5 Hours On The Ground In Chicago Shows Just How Cool Miles Can Be

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The DansDeals Forums is a messy community of 15,000. Newbies find it hard to navigate, but once you get the hang of it, it’s downright rewarding.

The discussions of breaking deals are rewarding, reading unique trip reports is very rewarding, but most of all the DOs or get-togethers are rewarding. That’s when names are matched to faces and when real friendships are created.

Earlier this week I suggested a DO in Chicago at Shallot’s to break yesterday’s fast day. I didn’t expect anyone besides the locals to actually want to travel to Chicago for a dinner DO, but in the end 10 people came to the DO including 7 who flew in just for dinner.  It was a crowd that ran the gamut from Modern Orthodox to Chabad, from Chasidish to Yeshivish to Roman Catholic. Because nothing unites people like miles and awesome food!

Nobody booked a ticket before yesterday afternoon.  Then the ball started rolling.

And that’s the great thing about a mileage forum. While paid tickets for a last-minute same-day turn would have run $500-$1,000, everybody used their miles of course.

My flight from Cleveland ran 9,000 Avios round-trip. That’s under 7,000 AMEX points with the current transfer promo. I mean for gosh sakes, I made many times that in just a few minutes at Target thanks to REDcard before the trip.

I mean I could have also used 100,000 Capital One points…but I’ll stick with the real airline miles thank you very much 😉

I was even able to upgrade my award to first class both directions and had the entire first class cabin to myself.

Left my home at 3:10pm EST, landed in Chicago at 4:45pm CST and Uber’d to Shallots by 5:10pm.

We spent the next 4 hours talking about our passions, miles, deals, travel, some sports talk, and good food. Doesn’t hurt that Shallot’s has some of the very best sushi in the world:

The Dynamite roll is pure sushi bliss:


Shallot’s sushi is expensive, but it’s like flying international first class on an airline like Cathay Pacific or Singapore. Once you fly first you’ll find it hard to fly coach again. And once you experience a few Shallot’s rolls you’ll never again appreciate any other sushi (save for Montreal’s Yakimono) in the world.  At least we can use miles for the flights 🙂


Rice Crackers are just sublime:



Tempura Asparagus is a must-have:



The steaks are top-notch as well.  I had the chimichurri churrasco which was excellent. Though not quite as good as the Wagyu or Delmonico options.




AJK, Hershelsdeals, and Rots5 went splitsies on a $270 monstrosity of lamb, veal, steaks, and sides loaded on the biggest food platter that I’ve ever seen. Pictures do it no justice whatsoever, only seeing 2 waiters struggle with it can possibly tell the story.  They were not able to finish it all…





Passion Fruit cocktail hits the spot:



The best strawberry shortcake you’ll ever try.  Chucksterace liked it so much he even ate his flower 😀



After stuffing ourselves silly, hearing about travels from New Zealand to Iran(!), and arguing about the best kosher restaurants in the world, the time flew by and it was time to rush back to the airport. We left Shallot’s less than 50 minutes before my departure time but I made my 9:55pm return flight with ease.

Of course a trip to Chicago isn’t complete without a Milt’s run. Except there was no time for that. So AJK and I had Uber bring Milt’s to Shallot’s. Probably the first time that’s ever been done 😀

Milt’s Rib Sandwich (special order only), Brisket Chili, and Burger (loaded with brisket chili, bacon, and crispy onions) are the best in the world. And their Fred Flintstone like slab of ribs is actually best when brought home, smothered in Milt’s BBQ sauce or garlic aioli, and then cooked for another day. (Find pictures of Milt’s food in previous Chicago trip notes).




Perhaps AJK summed it up the best on this DDF in this posting from aboard his return flight,

“Every time I think I should sit a DO out–because is it really worth flying for four hours (even in business), to eat for three–I am very pleasantly surprised.

Had an awesome time once again, and had the opportunity to meet some cool new people and greet some familiar ones once again.

