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I'm going to Chicago on my own in May

81 replies

NotMrPerfectAfterAll · 27/03/2026 18:38

And I've been really excited about it for months and months but now I'm getting really nervous. For reasons I won't go into I've lost my confidence travelling even though I've done NYC and places in Europe on my own. I'm female early 40s.

Can anyone give me reassurance please? Will they be nice to me at the airport?! Is Chicago as lovely as it looks?

OP posts:
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BitOutOfPractice · 29/03/2026 18:51

@NotMrPerfectAfterAll you know there’s quite a few Wendy’s in the uk. Admittedly they’re mostly London / SE. There’s one ten minutes walk from home for me. I’ve never been in.

onlygeese · 30/03/2026 02:16

There is nothing wrong with Wendy’s but Chicago has some really great burgers
best burgers

My favorite is red hot ranch but they are no frills. Au Cheval is a nice setting and very well known.

The home alone house is in a very naice area, you can uber there quite safely.

If you are staying in the Loop you won’t be able to walk anywhere that you wouldn’t want to be.

The best burgers in Chicago

Get 'em with a host of toppings.

https://www.timeout.com/chicago/restaurants/best-burgers-in-chicago

onlygeese · 30/03/2026 02:18

Feel free to post a map OP if you have any concerns about areas.

CharSiu · 30/03/2026 02:42

I have been to Chicago about 15 times as my brother lives there, well in Lake Forest which is a very nice suburb about an hour on the train from downtown. It’s fine except you just do not go to some parts of the Southside downtown ever. I can’t remember the exact names of the areas, always had a great time.

Lavenderandbrown · 30/03/2026 03:15

I love Chicago As mentioned the architectural tour and the “bean” and walking along the lake front. I also really like the bar in the Drake Hotel. Lovely wooded bar and you would be fine dining alone there sitting at the bar. I also love Restoration Hardware
restaurant but make a reservation. Bloomingdale’s on Magnificent mile is lovely large department store as is the Ralph Lauren store but I spent most of my money at Nordstrom Rack just on a side street. All walking distance of each other including the Drake.

Lavenderandbrown · 30/03/2026 03:19

I was there in October…there is some very serious seasonal decorating there….

I'm going to Chicago on my own in May
I'm going to Chicago on my own in May
I'm going to Chicago on my own in May
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