Looks like we're going to Chicago in late September for an adults trip. I've been twice but it was for work both times and I didn't have a lot of down time. It's also been about 6-7 years since I was last time I was there

Need some ideas of cool stuff to do and must hit eateries

Google says:
Millennium Park
Chicago Riverwalk
Wrigley Field
Art Institute of Chicago
Navy Pier
Sears/Willis Tower

What else ?

Giordano's and Lou Malnati's are the two deep dish pizza restaurants that are Chicago staples. Different people think one or the other is better..both are really good and I'd say go to whichever is closer to where your group is.

Not sure if your group would want to do a museum or not but the Science and Industries Museum is really neat, especially if you have any military history types in the group. The German U-boat there is really neat to see. Not your typical "kids" museum. The aquarium is also really nice.

River boat tours are also popular. Might be a little better that time of the year versus walking all around downtown. Chicago's downtown area is one of my favorites though because if you are staying downtown, it's a very "walk friendly" area with lots of things to do and eat close by.

I didn't do much while in Chicago, but I agree on Navy Pier - that was the one thing I did besides Giordano's, and I was underwhelmed by both (it was probably because they ordered bacon on the pizza and it was so overwhelming flavor wise - otherwise I think it would have been good). But I didn't find anything great on the pier.

Navy Pier is nasty and sucks. Don't waste your time.

And don't even bother wasting your time at Lou's. It's absolutely disgusting.

If you want the best deep dish in Chicago, head to Pequod's. You won't be let down! It's the best!! If you can't get into Pequod's, settle for Gio's!!!

His up the Signature Room at the John Hancock. Do the architecture tour. Tons of incredible restaurants but make reservations in advance. One of the best in the city is Aba. It's in the West Loop. Divine food and incredible atmosphere! <3

The museums by Soldier Field

Navy Pier sucks. It's Chicago's Pleasure Pier...avoid it unless getting your stinger wet that night depends on going there.

A great breakfast is Ann Sather's off of Belmont. I always get the Southern Decadence. For one of the sides, you have to get the cinnamon roll. It's nothing like you've ever tasted. Honestly, I'll got to Chicago just for one.

From another thread...

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You stated you wanted to do Wrigley, which I highly recommend. Wrigleyville is a pretty awesome place, especially during baseball season. One thing my wife and I did one time when we were staying in the Loop was to take the red line up to Wrigley (Addison stop), spend some time there, and then walk back to the Loop via N Clark down to the Gold Coast, then cut over to State or Rush and continue down, stopping or diverting here and there to see some of the neighborhoods. It's a long haul, but can be a lot of fun and a way to see the unique neighborhoods on the north side. We did this the first week of December the morning after the first snow, which was actually pretty cool. Really felt like Christmas.

I'd skip Willis Tower and go to Hancock Tower for the simple fact there's a bar a couple floors higher that's a 2 drink minimum, and when it's said and done, costs about the same as pay to go to the observation deck. Might as well have a drink while you're there.

We've done the whole pizza thing as well, and we prefer Giordano's over the others. But if you want a different experience, I'd suggest Chicago Pizza & Oven Grinder on Clark.

Tavern on Rush is another restaurant that will be a good dinner spot one night. Given where you're staying, it's a short walk for you. If the weather is nice, try to get a seat outside.

The Purple Pig is a place that's recommended here a lot. Never been there so can't comment any further than it's a hit with people here.

If you're in the Roscoe Village area, I'd suggest going to The Pony off of Belmont. It's nothing old or special, but is the official bar of the Chicago A&M Club and has been for quite a while. Might as well go and support a place that supports Aggies during the season. The same people that own this bar own Lottie's, so if you're a Chicago Fire (TV show) fan, it's the bar in the show.

One thing I love to do when I visit places is to go tour college campuses. I haven't been able to make one in Chicago, but going to University of Chicago and Northwestern are on my list.

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We went last year and used Chicago's First Lady Cruises for Architectural Boat Tour and it was top notch! I would highly recommend them and you can purchase your tickets online beforehand.

John Hancock Building/Center was fantastic and the view from the 96th Floor Bar was absolutely worth the wait and elevator ride up to the top. Drinks were expensive but that was also worth it just to hang out and look out at Lake Michigan and the city.

Millennium Park is cool, but yes, you just kind of walk around and take pictures and that's about it.

As far as restaurants go we tried to get into Au Cheval and it was a four hour wait, but it's supposed to have one of the best hamburgers in the US. We tried to get into Girl and a Goat also but they were booked, should have made reservations way before we got there. As one person said, Pequod's was WAY better than Lou Malnati's. We had a long wait at both pizza places.

By far our favorite bar/restaurant was 3 Dots and a Dash. It's a tiki bar and you have to walk down an alley and then go downstairs to get into it. If you're wanting to go there make reservations ahead of time, we were lucky and got in but we heard that's not always the case.

Enjoy your trip! Cheers!

We go to Chicago about yearly. The train from O'hare to the downtown loop is inexpensive and safe. Walking or public transport is pretty easy in Chicago.

For pizza, Pequod's is so much better. The location we went in the burbs is gone now.

If you enjoy art, The Art Institute is top notch.

The Field Museum is nice, but I wouldn't go without kids.

If you enjoy comedy, Chicago has plenty of options. We usually go to Second City and others around town.

Wrigley is iconic. It is old and run down, but I feel like I'm a part of a lasting history when there.

Watch Ferris Bueller's Day Off right before you go.

Portillo's - everyone we know that grew up in Chicago recommends this place. I had something like a cheese steak with Italian sausage also and a cake shake. Then we went to see Hamilton. That wasn't the best pre-play meal, but it was interesting.

We liked the Navy Pier, but mostly it was the walk to it through town and down the Chicago river. We walked out one side and back the other, only pausing to photograph the city and the lake.

Not "old" anymore. They've completely redone the inside of most of the stadium over the past 2 years.

Thanks. We will have to go again to check it out.

Wildberry Cafe for breakfast, right next Millennium Park.

Labriola for good Italian and their own take at deep dish pizza, which is really good.

Glad I saw this thread. Headed for first time Wednesday thru Saturday. Got my Cubs tickets for Friday already! That's my bucket list so whatever the rest of the family wants to do other than that I can't complain.

Thanks for heads up on Navy Pier. Is Wrigleyville ok for families or more for adults?

Darby said:

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Looks like we're going to Chicago in late September for an adults trip. I've been twice but it was for work both times and I didn't have a lot of down time. It's also been about 6-7 years since I was last time I was there

Need some ideas of cool stuff to do and must hit eateries

Google says:
Millennium Park
Chicago Riverwalk
Wrigley Field
Art Institute of Chicago
Navy Pier
Sears/Willis Tower

What else ?

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We were just there but had kids with us. If they weren't we would have signed up for the River booze cruise. There is a charter right at Michigan and River. The architecture river cruise is great too. The lines for Giordani were insane so we had deep dish delivered to the Hotel.

Like one poster said the Field Museum is great but we wouldn't have done it without kids.

Look at Groupon Chicago City Go Pass or City explorer. You can pick 3 attractions and save some money