Things to do in Chicago

Son has lived in Chicago for five years.
Boat tour is ultimate memorable Chicago experience.
Willis tower, touristy experience, and hancock tower gives you sweeping views ( be sure to go into women’s bathroom for that view)
Adler planetarium, not that exciting, but the walk, along lake back to millenium park, worth it. In fact, many bridal parties were at planetarium having photogrhers take pics with famed Chicago skyline.

Art musuem a highlight, but for unique Chicago memories , outdoor activities encouraged.

“Northwestern is quite a bit north of the city. In that part I’d suggest: Chicago botanic gardens ( in Glencoe) , Ravinia music Festival ( highland Park) Old Orchard ( a beautiful outdoor mall)”

It’s the first suburb north of the city, not quite a bit north. The drive up Lake Shore Drive / Sheridan Road is pleasant.

Old Orchard Mall is a perfectly nice upscale mall - but why would you come to Chicago to visit a mall that has the exact same stores as everywhere else? Like the OP can’t find the Gap and Ann Taylor and Bed Bath and Beyond elsewhere? This is not a tourist destination. If you’re coming to Chicago to shop, then go downtown, not to an unremarkable suburban mall that is identical to what can be found in any city.

“He doesn’t think our plan to go to Oak Park and see Frank Lloyd Wright’s House & Workshop is a good one, as he says the houses are spread throughout the area.”

Himom, the Home and Studio and The Unity Temple are walkable distances within in Oak Park. The neighborhood also has several easily walkable homes. They used to have maps at the studio, I’m sure they still do and they offer tours of the neighborhood, very easy walking. View is from outside the homes as these are privately owned. The Foundation offers several tours that are excellent. The Studio and Unity Temple is worth a visit, but check tour availability and hours for your dates. Unity has reconstruction going on and may be closing to the public.

Public transport from ORD area is slow and multiple bus and trains required. I would rent a car. You can check with the concierge as to cabs, but depending on where you are staying, they may be surcharges, between Chicago address and many suburbs has additional charge. Might be possible but probably expensive, especially depending on time of day and traffic. (My tolerance for expensive cab rides in cities I’m unfamiliar with is high - others will think I’m crazy to even consider this as an option.) There are estimators like the World Taximeter that might give you an idea.

If you were going to try to get to the Hyde Park area (Museum of Science and Industry, Oriental Institute, Smart Museum of Art), the Frank LLoyd Wright’s Robie House is worth seeing. Inside by tours only. Tours are quite good.

Do we get any discounts if we buy public transportation card online ahead of time?

I think a lot of your plan is dependent upon weather. If you’re in downtown Chicago (Loop, Grant Park, Mag Mile, Millennium Park, etc.) and it rains - there are places for you to duck inside; you can go into one of the museums or just enjoy tea in a nice hotel. If you go to Oak Park to visit the FLW houses and it rains, you’ll be miserable and in an area without a lot to do (yeah, Oak Park has a downtown, but it’s not like it’s an OMG-must-see-downtown).

"You can check with the concierge as to cabs, but depending on where you are staying, they may be surcharges, between Chicago address and many suburbs has additional charge. "

Or just use Uber.

If I was taking someone to Chicago who hadn’t been there before, this is what I would do to give them “a brief taste”:

-Drive from the South Side (or at least The Loop) all the way up to Evanston (or at least to Lincoln Park) on Lake Shore Drive (then into Sheridan).

That must be a good idea, at least part of the way, because that’s the first thing they did with a guy I know when he interviewed in Chicago, and he was impressed enough that he took the job.(ok not just for that reason)

Stop briefly at the Magnificent Mile, just to see it, and in Lincoln Park. Walk in the park , by the beach, and through the zoo , and the zoo-rookery, if it’s a really nice day. (I used to live nearby, so I like to mosey around there). go inland, walk around, get an idea of what the neighborhood looks like.

If no car, get driven. Do the trip in a few segments. But if I was taking someone I’d be renting a car,.

  • Eat deep dish pizza . Someplace. Someone said Gino's East. I used to like Giordano's. That's one night. then maybe Greek Town another night. And I liked The Berghoff's sauerbraten and we don't really have good German food here, so I'd probably try to get them to go there for the third.
  • I know it's a chain, but The Original Pancake House was hugely popular there and I haven't happened to see one since I left.
  • I really liked the Art Institute.
  • ditto Second City
  • ,Maybe see a play, there was some good theater there. Or a Cubs game?

So that’s what I would try to do. But I haven’t actually lived there since the early 80s. When I’ve gone back I;ve done some variant of above, as time permitted. without the first-time touristy parts. So those things were still there to be done,l but that doesn’t mean there aren’t lots of better things now too.

