Things to do in Chicago on a Layover

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Make sure you walk around under the Bean and look up. NorthShore gave me that tip when we were there one night. The effect is really cool. I almost fell over. :)
 
If you've never been to Wrigleyville, taking in Wrigley Field, even if just for the Stadium Tour if the Cubbies aren't playing, is a great way to see some of old Chicago. Ride the L ( Brown Line) and you also get a great view of the Skyline of the Windy City.

Lincoln Park, nearby, has a great Zoo if y'all are into Animals, but just walking around the park and the area on a warm Summer day is a treat!
 
You can walk around the Loop at night without worrying, especially during early evening like that. You'll be surrounded by tourists and other people out on a Saturday night. I've done it many times. It's fun to see people all dressed up for concerts, weddings, and fancy dinners. You could even venture north to the Gold Coast and Lincoln Park if you feel comfortable using maps/apps and public transit. The Hancock observation deck closes at 11:00, with the last elevator going up at 10:30. You'll be fine.
Agreed. I'd avoid bumming around South Chicago at night but tourists have no reason to be there anyhow. Just keep your wits about you like any other large city. It's not uncommon to encounter vagrants but it's rare to encounter violence in touristy areas. Keep your eyes open and tune your ears to your street smart voice and everything should be good.

I'm from Chicago and I have to say this repeated interest in skyscrapers and their observation decks is something I don't entirely understand--especially from folks who prefer to travel as close to the surface of the earth as possible.
Eh? I don't slither across the ground like a snake and sometimes I cruise above the clouds at FL400. We don't have anything like the Sears Tower or the Skydeck where I live so to me it's fun. That being said I don't understand the fascination with the Alamo or the Tower of the Americas either. Those things have always been here and don't seem that interesting to folks who live here. But those things aren't for us; they're for people who haven't seen it or had to drive around it a hundred times already.
 
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Lincoln Park, nearby, has a great Zoo if y'all are into Animals, but just walking around the park and the area on a warm Summer day is a treat!
Lincoln Park never gets enough credit in these discussions, either. Take the 151 from Union Station, down Michigan Ave, and get a view of the lake from the inner drive. It will drop you off right by the gate to the zoo (free.) In the summer, there are two beautiful gardens outside. The flower and tropical plant Conservatory is also right there.

Or you can go to the History Museum at North Ave, nearby. At Fullerton is the Peggy Notabert Nature Museum and butterfly garden. The beach is just across Lake Shore Drive. As is Theater By The Lake. Or take a little walk along Diversey Harbor.

Just a couple of blocks north are the Lions Club grand monument (check to see if it's open for inside tours.) As is the national shrine of St. Francis Xavier Cabrini. A beautiful big church, St. Clement, is a few blocks west. As are many other older historic churches. Around Lincoln Ave. (Near Halsted and the Fullerton Red/Brown Line Station) you'll find some great live theater and music, including the historic Biograph Theater building, where Dillenger was shot. Down Halsted are noted blues clubs.

De Paul University is also in this area, has some interesting buildings, culture, an art center, a music conservatory with live, free, performances. Check out the gorgeous historic houses here. You can even safely stroll through the alleys and see some cool porches and gardens.

Lets head back to North Ave. And the History Center. Walk a block west and you're at Second City. Take in an improv show. This is also historic Old Town. A walk through the neighborhood is well worthwhile. Go as far as the steeple and see one of the city's oldest churches, St. Michael's. Nearby, on Sedgwick just down the block from the L, is an historic bar and ribs place, Twin Anchors, where stars such as Sinatra have hung out. Indeed, there are plenty of excellent eateries in the area. Now, walk back to Welles Street. This was an eclectic, artistic area back in the 70s. It has mostly yuppified now, but there are still nice classic buildings, and all kinds of shopping/eating/entertainment business, including the noted comedy club, Zanies.

If you're not to tired to walk, go up to State Street, on North, and see the archbishop's mansion. Then saunter along State and Astor southbound to see historic houses of the Gold Coast. As you near Division street and its bars, you might happen across the Pump Room, where all the stars once came to drink and dine on their over night layovers between trains.

