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Going to Chicago...

Wrigley Field, tour of Soldier Field (limited), Navy Pier (just for the history), drinks in the lobby bar at The Palmer House, nice to stay there too, dinner at Gene & Georgetti's, dinner or drinks at the Signature Room, 95th floor, John Hancock building, and an evening at Buddy Guy's Legends, if you like blues.
 
If I was going to Chicago, I'd want a close-up look at the Cloud Gate sculpture.

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If you like any blend of music or history, you should check out The Green Mill -- the iconic jazz venue (not the pizza chain). It has been running since jazz was a thing. Its Uptown location isn't out of your way if you're driving Lake Shore Drive, and it's also near the Red Line.
The club itself is marvel: the interior hasn't changed much since it was owned by Machin-Gun Jack McGurn, one of Al Capone's thugs. Capone himself had a private booth here, and used an escape hatch behind the bar when the joint got raided (the trap door is still there).
The jazz is still top-notch. The last I checked, Thursday was swing night, with a full-on big band. You'll swear you were transported back to the jazz age.
You'll avoid a cover charge if you get there early (if that matters to you).
 
Ah! Hadn’t thought about that! We did the Fenway tour a few years back.
Wrigley Field tours area daily regardless if the Cubs are home or away. On game day the tours are not as extensive,ie, no locker room visits.
It’s an easy place to get to as well. Just hop on the El or subway downtown (going northbound)and get off at Addison. Then 2 minute walk from station. Parking in Wrigeyville is scarce and $$$$$
 
A few other Chicago gems:
  • Union Station - the stairway is famous for the shootout scene in The Untouchables. Just west of the Loop, near the Sears Tower (sure, it's technically the Willis Tower, but really...)
  • The Art Institute all by itself is worth a trip to the city, but even before you enter...
    • look up at the names engraved on the exterior: Donatello, Michaelangelo, etc... The creators of the Teenage Mutatant Ninja Turtles were sitting in a restaurant across from the institute trying to come up with names for their characters... they looked at the front of the building... and there they were!
    • look down at the intersection: Michigan & Adams is where Route 66 began;
  • Rosa's Lounge is a bit off the beaten path (northwest side of the city) but it's arguably the most authentic Chicago blues club still around (if your measurement of authentic is the spot where blues artists go to hang out & jam after they play gigs at Legends, Kingston Mines, etc.)
  • Merz Apothecary in Lincoln Square has been mentioned and, and even though the shaving selection has been shaved a bit lately (sorry), it's still a great selection with tons of testers. (Hey, even if you don't buy anything, how many places are there where you can check out the scent/texture of so much soft ware you may have wondered about without actually buying it?) Totally worth a trip if you're in the neighborhood. Speaking of which...
  • Malt Row is a burgeoning scene of craft breweries roughly stretching along the Ravenswood corridor on the North Side. If this is your thing, start with Begyle for your ales and Dovetail for some well-executed lagers and other Old World styles. They're just a block apart at Irving Park & Ravenswood.
 
The Art Institute Museum is worth a week on its own. I never understood why anyone would pay millions of dollars for a painting until I stood in front of Monet's Water Lilies, they look like you could swim in them. And the painting of St. Peter (?) praying, on the second floor just over the lobby, is breathtaking. As are so many more things there...

I suggest the Frontera Grill, on Clark Street - it's about the best Mexican food you'll ever have (the owner was invited to prepare the main course at the White House when the President of Mexico was visiting).

I dig the deep dish pizza at Ginos East.

And there's a great music scene, of course. Check out the schedule at Buddy Guy's, or any number of jazz clubs.
 
If you like any blend of music or history, you should check out The Green Mill -- the iconic jazz venue (not the pizza chain). It has been running since jazz was a thing. Its Uptown location isn't out of your way if you're driving Lake Shore Drive, and it's also near the Red Line.
The club itself is marvel: the interior hasn't changed much since it was owned by Machin-Gun Jack McGurn, one of Al Capone's thugs. Capone himself had a private booth here, and used an escape hatch behind the bar when the joint got raided (the trap door is still there).
The jazz is still top-notch. The last I checked, Thursday was swing night, with a full-on big band. You'll swear you were transported back to the jazz age.
You'll avoid a cover charge if you get there early (if that matters to you).
Excellent! I wasn't aware of this spot! Will definitely consider it! Thank you!
 
And thanks for all the other insight and suggestions. I am looking forward to checking out as many of these spots as possible! We are interested in it all: sports, food, art, music, architecture, beverages, and, I must confess, the shaving stuff. Maybe this'll be where I pick up that first puck of Haslinger Schafmilch.
 
Wrigley Field tours area daily regardless if the Cubs are home or away. On game day the tours are not as extensive,ie, no locker room visits.
It’s an easy place to get to as well. Just hop on the El or subway downtown (going northbound)and get off at Addison. Then 2 minute walk from station. Parking in Wrigeyville is scarce and $$$$$

Thankfully, we will be doing no driving. Even if we just get to Addison and Clark, I'll be happy.
 
Thankfully, we will be doing no driving. Even if we just get to Addison and Clark, I'll be happy.
If you make it to Clark & Addison it’s all changed now since Ricketts purchased the team. They built a big park on the Clark St. side to go with all the other eating/ drinking establishments in Wrigleyville. It’s like party central on game days.
 
Just had a second to check the Cubs' schedule. They will have finished a long homestand when we arrive. We'll still head over and check out the stadium.
 
...for the first time (other than O’Hare connections). Looking forward to a few days discovering the city. Staying close to the Oak Street Beach. We are probably going to the Field Museum, Art Institute, and Aquarium. What are the must sees and dos in Chicago? Food and drink tips? Might check out Merz Apothecary, but my shaving coffers are pretty full. Planning on a run or two on North Shore Drive and a swim in Lake Michigan. Any tips on enjoying this huge city appreciated!
If y
 
If you like popcorn, find a Garrett's popcorn shop and try their Garrett's Mix. Or even just the cheese popcorn alone. Freshly made, nothing beats it in my mind!
 
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