I would suggest taking the architectural river cruise. Fantastic....

Adler planetarium. Navy pier. Grant park (remember our guy!)

Ukrainian National museum.

Walk the waterfront and miracle mile.

Ride the L for fun and views.

What do you enjoy? Chicago is a great city with many everythings for all.

and I have been there a good 30 times. It is a great city. My wife asked me what do you want to do. We usually stay up on Wacker.
No trip to Chicago is complete without dinner in Greek town.

Shedd Aquarium has some beautiful displays, and it is indoors. I am poorly educated in art, but the Chicago Art Institute features artists so famous that Ninja Turtles were named after them! Have fun! (My cousin lives in Chicago so I have visited many times.)

If you are fans of Live comedy, Chicago has more comedy, clubs, than people. Zanes, Laugh Factory, 2nd City, and iO are places to consider. Kingston Mines and Buddy Guy Legends are good places for Chicago blues.


And if either of you are baseball fans, and the Cubs are in town on a trip to Wrigley is always worth it

I used to live above a Chinese grocery on Canal Street in Chinatown, while working at Steppenwolf.
Long ago, when I was ever so much younger than I am now!

Cloudgate (aka the Bean), Crown Fountain, and more.

Ride Dough Force One (believe it is still around) and sample numerous Chicago pizzas.

We did a great Seway tour years ago of the Lakefront/Grant Park and Museum Campus. It is great fun and you get a great overview of this gorgeous part of the city, and can cover so much ground. Just pick a place that keeps the groups small - those make sure you really know how to ride it before the tour heads out.

The view from Hancock observatory is fabulous, but you can opt instead of paying for observatory, go to the bar which is nearly as high up and still get the views.

Already mentioned above, but I will second that the Architectural River boat tours are great.

A lot of great suggestions. We appreciate them all. There's really so little to do that we like in this small city we're in (other than parks and get togethers with friends), I'm sure we'll fall in love with all Chicago has to offer!

I honed in on the Architectural River boat tours. Those sound really interesting.

Thank you everyone!

Try the Green Mill for Jazz, just a couple of blocks from the Red Line Station. Bring cash, there is a small cover charge.
Take a noon tour of the Chicago Theater on State Street---great tour!!!

....one of my favorite bars in chicago.

Try the Green Mill for Jazz, just a couple of blocks from the Red Line Station. Bring cash, there is a small cover charge.
Take a noon tour of the Chicago Theater on State Street---great tour!!!

You might want to walk a couple blocks north to check out the 'French Market' in lower level of Ogilvie station.
It's kind of a food hall - many varieties of meals to be had (ethnic, etc) or shop for fancy cheeses, sweets, wines, etc - stuff that you could enjoy there or take for later enjoyment. Has a busy kinda festive vibe.

for an entire afternoon! (LOL) cheese, wine, and sweets.... with my sweetie!

Is Illinois a legal state for pot, btw?

Dispensaries everywhere.
And, as supply has risen to demand prices have fallen significantly in the past couple years.
Flower is

....art institute as well.

on the NW side of town, on the corner of milwaukee and nagle and devon, there is an old drive thru hot dog stand called superdawg. go have a chicago hot dog there....you'll thank me.

There is NOTHING I have ever seen like Lakeshore Drive!

I would suggest taking the time to hit the Aquarium and the Museum of Science and Industry. Adler Planetarium is also pretty cool. This time of year Navy Pier is not as exciting as it is in the summer, but it is a Chicago landmark.

I do want to warn you that the wind coming off Lake Michigan really is a lot colder than you might expect. Seriously. There's a reason why Chicago natives have the reputation for grilling out in the winter. That wind makes 'em tough!

Have fun!


Laura