Anonymous
11/25/2025 08:40
Subject: Help us decide-Chicago or Aruba?
Anonymous wrote:I personally was disappointed with Aruba from the perspective of active pursuits like snorkeling, kayaking, etc.
I like to be able to just walk off the beach and swim to good-to-great snorkeling and Aruba was not that.
Half the island is also really desert landscape...which may appeal to some, but I was expecting a more jungle-like atmosphere which you get at most islands.
I really enjoyed Curacao for snorkeling and other active pursuits, and the Curacao City is fun too (though I would just visit for dinner/night activities).
Brain Freeze...Wilemstad (capital of Curacao).
Anonymous
11/25/2025 08:39
Subject: Help us decide-Chicago or Aruba?
I personally was disappointed with Aruba from the perspective of active pursuits like snorkeling, kayaking, etc.
I like to be able to just walk off the beach and swim to good-to-great snorkeling and Aruba was not that.
Half the island is also really desert landscape...which may appeal to some, but I was expecting a more jungle-like atmosphere which you get at most islands.
I really enjoyed Curacao for snorkeling and other active pursuits, and the Curacao City is fun too (though I would just visit for dinner/night activities).
I like to be able to just walk off the beach and swim to good-to-great snorkeling and Aruba was not that.
Half the island is also really desert landscape...which may appeal to some, but I was expecting a more jungle-like atmosphere which you get at most islands.
I really enjoyed Curacao for snorkeling and other active pursuits, and the Curacao City is fun too (though I would just visit for dinner/night activities).
Anonymous
11/25/2025 08:07
Subject: Help us decide-Chicago or Aruba?
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.
Found the Chicago native.
Anonymous
11/25/2025 07:39
Subject: Help us decide-Chicago or Aruba?
I used to live in Chicago (college then hung around a couple years) and love it, but I think my hangup is Chicago is more a place I'd take my kids than go on a couples trip. A lot of the stuff I like there is more family stuff (Art Institute, Science and Industry Museum, The Field, Lincoln Park).
Anonymous
11/25/2025 07:38
Subject: Help us decide-Chicago or Aruba?
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.
Disagree. There is TONS to do. Lots of museums, the lakefront, cubs/sox games, a free zoo, and definitely do the architectural boat tour.
Anonymous
11/25/2025 07:30
Subject: Help us decide-Chicago or Aruba?
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.
I’ve been to Chicago plenty of times. Couple of work trips and my son lived there for three months. Also, I’m not saying it’s a bad city, just not my choice for a getaway in June.
Anonymous
11/25/2025 00:22
Subject: Help us decide-Chicago or Aruba?
Chicago! Architecture tour on the river, Art Institute (miniature rooms are hidden gem), Shedd Aquarium, science museum, Second City, Chicago theater, Navy Pier, Grant Park, Mag Mile, Oak Street Beach, Wrigley Field Cubs game, River North Art galleries, Willis (Sears) Tower observation, top of John Hancock, so many amazing restaurants.
Anonymous
11/24/2025 23:38
Subject: Help us decide-Chicago or Aruba?
Love Aruba but 1- it’s v hot in June,
and 2- Chicago can be so much fun with tons to do for 4 days.
and 2- Chicago can be so much fun with tons to do for 4 days.
Anonymous
11/24/2025 22:08
Subject: Help us decide-Chicago or Aruba?
This is all dependent on what you like to do with your vacation time. I am biased to Chicago because I'm from that area, and I also don't like beaches. I don't like the ocean and the idea of sitting on a beach or pool all day is torture to me. So I will always pick a city. And I love exploring cities-- even small ones. I could spend 4 days in almost any reasonably sized - size city.
OP-- if truly depends on how you like to spend you time.
OP-- if truly depends on how you like to spend you time.
Anonymous
11/24/2025 21:15
Subject: Help us decide-Chicago or Aruba?
Anonymous wrote:
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.
NP
Proximity, I think, is one possible way to parse what you describe, mostly. In Ducumlandia, a near destination is awarded a highly favorable handicap. This includes Philly and Pittsburgh. Like mid-Atlantic beaches, North Carolina, OBX, Assateague ... near is near family, or near second homes, or near friends and/or family with second homes, near nostalgia, near first homes, or they are simply convenient destinations. Working adults with children have some limitations. For whatever the reason, nearness bias is a thing.
Costa Rica and Cayman (and Hawaii) are non threatening in ways that Samana DR and Dominica are not. Bermuda is a short flight (near) compared to other island destinations; Polynesia is just as friendly and interesting, and warmer in January. But Dcum favors light-jacket weather for beaches. A lucky coincidence for DCUM, Delaware is just a few hours drive away. It's like God planned it.
Chicago I would not call near. I don't understand this one. Perhaps it's transplants. This might explain the jackets on beaches thing. Compared to Lake Michigan in December, Rehoboth must feel like Bermuda.
Anonymous
11/24/2025 21:13
Subject: Help us decide-Chicago or Aruba?
Why are those the two options?
What about Montreal?
What about Montreal?
Anonymous
11/24/2025 21:08
Subject: Help us decide-Chicago or Aruba?
Anonymous wrote: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.
To the PP. I think the "weird" is because there are different sets of responders. The people who do elite foreign travel at high prices are tired of the "basics". And then the domestic trips are often the families with kids who need quick but fun driving vacations because they don't have $20K to drop on flights on two months' notice.
I've been to Bali, India, China, Russia, and even Tunis for a day but I haven't been to Costa Rica, Iceland or Portugal. I answer the Pittsburgh and Chicago questions. My vote is for Chicago over Aruba. I vacationed in Philly and NYC this year. I've hardly been to Philly before. And NYC is classic.
Anonymous
11/24/2025 20:58
Subject: Help us decide-Chicago or Aruba?
Anonymous wrote: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.
But OP's DH isn't a great beach person. My DH is the same and our approach to beach vacations is just different, so there's always a level of compromise needed for us both to have fun. But our approach to cities is the same so it's easier in a lot of ways.
I vote Chicago. Spring for a really nice hotel and plan something fun for a beach/water day, plus Second City show and architecture tour.
Anonymous
11/24/2025 20:38
Subject: Re:Help us decide-Chicago or Aruba?
Four days in Chicago is perfect.