Hello all,

I just finished reading an article regarding wheeled luggage (on a website called onebag I think) and I am having a bit of buyers remorse.
When traveling to Chicago in August I was planning to take my 25" to check and my 20" for a carry on, both have wheels. We were planning on taking the train into the city. Will the luggage be an issue for this type of travel?

Any tips on what/how to pack?

I don't understand why wheeled luggage will be an issue on the train. I mean, people bring all sorts of stuff on the train.

What did the article say?

A heavily loaded 25" can be difficult to wheel farther than short distances. Try loading both those bags and rolling them around!

I find that a medium rolling bag and small tote are much easier to manage. Especially if you encouter stairs or an escalator.

With those two bags, I'd be taking a taxi.

Agree with 2 rolling bags and a purse that is too much to handle on public transit. It's all too easy to lose control of one on an escalator or stairs - and then where are you?

If you have that much - just grab a cab - esp for more than one person.

I just returned from Chicago. I had one 24" bag that weighed 35 pounds and one rolling 'overnighter' briefcase. I took the train to Chicago Ave at 430pm (1.75) and a cab from the station to my hotel, at Michigan Ave & Superior (7.00).
There were 2 flights of 20-30 stairs at the Chicago Ave station. It was a hassle, but worth the savings IMO.
The train was a bit of a headache because it was PACKED like sardines.
VERY VERY difficult to manage 2 big bags!
I am very capable, an experienced traveler, so it was ok.
If you have the funds, just take a cab... if not, someone may offer to assist. Try to do it off peak, not during rush hour!
We took a private car back to ORD for 50.00, which was nice

Is that a 25" bag and a 20" bag for one person, or two people (you mentioned "I" and "my", but then you said "we")? If it's for two, it's doable, although as someone said, a full 25" bag is not that easy to pull for a long distance. Nevertheless, we have done it (all four of us, including kids) when we used to travel with more than we travel with now (now we hardly ever take anything larger than a 22" bag anywhere)

I was speaking about just for me, but I believe I've decided to take the 25" and the duffle bag that came with my 5 piece set. I just had it in my head that I'd need the extra space...I just need to make decisions about what I really need to pack and plan ahead. at least I can kind of set the duffle on top of the 25" to wheel around easier. I can now see how pulling two would be a hassle. The person I'm traveling with is take her large suitcase and a duffle for the same reason. I appreciate all your imput.