Road Trips Let us know where you've been on your Harley, the best places to visit on a bike, etc.

Chicago Digs

Thread Tools
 
Search this Thread
 
Old Jun 2, 2008 | 05:59 PM
  #1  
cathardo's Avatar
cathardo
Thread Starter
|
Novice
Joined: Sep 2006
Posts: 20
Likes: 0
From:
Default Chicago Digs

My son just graduated from U-Montana (proud dad) and as a graduation present, he requested a 'road trip’ with his old man (did I say proud dad?). Anyway we're kicking off a Rt66 (Chicago to LA), Rt 1-101 (LA to Seattle), and Northern US (Seattle-Albany), around the country trip starting mid July.

The only planned dates will be in Chicago and LA. My question to the open forum is where to stay near Chicago. We intend to kick off from Lake Shore Drive Sunday morning, and was wondering for a suggested place to stay Sat night. We’ll be spending the next 30 – 40 days on the road, so I’d rather not kick off the ride with a $$$$ hotel, however on the other hand, we need to be able to make it out of the windy city with our bikes and our lives. Any suggestions of a place near or within an hour (from the east) of the start of 66?
 
Reply
Old Jun 3, 2008 | 08:26 PM
  #2  
bigdoghd's Avatar
bigdoghd
Road Master
Joined: Sep 2007
Posts: 1,049
Likes: 1
From: Brookfield,Il.
Default RE: Chicago Digs

Wow that's awsome! Let me know how I can help, did you want to stay down town or stay in the suburbs and ride intoChicago during the day? Also we have a few nice rides along the illinois river with a few nice burger bars along the way that I would be glad to show you. I might be able to get you a killer deal on a major chain hotel if a get the dates. Not 100% but I would give it a try.
 
Reply
Old Jun 13, 2008 | 01:15 PM
  #3  
garyhendley's Avatar
garyhendley
Outstanding HDF Member
Joined: Feb 2008
Posts: 2,706
Likes: 1
From: Sunland, CA
Default RE: Chicago Digs

sound like a great adventure safe riding
 
Reply
Old Jun 21, 2008 | 09:09 PM
  #4  
jch82's Avatar
jch82
Intermediate
Joined: May 2008
Posts: 27
Likes: 0
From:
Default RE: Chicago Digs

That is exactly the kind of trip I would LOVE to take! I am envious!
&nbsp\\;
Safe riding!!
&nbsp\\;
Josh
 
Reply
Old Jun 27, 2008 | 06:16 PM
  #5  
mtgriz's Avatar
mtgriz
Road Warrior
Joined: Dec 2005
Posts: 1,644
Likes: 224
From: Coeur d'Alene
Default RE: Chicago Digs

University of Montana....all right, my alma mater. Congratulations to your son. Tell him if I catch you guys at the Mo Club, beers are on me. He'll know what I'm talking about.&nbsp\\;Easy for me to say since I'm in Texas these days..LOL.
&nbsp\\;
I know a little about Chicago and can say the obvious...staying downtown without spending $$$ is simply&nbsp\\;not possible. So, I'll recommend a place I stayed out in Countryside (just south of LaGrange) actually on the original US 66 that is about 40 minutes from the start of US 66 downtown,&nbsp\\;which I think is like Adams and Michigan Ave or perhaps Lake Shore Drive but I don't think Adams goes out to Lake Shore Drive. Regardless, sounds like you've done your homework and you&nbsp\\;know where you want to start from.
&nbsp\\;
Anyway there's a Hampton Inn in Countryside just west of the intersection of Joliet Rd. (old 66) and LaGrange Rd. Typical Hampton Inn..nothing fancy but a reliable place.&nbsp\\;I'm guessing you'll be about 30 miles from the beginning of 66. Some of the areas east of Countryside toward the city&nbsp\\;on the 66 route&nbsp\\;are a bit rough around the edges and I wouldn't recommend staying there. If you're looking for dinner, I'd go north on LaGrange Road to LaGrange, about 5 miles. Nice little suburb.
&nbsp\\;
One last thing...don't know if this has changed but motorcycles&nbsp\\;were not allowed on Lake Shore Drive when I used to visit from Missoula.....no motorcycles and no pickups. The Chgo. cop that stopped me had never seen a Montana plate on a Harley and let me go with a smile.&nbsp\\;&nbsp\\;Seems silly, so that may have changed. However if things have changed, ride south on Lake Shore Drive to the Planetarium and just&nbsp\\;take a look at the Chicago skyline from there. Spectacular.
&nbsp\\;
Have a great trip...Go Griz!
&nbsp\\;
&nbsp\\;
&nbsp\\;
 
