Chicago station layover

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Something I enjoy doing is picking up either breakfast or lunch to go and sit in one of the parks to watch the lake and the boats. You absolutely want to be inside at a hotel for the night. The Willis/Sears tower will be packed with very long lines if it is worth going to the top for the view. During the day, I enjoy walking over to Michigan Avenue, but I am a walker, just love stretching my legs. Do suggest you have a map of the downtown streets with you either on your phone or printed out. There is so much to see and enjoy without spending much. Walking Michigan Ave (Wrigley Building, the Chicago River, over a mile of shops and restaurants), there are the parks like Grant or Millennium (Giant Bean you see in so many people's pictures). Again, I love to walk, there is so much to see and not spend anything much except food. Another thing I do is walk off to see the sights then if tired or is really late, I spring for a taxi to take me back.
 
If you want to do more northernly Chicago city stuff (like Lincoln Park) or the HI is full I've also had many good stays at the Chicago Getaway Hostel.
 
Everyone worships the Sears Tower (and it IS a lot of fun), but I actually prefer the view from the Hancock Building, especially at night.

The observation deck at the Hancock is only eight stories shorter than the one at the Sears Tower, which isn't a huge difference, and the lines are MUCH shorter. The Hancock is about the same price ($19 vs. $19.50).

If you want to get the same view at a discount, just head up to the Signature Lounge and buy a cheap drink. ;)

Plus, I think the architecture is cooler in general, and it's on Michigan Ave. You could check out the shops and sights along Michigan and then end there. It's a nice way to cap the evening.
 
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Or at Lunch do the buffet lunch (we eat bigger at lunch when traveling since it saves money) and spend an hour next to the floor to ceiling windows, then head up to the lounge afterwards. Wives always want to drag their husbands into the Woman's Room on the Lounge Level to see the window with its view.
 
I'm going to have to stop saying thanks so much but you all are giving me such wonderful ideas and they are SO appreciated.

I've been to Sears Tower, but I'm not much for heights. Plus I'm more of a day than night person, so walking around is more my thing.

Glad to have another hostel in my pocket, Kat314159 - thanks for that. A hostel sounds perfect for me.

Lonestar648, I am like you, I love walking, watching and sight-seeing. Def plan on having maps, street guides, reservations, and notes I am keeping from these forums.

SaraZ I love looking at architecture, too, and walking around looking at beautiful Chi town from street level def sounds more fun. I've been there before on business years ago, but it was in and out, van to hotel to gig to hotel to van and gone.

Lastly, yes Ronbo I have to avoid extra legs on my rail pass. With my other stops I am already close to my limit and I want to hold one back in case of... whatever.

It prob doesn't need to be said, but this trip is a healing one for me after a very long struggle. Enough said. With all your ideas, and so many months to save, there is no excuse for me not to take trips like this more often. I'm so glad Chicago was suggested, and I'm not sure now why I was trying to avoid the layover when it's quickly becoming another leg of a very cool trip.
 
If you love architecture, definitely take one of the Wendella Boat Tours. :) I've been to Chicago countless times, but seeing it from the river made it look completely new again.

The Chicago Architecture Foundation offers cruises and walking tours as well.

Edited to add: I just realized you said "early spring". Depending on how early in the spring you come, the boat tours may not be running yet. I think they start in mid-March.
 
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The Willis/Sears tower will be packed with very long lines if it is worth going to the top for the view.
The city pass allows you to avoid the wait and cut to the front of the line, but it's only a good value if you're short on time and plan on visiting the majority of included attractions.

Everyone worships the Sears Tower (and it IS a lot of fun), but I actually prefer the view from the Hancock Building, especially at night. The observation deck at the Hancock is only eight stories shorter than the one at the Sears Tower, which isn't a huge difference, and the lines are MUCH shorter. The Hancock is about the same price ($19 vs. $19.50). If you want to get the same view at a discount, just head up to the Signature Lounge and buy a cheap drink. Plus, I think the architecture is cooler in general, and it's on Michigan Ave. You could check out the shops and sights along Michigan and then end there. It's a nice way to cap the evening.
The suspended cubes along the side of the Sears Tower are an awesomely mind numbing experience that I have enjoyed every time I've visited. The only problem is that it's hard to get the clueless teens who bogart the cubes out of the way long enough to fully appreciate it. As for the Hancock we have some history between us. I also have some bad blood with the Rookery, but I digress. Anyway, I went to the Hancock with a couple friends one night and we asked for a table with a view. Our first round of drinks and appetizers was a seemingly respectable $50. I had budgeted much more for the entire bill but the management were apparently incensed that we didn't immediately order from the rather lackluster entree selection and kicked us out. I'm no stranger to running up high bills in bars, restaurants, and hotels all over the world so being kicked out for lack of sufficient spending was a first for me.

It prob doesn't need to be said, but this trip is a healing one for me after a very long struggle. Enough said. With all your ideas, and so many months to save, there is no excuse for me not to take trips like this more often. I'm so glad Chicago was suggested, and I'm not sure now why I was trying to avoid the layover when it's quickly becoming another leg of a very cool trip.
I have a bit of a love-hate relationship with Chicago myself, but I wouldn't want it any other way, and truth be told I continue to avoid Chicago during the winter. When I was younger I probably could have handled it but these day's it's too cold and too windy for my warm weather skin. Feels like a sandblaster against my face. Anyway, I hope this trip hits the spot.

If you love architecture, definitely take one of the Wendella Boat Tours. :) I've been to Chicago countless times, but seeing it from the river made it look completely new again. The Chicago Architecture Foundation offers cruises and walking tours as well.
Agreed. I've taken multiple boat tours from different operators and ended up enjoying all of them for one reason or another. I wonder if there is a way to simply rent a pleasure craft and make your own tour.
 
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The cheapest place to eat within walking distance of CUS is Pierogi Heaven which is a hole in the wall place underneath the El north and east of the station.
Oh, I've gotta try this place!
Ditto! On the way home from the Gathering I'll head over there and chow down!
 
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