Be aware that Northwestern is about to embark on reading week (week of June 1), then finals week (week of June 8) then senior week / graduation (week of June 15). So the campus may be more subdued if you are there during finals week. I don’t know if U of Chicago has a similar schedule but it’s possible they do as they are also on a quarter schedule.
For entertainment, try to catch an improv or sketch show. Second City is always fun but there are tons of excellent groups, including Improv Shakespeare. All ages shows are not difficult to catch.
I concur about the architectural boat tour. If you like to be active, we rented bikes and rode along the lake all the way up to Wrigley Field, making a few scenery stops along the way and then watched the game in one of the pubs across from the park. My teen kids loved that! Millennium park is a fun outside thing to do in the summer, too.
N/G
Thanks for this timely thread. We leave this month for a short visit to the Windy City. We hope to try the architectural boat tour, as the weather is supposed to be nice. Have not tried the John Hancock Tower–sounds lovely and like something we ought to do. Have also not tried Navy Pier, tho did many of the other things listed.
One of the first things we do if we have visitors in town is do the architectural boat tour. Great way to get a feel for the city and its history. But I would go so far to say I would only do the ones through the Chicago Architecture Foundation. They are much more informative in my opinion, although, if you’ve never done one, you won’t have anything to compare it to.
https://www.architecture.org/experience-caf/tours/
Navy Pier is very tourist, IMO. I’d only go there for the giant ferris wheel, which gives you a neat perspective of the city as it looks from the lake. As far as doing stuff along the lakefront (bike/walk, etc.), if it’s a weekend, be prepared for it to be very crowded, especially if the weather is nice. But if it’s during the week, it shouldn’t be as crowded.
The Bahá’í House of Worship in Wilmette is far more interesting than something like Navy Pier, and is not far from Northwestern University. Also a beautiful place to see and learn about.
If you’re trying to get a feel for Evanston, walk south of campus along Sherman, Orrington or Chicago Ave. to get a feel for the shopping and restaurants that are available there. U of Chicago won’t have any of that type of downtown experience since it’s relatively isolated in Hyde Park. I think parts of Hyde Park are incredibly beautiful with historical old buildings and houses, but unless you have someone from U of C tell you which streets to drive on, and which to avoid, I might avoid that as some neighborhoods right next to the campus can be questionable and you wouldn’t want to get lost there. I spent many years commuting down there for grad school so I got a feel for it, and finally got comfortable driving around Hyde Park without worrying about going into a bad area because I knew the boundaries (they may have changed in the years since I was down there regularly). It can be done and is worth it for those who want to see that kind of architecture. Of course, it’s not difficult to find the house that Barack and Michelle still call home and drive by it if you’re driving around down there… just google for the address before you head out in the car.
I agree about Navy Pier. I’d only put it in if you had a smaller child with you who might like the Ferris wheel and the children’s museum. If you don’t, skip it.
Whats the strip or whatever that has lots of nice shops? Something mile? We had fun one evening just walking along there. Loved the architecture boat trip.
Yes to Architectural Boat Tour; Millenium Park; Bike Ride; Second City; Michigan Ave…
Per Goskid #1, instead of Willis/Sears Tower, go to Signature Room and have a drink. Paying for the drinks will cost the same as going to Willis Tower entrance fee. Also, the women’s restroom in the Signature room has awesome views…many were taking photos in there 
FYI for those not seated next to the window! And…if it’s a warm sunny day, those sun facing windows get warm…
I know it has been suggested, but if you or your kid has any interest in art whatsoever, you must, MUST, visit the Art Institute. You won’t find a more impressive collection of modern art anywhere in the country.
Thank you everyone for great ideas.
Magnificent Mile / North Michigan Avenue. Oak Street has the nicest boutiques.
OP, since you’re looking at Northwestern, their Chicago campus is right in this area - medical and law schools.
