Chicago is the second most visited City in America, but in my opinion, it should be first. Yes, New York has it all, but if you want a city with more character and outstanding architecture, then step away from Manhattan and give the Windy City a try. It ticks all the boxes and more.

Take the El train across the Windy City | Travel Nation


For you, Chicago may conjure up images of Al Capone, pizza and Prohibition. For me, Chicago goes much deeper than that. I moved to the Windy City with my family when I was 11 years old, and the city has stayed with me ever since. Sadly, a year later my parents decided it wasn’t for them, so we trotted back over the pond. Life went back to normal, but with one big change- my love affair with Chicago was born.

See Chicago's skyline reflected in The Bean | Travel Nation

Chicago has always stuck with me and I knew I would go back one day as an adult. But what to expect? I had memories of winters so cold that, by the time my dad walked me to school, he had icicles hanging from his beard! On the flipside, the summers were so hot that we spent our days playing cards in the basement to keep cool.

Here are my insider tips about the best things to do in Chicago:

Navy Pier

When I finally made it back to Chicago as an adult, I stayed in the suburbs, so I was chomping at the bit to get a slice of the Downtown action! That first view of the city, whether you're arriving by road or rail, is sure to blow you away. We drove past the famous Navy Pier, which is a great place to see the skyline at night. Arrive during the day, whizz round the fairground rides, grab a sundowner and then wait to see the city lights in all their glory when night falls.

See the Chicago skyline from the ferris wheel on Navy Pier | Travel Nation


River Cruise

If you’re travelling to Chicago, my first recommendation would be a lake and river tour. These tours sail through Chicago Lock, giving you a great perspective of the city’s most iconic architecture. Not only that, but you’ll learn about 200 years of the city’s history, with a prime focus on the great fire of Chicago. This blaze swept through the city in October 1871 and resulted in the building of the world’s first skyscraper using fireproof steel-skeleton construction. The cruise then takes you out onto Lake Michigan, where you can see the full 26-mile skyline stretched out before you. For any selfie lovers out there, this is the place to snap.

Take a boat trip on the river


Shopping on the Magnificent Mile

If you fancy some retail therapy, the Magnificent Mile will be right up your alley! This is the commercial district, where you’ll find all the top department stores and fashion outlets. While here, you can also visit some of the city’s famous landmarks such as The Chicago Water Tower, the Neo-Gothic Tribune tower (one of my favourites), the terracotta Wrigley Building, and the John Hancock tower (more on this later).

Admire the buildings along Chicago's Magnificent Mile | Travel Nation


Willis Tower

As a small girl, I will never forget the first time I stood at the bottom of the then-named Sear’s Tower, now known as the Willis Tower. Standing at 1,482 feet with 110 floors, this was the world’s tallest skyscraper for nearly 25 years. It was completed in 1973 and remained the tallest building in the Western Hemisphere until the rebuild of the World Trade Centre in 2014. I could have stood looking up at it all day, but my neck had other thoughts!

Enjoy views over the city from the Skydeck of Willis Tower


On my return to Chicago, twenty years later, the same feelings came rushing back. The structure of the tower was entirely ahead of its time and, in my opinion, most modern skyscrapers can’t compete. It’s just breath-taking. There is an observation deck on the 103rd floor and, on a windy day, you can feel the tower sway. In 2009, they installed glass bottom ledges, so if you’re g brave, you can look straight down to the ground.

John Hancock Centre

If you want to see the city from above and avoid the crowds, my top tip would be to visit the John Hancock Centre. Rather than queuing with hoards of tourists at the Willis Tower, you can have cocktails on the 96th floor in the Signature Lounge while you gaze out over the rooftops. There’s also a great restaurant on the floor below. Here, you get all the city views but, rather than paying for an observation ticket, you can sip a cocktail in peace. You might even run into Oprah Winfrey, as she has an apartment here!

Look down onto Navy Pier and Lake Michigan from the John Hancock Centre | Travel Nation


Deep dish pizza

You can’t talk about Chicago without mentioning pizza. This is the original home of the deep dish pizza - and boy are they deep! Gino’s East is one of the best, so be sure to head there with an empty belly. Gino has several branches across the city, now but if you’re on the Magnificent Mile, make your way to the original (and best) Gino’s East. Founded in 1966, Gino makes pizza so thick with cheese that you’ll feel stuffed for days. They have also kept the original graffiti on the walls, and you are welcome to sign your name when you leave.

Try a classic Chicago deep dish pizza | Travel Nation



If you’re into music, Chicago has you covered. Famous for its live jazz and blues clubs and renowned for some of the best house music DJs (the late and legendary Frankie Knuckles originates from here), Smart Bar attracts all the great names. Be sure to check out who’s playing during your stay – you might be in for a whopper!

Fancy a joke or two? Then head to Second City for some stand-up. Here, you’re likely to catch a rising star on their way up the ladder. Huge names such as Tina Fey,  Bill Murray and Steve Carrell all started playing to the crowds here. If you have enough time, you can even take comedy classes.

Head for a classic jazz and blues club in Chicago | Travel Nation

Tempted to book a trip to Chicago?

Chicago is a brilliant starting or finishing point for all kinds of USA road trips. We can arrange tailor-made USA holidays all over the country, including the Deep South, the West Coast and the Grand Canyon. Just get in touch with one of our travel consultants on +44 1273320580 or send us an email request and we'll get straight back to you. No challenge is too big!

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