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Chicago River
Chicago

Deep dive into eclectic Chicago and you’ll find a city that’s stuffed as full as a deep-dish pizza. Full of interesting architecture, prominent chefs, well-renowned festivals, stunning museums and a brewing scene that rivals America’s best, the Windy City is a treat and definitely worth a visit. For the hottest tips and tricks, read our Chicago travel guide and prepare for your getaway.

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Places to stay

Known as the city of neighbourhoods, each area of Chicago has its own distinct flavour. The cultural hub and centre of the city is the Loop district. Stay here for easy transport options, main attractions and designer hotels.

Near West Loop, the former meatpacking neighbourhood of Fulton Market is now a foodie hot spot and home to trendy hotels like The Hoxton. On the Southwest Side, staying in an Airbnb is the perfect way assimilate into the art-neighbourhood of Pilsen. Soak up its local galleries, seek out its mural-lined streets and tempt your tastebuds at its booming restaurant scene.

The super strollable neighbourhood of Hyde Park has lakefront paths, boutique hotels and architecture. Chinatown and the Old District are central and convenient neighbourhoods to base yourself with plenty of Airbnbs to choose from. Logan Square might not be as close to the action but, it’s a trendy neighbourhood for music, world-class restaurants, quaint inns and family-friendly activities. With so many unique areas to choose from, the accommodation options across Chicago are endless.

Things to do

You’ll find award-winning chefs, a thriving art scene, stunning skyscrapers, innovative interiors shopping and lakefront views massed throughout the city. Before taking on the windy city, coffee is a must. Venture to Wicker Park where you’ll find some of the best baristas in town at Fairgrounds Coffee & Tea.

After a caffeine hit, it’s time for some culture. Stony Island Arts Bank houses everything from local exhibitions to famous DJ’s record collection. For the city’s oldest treasures, visit The Art Institute Chicago or The Field Museum. On the riverfront, the Chicago Architecture Centre is home to models of some of the world’s most famous buildings. Looking to give the home a makeover? Rifle through the unique antiques at Scout on the North Side or Humboldt House in West Town. Amongst all the steel and concrete of the city’s spectacular skyscrapers, there are also pockets of green. Garfield Park Conservatory is a lush indoor oasis and perfect picnic spot.

There is no shortage of stellar food options in Chicago. Elske and Giant are the hottest reservations in town while comfort food can be found in Gene & Jude’s hot dogs or Pequod's deep-dish pizza. Stuffed and need a seat? Snag a prime position at The Second City where some of the biggest names in comedy, including Tina Fey and Bill Murray, got their start. For a spot of theatre, A Red Orchid Theatre is an intimate affair. Another booming industry in town is beer—breweries like Half Acre Beer and Revolution Brewing are the perfect places to pull up a stool for a cheeky afternoon brew.

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Where to go

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Festivals

Festivals and street parties are what summer in Chicago is all about. Come August, some of the biggest music acts in the world rock into town for Lollapalooza. Pilsen Fest sees the suburb taken over for a street festival that showcases the neighbourhood’s Latinx community. The smooth scene takes over during late August and early September when the Chicago Jazz Festival is on. 

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Day Trip: Milwaukee

Chicago is the perfect city to explore the rest of the Midwest, including Milwaukee. While the lakefront town is best known for beer and baseball, you’ll also find forest, great galleries and incredible dining options. Check out the collection at The Milwaukee Art Museum before sipping some of the famous brews at the Milwaukee Brewing Company. For some greenery, escape to Lakeshore State Park for a fish, kayak or hike.

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Getting around

From the airport: Uber, taxis, transfers and shuttles are available to downtown from Chicago O’Hare International airport. Public transport can also get you to the city via the Chicago Transit Authority buses and rail lines. 

In and around the city: the city's grid system is easy to navigate either on foot, bike hire by public transport. With numerous dedicated paths and more than 13,000 bike racks, Chicago is one of the country’s bike friendliest cities.

The 129 bus routes or the well connected ‘L’ train make it easy to get around town.  If you’re leaving central Chicago head for the high speed Metra train that connects with Chicago's outlying suburbs.

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