Huey123, since you are visiting us in the balmy south (compared to MN, that is), I've got a few suggestions for you.
First, you shouldn't get the idea that the "downtown" of Chicago is where all the action is - because it's not. Each neighborhood has it's own "atmosphere" and there is a lot going on in them.
With that being said, here's a few suggestions:
The City of Chicago usually has special activities planned for the weekends (and throughout the weeks) at that time of year. I'd recommend that you check their website to see what is going on when you are here.
If your daughter enjoys listening to jazz, I'd recommend that you two go to the Green Mill in Uptown (take the Red Line to the Lawrence stop - 1 block away). On Sunday evenings, they have the Uptown Poetry Slam, as well.
If you both enjoy international music (including blues and jazz), take a look at the HotHouse on Balbo.
If you like blues, Buddy Guys Legends. Buddy Guy himself is usually there sometime during the month of January.
Also, Pops for Champagne just opened up in the River North neighborhood at the historic Tree Studio building recently. Nice place to enjoy jazz as well.
And take a look at the Old Town School of Folk Music in Lincoln Square as well - they have very interesting acts.
Agree totally with the Art Institute. It's free admission on Thursday evenings 5pm - 8pm, by the way.
If the weather isn't too frigid, there is ice skating at the McCormick Tribune Ice Rink in Millennium Park, just north of the Art Institute.
I don't mention it enough, but check what is going on at the Harris Theatre at Millennium Park. Really good venue with wonderful acts - ballet, classical, etc.
You might want to go to a comedy club - maybe Second City or the I/O for improv or Zanies for stand-up comedy - but there are several others in town.
Now, if you are sports fans, I'd recommend that you stop in at Ditkas one of the evenings. Da Coach is often there greeting customers and there is a singer who does great Sinatra certain evenings of the week. Take a look at their website.
Now for restaurants (starting with the most expensive to the least expensive): For something really special, one of the best restaurants in town, Tru, has a dessert-tasting menu for $25. Reservations are required, appropriate dress. Next, for a wonderful special dinner, North Pond on the north edge of the lagoon in Lincoln Park, is just a beautiful place (take a look at the menus online for prices). I'd also recommend Aria (in the Fairmont on N. Columbus) for international fusion spin on comfort food. A La Turka on N. Lincoln has great Turkish food and bellydancers certain evenings (and hookahs, if you wish). Tango Sur in Lakeview on N. Southport is an Argentian steakhouse with live music on Thursdays - no reservations and BYOB - and Cullen's (an Irish bar) right next door has good entertainment every night of the week. Smoke Daddy has BBQ and the blues. Duke of Perth in Lincoln Park has all-you-can-eat fish n'chips on Wednesday and Friday evenings for under $10. For breakfast with unique offerings, try Orange (original location is on Clark and there is a second location in the South Loop on Harrison).
Turning 21 is a right of passage, and probably one of the last birthdays you will be genuinely excited for! So doing it in a city like Chicago, you have to do it right. So here’s a list of 21 things to consider for some inspo on your special day!
1. Buy your first (legal) drink!
You might want to do it at the stroke of midnight, but I’m a sleeper so I had a mimosa at Brunch. I’m Classy.
Courtesy Giphy
2. Have a great best friend.
Mine took a train all the way here just to celebrate with me. She’s amazing.
3. Buy the big 21 balloons.
It’s cheesy but you can celebrate your birthday for the rest of the month with those puppies. Or you can suck the helium out at the end of the night. Whatever you want.
4. Take pictures with the balloons at Chicago landmarks!
I am figuring at this point you will be slightly buzzed, so taking pictures in front of the bean won’t feel that weird and people love saying happy birthday!
Photo courtesy Tara Woods
5. Buy a shot glass.
You will want one to commemorate your big day!
6. EAT!
This is a big one- if you’re tryna get smashed the whole day you need to eat so you don’t die.
7. Write a letter to your 30-year-old self.
Mine consisted of what I think I’ll be doing, what my goals are now and just a reminder of who I am at 21.
8. Make a toast!
When you’re out with your bestie make a toast with some cheap champagne! (We’re all poor, I know).
Courtesy Giphy
9. Bar hop.
I made it to seven (SEVEN!) bars in the night.
10. Try a new drink at every place.
This might make your stomach upset, so try to keep with liquor and then beer.
11. Take activated charcoal!
Remember my amazing best friend? She taught me that taking activated charcoal when you’re drunk can help you not get sick the next day!
12. Hit up a drag bar!
I ended up at the Baton Show Lounge, and it was the most fun I had the whole night. Those ladies make sure you have the most fun possible!