Kudos to all who made the effort to show up, thanks to Chuck and CM for the rides, thanks to super helpful Walmart associate for helping me unload just under $10k, thanks to Chuck for the cohiba, thanks to Shallots for the food, thanks to an anonymous donor for the barter, and thanks to Mrs. AJK for not leaving me while I was gone.

I am so stuffed.


It’s quite an addicting game we play, but I sure don’t know of any more rewarding hobby out there. If only it lasts forever.

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69 Comments On "5 Hours On The Ground In Chicago Shows Just How Cool Miles Can Be"

All opinions expressed below are user generated and the opinions aren’t provided, reviewed or endorsed by any advertiser or DansDeals.


JEALOUS!! Maybe a pic of the guys – especially CV/CM 😉 ?


Did the same thing a month ago for my daughter’s birthday. It started out as to where we should go to dinner and when I suggested Shallofs and there was flight availability, it was a done deal. Would not have been able to do this without you!



If only my parents hadn’t been visiting us in Israel this week… 😉


Lol, that’s not gonna happen.
No need to be jealous, it was open to everyone.

@E R K:
Ain’t miles just the greatest 😀

Excuses, excuses 😉


Amazing! Didn’t expect that up anytime soon. That was quick


That looked awesome. Kudos to you all for pulling that off and stomaching such an extravagant meal after a fast (albeit a short one).


Wow, sorry I couldn’t make it. I was this close to stopping by for a few minutes.


That cheesecake can’t be parve. That’s just not possible 🙂


sorry, meant “shortcake”. Still having trouble believing that’s parve cream.


Dan looking forward to such amazing food on a fast just makes it even harder!

high end hobo

in the future, are newbies, (who think of themselves as quite knowledgeable) also welcome? i saw the discussion in the forums but i didn’t have 1.5K posts.


for a “foodie” you eat alot of fried food!


Dan, why wouldn’t you host a DO last week while in Miami ? i saw alot of Folks asking for one


Great write up! Until next time.


Story of epic proportions!


I believe its called Waygu, not Wagyu. But I’ll let this one pass as i can’t complain after that flower 😉

Leon m

Can you please explain how the red card works?
Also I know I asked you this before, but I am debating
Between the Starwood, Marriott and the citi American
Airlines card. Which do you suggest?
Thank you
Shabbat shalom


@Dan, were you surprised when you actually saw who they are in real life?

Also, are women allowed to a DO?


@Leon m: Why not apply for all of them? Better to diversify and have more options for earning and spending points:miles. For REDCard, read the wiki on the Forum. Lots of great info and guidance there, but you gotta invest the time. Shabbat shalom.


Why uber instead of renting a car? Just cuz of the time crunch?


This looks great, of course this will not last forever. ‘Forever’ needs preparation on quite another way ;-). Have a phenomenal Shaboss, may’en olam haba.


@high end hobo: They were just messing around. Even if you have one post you are welcome.


@Noturbizniss: b/c Dan has hundreds of dollars of Uber credit. Also for just a quick ride in and quick ride back Uber is faster and easier than renting.


AWESOME write up!
Informative and fun. Thanks Dan



Actually it is in fact “Wagyu”… the menu at Shallot’s is incorrect.



@Noturbizniss Uber credits.. And from Shallots to ORD or vice versa it would have been around $15-$20 each way. In the end it would be more convenient and cheaper to Uber.


That uber is probably <$20 with 0 hassle and I also wouldn't be surprised if he has a crap ton of referral credits.


AJK dared me 😉

Was my first time having a steak dinner after a fast.
Though winter fasts aren’t “real” fasts. More like skipping lunch.


Though the best imitation dairy product I’ve ever had is actually Shannon Road Ice Cream made in Cleveland.

People don’t believe it’s not the real thing and the flavors (Peanut Butter Cup, Cookie Dought, Toffee bar, Fudgenado, etc) are just awesome.

