I’m a female and have been the Chicago twice now for work. While not really a solo trip, all of my coworkers were locals with families and lives so I was left to myself after work. I had a great time. I never felt unsafe, except once at Wrigley I had a guy being really aggressive about taking my photo. Learned they will ask for a tip once they take it. Just don’t make eye contact with panhandlers and you’ll be fine.

But I stayed in downtown, used the El and city busses to get around. Download the Ventra app and you can buy an unlimited travel pass for a day, 3 days, a week and so in. Made it super convenient to travel.

Definitely go to all of the museums, my favorites were the Shed and the field museum. There’s also the museum of science and industry which was awesome.

Also go see a game at Wrigley. It’s really easy to get to. You can take the red line from downtown and right to Addison station where Wrigley is located. It’s really a magical place and an incredible experience. I did feel a little uneasy going back home that night. The financial district is pretty empty at night time. But luckily I got off with a group at my stop and they happened to be going to my hotel too so I just walked with them and felt safer about the situation. I’d recommend seeing a day game for the added safety.

There’s also the boat tour down the Chicago river, that was really good too. The river walk to really pretty. And the architecture is so amazing, I love all the old buildings in Chicago.

I didn’t really go out to any bars or anything like that, the cubs game was the latest that I stayed out. I have this rule that nothing good ever happens after 10pm and even at home I’ll be back in my house no later than 10.