Heading To Chicago? This Is Where To Stay, What To Eat And Where To Go
Chicago is a city that has it all. Buzzing with street food and Michelin star restaurants, a celebrated music scene, and famed architecture, the most populous city in Illinois has something to offer for every one of its locals and visitors.
Beyond the staples you would expect from such a metropolis, Chicago’s location perched on the edge of Lake Michigan gives it a vast water front and beach allowing the bustling city to have pockets of wide open space. Outside the city centre, fondly known as The Loop, there are 76 other neighbourhoods brimming with character worth venturing out to.
Below, is everything you need to know about Chicago, from the restaurants to eat at to the vintage shops to visit.
What to do
Aside from deep dish pizza - we'll get to that later - one thing Chicago is famous for is its architecture, and the city has made it very easy to see the best of it with its Architecture River Cruise. Drifting down the Chicago River, you're treated to views of the skyline that can't be seen from the hustle and bustle of the street while learning about the city's history. If it's your first time visiting Chicago, it's a perfect way to help you get to grips with its layout but don't worry, if you prefer your feet to be firmly on the ground, the next best thing is the city's River Walk, a riverside pathway lined with bakeries and coffee shops.
Outside of The Loop, Chicago has lots of neighbourhoods worth taking a day trip to. Pilsen is sat in the lower west side of the city and is a melting pot of culture. The first thing you'll notice is its colourful street art - buildings and walls are covered with huge mosaics celebrating the neighbourhood's Hispanic roots. But it's not just the street art that pays homage to its history, its food scene is second to none. Home to authentic taquerias and fine dining - plus some very good margaritas - if you're a foodie, Pilsen has to be on your hit list. While you're there, also drop in at the National Museum of Mexican Art.
On the other side of Chicago is Andersonville. A small town with a village-like feel, it's rich with independent shops, bakeries and restaurants. Lunch at Big Jones is a must and make sure you meander away from the main streets to catch a glimpse of the area's beautiful houses.
Back in The Loop, there's a number of iconic landmarks that you have to tick off your list. Head to Millennium Park - the home of Cloud Gate (more fondly known as The Bean) - to see great views of the city's skyline. On a sunny day it's worth strolling around the park to see the Jay Pritzker Pavilion and Crown Fountain. Film buffs should also visit the sets of some of their favourite movies and TV shows on an organised tour. From Batman to My Best Friend's Wedding, stand in some of Chicago's most recognisable spots as a tour guide replays the iconic scenes.
Where to eat
As Hulu series The Bear so beautifully demonstrated, when it comes to food, Chicago has something for everyone. Whether you're in the mood for Michelin-starred dining, or a slice of pizza (or both!), the options are endless.
There's a myriad of spots that claim to be the best hot dogs or deep dish pizza in town but we're here to tell you which ones are really worth trying. For hot dogs, take a trip to Portillo's. How busy it is only serves as a testament to how good it is. The menu is quite extensive but it's the dogs everyone can't get enough of.
When it comes to pizza, things get a little trickier. The myth is that Chicago natives can't get enough of deep dish pizza but alas, that isn't exactly the case. Yes, Chicago is the home of the deep dish and you'll find that most pizza places have it on the menu, however, it's mainly just visitors who order it. (Be warned, it's takes about 45 minutes to cook so you'll be in for a long wait.) The best spots are Giordano's and Pequod's Pizza.
For those craving some fine dining, treat yourself with a visit to Proxi. Combining the chef's two loves - food and travel - the menu is inspired by street food and the dishes wander freely through Asia, Mexico, India and beyond. We recommend trying the fennel and apple salad and the Indonesian grilled chicken.
On the northwest side of the city, head to Andros Taverna in the heart of Logan Square. Influenced by the tavernas of Greece, its menu is rooted in tradition and warm hospitality.
Where to stay
Found on the Magnificent Mile in the commercial district is The Peninsula. A five-star hotel in the heart of the city, it has everything on its doorstep, including very good neighbours - the hotel sits above Tiffany & Co. and looks onto Saks Fifth Avenue.
The Peninsula hasn't only nailed the location, which is imperative for a city getaway, the hotel's amenities will leave you struggling to leave. A semi-Olympic pool sits on top of the hotel with breathtaking views of the skyline through its floor-to-ceiling windows. An early morning swim watching the sunrise before a day of sight seeing, what could be better?
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