Reply
Old Jul 1, 2008 | 05:27 AM
  #6  
Moe Taters's Avatar
Moe Taters
Road Captain
Joined: Jun 2008
Posts: 623
Likes: 1
From: Carlin, Nevada
Default RE: Chicago Digs

I grew up in that very area.&nbsp\\; Coming from NY?&nbsp\\; Then stop anywhere BEFORE lake County Indiana.&nbsp\\; Porter or Laport Counties will have decent lodging and decent prices.&nbsp\\; You'll be 1 hour to 1 1/2 hour from Lake Shore Drive, or what Chicagoans call "The Outer Drive"...&nbsp\\;
&nbsp\\;
Moe Taters
 
Reply
Old Jul 6, 2008 | 10:37 AM
  #7  
silent1's Avatar
silent1
Road Warrior
15 Year Member
Liked
Loved
Community Favorite
Joined: Sep 2007
Posts: 1,584
Likes: 52
From: Here and there
Default RE: Chicago Digs

Agree with the poster above. Forget staying downtown unless you want to shell out over $200/night for a room. The rates in the suburbs are a little cheaper, but will still run you over $125/night.

If you're doing Rt 66, you might want to try staying in Joliet. Should be cheaper there, and you'll avoid a lot of the Chicago traffic.
 
Reply
Old Jul 12, 2008 | 11:10 AM
  #8  
marvincbr's Avatar
marvincbr
Road Warrior
Joined: Dec 2006
Posts: 1,321
Likes: 12
From: Shorewood IL
Default RE: Chicago Digs

I would be interested in you travels. I am trying to put together a trip to do the same thing (next year hopefully). My trip would start from the Joliet area, as I am there already and have traveled most of the old 66 route between here and Chicago anyway.&nbsp\\;
 
Reply
HD Forum Stories

The Best of Harley-Davidson for Lifelong Riders

story-0

7 Times Harley-Davidson Chucked Tradition Out the Window

 Verdad Gallardo
story-1

7 Surprising Harley-Davidson Products that Are Not Motorcycles

 Verdad Gallardo
story-2

8 Best Harley-Davidson Motorcycles Ever

 Pouria Savadkouei
story-3

10 Worst Harley-Davidson Motorcycles Ever

 Pouria Savadkouei
story-4

Killer Custom's Jail Break Is The Breakout That Refused to Blend In

 Verdad Gallardo
story-5

Crazy Bunderbike Build Looks Amazing, But Is It Impossible to Ride?

 Verdad Gallardo
story-6

Harley-Davidson Reveals Super Cool Cafe Racer Concept

 Verdad Gallardo
story-7

Engraved Rebellion: Inside Bundnerbike's Glam Rock II

 Verdad Gallardo
story-8

10 Motorcycles You Should Never Buy

 Joe Kucinski
story-9

10 Things Harley-Davidson Needs to Fix in 2026

 Verdad Gallardo
Old Jul 12, 2008 | 11:13 AM
  #9  
marvincbr's Avatar
marvincbr
Road Warrior
Joined: Dec 2006
Posts: 1,321
Likes: 12
From: Shorewood IL
Default RE: Chicago Digs

Trying to post is becoming such a pain!
 
