Chicago first time

samc

New member
We are heading to IN this weekend to pick up a new trailer and thought we'd stop on the way back and spend the night in Chicago. Any suggestions on places to try for food or lodging (remember we have a trailer)?
Thanks
 
Last edited:

harvest1121

Well-known member
I would not attempt to bring a trailer into Chicago its just looking for a problem. If you really want to see Chicago I would let you drop your trailer at my house if you want. I am 40 miles south of Chicago atleast you would not have a problem looking for parking. I am located at 55 and 80 if that helps you.
 

polarisrider1

New member
I rolled into the Heart of that City with a 2 place clam shell type trailer to deliver a sled this past spring to windingtrailgals house. Streets are narrow and not a ton of fun getting around. Also met up with Harvest1121 and he lives out in the burbs. I stayed at the Windham at 55 and ????? between Joiliet and Shorewood. Plenty of places to eat. You have to try Giordanos pizza for the deep dish and Portellos for the dogs. While your there visit Cardinal Liquors, Prices are about 1/2 of what we pay in Michigan.
 

peter

Member
If you want to go into the big city and see things, I would find a place to stay just outside the city where you can unhook trailer and go or take a cab or bus into city.
If you want a hot dog and cant find portillos, find a hot dog stand that has the Vienna beef sign. Order it with everything and do not order with ketchup. Dont want a dog try a wet Italian Beef with hot or sweet peppers. Pizza yes lots of good pizza here. I can only suggest the local pizza places by me.
There is millions of things to do in the city from shopping, sight seeing, bars, night clubs, tours, shows, talking to bums if you want, etc. etc. I dont know what intrest you but check it out online.
 

peter

Member
I rolled into the Heart of that City with a 2 place clam shell type trailer to deliver a sled this past spring to windingtrailgals house. Streets are narrow and not a ton of fun getting around. Also met up with Harvest1121 and he lives out in the burbs. I stayed at the Windham at 55 and ????? between Joiliet and Shorewood. Plenty of places to eat. You have to try Giordanos pizza for the deep dish and Portellos for the dogs. While your there visit Cardinal Liquors, Prices are about 1/2 of what we pay in Michigan.

Giordanos pizza? Pr1 there is much better deep dish then that. I told you if you got your boat to Wilmette harbor I would bring you portillos. Now if you take a ride across I'll have to bring you portillos and some deep dish.
 

polarisrider1

New member
Giordanos pizza? Pr1 there is much better deep dish then that. I told you if you got your boat to Wilmette harbor I would bring you portillos. Now if you take a ride across I'll have to bring you portillos and some deep dish.
I am in my office looking at my chart (map) of lake MI. been to Wilmette and Winthrop and can do it again for great pizza. I have a designated slip at the Columbia Yacht club. ( I made Vice Commodore status this year) go figure??
 

peter

Member
I am in my office looking at my chart (map) of lake MI. been to Wilmette and Winthrop and can do it again for great pizza. I have a designated slip at the Columbia Yacht club. ( I made Vice Commodore status this year) go figure??

Ok Commodore just let me know what toppings you want on that pizza. I can even drive you to Cardinal Liquors so you can bootleg some booze back home.
 

samc

New member
Thanks for the info. Plan is to stay out side the city as a 23 ft trailer would not be fun down in Chacago and then drive to where ever for food, sites, what ever she wants.
polarisrider1 - no need to apologize
Harvest1121 - thanks for the offer, have to see what the boss wants to do first, this is her idea. Can't say no since she bought me the trailer.
 

cuzzinolaf

Active member
If you're good at driving a truck and trailer you'll have no problem getting around the city. It will take some time to find a parking spot but you will eventually.

I say this from experience; I drove and parallel parked (yes, literally) my old 14' open (roughly 20' long) trailer after going to the auction in Bronson Michigan a few years ago. We went to Ed Debevics to eat on the way home.

http://www.eddebevics.com/flash.html
 

dcsnomo

Moderator
Back on track...
Yes, I have suggestions.

First, lose the trailer, somewhere, somehow.

Hit expedia or hotwire or the like on the day before your stay, get a cheap room in the Michigan Ave, Streeterville, or River North area.

Check in, go to Heaven on Seven on Rush (Rush and Ohio). Eat like kings, drink good beer (Abate)

Walk to Blues Chicago on Ohio and Clark, listen to the blues

Cab it to Andy's Jazz club on Hubbard and State, catch a set

Walk down Hubbard to the Billy Goat for an Old Style

Up the steps to Michigan Ave to The Big Bar in the Hyatt on Wacker

Cab ride to Buddy Guys Legends at 7th and Wabash.

Back to hotel neighborhood, find a late night bistro for coffee and a scone.

That should fill up your evening!
 

scott_l

Member
dcsnomo has some very good ideas........I would add taking a walk from the river to the old water tower on Michigan avenue. For those that have been to Chicago before this is nothing special, but for people that have never been to Chicago it's worth the hr or so walk. You will see a lot of "neat/old building" see the Michigan Ave/magnificent mile shopping district. My guess about an hr if your moving along obviously longer if you start stopping into some of the shops.

If you get a good price on a hotel "down town in the "loop" or general area just an FYI you will be paying $40-$50 a night to park your truck.

If you have never been to Chicago I personally think it would be worth your time.

I am heading there in Nov. for work but I am going to miss the lighting of Michagan Ave (Christmas event) by one day.
 

samc

New member
There are some great ideas, the water front and Andy's! Looking at staying on the outskirts of Chicago and driving into town for the afternoon/night and back to a hotel (just pay the tolls).
 

Stack

New member
If you are looking for a quick spot to drop the trailer and spend the night:

Holiday Inn
5300 West Touhy Avenue
Skokie, IL 60077
(847) 679-8900

You can be "downtown" in 15 minutes depending on traffic, just on the outskirts of town and perfect access to I-94. PM me if you have any questions. Many cool areas to visit outside of downtown (Lincoln Park, Old Town, etc....), definitly suggest Nookies on Halsted in LP for breakfast before you leave.

John
 

blkhwkbob

Active member
The Holiday Inn is a great suggestion. The Skokie Police station is a block away, so it should be safe for the trailer. This is a safe area anyway. Just don't eat at the restaurant on the corner (Sanders?) it's horrible.
 

Grant Hoar

New member
If they are still running the architectural boat tours on the Chicago River, try it. Great way to see a lot of the city from a different viewpoint
 

mustsled2

New member
I also live right outside of chicago and have plenty of room for a trailer drop. i have a house 1 mile south of i-55 on lagrange rd. in the town of willow springs. the 294 interstate exit would be either 95th or 75th st. also 1 mile from me .. I will be around all weekend except a couple of hours on saturday(milwaukee snow show). My name is keith and my number is 630-816-7696. Plenty of places to stay in the area,holiday inn holidome has a pool, in countryside il. Let me know. Always willing to help out a john dee follower as they have helped me many times.
 
Top