Ok, that doesn’t have the same ring to it as Things to Do in Denver When You’re Dead – great movie BTW; give it a name……

Moving on…..

So you are coming to Chicago in early May for Microsoft Ignite. Never been here? Been “here” but only been to O’hare\Rosemont\Schaumburg? Then this may help (but keep in mind these are all my opinions, and you know what they say about opinions).

Chicago Pro-tip #1:

Lets get this out of the way right now. We, DO NOT, under any circumstances, PUT KETCHUP ON A HOT DOG. Or mustard on an Italian Sausage “sangwich”. Its simply not done and you will be shunned if you ask and ridiculed if caught. 🙂 More on this later…

Where am I?

Chicago is the 3rd largest “city” in the US in population, but I don’t count Los Angeles as a “city” because it’s just a big suburb. I kid. However it is a very large city and due to the location of McCormick Place, it’s not the typical “walk across the street to classes” venue like you may be used to at MEC, LyncConf, or even many Tech Ed locations. I will elaborate a little further in the post, but it’s about 3 miles from McCormick Place to the northern end of “the loop” which I will call at the Chicago River. In the past, the location of McCormick place made it somewhat isolated from downtown in that there were few restaurants and places to go around McCormick. I won’t get into the socio-economic realities of “gentrification” etc but it used to be that you would leave McCormick Place, and go directly north into the loop/downtown. This is no longer the case and there are now many residential neighborhoods, restaurants and a whole ecosystem that just wasn’t there 20 years ago. However, most of what people would consider “downtown” is north of the river, which is River North, Mag Mile, Water Tower, etc. These are very much generalized locations keep in mind.

The weather at that time of year should be decent, but it has been known to rain/snow in early May here so I would bring a coat.


Getting Around

Chicago is pretty easy to get around in as we had the unfortunate benefit of the city burning to the ground in 1871. Because of this “clean slate”, and some pretty cool and forward thinking by the authors of “The Plan of Chicago” the city streets are in a grid layout. Madison Avenue is the North-South dividing line, and State Street is the East-West dividing line; Zero, Zero. So, for example, if someone said you needed to be at 425 W. Randolph St., you would know its 4 blocks west of State St. 225 S. Michigan would be 2 blocks South of Madison St. If you drive keep in mind each major street alternates one-way. Randolph is one way West, Washington East, etc.

Fun Fact: Wacker Drive is the only street in the city that has addresses in N/S/E and West

Public Transportation: I don’t ever use it so I am of no use here sorry. If you are coming from O’hare you can take the “EL”, Blue Line to somewhere in the Loop and connect if you need to get down to McCormick. There are plenty of apps that will help with that nowadays. Obviously there are many cabs and Uber is very popular here. I use Uber a lot and they almost always have cars around O’Hare and downtown.

Do I need to tell you to bring comfortable shoes? McCormick Place is HUGE so even getting out to the buses\cabs will be a haul so yes.


Where to stay?

Several people have asked me my opinion on this and, being a typical consultant, I have responded “it depends”. As of this writing, it appears that the Hyatt Regency McCormick Place is sold out, and as it’s the closest to the venue, that would have been my choice if you’re not a morning person and want to get to McCormick Place for sessions as quickly as possible. From the  MS Ignite website list of hotels below, you see I have marked the Hyatt MP and the Chicago River.


Again, it is about 3 miles from McCormick Place to the Michigan Avenue and the river, but keep in mind that if you are trying to get to McCormick Place in the morning and trying to get on a hotel shuttle it’s not going to take 12 minutes. Traffic can be brutal and getting across the river could take 10 minutes by itself. Walking is an option if time isn’t a factor and you can pretty much walk through Millennium and Grant Parks (they are connected) through the Museum Campus and Soldier Field (it’s not SoldierS Field by the way). It’s a pretty cool area and there’s a hidden surprise not far from McCormick near Soldier Field.


If it were me, I would stay around Millennium Park, or on the South side of the River. This also allows you to walk to a lot of places in the evening. Staying further West in the loop is fine, but you can assume some added time to get down to McCormick and there isn’t as many restaurants and bars in this area and the ones that are aren’t open as late. This may not be an issue for you but its something to think about.


Some highlights from some the hotels highlighted above (I have not stayed in all of them though):

– Hyatt Millennium Park. I thought it was fine. It’s in a good location and has a big bar called, wait for it, Big Bar. It is a pretty cool place though.

– The Fairmont. I have stayed here many, many times. Great location and the Aria restaurant within is pretty good and the sushi bar there is excellent.

– Monaco/Burnham. The hotel group that owns these and some others such as the Allegro take old Chicago buildings of character and turn them into hotels. Some pretty cool spaces in these hotels.

– Palmer House. Old school Chicago hotel. Off of Wabash, which is a great street to check out to see some great old Chicago architecture.


What\Where to eat.

Ok quick reminder: NO KETCHUP ON A HOT DOG!!. Are we clear yet?

I am biased obviously, and honestly these days its hard to find lousy food, but Chicago is home to many, many amazing restaurants. Many “celebrity chefs” have one or more restaurants here and it really is pretty crazy trying to get into some of them. Not that that has to be your thing obviously, but if you are a “foodie” (I hate that term), and you are going to be in Chicago for a week, you might want to check out some of these places.

