Boston or Chicago?

[RedIsNotMyFavouriteColour]

That's it, that's the question...

Favourite? Done NYC already

Bump

Chicago. It’s a bigger city so more to do and if it’s summer time then you also have all the beaches.

Boston.

Boston would be early October or Chicago would be early May

Neither. There's nothing that would get me to America over the next few years.

Chicago (I've been to both)

How long will you be there?
Who is going (what ages)?
What type of things do you like to do on vacation?

I've not been to Chicago. Absolutely loved Boston though.

I second that @Luggagerackistopheavy , in spades!

Still Chicago then although if you can push it to mid-late May to go after memorial day then even better as that’s when the beaches open, a lot of restaurants open their rooftops or outdoor spaces etc. and the city really comes back to life after a longgg winter! Still early May would still work for sightseeing and the usual and you’d hopefully have nice spring weather.

Five days, solo female traveller. Love eating and drinking, museums, scenery, parks, LOVE being by the ocean, shopping, most things to be honest. Big bookstores and just kind of exploring. Sitting in coffee shops people watching. Hate large crowds and seafood... refuse to drive in America.

You do you 👍

Oh I will.

I've not gone to Chicago, but loved Boston. It definitely suits a non-driver, has oceans of history, museums, beautiful in Autumn.

I went to Boston recently, and there's lots to do there. If you choose Boston, go to the Isabella Gardner Stewart Museum, as it is spectacular.

Havard is only a few stops away on the T and worth seeing.

Personally, I'd probably prefer Boston but I love Boston and the area. The ocean is there, but you could also do a day trip onto Cape Cod (there's a fast ferry to Provincetown which I've done for a day trip when I was working in Boston and I think that there are shuttles out to the nearest beaches but could also do an Uber/taxi).

Seafood is a big thing, but also some great other food (e.g. Italian in North End).

And you get the fall colours (my favourite time of the year in the region).

But honestly, you cannot go wrong with either of them.

I've been to both - quite a few years ago now. I liked both. Different vibe in both places. Boston is lovely and has some quaint / English vibe in some areas. Chicago is lovely downtown and along the lakeshore. My DS is there now and he landed in Boston and took transport to Nantucket which he says is lovely.

I’ve been to both dozens of times - I love both. I prefer Chicago generally but given the times of year you’re talking about I’d go with Boston. You’ll be a bit early for peak fall colours but it’s just absolutely perfect weather in early Oct in New England.

I think you’ll love either. Some great recommendations from people on here already.

Boston is lovely, very easy to navigate; a lot can be done on foot (Freedom Trail is worth doing), but the T can get you to places you wouldn’t walk to, like the Presidential Library, Harvard or Fenway Park. Terrific blend of the (relatively) old and the modern with lots of green. Although seafood is prominent, food choices are pretty much endless, so you’ll be fine on that front.

I know Chicago well, there is a lot more to do there but Boston is the one place in America that has a European feel and I also really like it. Have been to both many times as have relatives in each city.

Biggest seller for Chicago the Art Institute, bean and the aquarium.

We also went to Cape Cod which isn’t far from Boston and did Whale watching which was brilliant.

Thanks for your help guys I really do appreciate it, I think I'm going to go with Boston but it won't be this year, it will hopefully be the second or third week of October next year. I say that because it will be a very expensive trip (personally for me £2k+ for a 5 night trip is expensive). But I absolutely love Autumn and the Halloween season, so hopefully it will be worth it!

The Halloween decorations are amazing in October in Boston. Commonwealth Avenue and Beacon Hill especially. I’ve never done Salem that time of year because of the crowds but maybe worth a trip on a weekday.