Instead of NYC or L.A.
Chicago refers to itself the as the Second City. Most international tourists think of New York, or Los Angeles, or Disney World at first. Chicago, though, is a treasure trove of things to see and do. Of course, Wrigley Field is iconic, but you can cover a majority of the city on an architectural boat tour. The music scene is great—this city did give us a whole genre of blues—and The Second City improv troupe is a must for people who love comedy.
Instead of Madrid
Barcelona may not be Spain's capital, but it's certainly a cultural hub on at least the same level. From the art to the architecture to the dining, Barcelona has plenty to offer travelers. The Gothic Quarter provides a glimpse at the local Roman ruins, and there's an entire museum dedicated to Picasso.
Instead of Toronto
Montreal may not be the capital of Canada, or even of Quebec, but it is the largest city in the region and has its own cultural heft. It's regularly in the running for "most restaurants per capita" on the continent. It's also given us musicians from Leonard Cohen to Arcade Fire, and it's a very popular site to film TV and movies.
Instead of Brussels
A few years back there was a small-budget black comedy about a couple of criminals lying low in Bruges—appropriately called In Bruges. Amidst farcical stories of incompetent robbers and guilt-ridden hitmen was a love letter to a city that dearly deserves one. Bruges is rich with history, a global hub of trade in its heyday as a port. That wealth shows itself along the stone-paved streets and the incredible medieval architecture—so much of which survives that the entire historic center of Bruges is an UNESCO World Heritage Site.
8. St. Petersburg
Instead of Moscow
St. Petersburg was Russia's capital for a couple of centuries, but that honor now goes to Moscow. Still, St. Petersburg bears signs of the wealth and cultural weight that comes with being an enormous port. Russia's art is unique in all the world, from the paintings of Kandinsky to the gorgeous Eastern Orthodox cathedrals.
Instead of New Delhi
There's something about port cities. Maybe it's the influx of ideas and cool stuff from all over the world. Maybe it's just the views. Whatever the reason, Mumbai is a great place to visit. It's the heart of the Bollywood industry, meaning that you get the full force of the cultural experience without the crowding of New Delhi.
Instead of Beijing
Beijing may be the capital, but Shanghai is China's largest city—and the one where money changes hands. From the futuristic-looking skyscrapers in Pudong to traditional sites like Yu Garden, Shanghai offers everything a tourist may be seeking. This may be the equivalent of calling New York a "second city" to Washington, D.C., but Shanghai is cool enough to deserve a mention in its own right.
Instead of Cancun
Tulum may not be the most urban environment, but we've mentioned this resort town in Cancun's shadow so often that we would feel oddly remiss if we didn't mention it here. Tulum has all manner of luxe accommodations, but it also has a higher likelihood of actually talking to a local. Of course, the classic Mayan ruins are also nearby. Just be sure not to disrobe like so many kids these days (including Justin Bieber) seem wont to do.
Instead of Athens
The center of Thessaloniki was destroyed by a fire in 1917. What rose up in its place is a walkable, upbeat, optimistic city, with fantastic nightlife and easy access to the rest of northern Greece. In spite of the fire, there are Roman, Byzantine, and Ottoman remains throughout the city. The White Tower is particularly iconic, having guarded the waterfront for centuries. It now guards a pretty great stretch of cocktail bars.
Instead of Marrakesh
The city of Fez has been around for some 1,200 years. For much of that time, it's been the cultural capital of Morocco. At the heart of the city is the Fès el-Bali, the Old Fez, filled with mosques, markets, and ancient city walls. However ancient the medina may be, the city itself offers the newest and best in terms of food, trends, and more.
Instead of Bratislava
Slovakia may be the most underrated country for tourism in Europe. Between the Ottomans, Habsburgs, Nazis, and Soviets, they've changed hands a few times, yet they've embraced independence—and capitalism—warmly. Their "creative economy" focuses on incorporating arts, culture, and sustainability into their industrialization. Plus, their public spaces are filled with things that serve no purpose beyond getting a smile out of you.
Instead of Paris
It isn't easy sharing a country with Paris. No matter what you have to offer, you're competing against one of the most widely-romanticized cities in the world. But Marseille has plenty to offer, from the Frioul archipelago to the gorgeous Byzantine cathedrals. The city's been a happening place for a long time—there are actually cave paintings from the stone age nearby. You'll have to leave that off the itinerary, though—the cave is closed to the public, and the entrance is over 120 feet underwater.