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December 24, 2021
My partner and I will be in Chicago at the end of March. Looking for recommendations! [more inside]
December 22, 2021
My grown daughter is bringing her boyfriend home for Christmas. He's never been to Chicago and when I asked if there was anything he particularly wanted to do, she said he wants to see the Bean. What else can we do while we are there? [more inside]
December 4, 2021
My spouse and I plan to spend a day or two in Chicago, hopefully in the fall of 2022. Please help us make the most of it. We will arrive and leave by Amtrak. We will be there only a short time because we have other stops to make. [more inside]
August 25, 2021
I will have Friday and Monday free bookending a conference. I've not been to Chicago since I was a kid so I don't have a frame of reference for how crowded places typically are on weekdays. I have some risk tolerance for being in public spaces with masks (and don't involve eating or drinking indoors) if they're not too crowded but definitely don't want anything with a dense crowd. The current forecast is moderate rain Friday morning and likely scattered rain Monday. [more inside]
July 12, 2021
I'm living with an immunocompromised person, so my vaccinated self and a vaccinated friend would like to meet somewhere outdoors. I would also like to avoid grass/ticks and water/mosquitoes. Are there wide-paved trails or restaurants with extra-spaced outdoor seating, somewhere approximately halfway between Chicago and Normal, Illinois? Unremarkable but ok restaurants, as well as especially weird/cool suggestions, are welcome.
July 8, 2021
I live in Chicago, have an impromptu week off, and want to do some day trips with friends. What are my best options for leaving in the morning and getting back home by midnight with an amazing day behind me. OK if they’re in the city or outside of it, provided the above occurs :)
April 24, 2021
Where to stay in Chicago? [more inside]
July 14, 2020
We have a week off in early August and are in Chicago. What are some good, toddler-friendly, social distancing-friendly things to do? [more inside]
May 28, 2020
It is late spring and that means I start to dream about buying a lake house. We are in Chicagoland and it seems like most people go to Lake Geneva or to southwest Michigan, but are there lakes/towns that you have loved to visit that are less well-known? Preferences are down below. [more inside]
May 4, 2020
Every Mother's Day since forever, we have gone to Indiana Dunes National Seashore/Park. It is my wife's favorite thing in the world. This year of course we cannot do that, but I really want to find a place where we can at least still enjoy a nice view of a beach and the lake while we sit safely in the car. Do you know of a Chicagoland beach/viewpoint that is particularly nice from the parking lot?
November 12, 2019
I'm in Chicago at work for the first time ever, and I'm kind of bummed it's so cold and dark and that lots of the usual night tours and such are closed for the winter (because it's so cold and dark). Anything open after 5 you would recommend? [more inside]
October 19, 2019
I have one day to entertain two kids ages 3 and 7 anywhere in Chicago. I'd like to visit a neighborhood rather than the center of the city where we've spent most of the time so far. [more inside]
September 11, 2019
I'm going to a conference at Loyola University next week. I didn't register early enough to get in the main hotel. The shuttles they're setting up probably won't be enough for me. I could also use recommendations for vegan food in the area. Please help. [more inside]
September 2, 2019
What the title says! It's almost my birthday and I want to eat the best penne arrabbiata in Chicago. Bonus points for good atmosphere, burrata, outdoor seating, and easy to get to on public transit, but all of those things are negotiable.
August 21, 2019
I'm planning a little getaway to Chicago for a few days in October. I've never been, and am looking for ideas for places to stay, whether it be neighborhoods or actual hotels/B&B's. (And a bit of specific advice on things to do -- details inside!) [more inside]
May 17, 2019
Last minute plans for vacation went south. How best to salvage a mini Chicago vacation by myself? [more inside]
March 15, 2019
We are headed to Chicago second week in April with a 10 year old. I've always wanted to take him to the Field museum so that is on the list. What else is a really terrific and uniquely Chicago thing to do with a kid? Doesn't have to be ONLY for kids. I am not interested in a kids' museum, aquarium, or zoo, etc. unless it's a particularly good one - I just feel like we see plenty of those and can do that any time. I'd also love suggestions for any good, unusual, and fun restaurants that a kid might also enjoy. No car.
November 16, 2018
I'll be heading with a friend to Chicago on 12/1 for a concert. I'd like to go someplace fun and unique for dinner before the show. I would rather not spend more than about $100 for the two of us. [more inside]
July 20, 2018
I'm taking the IO Theater's intensive improv summer program right now in Chicago. Awesome fun. Me and my classmates are looking for recommendations on the hottest improv shows. Standup too. I've seen Improv Shakespeare and was blown away. Also Hitch*cock and Matt Damon Improv at Annoyance Theatre.
July 5, 2018
I'll be in Chicago next week for a conference and will have most of the day Tuesday and a small portion of Friday to do what I'd like. I am especially interested in places to photograph (but don't have to limit yourself to that). Any suggestions? I will be staying basically corner of Michigan and Ohio St - not too far from Chicago Riverwalk.