I'm going to Chicago on my own in May

NotMrPerfectAfterAll · 2026-03-27T18:38:38+00:00

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?

Devontownie · 27/03/2026 18:43

Oh my word! How exciting!

You will be absolutely fine as soon as you set off. You have probably done a lot of planning and organizing and it may be just sit and wait time now? Have you gone into over thinking mode?

Solo is scary, but it increases the potential for new experiences and new people ten fold. It's so worth it, and a dream to many of us. Like I said as soon as it's show time, the anxiety will melt away!

It will be amazing, when in doubt, plan some more 💪🏼🙂 Have an awesome time..

KitsyWitsy · 27/03/2026 18:44

I was in Chicago last may. It was freezing. But everyone was really nice to me. You’ll be fine.

gldd · 27/03/2026 18:47

My favourite US city - absolutely fantastic. Beautiful lakeshore, elevated trains, amazing architecture and architectural history, Hemingway's house and Frank Lloyd Wright houses in Oak Park, amazing sports across all US major leagues, fantastic music scene (esp. jazz at the Green Mill, blues at B.L.U.E.S on Halstead and Buddy Guy's), amazing food, really friendly people. Watch some classic Chicago films in preparation (Blues Brothers, High Fidelity, any of John Hughes' e.g. Ferris Bueller's Day Off) and have fun!

Original poster

NotMrPerfectAfterAll · 27/03/2026 18:49

I'm more concerned about the airport (O'Hare) to be honest as the last time I was at an airport I made such a stupid mistake and nearly missed my plane home. I'm still mortified about it!

OP posts:

Bitzee · 27/03/2026 19:05

They’ll probably be brusk in the airport because that’s how American airport staff usually are but as airports go it’s fine and not particularly hard to navigate. Lived there for years and managed many a flight on my own with my then baby/toddler. Chicago is AMAZING though. I hope you love it as much as I do!

Original poster

NotMrPerfectAfterAll · 27/03/2026 21:38

gldd · 27/03/2026 18:47

My favourite US city - absolutely fantastic. Beautiful lakeshore, elevated trains, amazing architecture and architectural history, Hemingway's house and Frank Lloyd Wright houses in Oak Park, amazing sports across all US major leagues, fantastic music scene (esp. jazz at the Green Mill, blues at B.L.U.E.S on Halstead and Buddy Guy's), amazing food, really friendly people. Watch some classic Chicago films in preparation (Blues Brothers, High Fidelity, any of John Hughes' e.g. Ferris Bueller's Day Off) and have fun!

Thank you! X

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GardeningMummy · 27/03/2026 21:46

I’ve been to Chicago and I can’t lie to you, it’s not a nice place….. The food is nice in parts and other parts of Illinois (especially rural & Amish areas) are lovely, I lived there for a while. Chicago is an incredibly dangerous place. Why on earth are you going there? It’s about as much of a tourist destination as Leicester or Milton Keynes!

GardeningMummy · 27/03/2026 21:47

NotMrPerfectAfterAll · 27/03/2026 18:49

I'm more concerned about the airport (O'Hare) to be honest as the last time I was at an airport I made such a stupid mistake and nearly missed my plane home. I'm still mortified about it!

The airport is not too bad. They have lines on the floor for you to follow to each area!

Original poster

NotMrPerfectAfterAll · 27/03/2026 21:57

GardeningMummy · 27/03/2026 21:46

I’ve been to Chicago and I can’t lie to you, it’s not a nice place….. The food is nice in parts and other parts of Illinois (especially rural & Amish areas) are lovely, I lived there for a while. Chicago is an incredibly dangerous place. Why on earth are you going there? It’s about as much of a tourist destination as Leicester or Milton Keynes!

Oh man

OP posts:

Riverhousepuppy · 27/03/2026 22:04

I have been a few times before and I am going again very soon. It is a beautiful city and people are so friendly. So many interesting places to visit and the food is incredible!
In any city there are always safe and unsafe parts but you will be fine and there is so much information available and where is good to go and where to avoid.
It is exciting and liberating and you will have a wonderful time. And O'Hare is a good airport too and my experiences have always been positive.
Enjoy :-)

Yuja · 27/03/2026 22:05

GardeningMummy · 27/03/2026 21:46

I’ve been to Chicago and I can’t lie to you, it’s not a nice place….. The food is nice in parts and other parts of Illinois (especially rural & Amish areas) are lovely, I lived there for a while. Chicago is an incredibly dangerous place. Why on earth are you going there? It’s about as much of a tourist destination as Leicester or Milton Keynes!

Well this is weird. Chicago is an amazing city.

TrashHeap · 27/03/2026 22:13

It baffles me that anyone would give tourism to that cesspit of a country now.

CallingOnTheMegaphone · 27/03/2026 22:14

I went to Chicago on my own and it was amazing! There is so much to do. My favourite thing was probably the architecture boat tour, I went on a lovely sunny spring day and it was so interesting.

My main tip would be to avoid the red line metro trains in the evening. Although nothing bad actually happened to me, I didn't really feel safe.

Original poster

NotMrPerfectAfterAll · 27/03/2026 22:16

What about the train from the airport to the hotel (near magnificent mile) would it be more sensible to just get an uber? Is it similar to NYC?

