Chicago trip ideas

Pro tip: if you need to go south on the train fairly soon after the game, walk a few blocks north to the Sheridan stop. This allows you to get on the train and sit down before it rolls up to the stadium and gets crowded.
Years ago I lived 1 block south of that stop on Dakin. Good suggestion!
 
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Lot's of good suggestions and info in here.

Wrigley tour is still good on gamedays? Looking at it you miss out on a few things.
 
If you want to spend the extra time and money, I highly recommend Chicago Detours. Amanda, the founder of Chicago Detours, is awesome. I plan to hire her for a private tour with several colleagues who are meeting in Chicago for a conference in October.

 
I think one of my favorite things is all the bars/restaurants where the whole front is glass that can be rolled up or accordioned away and snagging a table right there next to the sidewalk. Nothing like getting a few cocktails and appetizers and people watching.
 
Is the Twisted Spoke still there? That's a fun one to hit up.
 
When I have time on the way North to a game I do this for breakfast and get off at Belmont and go to Ann Sathers. LOVE that place. Incredible cinnamon rolls.

Ann Sathers is a classic. Sweet Mandy B’s has great cinnamon rolls too. Better imo
 
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They apparently have major plumbing issues and don't want to pay the cost to fix it and they're closing before the City more or less does it for them.
 
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Chicago is expensive as we all know. So I will throw this out there, in addition to the many other great things listed in this thread. The city has a lot of great free art to experience. So if you like to wander the city and see different things. Use the below like to find some different experiences and wonder around, spend your money on the hotel, Cubs and food/drink. Let Chicago’s entertain you for free.


In addition to that there is a ton of stained glass that is in building you can wonder through. That’s a good free past time as well.
 
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I agree. I've done them countless times in my life. I love that ones that will also take you thru the lock to get onto the lake then come back.
Agreed. The river tour is freaking awesome. Wife and I loved it, but we like architecture and there’s some cool city history.
 
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Use SpotHero for parking. I can usually find parking close to where I want to be for much less than hotel or drive-up rates.
Tonight, I got parking for $29 total in the garage underneath the museum of contemporary art. One short block from Wster Tower Place. SpotHero is great.