@high end hobo:

Was that much food in the post fried?

Probably because I haven’t been in Miami since last June?

Where to 😀


Definitely not.

@Leon m:


It’s always fun to put faces to the screen names.

Women are free to join in if they want. In general the miles community is very heavily male for whatever reason.

I’ve been to Flyertalk DOs and men outnumber women 10 to 1. Which is probably the ratio of men to women on most mileage forums.

I’ve yet to hear a good reason why it’s so male dominated.

Time crunch and I have a few referral credits to burn 😉
Renting a car with 5 hours on the ground would have killed an hour.

What I didn’t realize is that UberX is banned at O Hare. If I had more time I would have taken a shuttle to an airport hotel and then gotten UberX from there.

So Uber Black it was.

In UberX, about $16.
Uber Black is $50, hence the airport hotel run would be worth it with a little extra time to burn.


I never had a problem getting uber x in ord you just need to go to departures. they have ride share areas between terminals


Shakoyach! I presume DO is dine out?
I have been DDFer for 6+ months but missed this completely.
Guess there are DDFers and then there are DDFers. I can only aspire to a higher plane!


i guess thats why there was no posting of the cheap $367 flights to israel on transaero.


The reason is very simple. The men are the ones earning money, and planning vacations… at least by me… besides you have to be a little a “DRI-CUP” which are perfect for the man.

Anyways i wonder what was your reaction when you saw yesterday the Chasidish guy? as i know you hate chasidishe guys who are not Chabad as you said many times to me on DDF and almost insulted me 😉


@dan or if you had a few more minutes what you could have done was request a Uber pickup from a local hotel and then call the driver to come to the airport. I have yet had a drive who said no and they would drive to the terminal instead and pick you up.


Doesn’t have to involve a meal.
And 6 months in would have been welcomed just the same.

Are you kidding me?
I posted that twice last week:


Been alive since then, just the good connections sold out.

Why in the world would I hate chasidish guys?
Some of my best friends are non-chabad chasidish guys. The MH370 story’s travel agent, who I think is a really awesome person, is a “non-chabad chasidish guy”

Only people I hate are those that hate and disparage others.

Regardless, plenty of women in 2015 bring home the bacon and plan trips. I don’t see why the ratios are that skewed.

Cool, maybe I’ll try that next time.


great stuff all around guys, thanks for a great break-fast 😉

lets do this again…. next week in chops?


@chucksterace: my driver said you can request a yellow taxi thru uber at the airport

whats a DO?



Heh, I think they closed down.

Can’t use credits for that.

@whats a DO?:
A meetup.


Oh,I was at Midwood airport last week and Uber only allowed Uber Black so I took a train downtown for $4.50 (2people @ $2.25).I didn’t think of the shuttle trick. The train was probably as quick as the shuttle/Uber shpeil & much cheaper.


Hey Dan,

Looks cool!

Can I do this with my wife? Go in the afternoon NYC-ORD then stay overnight & fly back the next day…
Is it an interesting city to tour besides the food? Which hotel would you recommend? (I have all point currencies)



Of course. We’ve done that, hit up Milt’s and Shallot’s that way.

You’ll find several suggestions for stuff to do in the various Chicago trip notes found here: http://www.dansdeals.com/milesairline-tips

Tons of hotel options with all brands, depends on what star level you’re looking for.


@Dan: i thought it was a new one after it was dead last week. i saw it last week just no update that it was still alive yesterday. good stuff.


Was in Chicago last night. Cant believe I missed it.


Never dies last week, just the short connections sold out and most people don’t want to be stuck in an airport for 14 hours.

Gotta check DDF!


Isn’t Chabad- a chasid, why don you write chabad and chasidim


Dan, are you going to eat a Milts Berger or whatever you got at Milts reheated on Shaboss ? Since you were in Chicago on an erev Shaboss you should’ve sent a car to Romanians and loaded up on the absolutely best deli fit Shaboss.