OP posts:

HardyEustace · 27/03/2026 22:18

GardeningMummy · 27/03/2026 21:46

I’ve been to Chicago and I can’t lie to you, it’s not a nice place….. The food is nice in parts and other parts of Illinois (especially rural & Amish areas) are lovely, I lived there for a while. Chicago is an incredibly dangerous place. Why on earth are you going there? It’s about as much of a tourist destination as Leicester or Milton Keynes!

Are you having a laugh? Not a nice place? It’s one of the greatest cities in the world! Ignore this nonsense OP and have a ball. Enjoy the food, the architecture (do a river architecture cruise), the music and all that this fabulous city has to offer.

KitsyWitsy · 27/03/2026 22:21

GardeningMummy · 27/03/2026 21:46

I’ve been to Chicago and I can’t lie to you, it’s not a nice place….. The food is nice in parts and other parts of Illinois (especially rural & Amish areas) are lovely, I lived there for a while. Chicago is an incredibly dangerous place. Why on earth are you going there? It’s about as much of a tourist destination as Leicester or Milton Keynes!

In what parts? I think the OP is going to the city not the suburbs and the rest of Illinois. My partner is from Chicago so I’m there all the time. It’s absolutely fine. Don’t be scaremongered OP.

onlygeese · 27/03/2026 22:23

GardeningMummy · 27/03/2026 21:46

I’ve been to Chicago and I can’t lie to you, it’s not a nice place….. The food is nice in parts and other parts of Illinois (especially rural & Amish areas) are lovely, I lived there for a while. Chicago is an incredibly dangerous place. Why on earth are you going there? It’s about as much of a tourist destination as Leicester or Milton Keynes!

I live in Chicago, lived here for nearly ten years. It’s a fantastic place. It has been voted the best city in the USA to visit by Condé Nast for many years in a row now.
My family loves visiting from the UK and my dc have loved growing up here.
Don’t believe what Trump and his followers say about Chicago.

Overthemoun · 27/03/2026 22:23

Can I suggest the MPC app? We did it recently and were through customs so quickly.

catpupjoy · 27/03/2026 22:35

My dd (27) and her bf have just come back from a week in Chicago and then a week in NY. They are not experienced travellers…but they totally fell in love with Chicago and are already planning a return visit. (NY not so much)

worrisomeasset · 27/03/2026 23:31

We went to Chicago last August. The border control staff were perfectly polite. The architecture is gobsmacking, you need to take the architecture boat cruise. I knew nothing about baseball but going to a Chicago Cubs match at Wrigley Field was a fascinating experience. Our apartment was very near to Buddy Guy's Blues Legends Club and we thoroughly enjoyed an evening there. There's a lot going on lakeside, there was a free air display while we were there. You can spend hours in the Art Institute of Chicago (so many famous paintings there, including that Suerat one in the park) and you can spend a whole day in the Field natural history museum. The "L" train is remarkably cheap and makes it so easy to get around. It's not a major tourist city and that's one of the things that's really good about it.

Overtheatlantic · 27/03/2026 23:35

I’m so jealous! Chicago is a fantastic city. If you are inclined, the Obama presidential library and community centre is in the south side of the city. It opens officially in July but might be worth seeing the surrounding park.

HandfulOfMoths · 27/03/2026 23:45

GardeningMummy · 27/03/2026 21:46

I’ve been to Chicago and I can’t lie to you, it’s not a nice place….. The food is nice in parts and other parts of Illinois (especially rural & Amish areas) are lovely, I lived there for a while. Chicago is an incredibly dangerous place. Why on earth are you going there? It’s about as much of a tourist destination as Leicester or Milton Keynes!

Nonsense. I have travelled to many US cities and Chicago is my favourite. I felt very safe and there was so much to see and do. The food was great too.

OP, you will love it. Definitely do the Architecture Boat Tour.

GCAcademic · 27/03/2026 23:50

NotMrPerfectAfterAll · 27/03/2026 22:16

What about the train from the airport to the hotel (near magnificent mile) would it be more sensible to just get an uber? Is it similar to NYC?

I got a taxi from the airport. I read a lot of stuff online about how sketchy parts of the L are and didnt feel comfortable travelling on it with luggage after dark.

I went in the winter so the architecture boat tours weren't running and I did a walking tour instead, which was fantastic. Do both if you can as some of the buildings have stunning interiors.

honeyfox · 27/03/2026 23:55

We went on our honeymoon and loved it, did not expect to like it as much as I did. City centre felt very safe. Another vote here for the architectural boat tour, it was amazing. We stayed on the Magnificent Mile as well and visited Navy Pier too. Would highly recommend!

Crushed23 · 28/03/2026 00:10

GardeningMummy · 27/03/2026 21:46

I’ve been to Chicago and I can’t lie to you, it’s not a nice place….. The food is nice in parts and other parts of Illinois (especially rural & Amish areas) are lovely, I lived there for a while. Chicago is an incredibly dangerous place. Why on earth are you going there? It’s about as much of a tourist destination as Leicester or Milton Keynes!

Sorry but this absolute bollocks.