Reply
Old Jul 12, 2008 | 11:15 AM
  #10  
marvincbr's Avatar
marvincbr
Road Warrior
Joined: Dec 2006
Posts: 1,321
Likes: 12
From: Shorewood IL
Default RE: Chicago Digs

&nbsp\\;Will you be keeping in touch with the forum as you ride?&nbsp\\;
 
Reply
Related Topics
Thread
Thread Starter
Forum
Replies
Last Post
anubisss
Road Trips
6
Nov 4, 2009 03:19 PM
skydrifter
Road Trips
4
Apr 30, 2009 06:20 AM
msgtarmor
General Harley Davidson Chat
14
Feb 24, 2008 08:19 PM
Realeme99
General Harley Davidson Chat
8
Feb 5, 2008 06:28 AM
Fandango6
Road Trips
3
Mar 12, 2007 09:57 PM




All times are GMT -5. The time now is 07:13 PM.

story-0
7 Times Harley-Davidson Chucked Tradition Out the Window

Slideshow: Harley-Davidson built its reputation on nostalgia, but every so often, the company took a hard left turn into the future.

By Verdad Gallardo | 2026-05-20 11:18:19


VIEW MORE
story-1
7 Surprising Harley-Davidson Products that Are Not Motorcycles

Slideshow: The bar-and-shield logo shows up on far more than motorcycles, some of the company's most unexpected products have nothing to do with riding.

By Verdad Gallardo | 2026-04-29 16:50:35


VIEW MORE
story-2
8 Best Harley-Davidson Motorcycles Ever

Slideshow: Not every Harley gets it right, but these are the ones that genuinely earned their reputation.

By Pouria Savadkouei | 2026-04-15 14:23:21


VIEW MORE
story-3
10 Worst Harley-Davidson Motorcycles Ever

Slideshow: From the troubled AMF years to modern misfires, these bikes earned reputations for reliability issues, questionable engineering, or disappointing performance.

By Pouria Savadkouei | 2026-04-01 20:01:09


VIEW MORE
story-4
Killer Custom's Jail Break Is The Breakout That Refused to Blend In

Slideshow: Killer Custom's "Jail Breaker" build focuses more on stance and visual aggression than mechanical overhaul.

By Verdad Gallardo | 2026-03-18 19:20:32


VIEW MORE
story-5
Crazy Bunderbike Build Looks Amazing, But Is It Impossible to Ride?

Slideshow: The Swiss custom shop has taken a Harley Softail and stretched it into something so long and low that it looks closer to a rolling sculpture than a conventional motorcycle.

By Verdad Gallardo | 2026-03-07 16:15:30


VIEW MORE
story-6
Harley-Davidson Reveals Super Cool Cafe Racer Concept

Slideshow: Harley-Davidson's new RMCR concept revives the café racer formula with modern hardware-and it may be exactly the reset the company needs.

By Verdad Gallardo | 2026-03-04 12:23:37


VIEW MORE
story-7
Engraved Rebellion: Inside Bundnerbike's Glam Rock II

Slideshow: A standard cruiser becomes an intricate metal canvas in the hands of a Swiss custom house known for pushing Harley-Davidson platforms far beyond their factory brief.

By Verdad Gallardo | 2026-02-24 18:19:44


VIEW MORE
story-8
10 Motorcycles You Should Never Buy

Slideshow: There is no shortage of great motorcycles to buy, but we would avoid these ten.

By Joe Kucinski | 2026-02-19 14:50:51


VIEW MORE
story-9
10 Things Harley-Davidson Needs to Fix in 2026

Slideshow: Harley-Davidson's challenges aren't abstract; they show up in dropping shipments, shrinking dealer traffic, and strategic decisions that aren't yet translating into growth.

By Verdad Gallardo | 2026-01-13 18:33:17


VIEW MORE