Long Train Runnin

So this Friday I was planning on being by myself on an over night layover at O'Hare. My friend elected to join me today. He has never been to Chicago, but has always wanted to visit. We can get downtown by around 9:30PM. I know that's kind of a late start, but I set this trip up with no plans on heading downtown. I've been in the city itself around 6 times, and the one weekend night I spent in the loop was kind of underwhelming.

Anyway all of this being said if you had to try and show someone as much of Chicago as one possibly could on a Friday night. Hitting some bars is certainly very much on the menu. What would you do?

glg

How early is your morning flight? Would you want to stay in the city or would you want to go out for a while and head back to O'Hare for sleep or just not sleep?

How old are you/what's your scene? bars, clubs, sports, hipster, bro, beernerd, etc.

Long Train Runnin

The flight isn't to early. I have a room booked at the Hilton O Hare, so I figured dump the stuff in the room jump in an Uber toward the loop/magnificent mile area. Then at the end of the night head back to the room and crash since we'll be right at the airport should make the morning easier.

Craft beer is an interest that we both share. Obviously at that hour the bars will probably be the main thing to do, but was hoping we could some how also see a couple of the sights. Were both mid/late 20s.

chgoeditor

Chicago has a chronic problem with drunk tourists accidentally drowning in the wee hours in our river and lake, so maybe start with the sightseeing and then move onto the drinking. I'd recommend taking an Uber to Millennium Park, which is open until 11 pm. It's supposed to be quite mild on Friday, so it would be a perfect evening to stroll through the park, look at the sculptures and see some of the skyline.

You could also head to the Hancock Tower and have an overpriced drink at the Signature Room, which is on one of the top floors and offers panoramic views of the city.

If great craft beer is your thing, you'll probably want to get away from the Loop/River North/Mag Mile. I'd suggest heading to Publican, Map Room, Beermiscuous or Hop Leaf, which all have large and well curated beer selections. There are plenty of other bars and restaurants near Publican, which is located in the West Loop, plus the food is great. Map Room, Beermiscuous and Hop Leaf are all more neighborhoody spots. Alternately, you could go to the tap room/brew pub. I don't have hours in front of me, but Half Acre, Revolution, Goose Island, Haymarket, Dry Hop, Lagunitas, Atlas and Piece are all options worth investigating.

glg

I'll completely agree with chgoeditor, if it's a nice evening, head straight for Millennium Park, everything will be lit up. From there, Signature Room at the Hancock is a good option. The drinks are expensive, but remember that you're paying for the view. They charge $20 to get into the observatory on 94, so paying $10 for a beer on 96 ends up cheaper I'm told the women's room has a window, so nice view. No such luck in the men's.

After that, I would tend to say work your way back toward O'Hare as opposed to going to places that are off that general track, but that's me and traffic won't be a problem if you're going back late.

Generally back toward O'Hare: Publican, Haymarket (W Loop), Goose Island (Clybourn Corridor), Map Room, Piece (Bucktown), Revolution (Logan Square).
North along lakefront: Beermiscuous, Dry Hop, Atlas (Lakeview), Half Acre (North Center), Hopleaf (Andersonville)
Southwest: Lagunitas

If any of the breweries are ones you know and want to hit, definitely do those. Otherwise, some of these are reasonably close to each other. Publican and Haymarket are a couple of blocks apart as are Atlas and Beermiscuous. Piece to Map Room is about 1/2 mile (on Damen, mostly commercial, will have foot traffic). I would say skip Lagunitas unless you really want to go as there isn't much near it. ie, if you go there, it's probably your main stop.

From Piece or Map Room or Revolution, there are plenty of other bars on Milwaukee Ave to finish out your evening. If you want to save some $$, the Blue Line runs along Milwaukee up to Logan, so you can jump on the L back to O'Hare. This is also an option for inbound as well (check traffic, it's faster during rush hour, but by 9pm traffic may clear out enough to make a cab/uber faster)

JBord

I like this suggestion. I'd start at Publican where you can get some good food to start off the pub crawl. I'd probably end the night at Hopleaf, closest to the airport for the ride back.

Haymarket (which I'm not a big fan of) and Revolution, at least, have normal bar hours. Not sure about the others.

Given the late start, I might skip the Hancock this trip and instead opt for a rooftop bar. If it's a nice night, most should be open. There are a lot, you can Google them. I'm not as hip as I used to be, so maybe someone else can suggest some good ones with a skyline view .

Personally I think going to some good neighborhood bars and enjoying a view of the city from a rooftop, while sipping a beer, as soon as its warm enough to go outside is probably the best way to experience Chicago as a Chicagoan would.

chgoeditor

The challenge is that if it's a nice night and he's arriving at 10 or 10:30, most rooftop bars may be packed. That said, if I had my choice, I'd go to either Cindy's at the Chicago Athletic Association (directly across from Millennium Park with a great view) or JParker in the Hotel Lincoln (across from Lincoln Park).

Long Train Runnin

Wow thank you guys so much. This is pretty much exactly what I am looking for. I spoke some more with my friend, and said he was more interested in seeing Chicago "at bar level". So with that in mind I took a look at all of your suggestions. And it looks like the area around the Map Room has quite a few spots, so I think we might head that way. Since we are about 24 hours out looking at the traffic info at least for tonight the CTA looks like it would be marginally faster. Although obviously tomorrow is a different day. Seems like there are a few bars around the map room that should provide enough to make it an evening.

Thanks again for all the excellent and detailed ideas. ^ Really made this easier I don't think I would have found some of these spots without your help.

JBord

If you're leaving ORD around 9:30, a taxi would be the fastest (and most expensive) way to go. Probably will save yourself 15 minutes.

But the L from the airport is cheap and drops you off right where you want to start too.

Long Train Runnin

Yeah it will probably be a game time decision. Between the L and an UberX.

Non-NonRev

Mix it, take the train inbound and return via Uber

toomanybooks

I am too late for the OP I guess, but for next time consider a blues club. Plenty to choose from. I like Buddy Guy's, but mostly because it is convenient for my train and there are many good clubs.

Top-notch Chicago-style electric blues will change your life.

Long Train Runnin

Thanks to all the suggestions. We started out at the Map Room. Then went to 6 senses or something like that. Then over to Jack and Gingers for some food. Everyone we met said we should go to Division Street. So we headed over there...ugh not my scene. Felt like a bad bourbon street. Watching two girls get arrested that were absolutely freaking out. Hit a couple of the bars there, but didn't really care for it.

Thanks again though the map room was a cool spot I would have overlooked. Also made me realize how much bigger the Chicago metro area is.

JBord

Division is where we send tourists, not people smart enough to use FlyerTalk .

The fact that you liked Bucktown and didn't like Division (whether at Rush or Damen), means you're welcome back any time!

Long Train Runnin

Haha. Thanks. Yeah Division to me anyway felt kind of like a bad version of Bourbon Street. Except people at 1AM were behaving like it was 4AM in NOLA.

I hope that I am back in Chicago again soon. ^ Wouldn't hesitate to head back towards Milwaukee Ave area.