If you know Toronto and Chicago? Looking for the Chicago "Ossington" street or Leslieville

[threecluettkids]

We are headed to Chicago for the weekend. Two TO natives in late thirties. We want an vibe like Ossingotn or Leslieville. Yorkville is less our things. Seeking dinner/drink recommendations. Would like to be able to walk around before or after dinner in the area.

[ferret]

You're looking for a young & hip neighborhood with some trendy-ish dining drinking? We have a number of neighborhoods that would meet your criteria including Logan Square, Andersonville and Wicker Park. They're a bit spread out (not unreachable, but if, for example, you're staying downtown, you might waste and hour or two on public transportation) so you might want to clue us in on where you'll be staying.

[threecluettkids]

Thanks. We'll be staying at North Michigan & Ontario - so near Streetsville. For dinner, we would like to try a different neighbourhood. Arrive early and walk around. Maybe have a drink somewhere and then go to dinner . Ferret got it right with trendy-ish. The vibe is cool and different and young (not too young, we are late 30's). Prefer to that to something fancy and more uptight. But still want great food. Like the idea of small plates OR American (steak, fish etc). Mid range in price. We would want to be able to take a taxi from our hotel. Thanks again.

[ferret]

I'm in my late 40's so "young" to me is anyplace without an overabundance of toupees and early diners (and we have plenty of those).

[nsxtasy]

>> You're looking for a young & hip neighborhood with some trendy-ish dining drinking? We have a number of neighborhoods that would meet your criteria including Logan Square, Andersonville and Wicker Park.

Yup. Also Lincoln Park, Lakeview, Lincoln Square, West Town, Bucktown, and West Loop.

If you're concerned about the cab fare, the closest of these to Streeterville (not Streetsville, LOL) are the West Loop, West Town, and Wicker Park.

[threecluettkids]

Thanks for the tips. Here is the report back. Wicker Park and West Town were the two areas that we liked the best. In Wicker Park we didn't eat because it was the Wicker Park festival, but we had a great morning/afternoon there for shopping and it would have been the perfect hood for a meal, but it was going to be too crazy.

For West Town, we went to Randolph Street. We had drinks at Nell Cote and dinner at GEB. Atmosphere at Nell Cote was great, the appy that we had was okay. GEB was AMAZING. Loved the whole experience - would contemplate flying and driving back for the fresh donuts and the buratta and tomatoe salad.

On night two, we made the mistake of going to Vermilion - Indian and Latin cusine. Big mistake. The idea has potential, but was a total let down. Don't waster your night out. Also the vibe was odd. There have to be better options than this place.

Thanks again for your tips.

[nsxtasy]

Thanks for your report!

Incidentally, the neighborhood along Randolph Street, where you dined at Nellcote and GEB, is called the West Loop. West Town is a different neighborhood, roughly a mile north and a mile west of that stretch of Randolph Street.

[threecluettkids]

Thanks. It wasn't easy to keep track of.

[torontofoodbot]

I'm also from Toronto, heading to Chicago next week (Mon-Thurs). I'm looking for the same 'Ossington' vibe and wanted to get your take on the restaurant/bar selection at Wicker Park and West Loop. We'd like to have dinner at a neighbourhood where we can also stay afterwards for drinks.

For those from Chicago, since we're only there on weekdays, is one particular area better than the other in terms of staying open later?

[danimalarkey]

Personally, I'd aim for the Wicker Park/Bucktown/Logan Square areas. I think you may find a wider variety of options, and at different price points. I also find these neighborhoods a little more walkable while still being easily accessible via public transit and cabs.

[nsxtasy]

It might be easier to just describe what "vibe" you are looking for, rather than try to replicate a neighborhood from another city.