@85bears46 Thanks for the advice on the Loop El.
@uofcparent do you have any idea which airport you’ll be landing at?
Both airports get to the downtown via L no problem. From Midway take the Orange line:
From O’hare you can take the Blue and then Uber or Bus:
Uber works great in Chicago in a pinch. I met my D17 and her friend at Kurah, another great restaurant which is in South Loop and just down the street from the Hilton. They Ubered from BJ for $7 or $8 so pretty reasonable. This was on a Sat. night so presumably busy with surge pricing potential, etc.
Also, we tend not to worry too much about reading schedules. Google maps will tell you which public transit line goes where, and there’s probably a CTA app that lets you plug in your destination and will give you various options.
@jbstillflying Thanks for the tips! The one time that we flew to Chicago, we landed in Midway then took the El (can’t remember if it was the Orange or the Blue line) to downtown and then a bus to campus, we didn’t have time to look around or anything, it was literally go on campus, then leave campus.
In April, we’ll be landing in O’Hare (but subsequently, once school starts, I think our S will be flying from Midway instead of O’Hare, as it seems that Midway is a better commute from campus.)
Is The Hilton also accessible from O’Hare if we took the El?
The Hilton is accessible via L but depending on time of day it lets you off just short of your desintation - you can Uber or walk. Let Google or other apps be your guide.
If you are going from Midway straight to campus you can ride the bus or Uber. No need to go to downtown first unless it’s to drop off your luggage 
Delete - dup from above ^^
Thanks, @jbstillflying !
@uocparent If you are flying in Chicago through Midway, on the map the shortest route to U of C is to drive or take a Uber/cab along W 55th Street or Garfield Blvd. to go to Hyde Park. Unfortunately, a stretch of the Garfield Blvd. goes through the neighborhoods of Engelwood and Washington Park. Engelwood has the highest murder rate among all the Chicago neighborhoods and this is where the legendary gun violence in Chicago happens. Driving during daylight hours on Garfield is likely okay and I have done that many times. But it may not be the best idea after dark to pull over at Garfield and Halstad.
On Google map it will advise you after leaving Midway to drive on I-55 North (or in Chicago we call Stevenson) to go to downtown and then take LSD (Lake Shore Drive) south to Hyde Park. It will be a longer route to U of C. Yet that definitely will be the safest and fastest route unless you get caught in the morning rush hour traffic. Your Uber/taxi will likely take this route instead of driving on Garfield.
@uocparent From ORD to downtown it is much more straight forward: you just take the I-90 (or Kennedy according to us) from O’Hare to downtown. The only holdup is the traffic.
If you are staying in Hilton, then perhaps the best way to go there is take a Uber/cab. Hilton is not close to any Blue Line el train stop and you don’t want to walk 7 to 8 blocks with your luggage in the rain in April to Hilton.
I have taken both the 55 and the 59 bus from Midway to the Chicago campus, and back, any number of times. Engelwood may have a terrible murder rate, but I would wager that none of it happens on the 55 bus. I have never felt unsafe on that bus, and it generally has a lot of University-connected people on it.
The other way to get to the University from the Loop is to take the #6 bus Jackson Park express. It’s express on Lake Shore Drive from Roosevelt to Kenwood – a very pretty ride. In Hyde Park, it leaves you half a mile east of the main campus, but it’s easy to transfer to the 55 bus going west there, or just walk. (That’s a perfectly nice part of Hyde Park.)
If you are in Chicago for just a few days, you can buy a 3-day CTA pass that works on the Els and the buses, but not on the Metra. You have to buy it at the airport or the Amtrak station, I think. It’s a really good deal if you are going to be traveling around Chicago, but it does take you off of the Metra.
you can take the metra or the bus from millenium park to uChicago, takes about 45 minutes.
Your hotel is right across from the Art Institute. If you like art, or even just have a pop culture knowledge of art, you can easily spend a day or more in there. They have a collection of Monet and Seurat, and have Nighthawks and American Gothic (though its recently been on loan to somewhere else).
Robie house is on uChicago campus and worth a visit if you like Frank Lloyd Wright. You will need to buy tickets in advance on the website.
Second City is pretty far from where you’re staying. The main stage shows sell out pretty early, so check online in advance.
There’s a lot of fun shopping on the Mag Mile. I love visiting Eataly to sample cheese and cured meats.
I’d like to know how many out-of-town visiting parents were popped off on Garfield while driving from Midway. Hasn’t happened. We used to drive it 30 years ago - even first thing in the morning - when the murder rate in the entire area was much higher. Just wasn’t a concern. D17 has taken Uber and bus back and forth to Midway from HP* and she and I drove through Washington Park from the freeway on Move-In Day. As did I on my own Move-In Day. The only thing I regret is that the archdiocese has closed down St. Charles Lwanga Parish that used to stand at Garfield and the Dan Ryan. That was always the sign that we were near Home.
I drove through Englewood last Nov. - even off the main roads. I wouldn’t recommend the latter; however, I was never in danger of being shot. A lot of Englewood is in pretty bad shape with abandoned buildings, etc. However, there is lots of traffic on the main roads, most of it passing through the neighborhood en route somewhere.
Uber or bus from Midway is going to be fine. If Google is redirecting that might have more to do with traffic than safety.
*Route was Garfield.
@85bears46 at #28 is recommending what all the visitors who are worried about the “Big City” do. Yes - you can take the Kennedy and sit in traffic - or you can take the Blue Line/Uber or Bus and spend the savings on dining and fun times. The choice is yours. 
