(ARCHIVE) Milwaukee Vs Chicago

Why Milwaukee Vs Chicago? Why not just do both in equal measures?

At some point, you’re going to realise that visiting the United States is like ordering from an all-you-can-eat Japanese grill and sushi menu – it’s impossible to choose just one thing. That said, the ordering of your favourite is that lengthy comforting break you need from decision fatigue.

Let’s get analogical: The restaurant is Chicago O’Hare International Airport, and the menu is the Great Lakes of North America. You need to decide whether Milwaukee or Chicago is your comforting break.

Both cities are easy to get to from O’Hare and perfect for a longer stay at the start or end of your trip. Read on and decide on your pick for yourself.

Round One: Bars

Chicago has got the Blues. Make sure you check out the dark and magical Kingston Mines. As Chicago’s largest and longest-running blues club, you can feel the history emanating from the walls. It’s almost as if the building has soaked up those heartfelt blues, and the spirits of musical royalty live on through it.

Open seven days a week, with two stages for continuous live music, you’ll have plenty of opportunities to enjoy a casual Southern-style feast from Doc’s Rib Joint. The music is loud, the people are cool, and Kingston Mines will make you feel like a badass, walking in the footsteps of some of the biggest blues game-changers.

Milwaukee has one of the best bars I’ve been to in the States – Safehouse. To enter this bar, you will need a password that we are contractually forbidden from releasing. You may be able to press a local tour guide for the intel, otherwise, just try your luck at the door. Once you’re in, the vibe is secret agent mixed with escape room. The food and drinks are, you’ve guessed it, spy-themed, and you get to take away a branded glass with some of the cocktails.

The drinks are the cherry on top of this memorable night out. Go with a curious mind and don’t believe anything you see. Try every door, turn every corner, pick up every phone, and, for God’s sake, always carry a dollar!

Round Two: Food & Drink

Chicago. Do you remember your first Chicago Town Pizza? Pizza, with a high crust, that’s essentially short-cut pastry with even more sauce, cheese and toppings? Yes, Chicago!

Chicago’s deep-pan pizzas are from heaven. They absolutely smash this famous dish in every place that you’ll find it in the city. Whatever you do, don’t ask for a full pizza. You buy this pizza by the slice, and you’ll probably need a knife and fork to tackle it.

Milwaukee Public Market? Yes, please! By now, we’ve probably all frequented open-air markets peppered with kitchen pop-ups. Milwaukee’s version is a must-visit if you are in town for more than a few days.

Buy a bottle of wine (or two) after chatting with the vineyard staff and then head over to your preferred kitchen, pull up a stool, and soak up the atmosphere.

Round Three: Vibe

Chicago will blow you away with its chequered history and even more chequered architecture. Fill your heart and soul with blues, booze, and the smiles of strangers.

Chicago is big, bold, and glamorous. With ‘Trump’ emblazoned over one of its most impressive buildings, this city has a boujee air about it.

And of course, there's the bean.

Milwaukee will steal your heart and pierce your soul with its authentic response to a history of immigration and poverty. You’ll find long-standing breweries, incredible street art (don’t miss Black Cat Alley), and real people who want you to have the best time in the city they’re proud to call home.

Info: Discover both cities with American Experiences on their ‘Great Lakes Explorer Tour’.

For more information, visit americanexperiences.com. Hayes & Jarvis also offers a seven-night holiday to North America from £2,599 per person; find out more at hayesandjarvis.co.uk