Chicago for Boston for 4 nights?
Discussion
Interested in going to one of these places for 4 nights.
Dates: Either end of June, or possibl August/September
Going with my partner
We both love eating out, going drinking, touristy stuff like tours, looking round parks
Really would like to see an American sports game of some kind - maybe that Baseball is the only option depending on dates
Also love theatre, music bars
I've heard great things about both places.
Any opinions which would sway me one or or the other?
Dates: Either end of June, or possibl August/September
Going with my partner
We both love eating out, going drinking, touristy stuff like tours, looking round parks
Really would like to see an American sports game of some kind - maybe that Baseball is the only option depending on dates
Also love theatre, music bars
I've heard great things about both places.
Any opinions which would sway me one or or the other?
We visited both cities end of May/beginning of June last year. I’m not sure which I’d pick tbh. Boston is a nicer city I think in so much as it feels a bit safer wandering around, less high rise and greener. Both have excellent food and bar scenes, plenty of history and tours galore. When we visited the only real negative was the ridiculous cost of accommodation in Chicago, we timed it badly with a medical conference being in town. Boston feels a bit more European to me, Chicago a bit more American and very grandiose, I’m not sure I can split them even after giving it some thought.
Thanks all, Boston sounds the best option!
Curve ball ... My GF also mentioned Las Vegas. Definitely want to go but not sure on timing.
It will be very end of June into first week of July. Looks to be very hot then. I don't mind really hot if just lounging by the pool but walking around may be hard.
Anyone been around that time?
It may be better at another point of the year
Curve ball ... My GF also mentioned Las Vegas. Definitely want to go but not sure on timing.
It will be very end of June into first week of July. Looks to be very hot then. I don't mind really hot if just lounging by the pool but walking around may be hard.
Anyone been around that time?
It may be better at another point of the year
redrabbit29 said:
Thanks all, Boston sounds the best option!
Curve ball ... My GF also mentioned Las Vegas. Definitely want to go but not sure on timing.
It will be very end of June into first week of July. Looks to be very hot then. I don't mind really hot if just lounging by the pool but walking around may be hard.
Anyone been around that time?
It may be better at another point of the year
You can duck in and out of the casinos to get out of the heat. Even Boston will be pretty hot by then. I’d do Chicago of the 3. Presume you’ve done NYC?Curve ball ... My GF also mentioned Las Vegas. Definitely want to go but not sure on timing.
It will be very end of June into first week of July. Looks to be very hot then. I don't mind really hot if just lounging by the pool but walking around may be hard.
Anyone been around that time?
It may be better at another point of the year
2 GKC said:
You can duck in and out of the casinos to get out of the heat. Even Boston will be pretty hot by then. I’d do Chicago of the 3. Presume you’ve done NYC?
Yea I've been to NYC twice. Absolutely love it and would love to go back ... Just want to branch out a bit and try somewhere else this time I've been to Chicago a good few times, maybe 20, for work now and previously leisure travel. I would struggle to fill 4 nights in Chicago. It is no NYC no matter what the local press try to make out. Also has some very bad gang violence and shootings if you wander away from the downtown area. Boston, don't know, never been.
redrabbit29 said:
Curve ball ... My GF also mentioned Las Vegas. Definitely want to go but not sure on timing.
like to go to Las Vegas with your partner……It’s like taking a sandwich to a bbq.
A friend said that and I burst out laughing.
But I can see where he’s coming from…..
Boston for the win. 4 days might not be enough if you want to get out n about.
If you time it in fall with thechanging of the leaves, then travelling through New Hampshire towards Vermont is pretty special…
I spent 4 days in Chicago. Got an amazing flight/hotel deal in January and realised why it was so cheap when I arrived: absolutely freezing (-25 degrees).
I liked it - felt much less touristy than NYC. Would recommend an architectural tour. As someone said above, 4 days is more than enough.
I liked it - felt much less touristy than NYC. Would recommend an architectural tour. As someone said above, 4 days is more than enough.
redrabbit29 said:
Thanks all, Boston sounds the best option!
Curve ball ... My GF also mentioned Las Vegas. Definitely want to go but not sure on timing.
It will be very end of June into first week of July. Looks to be very hot then. I don't mind really hot if just lounging by the pool but walking around may be hard.
Anyone been around that time?
It may be better at another point of the year
I've been to Vegas in early July, never again. Having been to Vegas a few times before we weren't concerned about being there over the 4th July, it was hotter than hell and being their biggest public holiday the place was rammed, seriously rammed. We really underestimated how busy it would be. I'd advise against going at that time of year.Curve ball ... My GF also mentioned Las Vegas. Definitely want to go but not sure on timing.
