Great to hear that - well done! 
5 days will get eaten up pretty quickly by travelling around, so I think you’d be best off choosing one place and being able to go into a little more detail. If you had a car, I’d recommend Eryri (Snowdonia) and then maybe a quick fling down to Cardiff - but north/south without a car would take up most of a day…
Just to let you know, I chat every week to a lady from Chicago who wants to practice her Welsh. I realise that Chicago is a big place but how wonderful it would be if you were in the same area. She’s coming over to the bootcamp in September. It’s the Ffrindiaith thing.
Thanks for the help! This confirms that it will be best to just stick with exploring the Eryri area. Lots to see there already, and I’ll just have to make sure I can come back again in the future!
Despite being brought up in the south I would say get a train from Euston to north wales. It’s the Holyhead train. Get off at Bangor and base yourself possibly in Caernarfon or in Bangor. If you book early enough you might get change from an arm and a leg too.
The llyn peninsula is accessible as is snowdonia and Anglesey.
You will hear the Welsh that you are learning spoken. Very quickly! Also there are plenty of learners groups that meet and I’m sure if you get in touch with these they would be delighted if you joined them one morning or evening.
If you private message me your email I can send you a list of meetings that take place in Gwynedd and Ynys Mon.
Ahhh that’s great to hear! This means, of course, that I have to work up my courage and actually start talking to people 
Hi Anabel,
Carmarthenshire is a welsh speaking county with Welsh spoken in the towns and villages. I was born in Carmarthen before moving away for work . I spend all my holidays in Wales at Plas Uchaf in Llanybri at my farmhouse and Barn which was once owned by Dylan Thomas’s aunt Anne Williams.The Barn is available for holiday lets throughout the year. We are a mile from Llansteffan on the coast with its famous Norman Castle overlooking Carmarthen Bay and the Irish sea.Llanybri is a 20 minute drive from Dylan Thomas’s boat house at Laugharne.
Carmarthenshire is regarded as the royal county as Prince Charles has a place here. It is known as the garden of Wales too because of it’s green lush countryside undulating hills and valleys and home to the National Botanical gardens . It is right next to Pembrokeshire.
See our website www.plasuchafruralretreat.com
Croeso i gymru! Mwynau!
Three cheers @sandralanewillis for the shout out for Carmarthenshire. I live in Cwm Gwendraeth which in itself probably isn’t prime tourist territory, but with Carmarthen, and the Brechfa mountains and the Cefn Sidan beach along with Llansteffan and Laugharne it deserves many more visitors. Too many just go straight through on the A48 from the motorway to Pembrokeshire.
Greetings from another Chicagoan! I just took my first trip. I spent 2 weeks in Wales - one outside Caernarfon and the other outside Machynlleth, but we had a car and drove all over the place. Both were fantastic areas - beautiful in late June, and I can imagine how lovely it would be in October with the leaves changing! I would suggest looking at the train lines and planning your trip around those if you aren’t going to have a car. Just a warning - if you’re in north Wales and want to head south to Cardiff on the train, it’s an expensive ticket and a long trip that will take a full day. I definitely heard more Welsh being spoken around Caernarfon, but everyone pegged me as an American right off, so everyone approached me in English. Good thing, because the minute I set foot in the UK, all the Welsh I’d learned flew out of my brain and I couldn’t remember anything other than diolch 
I need to go back so I can practice!
I know this was directed at anabel, but I’m also in Chicago and would love to find someone I could practice with!
HI fellow Chicagoan!! Thank you so much for this! I really appreciate the info. 
Any chance you’d like to practice speaking with me, since we’re in the same city??
Wow, thank you so much for this!
Thank you @sandralanewillis and @margaretnock for the suggestion! I’m not sure I’ll have time this trip but will absolutely keep in mind for next time!!
Wel dw i di ffeindio bo fi angen ymarfer mor aml a phosib. Felly nes i cyfarfod pobl newydd a dw 'di siarad cymraeg efo nhw.
Dylet ti fynd. Mae’n neis i fynd ac mae pawb yn neis hefyd.
Pob lwc. Mwynha dy wyliau.
If you ever visit for long enough not to mind visiting places where virtually no one speaks Cymraeg, Gower is glorious! Area of Outstanding Natural Beauty! Ancient tombs, cairns, caves occupied before the ice age…castles…are you into history? prehistory?.. but only a few still speak Cymraeg, all in North Gower, except 2 I know of in south Gower who have moved from Gogledd Cymru.
I’d love to. I’m in the north suburbs - where are you?
I’ve also got a ton of tourist brochures that I can give you if we meet in person that might help you narrow down what you want to see/do.
An update: I will be in Wales Oct. 3-8, staying in Llandudno for the first couple of nights and then in Caernarfon. If anyone is in that area and would be interested in chatting please let me know, or if you have any suggestions for things I absolutely must see/do/eat while I’m there!
I’m so excited to visit Wales for the first time and hopefully be brave enough to use my Welsh!
Would love to. I am about 30 minutes from Llandudno so if you fancy a chat let me know.
We’re about ten minutes south of Caernarfon - Carmel - and you’d be very welcome to come round for a panad and a chat in Welsh…
I work in Caernarfon so can be in town any weekday lunchtime, and I’m only 5 minutes away - Caeathro - in the evenings. So panads & chats available on request!