Lake Michigan, wind your way into the CBD and downtown to crane your neck up at the skyscrapers that make the skyline famous. Next, give weary feet a break and join a relaxing boat cruise for the afternoon. Marvel at the skyscrapers from the water and cruise your way through the city. That evening, join a nighttime bike tour and discover the splendour of Chicago lit up at night.
Dive into Chicago's diverse cultural offerings with a morning spent at Museum Campus exploring three of the city's most important science institutions, dedicated to sea, land and the universe. Walk north through Millennium Park to the Art Institute of Chicago, arguably the city's most important museums, with the largest Impressionist collection in the country. Take a break from broadening your mind and wander down the Magnificent Mile, 14 blocks of retail heaven and ideal for finding some glad rags to don at Everest restaurant in the Chicago Stock Exchange that evening.
Embrace your third day with bravado and climb up to the 103rd floor of the Skydeck Chicago. See the city from dizzying heights and creep out onto the glass Ledge. Look down if you dare, the view is exhilarating! Next, head north to Lincoln Park Zoo. Free entry, 1200 animals and open 365 days a year, this Chicago stalwart is an affordable and fabulous way to spend the rest of your afternoon. Wander through beautifully kept enclosures, treat yourself in the zoo cafes and soak up the gorgeous parkland setting.
Head to breakfast specialist Yolk, at 1120 South Michigan Avenue, for a hearty American brunch of pancakes, omelettes or benedicts. The menu is vast and everything is sensational – you'll long to taste it all. After brunch, wander over to Navy Pier, a kaleidoscope of colour and bustling activity. Ride the Ferris wheel and take in a show at the Shakespeare Theatre, a celebrated landmark on the Chicago drama scene. Toast your last evening in Chicago with a cocktail and magnificent views at The Roof on North State Street.
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