We’re planning a trip in the spring or early summer. Chicagoans or lovers of the city, when would you suggest we go?
It’s hard to say. Both are nice, and both have unpredictable weather. I won’t swear it, but I think you’re a little less likely to get rained on in the summer. Depending on when you go in the spring, you might get a bit of snow.
Summer can be nice because you can sit outside when you eat and the city does a lot of events and street fairs. If it’s early summer, you probably won’t be hit by any heat waves. On the other hand, I always really enjoy the energy of the city in spring, when the snow is gone and people are just so excited to be out without needing hats and gloves, and baseball season is starting, and the flowers are blooming, and everyone takes their dogs to the dog beaches…it’s really fun to be around several million people in a good mood.
Weatherwise, from May 15th to June 15th you’ll find the best weather and somewhat similar weather from Sept 15 - Oct 15. Though Spring is a bit nicer.
If you like the beach Chicago’s lake Michigan is great though it takes awhile to heat up. I don’t find Lake Michigan getting really warm till the end of July and all of August.
Summers as of the last few years have been cool. I only think we a few days last year above 90ºF (32ºC). For the last few years Chicago’s been cooler than normal.
Remember museums are popular places in the Summer with the kids. Also during vacation times. The Chicago Public Library has free passes you can check out to the museums, so if you know someone in Chicago, with a library card (which is free) they can get you in free. Well the main admission is free, special exibits still cost.
We have only been to Chicago once so I can’t say about other times of the year but we really enjoyed going this last 4th of July. The weather was colder and rainier than we had planned for. The wind coming off the lake was something else. I don’t know if we would go back too early in the year after that.
TASTE OF CHICAGO was a great event. Food stalls from a great variety of restaurants. I wish I could remember the restaurant names but I really enjoyed the African and Columbian restaurant stalls. It was even better earlier in the week without the holiday weekend crowds.
The fireworks display over the lake was great. The mass of humanity watching it was even more impressive.
If you are into architecture & history, I would recommend the river boat tour. It gave a good overview of the city’s history & buildings.
We were very impressed with how nice of city Chicago is. We enjoyed the Field & art museums, aquarium, and planetarium. The only disappointment for me was the Museum of Science & Industry. I had always heard rave reviews of it but was definitely under impressed. It seemed more like a children’s museum.
You will enjoy the trip.
This past summer was unseasonably cool for Chicago.
Blues Festival is usually better weatherwise than Taste of Chicago. It’s also less crowded. Taste is nice too though. It depends what you want. Blues Fest has better entertainment IMO.