Solo Travel Destination: Chicago, United States

We are pleased to present a new Solo Travel Destination Post from Melissa, a member of the Solo Travel Society. Melissa is from Canada, and submitted the following report about Chicago, United States. Do you have a solo travel destination that you would like to recommend? Submit your description here, along with a few photos, and share it with fellow travelers!

Solo travel rating: 1 (1 is easiest, 4 is most difficult. Please see chart below)

Languages spoken: English

Cloud Gate, aka The Bean

Reasons to go:  When I was planning a solo long weekend in Chicago it surprised me when friends would comment that they never thought of the city as a travel destination. Why wouldn’t you? Chicago has so much to offer: theatre, art, music, shopping, food and unending lakefront.

The city is easy to navigate with the transit system connecting right up to the airports. Downtown is about an hour’s journey from O’Hare and 30 minutes from Midway. Between rail and buses the city is a breeze to get around, especially if you have access to Google Maps while there.

There’s lots to do as a solo traveler as well. I went on a Segway tour of Grant Park and the lakefront, chilled out in a glass box on the side of the Willis Tower (though it will always be Sears Tower to me) 103 storeys above the ground, rode a hop-on-hop-off bus to get acquainted with the downtown core and spent a good bit of time shopping on the Golden Mile. If you’re at all interested in art be sure to set aside a few hours to check out the Art Institute of Chicago. Going it alone may even be the best strategy here because you can spend as much or as little time in each section as you like. Friends may have gotten bored with how long I found myself lost in the Van Gogh paintings.

There is also lots of live music, blues in particular and great restaurants. Try the deep dish pizza as it’s a pizza experience like no other. Chicago is also home to Steppenwolf, a renowned theatre troupe and The Second City, which has turned out countless comedy stars. Check out their offerings while you’re in town.

If you stay in the Loop or River North there will be lots of people around at night so I felt safe walking by myself between the subway station and my hotel. As with  any city be aware of your surroundings and try to stick to populated streets.

I would go back in a heartbeat.

The grand staircase at the Art Institute of Chicago

Architecture buffs will love Chicago.

The famous sign outside the Chicago Theatre.

Solo Travel Destination Rating System

Safety - 1 (1 very safe, 2 safe in most areas, 3 be cautious at all times.)

Language - 1 (1 English is first language, 2 English speakers easy to find, 3 English speakers rare)

Navigation – 1 (1 easy to navigate by transit or car, 2 poor transit, car necessary, 3 not easy to get around)

Culture – 1 (1 Similar to North America or Western Europe, 2 Different from above but relaxed and easy, 3 Challenging)

Average Rating – 1 (1 is easiest, 4 is most difficult)

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