32 @JBStillFlying
In many ways I agree with you. If I have to catch a flight out of ORD in the afternoon, I will get out of my office in the Loop and go take the blue line from the Monroe Street station and watch the traffic jam on Kennedy from the el train. El is the way to go if you don’t have a lot of luggage and you know your way in and out of Chicago. I wouldn’t dream of taking a cab to ORD after 2:00 pm.
However, I assume @uocparent is not a native Chicagoan. And she has specific requirement as she is likely staying in Hilton Chicago. The closest blue line station will be at LaSalle Street which is right next to CBOE. It is a good .6 mile walk from there to Hilton. April weather in Chicago is unpredictable. I wouldn’t advise her and her family to take the chance of walking 8 blocks with their luggage in the rain or snow from LaSalle Street station to Hilton Chicago.
To save some money taking Uber is fine but sitting in an Uber is no different from sitting in a yellow cab when you are stuck in a Kennedy traffic jam.
So much for transport to and from airport, now back to the original program
Chicago Loop and Hyde Park are walking towns. So @uocparent, be prepared to walk a lot. Please wear comfortable shoes. Thank God this is Midwest and dress code is extremely casual unless you are going to super high end places.
A few suggestions of totally free attractions:
- On a nice day take a leisurely stroll along the Chicago River Walk and just take in the urban architecture along the river: Tribune Tower, Wrigley Building, Marina City, 333 West Wacker, etc. There are plenty of places to sit down and take a break. If you have iPhone trouble, no problem. Cross the Michigan Avenue bridge and there is the brand new iconic Apple Michigan Avenue Store.
- In Hyde Park, I would recommend going to Nuclear Energy (Sculpture), Smart Museum or Oriental Institute. If you are into finance and economics, visit Saieh Hall and you can see the Nobel Prize medals won by Milton Friedman and Gary Becker. Actually, Saieh Hall itself is worth a visit. It used to be the Chicago Theological Seminary but has been bought by the University and is now home of the Becker Friedman Institute and Kenneth Griffin Department of Economics. Jokingly called the "Money Church" by the irreverent students, it is a gorgeous historic building with high arches and detailed stone carving. And there is a Starbucks inside to get your caffeine recharged ;).
@MusakParent One of my kids graduated from UChicago (science and theatre) and the other attends Northwestern (music and theatre). Let me know if you have any questions about them.
“However, I assume @uocparent is not a native Chicagoan. And she has specific requirement as she is likely staying in Hilton Chicago. The closest blue line station will be at LaSalle Street which is right next to CBOE. It is a good .6 mile walk from there to Hilton. April weather in Chicago is unpredictable. I wouldn’t advise her and her family to take the chance of walking 8 blocks with their luggage in the rain or snow from LaSalle Street station to Hilton Chicago.”
@85Bears46 and @uocparent : Blue Line from O’hare to Washington/Lake, change to Red Line (95th/Dan Ryan), get off at Harrison. Hilton’s about 1/4 mile away on Balbo and Mich.
I am not a native Chicagoan, so thanks to all of you for your advice! My spreadsheet is getting huge with directions, times, distances and attractions, lol!
For this trip, we’re staying at the Hilton because that was one of UChicago’s recommended hotels. So upon landing, we’ll be going from Midway to Hilton, and the next morning, UChicago said they’ll provide shuttles from the Hilton (at 720 South Michigan) to campus.
For some reason, my hubby is opposed to being in traffic during the afternoon and rush hours, but if there are questionable areas, we might Uber it. (post #31 ‘never in danger of being shot’ rotfl! --yep that’s the standard by which everyone uses to determine a neighborhood’s safety threshold.)
Probably after this trip, we’ll be more familiar with the layout o’ the land and will be able to figure out whether other hotels might be better depending on what we’re planning on doing.
Thanks for all the touring destination suggestions. So looking forward to seeing them. We’re definitely going to be walking alot, as it really gives us a flavor of the city/area we’re in. We’re not going anywhere upscale, just wanted to explore the city, so I guess we’ll leave our tux and gown at home! 
Wow, there’s so much I am interested in seeing, so I obviously need a few more trips to Chicago! (or should I say Chicagoland?)
Navy Pier - take the boat tour to Lake Michigan. Best skyline photo op of Chicago is 1 mile into the lake.
Chicago River - take the kayak tour or the architecture boat tour.
Lake Shore - rent a bike and bike from Lincoln Park Zoo to Navy Pier to the Museum Campus to even Hyde Park promotory point. Its all flat terrain so if you are healthy or used to worse terrain, it would be an easy route.
Sears Tower - just do it. Its good if you are a tourist. Dont listen to locals when it comes to this building.
Interesting Food Experience:
The Wierner’s Circle at 2am. They sell hotdogs to people coming out of bars. Order the chocolate shake if you are brave; prepare to be berated. It’s a weird experience for sure but its a story worth bringing back home with you.
@UofCparent I stay at the Marriott Mag Mile on N Michigan right by Booth once a month. You can leave at the height of Rush Hour and make it to Hyde Park in 20 minutes. Lake Shore Drive (LSD) flows well.
Try that in Manhattan and it will take an hour to just hit a tunnel/bridge.
Majority of the traffic is headed out to the burbs.
Have fun !!!
Edit : additional restaurants not mentioned above:
Gyu-Kaku Japanese BBQ, 210 E Ohio St
Lao Sze Chuan, 520 N Michigan Ave
I did both of these last week and excellent !!!