You can get a City Pass and customize it to suit what you want to do: if you have a COSTCO membership, you can get it online and save quite a bit of $$ !!
My daughter lives in Chicago- Wrigleyville- and you should be aware that the area is crazy when the Cubs are playing! Even the Taco Bell rents out their parking lot spaces! Avoid driving in the area and use public transportation. The same for the zoo- take the bus there and walk into the zoo, which is free, because if you drive, parking is very expensive ( $30+). If you buy transit passes when you first arrive in the city, you can keep them and just add more money on them each time you’re in Chicago. The zoo is really nice and a great way to spend a few hours.
The Field Museum is also excellent and right now they have the traveling “Vikings” exhibit which is well worth seeing (I was through it two weeks ago). The museum is famous for it’s complete T-Rex, “Sue”, and it’s hall of dinosaurs as well, and they have an amazing native American collection.
I’d recommend the Shedd Aquarium too! It’s considered the finest in the country, and I must have spent an hour just watching the sea otters playing!! The reef exhibit was the “extra” that we chose and it was well worth it- went through it twice!
The Art Institute has a special traveling exhibition on Ireland and Celtic art right now.
There is a bus that runs to the museum campus- lets you off at each of the buildings and is so much easier than driving there and paying the rapacious fees.
If I can answer any more questions, feel free to PM me.
Thank you @Mezzo’sMama our hotel is right across from the Art Institute of Chicago so we definitely plan to visit it. Chicago blues festival, Ribfest and Wells street Art show will take place on the weekend we are in town. Any input on those activities?
Ummm… have lots of patience because downtown near Grant Park will be a nightmare. The Blues Festival is awesome, but will take up a good chunk of the park and surrounding area with vendors/gates/people, etc. It’s a massive event. I haven’t been to it in many years, but I highly doubt it’s gotten smaller than the last time I was there! If you have to be at certain places at certain times (like dinner reservations), give yourself plenty of time with it being that particular weekend.
Use the rental car to visit the universities and suburban sights. Take public transportation (or cabs/Uber) for pretty much everything else.
When in Hyde Park for the U of C, plan for a neighborhood/lakefront walk if the weather is nice. If not, try a museum: the Oriental Institute for Egyptology or the Museum of Science and Industry (expensive but worth it if you enjoy science museums).
Have a simple lunch at Noodles Etc. on 57th Street or Plein Air Cafe in the seminary building.
We are thinking of light lunch at the lounge at the Signature Room and Chicago Architecture Foundation boat tour on our first day. The 2nd day we are thinking of the Frank Lloyd Wright House & Workshop. 3rd and 4th days are meetings. The last day, there is a food truck fest that we may attend or we may go to Busse Woods and bike. What do you think of these plans? 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.
I’m just surprised at how long it takes to go the 7-12 miles in Chicago on the line and buses. When we stayed on Michigan Avenue, I guess it was much more centrally located. We walked a lot and did catch the light rail.
I read that Navy Pier is rundown and currently under renovation. We have opted to avoid it for both reasons.
Dang, just spoke with BIL & sis who lived in Chicago for 5 years. They can’t understand why we want to stay so far away from downtown (because we’re attending a conference & staying at conference hotel near ORD). They also don’t understand why we don’t have a car to get around–have never driven in Chicago and only taken the “L,” buses and taxis. 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. He also doesn’t think catching the L to go through west Chicago to Oak Park is a good idea.
Oh well, will talk with the concierge. Am looking forward to the Signature Room & Chicago Architecture Foundation boat tour. Those sound fun, even tho it will be a significant commute to get to them from our hotel & back. I’m sure the concierge will have suggestions and ideas.
I would knock Frank Lloyd Wright / Oak Park off your list if you’re staying near ORD without a car. Way too inconvenient to get to.
So much great food in Chicago - if food is something you enjoy, try to stay away from any chains and partake in all the local choices. From the upscale to the Chicago dog (hotdog!).