Windy City beckons

[Prazia]

Windy City is beckoning me soon. I will be there for one night (afternoon - night - afternoon)before traveling further west. I am trying to plan my time there when I'll be by myself. I am also planning to fly pretty, not dress pretty, but may be business casuals. I hear Michigan Ave is a nice place to be in the evening and I'm thinking of walking along the Riverwalk in the morning. I would really like to experience dine-in experience at a decent restaurant that is friendly and accepting. Suggestions and advice from your own experiences in the city would be so welcoming. One thing I always struggle with is getting photos taken while out and about. I sometimes ask strangers and they often oblige but I hesitate to ask each time. It would be so much easier with a companion, I think.

I was contemplating taking the blue line from the airport but it might not be convenient with more luggage since Prazia always needs an additional luggage. How much does a cab or a shared ride go for from the airport to downtown?

[Heather76]

The approximate taxi fare from O'Hare to Michigan Avenue (Magnificent Mile) is $50.00. I can only suggest if you are out by yourself, be sure to keep aware of your surroundings.

[docrobbysherry]

Selfie phone holders sell for $5 up. $10 if u want a collapsible column. I've got one that works great!:)

[TheHiddenMe]

I've been out dressed in Chicago and haven't had an issue. I've also taken the trains without an issue but if you have luggage that is a consideration.

Yes, walking Michigan Avenue is great. Chicago and Illinois are progressive places so wherever you chose to go or eat it shouldn't be an issue. There is a Cheesecake Factory in the Hancock building and I've always felt accepted there. State Street south of the river has a number of stores to visit too. Also, Millennium Park is a fun walk, or walking along the lakefront.

Have fun. You'll be fine.

[OrdinaryAverageGuy]

Chicago is a dangerous city no matter how you're dressed. Please be aware of your surroundings at all times, especially if you're out alone.

[Robyn n TN]

Prazia, if your on facebook you might check out ChicagolandTgirls .

[Terrihoney]

I wouldn't go into the city for any reason. The burb's have plenty of places to go. PM me. I live in the near South suburbs. Never hand your camera or phone to anyone. Take a cab or Uber to get around. Hotel rates are more affordable outside the city.

[Connie D50]

It's a great city to have fun in, enjoy your trip.

[StephanieCLT]

I was in Chicago for work about every other week between October and February. I went out plenty at night and never had a problem (plenty of posts in the pictures gallery of my experiences). Yes, Chicago is a big city with crime, so be aware of your surroundings (Ubers are your friend). Enjoy and let us know how it goes!

[NancySue]

Chicago, the Windy City. I echo, have fun, but be careful. They can spot a visitor a mile away. Go Cubs.

[melissalynn]

I'd check out the Andersonville neighborhood. Lots of eclectic shops and dining places and it's largely LGBT friendly.

[Prazia]

Thank you everyone! Much appreciated.

StephanieCLT, I read all your posts and I am so impressed and inspired.

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I'd check out the Andersonville neighborhood. Lots of eclectic shops and dining places and it's largely LGBT friendly.

I do plan to check out a couple places there if time permits. How's the transit going north from downtown crowd and safety-wise?

[TheHiddenMe]

The Lakeview area about 3200 North is also LGBT friendly.

My sister lives in the Wrigleyville area and I've been going to Chicago for 60 years. Public transport, either busses or trains, are safe. I've been on them inboth boy and girl mode and never had an issue. Yes, there are some rough areas, but don't go to those areas!

In the picture folder I've posted about my several trips to Chicago dressed. You can read about them.

You'll be fine.

You'll

[ColleenA]

My only suggestion is about getting photos. If you want someone to take your picture, ask a bartender, hotel clerk, etc. In other words, someone with whom there is no risk they'll steal it.

[Opdresser]

Most of Chicago is quite safe. There are a few areas that are horrible but the touristy areas are fine. I live in the suburbs but going into the city a fair amount.

[Prazia]

The Lakeview area about 3200 North is also LGBT friendly.

My sister lives in the Wrigleyville area and I've been going to Chicago for 60 years. Public transport, either busses or trains, are safe. I've been on them inboth boy and girl mode and never had an issue. Yes, there are some rough areas, but don't go to those areas!

In the picture folder I've posted about my several trips to Chicago dressed. You can read about them.

You'll be fine.

You'll

I felt safe all the time I was out and about the city and in the neighborhood north of the city. I took the metro several times and it all felt very normal which I guess is a good thing. I loved the city and I also found it very welcoming.

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I'd check out the Andersonville neighborhood. Lots of eclectic shops and dining places and it's largely LGBT friendly.

I got to spend a few wonderful hours there checking things off my bucket list for this trip! Thank you for the suggestion.