I have a co-worker who came to Chicago on business trip, and unfortunately does not have the opportunity to spend a weekend here. I would like to take her to downtown (she is staying in Skokie area) for at least several hours. We can leave work around 4:00 pm, and it would probably take us about 45 minutes to get to downtown (on 94), so it will be pretty dark by then. What is the best time to spend a few evening hours in the city? She is from Memphis, and it is her first time in Chicago. I am thinking to briefly stop by State street to see the tree and the area, then stop by Millennium Park, then go for a walk along Michigan avenue followed by the dinner at Gino's East. I would love to incorporate the drive along the Lake Shore Drive somehow. I can't figure out the logistics with the parking. It looks like I may need to re-park like 3-4 times, which will get too expensive. Any other ideas or suggestions?
Thanks in advance for you invaluable help!

Helen63, do you think that 45 minutes will suffice for driving into Chicago during rush hour?

However, since you are driving, here is my suggestion:

Drive into Chicago and park on the north side somewhere around Belmont. (You might just find a parking place on N. Broadway if you aren't too late getting into Chicago -and there is a parking garage at Hawthorne Place/Broadway, right next to the Best Western Hawthorne Terrace, if not.) Then take the #145 or #146 SB CTA bus from the Belmont bus stop on Sheridan.

NOTE: If you park in the parking garage at Hawthorne Place/Broadway - all you have to do to catch the above busses is walk one L-O-N-G block east on Hawthorne Place to Sheridan (aka inner Lake Shore Drive). This is a historic area with large, beautiful houses - decorated for the holidays at this time of year. There is a bus stop at the southwest corner of that intersection.

The bus goes non-stop down Lake Shore Drive to Michigan Avenue - so you get the drive down LSD - then it continues south to State Street via Wacker.

You can see the windows on State; walk east 3 blocks to Millennium Park. Then I'd take any of the busses from the bus stop at Randolph/Michigan up to just north of the Chicago River and get off at the Tribune Tower. Walk north on Michigan Avenue to the John Hancock Building and go to the Signature Lounge on the 96th Floor for drinks.

Are you sure that you want to go to Gino's East for pizza? There are so many other choices available. If budget wasn't of concern, in fact, what I'd do next is after the drinks go to ZooLights at the Lincoln Park Zoo for a short while, followed by dinner at North Pond. But, of course, this is pricey and may not fit in with your plans. But I'd still try to fit in ZooLights to cap off the evening - it's free and beautiful.

Then you just have to reclaim your vehicle on the northside. (You can take a cab back to wherever it's parked to save some time.)

If you were looking for something a little different in the pizza department, Chicago Pizza and Oven Grinder is only 2 blocks west of the Lincoln Park Zoo on N. Clark Street. Easily walkable; although there may be wait lines if you go later in the evening. Cash only.

Tell your friend it's right across the street from where the St. Valentine's Day Massacre happened, too.

Helen63, if you're starting in Skokie what about taking the train downtown? You could catch the Yellow Line from Dempster to Howard, then transfer to the Purple Line to downtown. It runs express from Howard to Belmont, then local to the loop. Your co-worker could experience the "L" and unlike the Red Line, would see the city as you approach.

You could also park at the CTA garage at Howard and pick up the Purple Line there. The cost at either Skokie or Howard is $2.

On the way home, you could catch the Number 147 bus anywhere on Michigan Avenue north of Randolph. It runs express on Lake Shore from Oak Street to Foster and ends at the Howard Terminal. The last Yellow Line leaves Howard at 10:00.

If you opt to follow exiledprincess's plan and drive, just a couple words of caution. If you park on the street, read the signs carefully for rush-hour or resident-only restrictions. Also keep in mind that most of the meters in that area have a 2-hour max and are enforced until 9 pm.

A couple of the better areas to find unmetered spots are the west side of Lake Shore Dr from about W Sheridan south to around Cornelia (the east side of LSD has no parking during evening rush) or Clark between Waveland and Irving Park.

Don't drive on 94 at that hour - take Lake Shore Drive in and you'll catch the last glimpses of the skyline as the sun sets. Exit at Monroe Street, turn north on Columbus and park your car in the Millennium garage.

From there you can walk a few blocks west to Daley Plaza for the tree, see State Street, then head north past the Chicago Theatre to Wacker Drive and Michigan Avenue, ending at whatever restaurant you decide on. Walk back straight down Michigan; if you are too tired for the walk, a quick cab ride will do.

To be honest, I had thought about mentioning to helen63 to take the train in, but I figured that she and her co-worker would get into Chicago closer to 5:15-5:30pm than 4:45pm; and that would leave them only a little more than 4 hours for what they wanted to accomplish (including dining).

Re: the Sheridan suggestion and other major streets. helen63 needs to be aware that Sheridan (Clark also?) is a snow route and woe to anyone who parks there when it's being enforced. That's why I mentioned along N. Broadway - as well as the parking garage at Hawthorne Place/Broadway. Problem is that on N. Broadway in this area, if helen63 gets there after 5:30ish, it's unlikely she'll find any street parking for the evening.

Going south on Lake Shore Drive into the Millennium Park area. There usually is bad traffic back-up from just north of Fullerton to Oak and past on LSD (reverse commute problems, you know) starting about 4:15-4:30 pm at the latest. And it lasts until 6:15-6:30 pm-ish. even later. See it all the time. That's why I mentioned only driving as far as Belmont.

Thank you so much for all suggestions! Great ideas as always, and the best information!
I did not want to expose my co-worker to the Chicago public transportation too much, so that's why I was thinking of driving. I think we will end up taking the train to downtown, then use some of your ideas for the sightseeing, and then have my husband pick us up, and maybe take LSD back on the way to the suburbs.
Thank you so much again for your help!