Chicago and Boston in September

[ChicagoBoston]

Anyone want to help me plan a holiday there next year?

Me, DH and DD (who will be 18 then)

Flying from Stanstead or Manchester to Boston. Or Chicago then Boston.

3 nights in each city then a couple of nights (or more) on Cape Cod.

Will it be ruinously expensive?

I've not been to Chicago, it's a long way from Boston. We have been to Boston and Cape Cod at that time of year. We did the historic trail in Boston - it's free and a great way of seeing the city and key places. Cape Cod was a great contrast to the cities we visited. We stayed in a log cabin.

On the same holiday, we also went to NYC and Philadelphia, which we loved. We spent a night in Newport, Rhode Island on the way to Cape Cod.

Chicago has a lot to see but it depends on what you like doing.

Really good museums, several of them next to each other. A fabulous free zoo. A river with fun boat tours, or informative boat tours (architecture). Some free concerts in the park, but not sure how many are left in September. Also they’ve recently moved the Taste of Chicago to September (from July) so not sure if that’ll cause hotel prices to be higher.

There’s free fireworks every Wednesday at Navy Pier. Jazz and blues clubs, comedy clubs etc if that’s what you like! Classical music outside the city easy train ride).

There’s every kind of food from very famous chefs to very reasonable fast food.

I haven’t tried it in ages, but Groupon used to offer really good deals on some of the sights, like Willis Tower, the boat tours etc.

Also a lot of the museums have free days, so if you know what interests you, it’d be worth seeing when the free days are.

And I’d say September perfect weather time to visit. Can still be a bit hot at the beginning but usually lovely towards the end.

If you have 9 nights I would do 4 in Chicago, 3 in Boston and 2 on the Cape. If it's the end of September you might have some foliage so could go to the Berkshires in western MA. It will be expensive but cheaper than nyc or California.

For flights, you'll ideally need to fly to (for a example) Chicago, then a domestic flight to Boston (only an hour and will be pretty cheap), then bos-london.

We did Chicago earlier this year. It was AMAZING. I could honestly live there. The Ivy Boutique hotel is great, We opted for a King Suite which has a separate living room area. It was about £150 a night.
So much to do : Navy Pier, the Ferris wheel, the Bean, rooftop bars and restaurants. We did the Gangsters and Ghosts walking tour which was fab. Also, the sunset cruise with Wendella was great.
I have also been to Boston, but not recently enough to comment (in the 90's).
If you fly into Chicago, I would look at flights with Aer Lingus. You will stop at Dublin and do all the immigration in Dublin. Plane was excellent. Be prepared, Chicago airport is utterly shit. Definitely download the Uber App if you don't already have it. You can use it for everything, even bringing breakfast to your room, or ordering a few bottles of wine from a supermarket.

It's quite a distance between Chicago and Boston, you loose a full day travelling.

We did 4 days in Boston which included one day in Salem (1/2 hour by train) plus 1 day in Concord and Plymouth by car.
We did one day in Cape Cod, it's quite a lot of driving, it's bigger than you think.

I would concentrate on either Chicago or Boston/Cape Cod, you have a lot more time instead of rushing it.

Boston was expensive like the US is at the moment. But we absolutely loved it.

We were in Boston in September. It rained. A lot!

The Boston Tea Party experience was interesting.

Go and see a game of baseball at Fenway Park. The game itself is a bit rubbish, but all the spectator participation is good fun.

The freedom trail is easy to download and follow.

Bankrupt yourselves and go for a drink at Cheers (if you are old enough to remember the TV programme).

We flew back from Boston with Aer Lingus via Dublin. Fantastic flight and check in was a dream. (Unlike the miserable lot at Lufthansa. Would never fly with them again]

Boston hasn't changed much since the 90s lol