Chicago is one of my top American cities. I’ve been at least five times and on the surface it appears a bit like New York with it’s really tall skyscrapers, but it’s got more of a lazy and open feel once you get to know it.  Plus, it’s in a league of its own when it comes to food. What’s particularly noteworthy about this city is that it’s famous for several iconic dishes: the deep dish pizza, the Chicago-style hot dog, and interestingly, popcorn.  And I’m going to tell you where to eat them all.

Where to have a deep dish pizza: Lou Malinati’s


No one should visit Chicago without trying it’s most famous dish – the deep dish pizza. Lou Malinati’s is known as the oldest family name in Chicago’s pizza history, opened in the 1940s by a man called Lou Malinati! It’s the pizza spot that all locals will recommend.  To me, the deep dish pizza is more of a pizza pie, they take 45 minutes to cook because the dish is so deep.  It’s unique butter crust sets it apart from it’s competitors’ pizzas.

Location: Various, it’s a chain
$15 – $30 per person

Where to have tacos: Milwalky Taco

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Mexican food in the states is always 200 times better than in the UK, so I make it a point to eat as many tacos as possible when out there.  Milwalky Taco is actually a little outside of central Chicago, in the quaint suburb of Libertyville, which is lined with loads of pretty shops and trees so is definitely worth a visit.  The tacos are also the best I’ve ever eaten so its worth the 40 minute drive from the city.  The tacos are pretty cheap, ranging from $3-5 and they’ve got a massive menu with all sorts from shrimp to lamb, to cactus tacos.  The pork taco was my ultimate fave and I still think about it a year later!

Location: 605 N Milwaukee Ave, Libertyville, IL 60048, USA
$3 – 5 per taco

Where to eat at a classic American diner: Portillos

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No trip to the states is complete without a visit to a diner.  Portillo’s is a chain that first opened in Illinois in the 60s as a ‘dog house’ serving another Chicago classic – the beef hotdog, which is of course still on the menu. There’s loads of other traditional diner dishes like burgers, fries and chicken strips (yum). What I loved about it is the look and feel of the place, as a typical over-excited tourist, it really does look like a diner you’d see in ‘the movies’.

Location: Various, it’s a chain
Approximatley $10 per person

Where to have drinks with a view:  The Signature Lounge at the John Hancock Centre

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Chicago has an incredibly pretty skyline, there’s views of lake Michigan and loads of skyscrapers including the massive Willis Tower.  The John Hancock Centre has a bar on it’s 96th floor, they don’t take reservations so you can just walk in.  I found the best views were actually from the ladies loo! (Sorry fellas).

Location: 875 N Michigan Ave, Chicago, IL 60611, USA
Fairly pricy, cocktails are around $18.

Where to have a fancy dinner: Cafe Spiaggia

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Cafe Spiaggia is the sister restaurant (and cheaper version!) of Spiaggia, a Michelin starred restaurant under Joe Flamm, the Top Chef winner. It’s still fairly pricey and fancy but in a more affordable range, it’s great for a special occasion.  Their Italian dishes are really well made, featuring lots of meat, fish, salads and hand made pasta dishes. There’s something for everyone.

Location: 875 N Michigan Ave, Chicago, IL 60611, USA
$70 – $80 per person for 3 courses and drinks

Where to have a light lunch: The Purple Pig

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The Purple Pig is based on Mediterranean fare, but that’s a loose description.  This is one of the ‘in’ restaurants in Chicago at the moment, probably due to their experimental cooking.  The flavours culminate perfectly and really are unlike any other dishes I’ve had before.  It’s got an informal vibe and a tapas style menu that’s good for sharing.

Location: 44 Michigan Ave, Chicago, IL 60611, USA
$20 – 30 per person

Where to have popcorn: Garrett’s


Interestingly, Chicago is known for it’s popcorn, mainly thanks to the guys at Garrett’s popcorn who opened up over 70 years ago in the city.  If your knowledge of popcorn mainly centres around the sad microwave bags you get at the supermarket, your mind is about to be blown after trying the hand crafted popcorn here.  They’ve got tons of different flavours from Buffalo Ranch to Caramel. It’s worth popping in and stocking up.

Location: Various throughout the city
Bags priced according to weight

My top things to do:

Millennium Park & Cloud Gate


Anish Kapoor’s Cloud Gate (aka a massive shiny bean sculpture!) is so worth the hype. The city’s skyline is reflected from all angles and it’s an incredibly simple yet elegant work of art.  Plus, you can wander round the Millennium Park afterwards.

Visit a blues bar

Chicago will always be considered a Blues town and an informally known ‘Blues Alley’ is probably the best place to visit for a good time. Kingston Mines is an iconic institution that’s a bit of a dive bar that’s got live music most nights till late.

Navy Pier 

Navy Pier is the perfect place to visit when the weather is nice, for great views of the Chicago skyline, a few arcade games and a boat trip across Lake Michigan.  There are lots of nice cafes round here and it’s a great place to spend an afternoon.

Willis Tower

Be careful with what you call this one, as the locals will forever refer to it as the ‘Sears Tower’! This is the tallest building in the city, and has some fantastic views from the top. If you are brave, they also have a glass platform protruding out of the side which you can walk over…

The Shedd Aquarium

This is probably my favourite aquarium in the world, its HUGE, they have dolphin shows, they have seals and penguins and there’s plenty of activities going on for kids. If you do visit, plan to spend a few hours here as there’s lots to see.

The Art Institute of Chicago

Chicago’s Art Institute houses a huge collection, ranging from Van Gogh to contemporary works. They often have some great exhibitions here so it’s worth keeping an eye out for what’s on.  If you’re really into art they also have some courses and lectures on throughout the year.



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