It will be very end of June into first week of July. Looks to be very hot then. I don't mind really hot if just lounging by the pool but walking around may be hard.
Anyone been around that time?
It may be better at another point of the year
Boston v Chicago: Boston clear winner, lovely compact city, full of history, very walkable, not cheap.
If you do go to Boston then I can recommend this tour:
The politically incorrect food tour it’s run by a guy called Anthony and he’s typical Italian American, smokes too much, swears, mildly xenophobic (dislikes Canadians because they’re cheap) but he knows all the best spots in the North End which is the Italian bit of Boston.
We also did the Harvard tour which can be booked online or from the Harvard store next to the MRT station. It’s run by current students.
The politically incorrect food tour it’s run by a guy called Anthony and he’s typical Italian American, smokes too much, swears, mildly xenophobic (dislikes Canadians because they’re cheap) but he knows all the best spots in the North End which is the Italian bit of Boston.
We also did the Harvard tour which can be booked online or from the Harvard store next to the MRT station. It’s run by current students.
GilletteFan said:
Boston is too quaint and boring. Chicago is more interesting of the two.
Totally agree. I used to go to both cities on business, and holiday sometimes. I always though Boston was like being in the London suburbs and disappointing , whereas Chicago is real USA.Of the 20+ USA cities that I have visited, Chicago remains my firm favourite.
R.
We did a couple of nights Boston and three nights Chicago as part of our cross country trip last summer.
Allowing for the travel tiredness we had in Boston as we’d just arrived, we’d still go back to Chicago first.
As above, Boston has all the history and whatever, but the freedom trail felt like a school trip.
Chicago was pretty impressive. When you get to Tribune and Trump towers, wander along the river, stopping for a drink by the riverside, it’s a nice place to be.
We went to Wrigley Field to watch the Cubs. This was mid August. Sat in the bleachers and it was unbearably hot. Wish we’d sat in a covered stand.
Allowing for the travel tiredness we had in Boston as we’d just arrived, we’d still go back to Chicago first.
As above, Boston has all the history and whatever, but the freedom trail felt like a school trip.
Chicago was pretty impressive. When you get to Tribune and Trump towers, wander along the river, stopping for a drink by the riverside, it’s a nice place to be.
We went to Wrigley Field to watch the Cubs. This was mid August. Sat in the bleachers and it was unbearably hot. Wish we’d sat in a covered stand.
Not particularly a fan of either city, as neither compares to New York, even though people say Chicago is like a smaller version of New York, but is has nothing like the buzz or atmosphere in comparison, in my humble opinion.
I have been to both cities though and out of the two would probably choose Chicago. Boston itself is a nice city and does have some decent food and amazing craft beer if that is your thing. Also it does win on the baseball side too, if you are planning on taking in a game. I'm a Yankees fan and I was lucky enough that they were playing the Red Sox when I was in town. Fenway park is the oldest and most iconic baseball ground going and glad that I can say that I've been there. However I felt that it was a bit boring and didn't particularly find the locals to be that friendly. I would say that I feel there is more to do and see in Chicago and it is quite a bit bigger than Boston. The food scene there is also impressive and pretty diverse in terms of cuisines available. The architecture is impressive and the range of skyscrapers is interesting. I highly recommend visiting the "Art Institute of Chicago" if you do choose Chicago and are into your art. The place is huge and has an incredible amount of items on display that you could spend near enough a day there on its own.
Other American cities that I visited and enjoyed are San Francisco (my second favourite after New York, although a totally different vibe), Detroit, Philadelphia and New Orleans.
I have been to both cities though and out of the two would probably choose Chicago. Boston itself is a nice city and does have some decent food and amazing craft beer if that is your thing. Also it does win on the baseball side too, if you are planning on taking in a game. I'm a Yankees fan and I was lucky enough that they were playing the Red Sox when I was in town. Fenway park is the oldest and most iconic baseball ground going and glad that I can say that I've been there. However I felt that it was a bit boring and didn't particularly find the locals to be that friendly. I would say that I feel there is more to do and see in Chicago and it is quite a bit bigger than Boston. The food scene there is also impressive and pretty diverse in terms of cuisines available. The architecture is impressive and the range of skyscrapers is interesting. I highly recommend visiting the "Art Institute of Chicago" if you do choose Chicago and are into your art. The place is huge and has an incredible amount of items on display that you could spend near enough a day there on its own.
Other American cities that I visited and enjoyed are San Francisco (my second favourite after New York, although a totally different vibe), Detroit, Philadelphia and New Orleans.
Gassing Station | Holidays & Travel | Top of Page | What's New | My Stuff