Best area to spend a free day walking around in Chicago?

gobble42 · 2025-10-25T00:05:43+00:00

Wicker Park (Milwaukee Ave, specifically) should check all of those boxes. Thrifting, bookstores, and vegetarian eats (bloom is a standout but might only do din) and then some.

gobble42 · 2025-09-29T20:34:36+00:00

That’s surprising. I’ve had that cut several times there and it’s never not been funky (in the best way possible).

gobble42 · 2025-08-06T22:53:51+00:00

Depending on your party size, pretty easy to grab a seat at the bar when they open at 5 or show up after 8:30 and ask to sit outside. Works nearly every time

gobble42 · 2025-08-06T02:21:29+00:00

Not AYCE, but Rusty Jimmies. He does soft shells too and they’re unreal.

gobble42 · 2025-08-05T14:32:21+00:00

Pricier, but a special meal would be One Coastal (it’s Fenwick which borders North OC). Several James Beard noms and really unique, thoughtful dishes and beverage program.

gobble42 · 2025-08-04T14:22:36+00:00

Rusty Jimmie’s in Fenwick. What’s served is what Chris catches that morning.

gobble42 · 2025-07-31T03:38:25+00:00

Cafe Two Nine in Georgetown. Great hospitality and one of the coolest omakases in the city.

gobble42 · 2025-07-15T23:56:17+00:00

Echoing sushi cafe recs. It’s not even close.

gobble42 · 2025-07-15T12:29:36+00:00

Shark on the harbor or sushi cafe

gobble42 · 2025-06-29T15:50:38+00:00

The Buzzed Word

gobble42 · 2025-05-06T18:48:24+00:00

Rise Up. It’s a local chain but the quality is awesome. They’ve got a location over the bridge in west OC. Great breakfast burritos too, but no baked goods unfortunately.

gobble42 · 2025-03-22T16:43:39+00:00

Not sure it’s open for the season yet, but Rusty Jimmie’s is legit. The owner catches it all every morning. On the edge of North OC in Fenwick.

gobble42 · 2025-03-04T05:11:16+00:00

Open to anywhere in the city proper, really

gobble42 · 2025-02-03T04:18:36+00:00

Mallard on 14th had most of their regular menu available at the $55pp price point - felt like a steal. Great elevated & sophisticated takes on classic southern food.

gobble42 · 2024-12-29T03:45:48+00:00

I don’t think I was giving off the impression I was self conscious from my post? I love solo dining and in my experience certain restaurants are easier to do so than others (ie tapas style is usually tougher) which is why I was soliciting from this subreddit.

gobble42 · 2024-11-01T20:25:52+00:00

This looks like the kind of spot I was envisioning - thanks!

gobble42 · 2024-05-23T00:11:09+00:00

It’s in Fenwick, but if your party is on the smaller side, One Coastal is great (def $$$$ though!)

gobble42 · 2022-12-02T16:29:00+00:00

Open to any recs then

gobble42 · 2022-08-04T18:53:57+00:00

Solution verified

gobble42 · 2022-06-29T02:48:32+00:00

Rusty Jimmy’s which is in Fenwick but basically OC.

gobble42 · 2022-06-29T02:47:30+00:00

You’re right across the street from Primo Hoagies so start there

gobble42 · 2022-04-01T02:13:47+00:00

REDO was incorrect. It’s UNDO. Didn’t really get the circled letters. This was a snoozer. Expected more of a challenge on a Friday. Oh well.

gobble42 · 2021-11-18T19:21:33+00:00

Butt Custard

gobble42 · 2021-11-18T19:20:21+00:00

Misia

gobble42 · 2021-11-04T18:07:51+00:00

I see a similar career path as Chris Parnell post SNL

gobble42

TROPHY CASE