Chicago. What do I want to see?

Shedd Aquarium

The Art Institute of Chicago is awesome!

What's the 360?

Main Museums: the aquarium (Shedd), the planetarium (Adler) and the natural history museum (Field) are all clustered together about 12 blocks south of the Loop (a.k.a. downtown). The Art Institute is right about n the Loop next to Millennium Park (the park is cool but God knows why "The Bean" has become our claim to fame). The Museum of Science and Industry Is 65 blocks south of the loop (Uber?). It's a really fun museum, but you can drop a lot of money there. Check to see which special exhibits are at the Field, the Museum of Science and Industry, and the Art Institute. Especially in tourist season, you need to reserve ahead.

Beaches: Oak Street Beach is right at the tip (so, just north) of the Michigan Avenue stores, so a few blocks north of the John Hancock Building. North Avenue beach is six blocks north of that; it's bigger and has more locals. Water will be cold - probably in the 60s. The lakefront path is a walking/biking path that extends the entire length of the lakeshore. Good for people watching. The walk between the two beaches I mentioned is fun. You can rent bikes and other wheelie things at both locations.

Boat Tours: if you do the architectural boat tour on the river, use Chicago Architecture Foundation. Check out their walking tours, too. The Wendella is a fun boat trip on the lake.

Navy Pier is a soul-sucking, wallet-emptying devil, but it's quite the draw, nonetheless.

Lincoln Park (the actual park, not the neighborhood) is huge. There's a free zoo, a lagoon with paddleboats, a conservatory, etc. It's west of North Avenue Beach on the Lakefront Path.

Google "Chicago summer festivals 2017" to see what's scheduled for your trip dates.

Go to the observation decks at Willis Tower or John Hancock Building. Have a pricey drink of the 96th floor of the Hancock.

Eataly (off Michigan Avenue) is a fun stop when you're in the area and hungry.

Chicago is the "second city of theater." You don't have to go to Hamilton or one of the pricey "Broadway in Chicago" productions. There's excellent theatre all over.

It could be beastly hot and humid in August (it is now). Then again, the last few summers have been strange.

Let me know if you have specific questions.

Chicago is an excellent city to visit -- I agree with everything AmeliaBloomer suggest with the addition -- WALK -- Walk the Magnificant Mile - see Garrett's popcorn (totally the best caramel popcorn anywhere!) -- Is Lord & Taylor's still in Chicago -- I LOVE Lord & Taylor's!! See the Art Institute -- all the museums are good but see the Art Institute!! -- House of Blues Brunch -

Chicago is a FUN city !!

You have heaps of good ideas. I am going to throw out another beach possibility. Indiana Dunes. It's not a long drive, but if no car, you can take the South Shore train out there. I have not done it, but there are people who do and I have always wanted to. I think the stop may be Beverly Shores, but call or look at their website to be sure.

We just got back and I am glad I didn't see all the suggestions. We only had just over half a day to see things. We had a new sailor with a curfew. We did have Garrett's popcorn as a friend met us at the train station with it. Oh my goodness!! So good!

We did walk the Navy Pier. It was a gorgeous morning to do it. We went to Millenium Park and saw the Bean. It was a very cool thing but too many people there for my liking. I have crowd anxiety so I stayed at the fringe to see it.

We walked around downtown and saw the buildings and then hopped a train back to Great Lakes. My DD and I are talking about a girls' trip up at some point. We really want to see all the sights mentioned in the above posts.

If you do go to the beach, please take the water seriously. Lake Michigan is having a record year (or near record) for drowning deaths due to the rip currents. They are much stronger on the Michigan side of the lake, but exist on all sides. Far too many people think that a Great Lakes beach is not a "real" beach and not on a "real" body of water. It's real, it's beautiful, but it needs respect and caution.

You could get the Www.citypass.com/Chicago and use it to access the top museums. We used the Atlanta City Pass a few years ago and it was a great bargain.

YES! On the Chicago Architecture Foundation boat tour. We've done it a couple times. The twilight one is very cool. And be sure to have time to just walk - the Riverwalk area is neat. We went all the way to the harbor and along the lake front.

We've also done a lake boat trip, that goes along the shore line. I like seeing the city from the water, whether on the river or lake.
We've done the trolley tours too. I think they are a good way to get a quick look at a lot of places, and you can decide where you want to spend more time.

one tip - if you go to the Shedd Aquarium, be in line before it opens or you'll waste hours standing inline outside in the heat. We also enjoyed the science museum and cycling round the lake.

I understand that, but the price is still steep for a 90 minute boat ride.

My favorite restaurants in Chicago are: The Hampton Social, Mercadito, and Siena Tavern.

Eat pizza at Lou Malnatti's.

For a fabulous breakfast, try Sweet Maple Cafe on Taylor. It's a bit away from downtown, but worth the trip.

Don't be afraid of the trains. They are super easy to navigate.

Chicago is amazing. Do not miss the architectural river boat tour. It's amazing.

Depending on your DD age, The American Girl store is a fun stop. Portillo's is awesome for Italian Beef sandwich and is famous for their Chicago hot dogs. You might want to see the Bean and the Buckingham Fountain.