I like both but I think for a short trip like that I would pick Chicago. You will spend realistically 2 full days in travel to and from Aruba. The passport control coming home is insane (they do all the checks for US there so it’s like 5 different lines).
I do think it’s fun though — we went jet skiing and snorkeling and there’s lots of restaurants.

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:In Chicago, do not miss Portillos for a Chicago dog or an Italian beef.

Exhibit A as to why I can’t wrap my head around choosing Chicago over the Caribbean for an adults only 4 night getaway.

I mean, yes, Portillos is a Chicago thing, but it’s basically fast food.

Chicago is a place you piggyback on a day or two when you are in town for business. You see a baseball game, go to a museum, do the boat/architecture tour, shop, and seek out good restaurants and make sure you have reservations. There’s nothing sexy or exciting about it though.

Aruba is probably the last place on my list if I’m going away for 4 nights. Where can you get a direct flight from your home airport, op? Start there. Heck, French side of St. Martin or Bermuda would be quick and lovely.

Agree. Chicago is fine, but wouldn’t go there for vacation. A lot of people do love Chicago, but I’ve found these are usually people from Chicago. They have a very protective/defensive nature regarding their city. They don’t like that Chicago isn’t a world class city, like NYC and L.A.

Ignorance ^^.

I have zero doubt this PP has never been to Chicago. Classic DCUM -- dishonest ignorant people saying stupid things with authority.

DP

I bet most posters on dcum have been to Chicago. It’s a car ride away—or a short, cheap flight. It’s a city that routinely hosts conferences, and it’s routinely suggested as a great long weekend or summer vacation destination (presumably for families that aren’t fans of beach destinations).

Chicago is a fun city. I tend to have fun whenever I’m in town on business. I’ve extended my trips when I bring my family with me so we can spend a couple days going to games, museums, etc.

But if I have 4 nights in June to get away with my spouse, I’m not going to Chicago. NYC perhaps—if we have tix to a show or reservations at fabulous restaurants. But in all honesty, I’m flying to a beach: either opting for full-on island relation or perhaps choosing a place with a mix of beaches and activities.

If we are playing the Dcumlandia card, then I’d like to pose the following:

How come Dcumlandia is an evenly mixed bag of those who claim places like London, Paris, all of Italy, and the dreaded Costa Rica/Iceland/Portugal trifecta of “basic” are a laughable “waste of time” yet Chicago (and for whatever reason Philly and Pittsburgh) is a fan favorite for weeklong vacations?

So weird.

I went on a long weekend w DH when kids were little and we had a blast. It included Portillos which was fun for us. To each his own.

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:In Chicago, do not miss Portillos for a Chicago dog or an Italian beef.

Exhibit A as to why I can’t wrap my head around choosing Chicago over the Caribbean for an adults only 4 night getaway.

I mean, yes, Portillos is a Chicago thing, but it’s basically fast food.

Chicago is a place you piggyback on a day or two when you are in town for business. You see a baseball game, go to a museum, do the boat/architecture tour, shop, and seek out good restaurants and make sure you have reservations. There’s nothing sexy or exciting about it though.

Aruba is probably the last place on my list if I’m going away for 4 nights. Where can you get a direct flight from your home airport, op? Start there. Heck, French side of St. Martin or Bermuda would be quick and lovely.

Agree. Chicago is fine, but wouldn’t go there for vacation. A lot of people do love Chicago, but I’ve found these are usually people from Chicago. They have a very protective/defensive nature regarding their city. They don’t like that Chicago isn’t a world class city, like NYC and L.A.

Ignorance ^^.

I have zero doubt this PP has never been to Chicago. Classic DCUM -- dishonest ignorant people saying stupid things with authority.

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:
June in Chicago can be very hot, it just kind of depends.

You think Aruba would be cooler in June? It's much closer to the Equator.

Possibly, or not. Aruba is the same year-round, 83 and sunny with a few puff clouds. The only difference is during the “rainy season” you might get an hour or two afternoon storm.

I live near Chicago and June can either be 95 or 75. And of course, we have a lot of volatility to the weather then. When it is nice, it’s lovely. Overall it’s probably an average of 10 degrees cooler than DC and otherwise similar.

I went to Aruba in late March/early April and it was 90-93 degrees every day. I wouldn’t expect low to mid eighties in June.

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:In Chicago, do not miss Portillos for a Chicago dog or an Italian beef.

Exhibit A as to why I can’t wrap my head around choosing Chicago over the Caribbean for an adults only 4 night getaway.

