Help on basic Itinerary

It is a lot of backtracking. Why not fly into Barcelona and out of Madrid? You would book this as a multi-city trip, sometimes only available in the airline’s full website (not app) and under advanced search options. It’s rarely much more than a round trip, and saves you a day and train ride. You could also look at flying out of Granada.

I'd echo the first responder in that I would also start this trip in Barcelona. If you are Chicago-based (my guess based on the last day of the itinerary), both American and United offer seasonal nonstop Chicago-Barcelona flights that appear to operate in late October. I'd recommend changing to one of those flights.

Have you already booked your flights?

Flights are already booked. We are Minneapolis based, I tried the multi-city flight option but just couldn't get the cost/dates to work. Actually had to add a couple days in Spain to get the ticket prices down.

I would cut out one of the three overnight clusters in Madrid. If the 5K is a must for you, then what you could do is fly into Madrid and then depart for Barcelona either on a 75-minute flight at 15:55 for $100 or take a high-speed train taking 2:45 immediately to Barcelona from Madrid’s Atocha station. A flight will be much easier.
Flying to Granada doesn’t work as well on 10/21 as the only direct flights leave in the morning.
After Barcelona you’re pretty much locked in to returning to Madrid, then going to Granada (3:30) by high-speed train and returning to Madrid the night before your return flight home.
You’ll be an expert on Madrid’s newly-remodeled Atocha train station by the end of this trip!

www.Skyscanner.com for flights
www.TheTrainline.com for train schedules

Agree with Kenko- travel onwards to Barcelona on arrival day.

Wednesday, 10/29/25 Granada
Thursday, 10/30/25 11:35 am Flight from Madrid to Chicago

You should be IN Madrid Wednesday night

Whatever itinerary you end up with you need to make specific plans for the Alhambra and La Sagrada Familia. Buy the Alhambra tickets ASAP. The La Sagrada Familia tickets must also be purchased in advance. Right now they're selling through September. Make sure you use the official websites.

All these replies are very helpful. The 5k is now probably out. Having a "must do" right in the middle of our time is just too complicated. Now I am having another thought. Knowing we plan to come back to Spain in the future, what if we just skip Barcelona and instead include Madrid, Sevilla, Cordoba and Granada in a loop? Which direction would you go? Madrid for 2-3 days, then to Granada for 2-3 days and then drive to Sevilla for 2-3 days and then train back to Madrid with maybe a day in Cordoba? Maybe an overnight in Ronda?

We can fly into Barcelona on another trip and do the Northern loop including the Basque Country and Galicia.

With nine days in October and flying into and out of Madrid— sticking to Madrid. Cordoba. Seville and Granada is a good plan. They’re all 3.5 hours or less from each other and your itinerary will flow a lot better and be more enjoyable. Plus, late October is a good time weatherwise for Andalusia.

Barcelona by itself can easily take four days or more to tackle, so it actually will be better to save it and Catalonia for another time,

On the fastest high-speed trains, Madrid to Cordoba takes 1:45; Cordoba to Seville takes :55. Seville to Granada takes 2:30 and Granada back to Madrid takes 3:30.

To optimize your time, if you can depart for Cordoba right after your flight arrives, you’ll hit the ground running and only have to endure a couple hours of traveling after your flight arrives, This way, you can save Madrid for the very end of your trip when you have to be there anyway prior to your return flight home.

So, one way to map out the nights would be Cordoba 1 to 2 nights; Seville 3 nights; Granada 1 to 2 nights; Madrid 3 nights. Granada is the smallest city of the four, so, if you reserve the Alhambra for the afternoon you arrive in Granada , one night could work.

There’s not much slack time here, but I highly recommend seeing Toledo. It was Spain’s capital for centuries before the capital was moved to Madrid, and it’s only 35 minutes from Madrid.

Very inefficient plan.
Consider open jaw flights, fly into Barcelona then out of Madrid or vice versa.

You need more than a day and a half in Barcelona. Suggest 3-4 days.

Reserach what to see in Madrid, do the Prado, take a city tour, visit the Royal Palace.
Toledo is near Madrid and fantastic, you can do it on a day trip. It is a must see for Spain. Also, Segovia is a great day trip just north of Madrid.
Granada is great, but with 9 days suggest doing it on another trip that would also include Seville.

@geovagriffith, The OP wrote two posts above yours that they’re now leaning toward saving Barcelona for a future trip and doing a loop route on this one.

I wouldn't plan to see the Alhambra on my only, partial day in Granada. I spent more than half a day at the Alhambra, and there are other things to see in the city. That sort of compressed schedule would be a bit risky even if you were sure you'd only need a few hours for the Alhambra. In the (unlikely) event of a significant train delay or other issue, you'd be out of luck. The Alhambra sells out virtually every day, often weeks or even months in advance; replacement tickets for later on the current day would almost certainly not be available.