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May 9

Specific spot to experience the levels of Chicago?

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 has best

May 1

How to spend a free day in Chicago

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 has best

April 27

Critique my Chicago trip, please!

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

March 21

Recommended Chicago River Architecture Boat Tour

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

August 9, 2022

30 relaxing hours in Chicago

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 has best

July 24, 2022

Where to stay in Chicago in September?

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 has best

December 24, 2021

Chicago Recommendations

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

December 22, 2021

He wants to see the Bean

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

December 4, 2021

Help us plan 24-48 hours in Chicago

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 has best

August 25, 2021

Two slightly rainy days in Chicago during Covid

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 has best

July 12, 2021

Outdoors, but not nature, between Chicago and Normal, Illinois?

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.
posted by zeek321 around Chicago, IL at 7:07 PM - 2 answers has best

July 8, 2021

Day trips from Chicago

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 :)
posted by sirion around Chicago, IL at 7:03 PM - 14 answers

April 24, 2021

Where to stay in Chicago?

Where to stay in Chicago? [more inside]
posted by cozenedindigo around Chicago, IL at 3:06 PM - 19 answers has best

July 14, 2020

Chicago staycation with a 1.5 year old: What to do outdoors?

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]
posted by huskerdont around Chicago, IL at 10:16 AM - 6 answers

May 28, 2020

Underrated lakes/towns for a lake house in Michigan/Wisconsin/Illinois?

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]
posted by AgentRocket around Chicago, IL at 12:16 PM - 7 answers

May 4, 2020

Chicagoland beach we could "visit" from the car?

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?
posted by AgentRocket around Chicago, IL at 12:10 PM - 5 answers has best

November 12, 2019

What should I do this week at night in Chicago?

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]
posted by clarinet around Chicago, IL at 3:08 PM - 9 answers has best

October 19, 2019

Where to spend a whole day in Chicago with two young kids?

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]
posted by Shusha around Chicago, IL at 7:25 PM - 13 answers has best

September 11, 2019

Getting around Chicago, stuff to do near Evanston, plus vegan traveler

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]
posted by FencingGal around Chicago, IL at 6:37 AM - 14 answers has best

September 2, 2019

The best penne arrabbiata in Chicago

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.
posted by goodbyewaffles around Chicago, IL at 4:31 PM - 2 answers has best