Sadly mourn the passing of some of the places I liked that are gone:
Wise Fools Pub (too loud for me now anyway), Earl of Old Town, Busy Bee Diner,Belden Deli…

I was raised in Chicago, when we go back our culinary checklist is pretty low rent, but it’s stuff you can’t find anywhere else. There are multiple good sources for any of them (competition is fierce) so just ask a local. If you’re a vegetarian, I can’t help you:

  • Italian beef w/sweet peppers (get the hot “sport” peppers if you like it hot.)
  • Chicago hot dog “all the way” (warning: do not request ketchup or you may be asked to leave)
  • Pizza, the thin crust variety, with good sausage - not the thick crust stuff (we always called that “Sicilian pizza.”)

Even if you’re not a baseball fan (arguably, the Cubbies are marginally a baseball team) hanging out at the Cubby Bear across the street from Wrigley on a game day is the ultimate people watching experience. If you can do a game, even better.

The architectural tour via the Chicago River is a treat. (Moon the Trump Tower for me.) The museums are excellent, especially the Field Museum, but unless the weather is bad, I would pass, as it take a full day to explore each one.

Definite NO to Navy Pier. Touristy.

Millennial Park is great, gotta get the standard “bean reflection” picture. The entire lakefront is great for walking around.

The view from the Hancock Building is better that Sears (or whatever they call it now.)

There are many great neighborhoods, not sure what the current “hip” ones are but it’s fun to check them out. There is great shopping to be had everywhere, depends on what you’re looking for.

The drive south on LSD (Lake Shore Drive) if you’re coming from Evanston to downtown is lovely.

Yes to Second City in Old Town.

Lot’s of great music, Of course the blues clubs are legendary, but the Irish music scene is big in Chicago and the pubs are a blast.

Have fun, best thing to do is to not overplan, let the good times roll.

Re post #45 - " 'You can check with the concierge as to cabs, but depending on where you are staying, they may be surcharges, between Chicago address and many suburbs has additional charge. "

Or just use Uber.’ "

Thanks Pizzagirl - I’m showing my age and Luddite tendencies… Eventually I will join the 21st century!

“It looks like it will take 60-90 minutes to get from our hotel to any of these destinations and we figure that the Signature Room and boat tour are pretty close together.”

Staying near O’Hare is not convenient to much of anything except the airport and conventions. I agree that taking the blue line all the way downtown and then out again to Oak Park is more of a haul than it is worth. Drive or Uber that route. That said, taking the L through west Chicago in the daytime is safe, if not scenic.

“Pretty close together” is subjective. For me, that’s a lovely walk. It’s probably 3/4 of a mile.

Be aware that the Signature Room is about the view, not the food. You can get much better food at lower prices elsewhere. It’s fine as an alternative to the Hancock observation center.

From recent experience,

  • Uber rocks! Used 6 times, spent a total of $29.57. Longest wait was 4 minutes.
  • CTA http://www.transitchicago.com/ $5 from ORD to downtown, flying by all those idling cars
    on the freeways.

“Chicago blues festival, Ribfest and Wells street Art show will take place on the weekend we are in town. Any input on those activities?”

Yes, This may help plan my next trip to Chicago, actually.
Me, I; might be at the blues festival Saturday night for sure. I was just planning our summer and might be seeing Buddy Guy around here someplace. Seems like you need to bring some folding chairs though.

I don’t know where you’re from, but the midwest does ribs better than they do here in the Northeast. So ribfest could possibly be tasty. Though possibly excessive, and with loud rock music?

Re: Art Fair, based on distant past I would go to the Old Town Art Fair instead. I was actually just looking for it last night, by coincidence for my own summer planning, couldn’t find it till just now. Same weekend, apparently. That’s somethng I would definitely do.

The others, while probably fun, would possibly compete with other things you might do that might be more typical Chicago,or that you just might prefer,so it depends on what you want to do.

@monydad We are from California. Thank you for information regarding Old Town Art Fair. I think we will go to this one instead. That is interesting that so many festivals happen at the same time. Glad that we will be in town for that.

So far, we have not had the urge to catch uber or lyft, but who knows? The taxi fares look to be pretty high for some of the venues.

I had to pop in again when I saw the Belden Deli mentioned. I worked there years ago while a grad student at DePaul. I miss that and My Pie, which was a little further north on Clark.

All these great ideas are coaxing me out of the suburbs to visit some of these great places again. And… I still need to see the Bean!

@ballerina16, Uchicago has graduation that weekend (June 13), along with final exams and dorm move-out for underclassmen. It will be a very crowded and chaotic campus from June 10-14th, imo. Just want to give you a heads up.

And I thought I was the only one who hasn’t seen the Bean yet! Maybe we should organize a Chicago meet-up at the Bean!

The bean is very cool and when we had a hotel on Michigan Ave, we must have passed it daily! I do enjoy the area around the lake.

Oh, Belden Deli and My Pie! You’re bringing me all the way back to middle school. I was a block from those places every day.

Great suggestions already! A few other cool things include RL restaurant (Ralph Lauren restaurant - late lunch is an easier reservation), afternoon tea at The Drake hotel is a very special thing to do with a daughter (make a reservation), if you do go to one of the museums on the museum campus and it is a nice day - take a water taxi from the museum campus to Navy Pier for a quick walk around, try to have deep dish pizza, Evanston has lots of great restaurants and shops too.