Israel Cohen


As a frum jew, is not your time better spent learning or doing a chessed with other, rather that spending time and money flying around the states for a restaurant and discussing how delicious the food is. It sounds very shallow.
Use your talents for the ultimate spiritual endeavours.

Good Luck
Israel COhen

Israel Cohen

Is not your time better spent learning and doing chessed, rather than flying around the states for a restaurant and talking about food in forums.

It sounds very shallow to discuss food to such an extent with pictures.

Use your talents for ruchmiyas.
Good Luck
Israel Cohen

to Israel Cohen

Do you not know that fressing is the tachlis of life? Do you not know that flying around on a taanis tzibur in order to pig out is what the gemaras and rambam refer to as the teshuva of a taanis tzibur? How can one miss the boat so much? Beyond my comprehension.

Dan's the Man

@Israel Cohen: Why aren’t you learning instead of posting “great” comments?


Looks like a great trip!
Can you please confirm if CC can still be used to load funds to the Target Prepaid Redcard? On their website CC is not one of the options.
Thanks and good Shabbos.



If you are sincere, then you’ll pm Dan privately, and not publicly denounce his actions on his site


When is the best time to visit Chicago?


The first three pics are all fried, the steak have fried food, etc.

The menu says maygu, because its not wagyu. There’s no real wagyu in the US



Slab of Milt’s ribs my friend 🙂

@Israel Cohen:
Imagine how bright you could make the world by perfecting yourself instead of criticizing the business of others.

Then again it’s must easier to criticize others (especially on an anonymous internet site) than to actually work on your own midos which are clearly lacking. As anyone who actually cared about my spiritual health would email me and not post silly comments.

They can.

Depends on your tolerance for cold!

That’s a non-fried sushi roll with something heavenly on top.
Most of their specialty rolls have something fried on it.


Just curious. Flyer Talk ppl know who you are by the DO? If yes aren’t they upset on you for going to a competition and revealing the secrets on your own site? I guess I’m missing some info.


Of course.

A DO isn’t about secrets, though you may learn a thing to 2. It’s mostly just having a good time with like-minded people.

If someone tells me something and asks that it remains a secret then it remains a secret. Did you really think I’d write about them on the site?


Dan how did you upgrade to first ? You have added miles ? Or they just upgraded you bcs there was no seats in economy?


Agent took a sticker upgrade for both ways 😀
On an award, go figure!

Heilghe Shabbos

Hey Dan This last response was posted within 18 minutes of shkia in Cleveland, com’on a little respect for Shaboss don’t post after candelighting. 🙁


Someone had to say it. A taanis is just not the time to fly first class to an eat fest. How about the day before a taanis next time if you must. Must of us here on DD are not so holy that we don’t succumb to our physical cravings every so often, but there is a time and place for everything.


seriously guys?? why is this about haskofa? & not even yours its about other DD members. worry about yourself, your kids, or friends that need someone to talk to. +there is way too much judging on this site. this is meant to be a religious gathering to talk about yideshkeit.


If Dan posts a deal and nobody complains about it, is it still a deal?



I probably wouldn’t fly on a fast day as well for a DO but to each their own. You may feel it’s not the right time but others may feel it’s fine. There is nothing wrong with sharing your opinion of course on what you feel and what you would do.
Meanwhile how holy or not one is has nothing to do with it. There were plenty of people who you and I would both agree were holy who may have done things you wouldn’t do and vice versa.

That aside-
Great TR! @Dan – It’s at moments like those that you can appreciate how valuable miles are.


Da Bears


What does DO stand for

Israel Cohen


I apologize for criticizing you in the public forum.
I was not aware that you your email is available.
Please send me your email when you have a chance.
All the best

SoCal Dude

I gotta work on my wife to get a kitchen pass to do an out-of-town DO like this…we have so greatly benefited from DansDeals & DDF. I’m in awe & envious of ALL of you who attended!