I mean, yes, Portillos is a Chicago thing, but it’s basically fast food.

Chicago is a place you piggyback on a day or two when you are in town for business. You see a baseball game, go to a museum, do the boat/architecture tour, shop, and seek out good restaurants and make sure you have reservations. There’s nothing sexy or exciting about it though.

Aruba is probably the last place on my list if I’m going away for 4 nights. Where can you get a direct flight from your home airport, op? Start there. Heck, French side of St. Martin or Bermuda would be quick and lovely.

Agree. Chicago is fine, but wouldn’t go there for vacation. A lot of people do love Chicago, but I’ve found these are usually people from Chicago. They have a very protective/defensive nature regarding their city. They don’t like that Chicago isn’t a world class city, like NYC and L.A.

DP

It’s certainly true that people are highly biased when it comes to local and near-local destinations.

Anonymous wrote:

Anonymous wrote:In Chicago, do not miss Portillos for a Chicago dog or an Italian beef.

Exhibit A as to why I can’t wrap my head around choosing Chicago over the Caribbean for an adults only 4 night getaway.

I mean, yes, Portillos is a Chicago thing, but it’s basically fast food.

Chicago is a place you piggyback on a day or two when you are in town for business. You see a baseball game, go to a museum, do the boat/architecture tour, shop, and seek out good restaurants and make sure you have reservations. There’s nothing sexy or exciting about it though.

Aruba is probably the last place on my list if I’m going away for 4 nights. Where can you get a direct flight from your home airport, op? Start there. Heck, French side of St. Martin or Bermuda would be quick and lovely.

Agree. Chicago is fine, but wouldn’t go there for vacation. A lot of people do love Chicago, but I’ve found these are usually people from Chicago. They have a very protective/defensive nature regarding their city. They don’t like that Chicago isn’t a world class city, like NYC and L.A.

Anonymous wrote:In Chicago, do not miss Portillos for a Chicago dog or an Italian beef.

Exhibit A as to why I can’t wrap my head around choosing Chicago over the Caribbean for an adults only 4 night getaway.

I mean, yes, Portillos is a Chicago thing, but it’s basically fast food.

Chicago is a place you piggyback on a day or two when you are in town for business. You see a baseball game, go to a museum, do the boat/architecture tour, shop, and seek out good restaurants and make sure you have reservations. There’s nothing sexy or exciting about it though.

Aruba is probably the last place on my list if I’m going away for 4 nights. Where can you get a direct flight from your home airport, op? Start there. Heck, French side of St. Martin or Bermuda would be quick and lovely.

In Chicago, do not miss Portillos for a Chicago dog or an Italian beef.

I've been to Chicago in June and it was great. One day of rain but otherwise beautiful weather. Definitely take an architecture cruise on the river, check out whichever museums appeal to you and take some crazy pictures of the Bean.

Anonymous wrote:

Anonymous wrote:
June in Chicago can be very hot, it just kind of depends.

You think Aruba would be cooler in June? It's much closer to the Equator.

Possibly, or not. Aruba is the same year-round, 83 and sunny with a few puff clouds. The only difference is during the “rainy season” you might get an hour or two afternoon storm.

I live near Chicago and June can either be 95 or 75. And of course, we have a lot of volatility to the weather then. When it is nice, it’s lovely. Overall it’s probably an average of 10 degrees cooler than DC and otherwise similar.

Anonymous wrote:

Anonymous wrote:Four nights in Chicago is too much imho.

What about Charleston—perhaps stay at Kiawah for some beach/nature?

San Juan plus the beach? Easy flight.

Grand Cayman is always great.

Have you been there? Chicago is a world class city -- four nights is not at all "too much."

+1

We did 5 weeks in Chicago (dm, so working during day) on the way to Oregon. Chicago has plenty to offer.

Anonymous wrote:

Anonymous wrote:
June in Chicago can be very hot, it just kind of depends.

You think Aruba would be cooler in June? It's much closer to the Equator.

It just depends. I used to live in an apartment with no AC in Chicago and by late June it could either still be nice or could be spiking into the 90s.

Have you considered Bermuda as an option ?

Anonymous wrote:In June--I would do Chicago. In a colder time of year, I would do Aruba.

+1 June is the right time of year to enjoy Chicago.

If you do choose Aruba, keep in mind that it’s close enough to the equator that the sun is much stronger. You see tons of bright red sunburned tourists. You have to be religious about sunscreen. And it’s too windy to keep a hat on your head.