Trains rattle and rumble as they pass overhead. Tall buildings – some Art Deco treasures, others shiny glass tower – rise triumphantly over the river that flows through the heart of downtown. It sounds corny but to walk the streets of Chicago is to admire the spirit, enterprise and power that built one of the great American cities.
Chicago is smaller than New York City and Los Angeles, and therein lies its charm. Simpler to navigate and less crowded, it’s easier to appreciate all the city has to offer – and there’s a lot. Chicago rivals anywhere in terms of culture; Hamilton: An American Musical is showing at the CIBC Theatre, the Art Institute of Chicago is one of the word’s top-rated museums and it’s in good company with the American Writers Museum and the National Museum of Mexican Art. The jazz scene thrives year-round, and improv and sketch comedy space Second City has launched the careers of top American comedians including Tina Fey. Low-key cool neighbourhoods like Wicker Park, Bucktown and Logan Square are thriving with hip restaurants, bars and boutiques. Here’s what you need to know before you go.
It takes around 20 hours to fly to Chicago from Australia’s east coast cities. Fly direct to Los Angeles, Dallas or San Francisco with Qantas and then onwards with American Airlines.
From Australia’s east coast cities it takes approximately 20 hours to fly to Chicago on Qantas, with a stopover in either Los Angeles, Dallas or San Francisco and then
Entering the United States
Australia is a participant in America’s Visa Waiver Program, meaning eligible Australians don’t need a visa for visits of 90 days or less. We must, however, obtain an Electronic System for Travel Authorization (ESTA) through the Department of Homeland Security site. Approvals can take up to 72 hours so apply with plenty of lead time in case there’s an issue. Approved ESTAs are valid for two years and multiple entries. ESTA-approved travellers also need a (machine-readable) ePassport. Check the Smart Traveller website for detailed entry and exit requirements.
If you overstay, the American government could arrest, deport or even bar you from returning to the States.
Landing at Chicago O’Hare International Airport
From Chicago O’Hare International (ORD), shuttles are available to downtown. The airport is also well-serviced by taxis and ride-sharing apps like Uber. Public transport can get you into the city via the Chicago Transit Authority buses and rail lines.
At the time of writing, the Australian dollar was buying around 71 US cents but consult a reliable currency conversion service for up-to-date foreign-exchange rates.
Check with your bank that you won’t be hit with extra fees when using your credit card in the US. Your Australian bank and American ATMs will each charge you for withdrawing money from your debit card, too so it might be worth organising a travel card with low or no fees to use while you’re away.
Always inform your bank of travel plans, just in case overseas purchases are thought to be fraud and your account is frozen, putting an end to any shopping spree plans.
Tipping in the US is so complex it needs its own guide, which you’ll find here.
American hospitals are of a similar standard to those in Australia but costs can quickly become astronomical. It’s essential to take out comprehensive travel insurance before a trip to the US and fill any prescriptions before you leave.
The city's grid system is easy to navigate and find your way either on foot or by public transport.
Bike-share program Divvy has stations all over the city, making it easy to use the more than 320 kilometres of on-road bike lanes, numerous dedicated paths.
There are 129 bus routes that crisscross Chicago, making it easy to get about. Alternatively, the well-connected ‘L’ train has eight lines running around the city with more than 145 stations for quick and easy connections.
The best value transport option is a one-day, three-day, seven-day or 30-day unlimited-ride pass for trips on Chicago Transit Auhtoirty buses and trains, which is loaded onto a Ventra Card.
From late March to early June, Chicago experiences mild temperatures and greenery returns as spring arrives. In summer (June to September) the city comes alive with free live music and other public arts programming in the parks, and courtyards, rooftops and outdoor swimming pools open for business. Autumn (late September to early December) is cool but picturesque as the foliage turns red, orange and brown. Late December to February marks the winter season, when snow fall is frequent, the temperature gets above zero degrees and the wind chills make it feel a few degrees colder than it actually is (pack some thermals).