You may choose to head east back to walk along the busy lakeshore path as far as the Drake hotel. Or, if you continue instead to Rush Street, make sure to go as far as Pearson, just a block short of Chicago Ave. There you will behold a beautiful gothic building, which once housed the high school I attended. If you're there sometime early Saturday, or on a non summer Sunday around seven, you might even be able to visit the chapel, a copy of a historic Paris church with stunning stained glass.

Across the street is Lewis tower, downtown home of Loyola University.

From here you'll surely see the historic water tower. Across the street, in the accompanying pumping station, is a visitor's center, a live theater, and hottix (where you can purchase discounted tickets to all sorts of theater.)

NOW you can visit the Hancock building, if you need a nightcap, which is just a block away.
 
I'd avoid bumming around South Chicago at night but tourists have no reason to be there anyhow.
You do realize just how far from the downtown area and Union Station that is, don't you?

Given, there might be some particular reason someone would be in certain areas (which can even be dangerous days.)

And there are, clearly, parts of the south side which are just fine and worth visiting (Hyde Park/University of Chicago/Museums, Bridgeport/White Sox/Arts Centers, Pullman, for example.)

Similarly, one might suggest avoiding the west side, for safety reasons. But one can certainly go most places, safely west at least to Ashland. And there's no serious threat in taking the L to the Garfield Park Conservatory. Or joining the many commuters who ride through these parts to see interesting sites in Oak Park.
 
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Manny T and NorthShore, good ideas from both of you. For some reason, granddaughter has a fascination with high places. Maybe because her mom won't let her fly! We have been in the Sears tower and the Space Needle. During our trip in June, we will tour the Empire State Building and the Washington Monument, although I'm trying to convince her the old post office building in DC has views almost as good as the monument without the long lines.

While in Chicago, we also plan on a water taxi ride, looking for the beginning of Route 66, and seeing cloud gate.

Her idea of gourmet food in Chicago is giordanos pizza and Carmel corn from Nuts on Clark. (OK, that's my idea, too)!

Keep the ideas coming. I love it!
Re Washington Monument, I think you can get a timed ticket online. We did that over 10 years ago.
 
I'd avoid bumming around South Chicago at night but tourists have no reason to be there anyhow.
You do realize just how far from the downtown area and Union Station that is, don't you?
Would be a heck of a walk or a relatively quick ride on the train. Or at least that's my memory of it.

Well, if you like high places, and have disposable cash you could always consider a helicopter tour.
I think Micki's mom would put a restraining order on Patti if she did that. If she won't let her daughter fly, she sure will not want her in a helicopter.
Is this an inside joke or is this based on some sort of emotional anti-vaxxer pseudologic?
 
Well, if you like high places, and have disposable cash you could always consider a helicopter tour.
I think Micki's mom would put a restraining order on Patti if she did that. If she won't let her daughter fly, she sure will not want her in a helicopter.
Is this an inside joke or is this based on some sort of emotional anti-vaxxer pseudologic?
See Patti's post (#50). I did not see hers before I posted mine, just worded mine differnetly than she did. Yeah, you could say it's an "inside joke", though Patti has made this fact known publicly here on AU, which is how I knew.

NorthShore, if I took Miki on a helicopter ride, her mom would never trust me with her again. I'd lose all "grandma privileges". (also there's no disposable income around here, which is why this might be our last long distance train trip).
 
You might lose all grandma privileges. But she would remember you and the experience FOREVER! You'd be LEGENDARY!

(And, hey, if it's your last trip, anyway....)
 
We had planned a taxi ride to check out the Handock tower, but it was too foggy/cloudy. So my wife spotted a "Museum of Blues" at 205 Michigan on Google. So we walked there. No museum, and the lady at the desk said we were not the first visitors to look for it. The museum that never was? We has a nice walk and stopped at the Marq for a burger on our way back. Still turned out ok.
 
I'll second the river architecture tour; my Chicagoan friend took me last summer and insisted it was the only "touristy" thing actual Chicagoans enjoyed as well. It was neat!
 
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