I won’t get into a pizza war, if you like thin crust pizza we have that. If you like New York Style “utility” pizza we have that as well. We are known for our pan and stuffed pizzas. I would suggest you try Lou Malnatis at the very least, Giordano’s if you want a good example of stuffed pizza. There are dozens of other great pizza places though and none of them are papa johns, dominos or sbarro. I don’t have anything against these per se, ok yes, pizza hut is wretched, but when every mom and pop pizza place has better pizza than dominos how do they survive here? Makes no sense to me.

Best Hot Dog anywhere? Chicago. Just no Ketchup. At minimum (for me), mustard, onions, celery salt on a poppy-seed bun. “Chicago Style” can have sport peppers, neon relish, and tomatoes. Look for the Vienna Beef logo and you should be ok.

Some of my favorite restaurants or places I would not miss if I have never been here, in no particular order.

Girl and the Goat. Top Chef winner Stephanie Izzard. Great food, pretty reasonable, laid back, usually need to book way in advance. Will need to cab there from any of the Ignite Hotels.

The Publican. Shrine to all things Pig. And Seafood. And Beer. Paul Kahan (Avec, Blackbird, etc). One of the best. Reasonable, laid back but loud and communal seating. If there are 4-ish in your party you can ask for a “PIG PEN’ which is closed off booth which is cool. You’ll need to cab, as it’s in the same area (Fulton Market) as Girl and the Goat.

Sienna Tavern. “Modern” Italian. And awesome. Generally reasonable and laid back.

Piccolo Sogno. More “classic” Italian. Hand made pastas, awesome pizzas. Very reasonable.

Greek Islands. Greek (duh). Chicago has a good-sized Greek Town and all the restaurants are great, this one is my favorite. All things being equal, if I had to pick my favorite restaurant of all time, it would be Greek Islands hands down. I have been going there since I was a kid (and I am old now) and it never disappoints. Very reasonable and very casual. It’s a long walk but it’s definitely walkable from all but the McCormick hotels. In fact, its fun to cab there, eat a ton of Gyros, saganaki and down several bottles of Roditis, then walk back to your hotel. You can hit the river, Sears (Willis) Tower and more on the way back.

The Purple Pig.  Great location right across from the Tribune Building and next to the Wrigley Building. Beyond good and very reasonable. House made charcuterie. Great wine list. They don’t take reservations so its best to go later like 9-10 or you may wait a while.

China Town. We have an awesome China Town that’s just a mile or so west of McCormick Place. You could walk it, not sure I would, but you can. There are dozens and dozens of restaurants, one that was well reviewed recently on a local TV show is MingHin Cuisine.

Quartino. Italian small plates and pizza. Very reasonable and laid back and also open late. Great place to head after the bar. Walkable from a lot of the hotels or a very short cab. It looks like an Italian TGI Fridays inside, but the food is good.

Jim’s Original. Every city has their institutions, Jim’s is one of Chicago’s. You will see “Maxwell Style” on the menu of every hot dog stand in Chicago and this is why. The original place on Halstead and Maxwell was literally a plywood shack and going there was, lets call it “an adventure”. “Maxwell Style” is mustard and grilled onions, as in “Maxwell Style Polish”. It’s a very short cab ride from McCormick Place. I would ask for a Polish and Pork Chop sandwich on my death-bed.

Italian Beef. I will put vote Al’s as one of the best especially downtown. I don’t like dipped. I will do “sweet and hot” and just like you always double down, always get the combo.

Formento’s  Just opened in the beginning of the month of January. Can’t say enough great things. Food outstanding and service even better. We have a lot of Italian places in Chicago that are great, but Ferments is a new standout.


I have been asked to add some steak places and we have tons so there are a lot to choose from.

My current favorite is Bavette’s Bar and Boef. Its not cheap but not insane and so very cool. They have also opened a “burger” place, Au Cheval thats supposedly amazing (haven’t been there) but no reservations and wait can be long. Here is an additional list of steak places thats very legit.

Gibson’s – Always great.

Benny’s Chop House. I have been there, with foodie-at-large @alexlewis no less, and I thought it was amazing.

Chicago Cut. Haven’t been there but have heard its great.

Ok I didn’t even know we had a Del Frisco’s Double Eagle. Been to one in Denver, and its amazing but a lot of these places all get their beef from Allen Brothers so theres a lot of similarities.

There are so many places there’s no way to cover them all. We have a decent food truck “scene” but they are scattered so sometimes is hard to find them.

I am hungry now.



Chicago Pizza Primer

Thought this was interesting.

A Guide to Chicago Pizza: From Deep-Dish to Tavern-Style and Beyond.

The 10 Hottest Bars in Chicago from Zagat. If thats your thing.

Another Update: More ChinaTown recommendations thanks to Johnny Chan.

Mayflower – Cheap, good one of my personal go to restaurants

Seven Treasure – Late night til 2 AM with classic won-ton noodles soup and BBQ

Chai Cafe – Another great night spot open til 5AM on Friday and Saturdays


What to do?

Other than eat, not much. Kidding. In early May, it may be cold, especially along the lake and the beaches aren’t open yet but you can walk along them. Navy Pier is always nice if you’ve never been there before.

You can take a water taxi from different bridges to stops along  the river. If the weather is decent its pretty cool and a good way to see the city and cut through traffic.


Will I die?

Like I said earlier Chicago is a big city, and as such you need to pay attention when you are walking around, especially at night. There are no areas around downtown you shouldn’t go, but always pay attention to your surroundings. You hear a lot of crime related news from Chicago and this is all true, but this is well away from downtown.

if anyone actually reads this, please comment and ask questions or add a restaurant pick etc.

Anything else you want to know?