Solo female off to Chicago next May...

[AmericaIsSoAwesome]

Early to middle of the month (can't do later in May but not hugely fussed about beaches or roof top bars). Also fine with mild weather.

The museums, the markets, the zoo, the aquarium, the kayaking, the shopping, the FOOD, the bike riding, the views.

This is a good idea for a trip isn't it?! Five days, four nights. I cannot wait.

Tips welcome...

Make sure you do an architecture boat tour. That was the highlight of my time in Chicago.

Brilliant idea. Yes to architecture boat tour, rent a bike, do the river walk, visit the bean in Millennium Park - and the art institute is incredible. I visited Chicago solo and had a fantastic time. Lots of restaurants have a bar which is nice to eat at, feels sociable. You’ll have a brilliant time.

You'll have a ball.

The weather will be nice, trees will be budding, the lake will be sparkling, and kids will still be in school.

I second the recommendation of the Art Institute - plan on spending a whole day to get best value.

Maybe consider a trip by local L train (Green Line) to Oak Park to see the famous Frank Lloyd Wright historic district, including FLW's home and studio, and the Unity Temple, a UNESCO World Heritage site. The Unity Temple offers tours daily. You can do a self guided audio tour of the historic district, full of houses designed by Wright, or join a guided tour. The Home and Studio offers docent led tours. Well worth a visit (check if advance booking is needed for Home and Studio and Unity Temple tours).

Thanks for tips so far, one question please. How safe is the subway (blue line) from O'Hare to Magnificent Mile? I did the E train from JFK to Manhattan a couple of years ago after being told it was fine. It wasn't fine it was very frightening, but I feel like Chicago will be slightly less intense than NYC (NYC was still awesome!)

Bumping for the morning!

The blue line from/to the airport was OK.
I felt quite unsafe on the red line at times, even fairly early in the evening (6pm). No-one actually bothered me, but I was very wary.
My favourite things in Chicago were the architecture boat tour, walking on the 606 line and the museum of Mexican Art. I also did a food tour which was great.
I found the Art Institute very crowded and quite hard to navigate but went the day it's open late, maybe if you go first thing in the morning it'd be better.

I'll be doing any museum type stuff very early, I'm a morning person

I went years ago but loved the riverboat tour and a tour to a Frank Lloyd Wright house. Some shops were open 24 hours a day- my DH had an early breakfast meeting so I went out and was in the Gap at 7am! Not sure now post Covid if that’s true except for Walmart and the like. Anyway really liked the city.

I did a couple of days alone there as part of a wider trip, and had a great time! Did the usual boat and bus tours, the bean, skydeck, the usual shopping bits and a museum solo. I chose to stay on the mile so i was close to things, and to feel a bit safer alone, but honestly, it was one of my fave solo experiences, i loved it!!

Some of the museum are a bit later opening on the weekend - just to bear in mind!

I was there in February (DS moved from NY to Chicago) and it’s fine. Didn’t feel unsafe anywhere on public transport. Different in NY, much more intense. Go, enjoy your trip, it’s a great city.

Yes I thought it seemed that way. Thank you x

I went solo about ten years ago. Ace things I remember:

Segway tour of the lakeside
Planetarium
Ticket to Second City improv show.

The contemporary art museum is stunning, it’s a phenomenal collection. The food is amazing too. Lots of public art, including the bean - there must be an online walking trail you can follow or something?

And Whole Foods. My favourite place on earth.

I’d add to your list see a show at the Second City and whilst you’re in my old neighbourhood you have to eat at the Twin Anchors (the best ribs!) and drink at Marge’s Still (Chicago’s oldest pub).

I always get an uber from the airport but then I haven’t ever lived convenient for the blue line. It doesn’t have a rep as being dodgy though (unlike the red line).

Yes, the Blue Line is fine. Lots of people use it to get to the city from O'Hare. You'll have a few blocks to walk to get to points on Michigan Avenue as it turns south at Ashland and Milwaukee iirc, where it goes underground. Clark/Lake, Washington, Monroe, and Jackson are the closest stops to Michigan Ave. The train is a lot cheaper than a Lyft or Uber.

The Art Institute opens daily at 11am, so it's not exactly an early bird attraction.

Agree wrt the Red Line.

What's so bad about the red line? Just a bad area it runs through I presume? There are attractions I can see are available via the red line but to be honest I'm a big walker so it's only really the airport journey I'm concerned about. But it would be good to know anyway in case I feel lazy one day!

I would love to do this. Where are you staying?

The red line runs north and south. It goes as far south as 95th street and north to Howard. It is the busiest L line, running 24/7.

The issue is a certain amount of spillover from problem areas in the southern half of the run into the northern half. Late evening and hot summer weekend nights can feel a bit hairy on the red line, and you get your share of homeless people on the trains too.

It's definitely a really useful line to access Michigan Avenue, and during weekdays you'll probably be fine.