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Should I book an impulsive random solo trip to Chicago for 5 days?
#poll
Yes
No
202 votes
upvote 3 downvote

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Anonymous 11w

You will regret the things you never did, rather than the things you were bold enough to do.

upvote 9 downvote
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Anonymous 11w

Go to 63rd street

upvote 3 downvote
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Anonymous 11w

Its not impulsive if you are taking the time to ask

upvote 3 downvote
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Anonymous 11w

Only if you can afford it

upvote 1 downvote
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Anonymous 11w

Invite ya friends

upvote 1 downvote
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Anonymous 11w

Have you been to Chicago?

upvote 1 downvote
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Anonymous 11w

Do it. Nows the best time. If you want some recs and where to stay and what to do lmk. Been here for a few years and work in the nightlife industry. Easily the best city I’ve been to in the country and I’ve been to many

upvote 1 downvote
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Anonymous 11w

Chicago native here, YES, absolutely 100%. There’s riverboat architectural tours that are really fun if you can afford it, otherwise you NEED to go to Shedd aquarium, the field museum, and MS&I Chicago’s THE best city in the entire world for food, no matter your price range. Honestly the best thing you could do is approach some locals and ask them for suggestions on things to do and places to eat. Also check out @boredinchicago on TikTok, they’ve got a TON of cool stuff

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Anonymous replying to -> #5 11w

Nope

upvote 1 downvote
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Anonymous replying to -> #3 11w

What friends

upvote 1 downvote
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Anonymous replying to -> OP 11w

Get some

upvote 1 downvote
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Anonymous replying to -> OP 11w

If you aren’t afraid of heights definitely do The Tilt in the Hancock Building

upvote 3 downvote
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Anonymous replying to -> #5 11w

And if you are afraid of heights then still go to the observation deck

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Anonymous replying to -> #10 11w

Wait I lowkey wanted to go to the art institute. Would you say the ones you listed are better than the art one

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Anonymous replying to -> OP 11w

Put the art institute on the list too tbh, I just didn’t mention it cuz I was running out of characters to type with 😪

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Anonymous replying to -> OP 11w

Oh, and if you’re not acquainted with Portillo’s already, become acquainted. I’d highly recommend getting an Italian beef or some Chicago style hotdogs, cheese fries, and a chocolate cake shake (or piece of chocolate cake). I actually used to work at Portillo’s too so I can give more recommendations if you want lol

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Anonymous replying to -> OP 11w

Gun to my head tho, this is how I would rank the attractions. It’s also worth noting that I’m a biology/science nerd so your mileage may vary 1. Shedd aquarium 2. Field museum 3. Museum of science and industry 4. Art institute

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Anonymous replying to -> #10 11w

Thank you pookie. I just bought my plane ticket and reserved my hotel. Staying for 4 days and will be making the most of it 🫡

upvote 2 downvote
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Anonymous replying to -> OP 11w

Have fun! Take L train at some point too, quintessential Chicago experience. Maybe even see a Cubs game too if tickets are reasonably priced and you’re into that sort of thing. Either way, bring good walking shoes and clothes for all kinds of weather cuz the city can get pretty cold at times because of Lake Michigan

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Anonymous replying to -> #10 11w

Is it usually safe in Chicago? I saw there was a mass shooting last night and now I’m terrified

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Anonymous replying to -> OP 11w

I promise it usually really is, Chicago gets a bad rap but it’s still a lot safer than a fair amount of cities throughout the country ESPECIALLY after a mass shooting, security is going to be on high alert, and a mass shooting is a crazy rare anomaly anyways. If you’re really concerned tho you could always wait a few weeks/months and reschedule your trip

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Anonymous replying to -> #10 11w

I already bought my tickets to the museum and boat tours lmaooo. Plus tickets are non refundable now. Imma be there for 5 days. I think I’ll just only go outside when there’s daylight out and pray I don’t die

upvote 3 downvote
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Anonymous replying to -> OP 11w

I promise you even if you go out at night it’ll be fine, just stick to crowded streets lol

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Anonymous replying to -> OP 11w

OP I work a half a mile away from the shooting. Life went on and there was just more a police presence. These things happen but are usually targeted and off the beaten path. Still walked home at 4 am bc I can use Michigan Ave, one of the most popular streets in Chicago.

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Anonymous replying to -> #10 11w

Ur recommendations are exactly what I would have said maybe plus a sky scrapers experience like the John Hancock

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Anonymous replying to -> #9 11w

Seconded. Tilt at the Hancock building was cool as fuck, would HIGHLY recommend even as someone who’s #1 fear is fear of heights

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Anonymous replying to -> #10 11w

If you’re 21+ cloud bar is amazing aswell

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Anonymous replying to -> #9 11w

Also gotta see grant park. Millennium park to the shed is an incredible walk

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Anonymous replying to -> #9 11w

Just gonna say it cause I’m a bit drunk and went out in River north / the loop tonight but this is the greatest city in the country. I’ve been and lived in many. None like Chicago

upvote 1 downvote