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.