Chicago for One
May 17, 2019 7:24 PM   Subscribe

Last minute plans for vacation went south. How best to salvage a mini Chicago vacation by myself?

I (somewhat impulsively) bought tickets to see a The Distillers at Metro in Chicago a couple of months ago. I only know two people in Chicago, one of which will be out of town, and the other is in school and cant get together most of the time, and pulled out of going to the concert. I’m kind of freaking out. The whole point of the trip was for us to see a concert together, and due to bad timing, it looks like I’ll be alone in Chicago next week.
Here’s where you come in. I’m afraid of having a mostly lonely trip. I’m a big people person. How do I spend a trip to a city I’ve never been in by myself?
Pertinent details:
I’ll be staying in Wicker Park (by the blue line) from Tuesday the 21st to Friday the 24th.
The Distillers show is Wednesday the 22nd. I’d really like to go with someone instead of just selling the ticket and going solo. How do I do this?
Are there any meetups/ social things I should know about?
Any general Chicago tips I should know?
Many thanks in advance for any advice you have to give!
posted by Champagne Supernova to Travel & Transportation around Chicago, IL (14 answers total) 2 users marked this as a favorite
Wicker Park is awesome. I lived there for a time in 2018 so I doubt much has changed there. Check out Myopic Books and Quimby’s if you’re into books and zines. The Subterranean always has shows. I always used to check the walls there for flyers for interesting get togethers. I was also particularly fond of the Gene Siskel Film Center and Cinema Obscura. Logan Square is also not too far and a very hip area.

Also in terms of tips, of you’re going to use the Subway, avoid the green and red lines when heading toward Southside. They can get...a bit precarious.
posted by Young Kullervo at 7:33 PM on May 17, 2019 [2 favorites]

It's actually OK to take the red line to the south side (eg. if you want to get to a Sox game or UChicago). Just maybe avoid certain stops--63rd or south of that can get dicey.

There's lots to explore in Wicker Park, and it's all walkable. If you're a museum and galleries person, you can have plenty of wonderful alone time at the Art Institute, Museum of Science and Industry, and the Field Museum. After going to the Art Institute you can always head across the street to the library at the Athletic Association. If it's a nice day you could grab a drink on the rooftop and have a great view of the bean & the lake, etc. You can also meet folks there, maybe at the games room.

There's always stuff going on in the city in the summertime. Not sure what's on ATM, but some things are actually hard to miss. Check out the Reader for events.
posted by Miss T.Horn at 7:57 PM on May 17, 2019 [1 favorite]

As far as how to use the ticket - if you’re single, maybe try Tinder?
posted by samthemander at 8:00 PM on May 17, 2019 [2 favorites]

I disagree that the green line or red line need to be avoided. I have ridden them countless times and have only had one worrisome situation in eighteen years in this city.

If you are a people person, you've come to Chicago at the right time. Everyone comes out when the weather is nice. Wednesday is going to be a beautiful warm day, perfect for a walk on the beach or the lakefront trail.

If you like architecture, consider a walk along the river downtown or the architecture foundation boat tour. Touristy but so worthwhile.

If you are staying through Friday evening there's a free house music festival concert in Millenium Park. Link

Bars near Wicker Park: If you like to sit out in a beer garden with a lively atmosphere, I recommend Happy Village. If you like do dance, I recommend Danny's. If you like a good cocktail and a nice patio, I recommend the Whistler, which is a short jaunt up Milwaukee Avenue. If you like frozen slushy cocktails, a yard with outdoor games, and yuppy people watching, I recommend Parson's. All pretty friendly places.
posted by mai at 8:00 PM on May 17, 2019 [3 favorites]

I forgot to mention one of my favorite things to do when the weather is nice: just bike around. Chicago has a bike rental program called Divvy.
posted by mai at 8:02 PM on May 17, 2019 [2 favorites]

If you're into plants and naturey stuff, I highly recommend the Garfield Park Conservatory. If you end up doing more than you expected alone, it's a great place to wander slowly amongst the lush environment and do some self reflection.

And like a previous person suggested, maybe you can talk a native Chicagoan via Tinder into showing you their city during your stay?
posted by pdxhiker at 8:18 PM on May 17, 2019 [2 favorites]

People have in the past posted in IRL section and us available Chicagoan mefites have gotten together. Don't be shy! (I unfortunately have a small child and work nights, but can attest that everyone is lovely!)
posted by AlexiaSky at 8:30 PM on May 17, 2019 [4 favorites]

Nthing that Chicago mefites are a simpatico bunch.
posted by brujita at 8:43 PM on May 17, 2019 [2 favorites]

Thursday nights at 8 PM there is a free, open improv jam at Second City (the North Avenue bus goes right there from near the Damen Blue Line station). It's very structured and friendly, and it's fine if you've never done improv before.

Tuesday nights at 7 or 7:30 PM there is a music improv show called MINt at The Annoyance (by the Belmont brown/red line station).
posted by amtho at 9:49 PM on May 17, 2019 [1 favorite]

Biking along the lake is truly a great bike ride. Also, you can take a break and spend some time on the beach. Beach time always makes me feel like I've gotten some solid vacation time in.

Check out TimeOut. They usually have a nice list of things to do. There may be a film festival at the Music Box Theatre. If I can go to the show I'll let you know :-)
posted by xammerboy at 10:33 PM on May 17, 2019 [1 favorite]

Check out the Flat Iron building, full of artists. You might meet some cool people there, who knows, maybe someone will want to come with you (long shot, but check it out anyway). Here is their FB page.
posted by Marie Mon Dieu at 2:10 AM on May 18, 2019 [1 favorite]

I just returned from Chicago. A people person will have no problems chatting with the natives. They will approach you. Chicagoans were even greating women on the street with a "Happy Mother's Day".
posted by Raybun at 5:10 AM on May 18, 2019 [2 favorites]

Response by poster: Thanks everyone! I now have a great list to use to work my way through Chicago. I’m so appreciate of all of the responses, you all rock! Thanks AlexiaSky and brujita, I have posted a meetup on IRL for Chicagoans (as well as an extra concert ticket post for any interested Mefites)!
posted by Champagne Supernova at 7:52 PM on May 18, 2019 [1 favorite]

I would suggest taking the ferry from Downtown to Chinatown. Chinatown (especially the new addition on Archer); has some fantastic food. Architecture Boat Tour conducted by the CAF is a nice thing to do. Something that is quite uniquely Chicago.

If you like Blues, Buddy Guys Legends in the South Loop and Rosa's in Logan Square are worth checking out.

Museum Campus, especially the Shedd Aquarium is worth visiting.

Food in Wicker Park is great. From cheapo places like Sultan's to more upscale places like etta, it is quite diverse.

Unfortunately, I am out of town. Otherwise I would have PMed you my number to call me for suggestions.

Edited to Add; The new Riverwalk is fantastic.
posted by indianbadger1 at 2:01 PM on May 19, 2019

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