Boston v Chicago

Zazie

In November we will have a few days to spend in the US after a Transatlantic cruise.

On a previous trip, we did New York for 3 days. This time, we are thinking of either Boston or Chicago. We haven't been to either of these before.

Where would you go if it were you (and why)???

Nick_C

Chicago is a great city, but it can be bitterly cold in the winter. OTOH, the train journey (if you have the time, allow 24 hours with delays) up to Chicago is beautiful at any time of year.

Not been to Boston. On my to do list. Might be milder than Chicago in November.

I would make a decision based on price, including the price of the flight home.

The flight home from Chicago is about 75 minutes longer than the flight from Boston, which might also be a consideration. Personally, I like a longer flight as there a better chance to get some sleep.

jackieblack

I spent 6 days in Boston last summer. Loved it and would go back in a heartbeat. So much to do and see

Not been to Chicago (yet )

Zazie

Thanks for the quick responses!

We have found that Icelandair usually works out the cheapest for a one-way flight to/from the US.

I had already checked the cost and it's not a deal-breaker (Boston - Glasgow £299, Chicago - Glasgow £330). Chicago flight is 55 mins longer, also not a deal-breaker.

tomtontom

Been to both several times, and I'd favour Chicago over Boston. Both are lovely places, both will be cold (but not nearly as bad as they've had it this past week), I'd say they're pretty even in things to do but for shopping Chicago wins hands down.

What things do you enjoy doing?

Nick_C

If you are fan of cruising, why not save Boston as a starting point for a Fall Boston - Montreal cruise on some future occasion.

I concur that Chicago has great shopping. Also good culture. I'm not a huge art buff, the Art Instute has some iconic pieces, including some nice Chagall glass and Seurat's "Sunday Afternoon ... " https://en.wikipedia.org/wiki/A_Sunday_Afternoon_on_the_Island_of_La_Grande_Jatte (featured in Ferris Bueller's Day Off and the inspiration for Sondheim's "Sunday in the Park with George").

And you have to try the famous Chicago Pizza Pie at Pizza Uno or Pizza Due.

And the aquarium is also very good.

And if its really cold, Lake Michigan is quite spectacular when its frozen (and when its not)

Edit; And take a ride around the Loop on the L.

And Macy's in Chicago is possibly the most beautiful department store in the world.

blindman

Zazie wrote: »

Thanks for the quick responses!

We have found that Icelandair usually works out the cheapest for a one-way flight to/from the US.

I had already checked the cost and it's not a deal-breaker (Boston - Glasgow £299, Chicago - Glasgow £330). Chicago flight is 55 mins longer, also not a deal-breaker.

When in November?

Been to Both cities around these times, colder as it gets later in November.

Chicago
Plenty of shopping
Iconic buildings\architecture. (Frank Lloyd Wright)
Pizza\beer
Wrigley Field
Lake Michigan tour (cold though!)
Good Metro to get around
Historic Route 66 start\finish.

Boston
Historic Cambridge
"Cheers" Bar (don't go in )
Historic walk\trail

Difficult choice TBHO Both have expensive hotels :cool:
I'd say Chicago if you do not have a car.

Doshwaster

Boston is one of my favourite small-ish cities in the world but I'm not sure I'd go in November as the weather is unpredictable.

Never seen anything of Chicago apart from the airport so I can't comment.

cuffy_2

Also been to both and Chicago every time.

Nothing wrong with Boston - just my preference. In fact my wife is already nagging me to love at going back again although I think I will be avoiding it in November; went in October and that was cool enough without being too cold.

daveyjp

Only ever been to Chicago and had a great time, but it was May so we could at least walk around the city centre and go to the baseball.

In November you may be more restricted on where you can go and enjoy it! My wife was there just after Christmas and it was -12 degrees, -20 to -25 with windchill and it was so cold walking across the street was too far.

Duckyduck

Ive been to both - Chicago repeatedly as its one of my favourite cities in the world, once was enough for Boston.
If you were going in summer I'd say Chicago wins hands down, I love absorbing the atmosphere and the views down at the lake, but there won't be much going on there in winter. In November Boston might be better. Boston will be cold too, but probably not have the windchill of Chicago.

Was going to list why Boston would be better, but I'm struggling a bit! I'll list some pros for each and let you make your own mind up!

Boston has:
History
Better sports teams (basketball, American football and ice hockey season)
Lower sales tax (so cheaper shopping, and really it's the same stores in both)

Chicago:
Architecture - inc good views from the top of the Sears tower and John Hancock Building, Frank Lloyd Wright
Lots of shops (though high taxes by US standards)
Good Aquarium/museums
Chicago Pizza (I'm not a fan personally - much prefer the thin crusts of New York)
Midwest generally more friendly than the East Coast