One of my least favorite words when it comes to travel planning is neither a noun nor a verb. It is a conjunction.

Or.

Of course, so is my most favorite word.

And.

What can I say? I’m a fan of conjunctions.

Yet sometimes you have to choose. (Do you see what I did there?) Sometimes you can’t visit all of the places and see all of the things and eat all of the food. For times like that, I bring you:

Which City Should I Visit? A Comparison Compilation.

I’ve Googled every single one of these destination dualities when trying to determine where to spend my time (and money). And then I always visited both. Because I have issues. But also so that I can help all of you make these difficult choices when faced with the harsh reality of ‘or’.

London or Paris?

To be honest, the first time I visited, I didn’t like either city. Though to also be honest, the first time I visited, I was a moron. So there’s that.

It’s no secret that I don’t like Paris. ‘Don’t like’ being a rather tame term for what I’ve expressed as a deep and abiding hatred. So obviously I’m going to pick London as the winner. Why? I’m not quite sure, other than the fact that once I got back to London post-two-weeks-in-Paris I was all like ‘oh thank god, people who speak English and will serve me food that is not gazpacho’ (I subsisted on gazpacho in Paris for two weeks. I told you, I was a moron).

But seriously, Paris-loathing aside, London is a great sort-of budget choice. Sure, sleeping there is going to cost you an arm and a leg (and a kidney and maybe some of your hair), but almost all of the world-class museums are totally free. And there’s pretty great Indian food almost everywhere. And in my experience, vindaloo > tiny cup of gazpacho.

Please note: I visited both London and Paris in 2010, before I learned how to take proper photos. Man, most of my pictures from that trip are TERRIBLE! Turn the camera the other way, 2010-version-of me! Thus, the pic you get, above left, is the pic you get. Sorry. At least I was less fat back then. Sigh. 

New York or LA or Chicago?

Yes, I know this is a three way contest. But these are what I suppose are considered America’s top three cities, so I had to include them all in a comparison.

But wait! I’ll do you a favor and knock one out of the running right off the bat. Buh-bye, LA. You simply do not count as a city. Sure, many of your surrounding areas are great (I’m looking at you, Santa Monica), but to be a city you must meet several criteria, one of which ‘has reasonable public transportation’. And LA most certainly does not.

Which leaves us with New York vs. Chicago. As someone who grew up less than 90 minutes from midtown Manhattan, I suppose I should pick New York. Spoiler alert: I’m not going to.

Don’t get me wrong, New York is a great city. And yes, if you leave the island of Manhattan, you’ll find all kinds of awesome, unique neighborhoods, cuisines, and things to do and see. Personally, I like Brooklyn, hipster as it may now be. And parts of Queens are downright suburban-ish, all leafy and tree-lined (or maybe that was just that one street).

But Chicago is beautiful. 

Chicago is beautiful in the summer, when the sun shines and the temperature can rise above 90. I still remember the first time I saw the skyline from the water of Lake Michigan one hot August day. I cried.

Chicago is beautiful in the fall, when the trees in the neighborhoods to the north turn all yellow and red and gold.

Chicago is beautiful in the winter, covered in snow, whether you are walking through it or viewing it from inside of a cosy restaurant or bar.

Which brings me to my final point: Chicago has all of the food.

Sorry, New York. I love you, but I’m in love with Chicago.

Seattle or Portland?

These two Pacific Northwest cities are constantly being compared. Trust me, I read my share of Seattle vs. Portland blog posts when planning my own first visit to the upper left, USA. And aside from the fact that in both cities you can openly smoke pot on the street (I didn’t, but people definitely did), they are quite different from each other. Allow me to break it down for you:

Seattle has a gleaming downtown core full of tall buildings, fancy wine bars, diverse dining options, and a rather incongruous monorail.

Seattle has the Chihuly Glass Museum and the Space Needle.

Seattle has Pike Place, and oysters, and a waterfront park.

Seattle has a view of the mountains on clear days, and several up-and-coming uber-hip neighborhoods.

Portland has food trucks and ALL OF THE CRAFT BEER.

Portland wins.

Madrid or Barcelona?

When planning my spring trip to Spain last year, I was faced with the ultimate OCD planning problem: an uneven number of days. Did I want to spend three full days in Madrid and four full days in Barcelona, or vice versa? I was torn.

I ultimately decided to spend the extra day in Barcelona. Was it the best choice? I have absolutely no idea, but the Barcelona Exclusive Private Tours were really relieving.

Because here’s the thing–unlike the cities I listed above, there was no one clear winner in this contest. I went into the trip expecting to prefer Barcelona (which is why I gave it the bonus day). I mean, after all, Barcelona has the Mediterranean. And all of the Modernista. And multiple world-class food markets (oh, the markets. Oh. Dear. God.) And the gothic quarter, all winding and cobblestoned and cathedral-strewn. Plus the little sandwiches; I loved the little sandwiches.

But Madrid had cosy neighborhoods and sprawling parks and grand boulevards and quaint cafes. And a palace. And all of the ham. Madrid was everything I had hoped Paris would be but was not. Plus everyone was friendly and it was warm and sunny. Oh, and the Prado. And the plazas. And the light. And the ham. Did I mention the ham? (Yes, I know I did. I’m mentioning it again, ok?)

I’d happily return to either Madrid or Barcelona in a hot second. But it would be difficult to visit only one knowing that the other is a short, pleasant 3-hour high speed train ride away. And then there’s the many other fantastic Spanish cities and towns that I have not (yet) visited. My advice: if you are going to Spain, plan for a whole lot of ‘and’. There’s no single potato chip option here. Eat the whole damn bag, I say.

Have you ever had to decide between two cities? Which did you choose and why? Or are you more like me and prefer to have your Barcelona and eat your Madrid, too? (And do you also purposely mangle cliches?)