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I'm arriving in Chicago by train and it looks pretty straightforward to get from Union Station to my hotel by bus according to google maps directions but I haven't ridden a city bus in ....30 years? Hold my hand? [more inside]
posted by Jenny'sCricket around Chicago, IL at 4:25 AM - 17 answers

I made potential plans to celebrate an anniversary of sorts with my husband in Chicago at the end of May. I knew cicadas were coming this year, but as I live well out of the way of anywhere they would be, it wasn't in my mind until I saw a headline about two broods emerging simultaneously in Illinois around that time. So...is this going to be awful? [more inside]
posted by tubedogg around Chicago, IL at 8:19 PM - 8 answers

2 families (kids are 6, 8, and 8) are hoping to rendezvous at a park in greater Chicago next Tuesday. Can you help us find somewhere, given the following snowflakes? [more inside]
posted by juliapangolin around Chicago, IL at 7:44 AM - 7 answers

Going to Chicago this summer. I've spent a lot of time there but it will be my first time back in years! 7 years, to be precise. What's new? [more inside]
posted by capricorn around Chicago, IL at 8:26 AM - 11 answers

Hello, we are looking to spend a week or two in Chicago and are trying to figure out the best place to get an AirBnb. We have been to Chicago a lot, but generally have stayed downtown. Which is what we will do if it makes sense, but we have a car this time. We'd like to be in a walkable part of the city and leave the car parked when we can. [more inside]
posted by ugf around Chicago, IL at 8:40 AM - 9 answers

Heading into chicago and need to entertain a 2-year-old and a gaggle of adults on a cold winter's day in Chicago. we are starting with the shedd aquarium and staying ar the embassy suites near navy pier. what else should we be doing? have car, have stroller, and do need to eat. All suggestions welcome! Thank you, Metafilter!
posted by wowenthusiast around Chicago, IL at 11:27 AM - 6 answers

We're staying near Millennium Park in early December and would love hearing about any personal experience with walkable things to do, places to eat, etc. I've done quite a bit of obsessing on Google Maps over the past few months, but have never been to this part of Chicago. [more inside]
posted by Eyelash around Chicago, IL at 6:19 PM - 12 answers

About a month ago, while looking for a hotel in Chicago for October 6-8, all the hotel rates I saw were about twice as high as normal (~$400/night instead of the usual ~$200/night). What's going on in Chicago next weekend to make the rates so high?
posted by ShooBoo around Chicago, IL at 11:23 AM - 5 answers

What should I do as a Chicago first-timer if I have only a Saturday afternoon to kill? And where should I store my luggage if I'm not staying in a hotel there. [more inside]
posted by greta simone around Chicago, IL at 11:10 AM - 20 answers

Thinking about doing a last minute Chi—>Minneapolis—>Chicago, leaving tomorrow and returning Friday. I’m not pressed for time (lol obviously) but not looking to court a living nightmare. Three hours late, okay; 13 hours late, no thanks. Is this a terrible idea? I know about the derailment/delays yesterday, not sure how they’re impacting things at this point… What should I expect in terms of lateness leaving Minneapolis and heading east? Choo choo, my friends.
posted by Charity Garfein around Chicago, IL at 10:51 AM - 9 answers

What's a good and safe location for someone who's new to Chicago to take a flight or two of stairs down to experience the various levels of the city? [more inside]
posted by Brandon Blatcher around Chicago, IL at 8:09 AM - 5 answers

I've got a free day next monday to spend in Chicago, and i'd like to enjoy it, so hope me... [more inside]
posted by OHenryPacey around Chicago, IL at 8:20 AM - 18 answers

I’ll be headed to Chicago next week for the Moonrunners music festival and for various wanderings, shenanigans, and cultural enrichment. I have never been to Chicago, and - as a Planner - I am asking for help to make sure I am maximizing my vacation days. My itinerary, with questions, is below the fold. [more inside]
posted by sacrifix around Chicago, IL at 7:16 PM - 26 answers

I will be in Chicago at the end of June, where I will be meeting up with a group of about 10 to 20 people (still in flux). We'd like to purchase tickets for one of the river architecture boat tours. There seem to be several different companies selling tickets. Is there one you'd recommend? Also, we'd like to do a group dinner after. Are there any restaurants you'd recommend near the end of the boat tour that are under $40 per person? Thank you in advance!
posted by cursed around Chicago, IL at 9:54 AM - 16 answers

In October, we are flying into Midway, arriving about 3pm on a Sunday, and flying out of O'Hare at 10pm the next day. We will be finishing up a potentially hectic and stressful three weeks in the states before our long flight back to the UK so would like to have a fun and relaxing time to wind down. [more inside]
posted by cilantro around Chicago, IL at 9:01 AM - 6 answers

We (spouse and I) will be visiting Chicago in late September to see Pavement at the Chicago Theatre. We rarely travel, and haven't been on a plane or anywhere out of our home state since pre-pandemic. This is a big deal for us, and we are excited to see our favorite band one more time! I've visited Chicago once, but it's been more than ten years ago. Can anyone recommend a nice hotel in the Loop? [more inside]
posted by little mouth around Chicago, IL at 7:35 AM - 7 answers

My partner and I will be in Chicago at the end of March. Looking for recommendations! [more inside]
posted by kittensofthenight around Chicago, IL at 1:25 PM - 8 answers

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]
posted by Serene Empress Dork around Chicago, IL at 6:44 AM - 17 answers

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]
posted by NotLost around Chicago, IL at 8:20 PM - 19 answers

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]
posted by Candleman around Chicago, IL at 10:37 AM - 11 answers