When to go
Any Chicagoan will tell you summer (June to September) is the best time to visit, when you can people-watch in Millennium Park and see the Cubs baseball team play at Wrigley Field. But the weather is pleasant enough for exploring on foot through December (although by then you’ll need a good coat). Chicago is magical at Christmas – lights adorn every tree and store window, a German Christmas market is held in Daley Square and there’s an 18-metre tall Christmas tree in Millennium Park (shorter than the Rockefeller Tree in New York by only a few metres).
If you’re not put off by the cold, low tourist numbers January – March make it a good time to get a deal on accommodation and negotiate your way to a hotel room upgrade.
Practice common sense in Chicago as you would anywhere else – don’t walk alone in unfamiliar neighbourhoods at night, don’t accept unsolicited offers of help or to buy something and keep expensive items concealed.
Don’t let statistics about gun and gang violence in Chicago deter you – it’s mostly limited to the South Side neighbourhood. The only thing tourists might want to see in that area is a White Sox baseball game but there’s an L train stop outside the stadium and plenty of people and security around on game days.
It’s safe to drink the tap water in Chicago, although a recent study did find higher than advised levels of lead in 70 per cent of homes. Water in public places is safe to drink.
If you’re visiting from October through March, you’ll need a puffer jacket, thermals, beanie, gloves and snow boots (or gum boots as an alternative) and as many layers as you can pack.
Chicago is a walking city so practical footwear is essential.
Purchase comprehensive travel insurance before you leave for the US to ensure you’re covered for medical bills, cancelled flights and other unexpected events.
Where to stay
River North and the South Loop are the most convenient parts of the city to stay in. From here, Millennium Park, the River Walk, the theatre district, the Art Institute of Chicago, Willis Tower (with its 103rd floor Skydeck observatory), the American Writer’s Museum, the best shopping and more are within walking distance.
Wicker Park/Bucktown has become an appealing place to stay following the opening of The Robey, an award-winning boutique hotel in a renovated landmark building. It’s only f15 minutes by Uber or 25 minutes by public transport to downtown and offers a rare view of the Chicago skyline from the rooftop and most guest rooms. The area is known for its indie book shops, speakeasies, dive bars and cosy restaurants.
Phone calls and mobile data
Before you land, disable data roaming and don’t answer incoming calls on your mobile phone if you want to keep your monthly bill in check. Invest in a prepaid travel SIM card if keeping in touch with home is important.
If you need to make calls in Chicago, buy a US SIM card for local calls and mobile data. Remember, this will only work if your phone is not locked to your Australian carrier.
Australian mobile phones operate on a GSM network. In America, both GSM and CDMA networks are in operation. This means that your Australian handset won’t work on a CDMA network such as Verizon. See WhistleOut for more in-depth information on using your mobile phone overseas.
Consider buying a cheap handset from one of the US’s many big-box stores, such as Walmart. It will come with credit preloaded but keep in mind that in America you’re charged not just for making calls and sending texts but also for receiving them.
To call Australia, dial +61 followed by the phone number – including the area code minus the zero. So, to call a Sydney landline telephone, you would dial +61 2 then the phone number. To call a mobile phone, use the same country code and dial the mobile number minus the first zero.
Power sockets in the US (120V) have a lower voltage than those in Australia (230V) and a higher frequency (60Hz compared with Australia’s 50Hz). Most gadgets are designed to work on a range of frequencies and voltages but double-check if you’re in doubt. Power plugs and sockets also have a different configuration so an adaptor will come in handy.
Handy apps and websites
Uber For getting around when your legs need a rest.
Smart Traveller for safety information.
XE for currency conversion.
Chicago O’Hare for information on flights, weather, traffic, parking, terminal locations and airport shuttles.
Citymapper for public transport and walking directions and trip durations.
Choose Chicago for things to do and specialised itineraries.
Art Institute of Chicago Tours for a self-guided audio tour.