Mrs. Heismenberg and I are taking a trip to Chicago in mid June (kid-free!). Neither of us have ever been. While we are there we will have 2 full days to do whatever we want and 2 half days to find things to do.

What are the must sees and eats? We will be staying on North Michigan Avenue near the Chicago River, so I assume everything will be within walking distance or we could take the bus/train.

Things currently on my want/to-do list:

1. Wrigley Field (the Cubs will be away while we are there though...)
2. Willis Tower
3. Boat/City tour (are these any good?)
4. Navy Pier
5. Millennium Park

What are the best places to eat? I guess we can't go and not get deep dish pizza or a hot beef sandwich.

Opinions will differ, but my picks for pizza and hot dogs:

Pizza: Lou Malnati's - I think there are three in Chicago. Get the butter crust.
Hot Dog: Hot Doug, Inc. I got 3 randomly selected hot dogs and they were by far the three best hot dogs I've ever had.

ETA: Ugh I just read Hot Doug's is permanently closed.

Architectural boat tour very well worth it

Navy pier not so much at all.

Suggest Second City comedy club as an option as well.

Marauder Blue 6 said:

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Portillo's for hot dogs, beef sandwiches, and chocolate cake shakes.

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This

Malnatis, Giordanos or Uno for pizza.

The architectural boat tours are great. Really interesting, and a great way to see the city, also has a bar.

Navy Pier is just a tourist trap. Nothing there you can't get in your local mall.

Go to the top of the Hancock building, it's free if you go to the bar instead of the observation deck.

Trump International Hotel

Beatrix for brunch
Topo or any Rick Bayless restaurant
Girl and the goat

We did Malnati's, Portillo's, caught Hamilton and did most of the tourista stuff. The locals are great, they don't like the beam, the cubs or the trump tower. (White Sox all the way.) My stomach still hurts from Portillo's. The Navy Pier isn't much, but the walk from your mag mile hotel along the river is worth it.

I love Chicago and always have a great time when I go there.

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.

Pequods is the best deep dish in the city. Hands down.
Skip Sears Tower. Head to John Hancock building and go to The Signature Room. Great View.
Gene & Georgetti is an old school Chicago Steakhouse. Delicious Food. Cool atmosphere.
Bavette's is to die for.
Aba is amaaaazing. Make reservation at least a month in advance.

If you're looking to start your morning off right, head to Cere's in the CBOT. It's a one and done type place. It's only open M-Fri.

If you're going to a day game at Wrigley and want a hearty delicious breakfast, head to Ann Sather. It's right off the red line stop @ Belmont. Eat, enjoy, it's also BYOB. Hop back on train to Addison and go enjoy the trashy bars at Wrigleyville.

Keep in mind it takes a minimum of 45 minutes to get a deep dish pizza, most will let you order in line then when your table is ready you don't have to wait as long.

We did a "dinner" cruise for brunch one morning. It was around $50 head and you go out on the lake for a buffet lunch and drinks after. It was a great way to get out and see the city. The food was so so, but we enjoyed the trip.

The architecture tour was great. We also did the bar at the Hancock tower. It was very relaxing. We walked the length of Michigan Ave from the Hancock tower to soldier field. Overall Chicago is a great city.

Thanks for all the feedback. Can't wait to go. Guess I'll have to wear an Aggie hat while I'm there just to see if I get any Gig Em's or Howdy's. I heard the water taxi is the same route as the Architectural boat tours but 1/4 the price because they don't narrate the ride. Is this true?

Also, one thing that I've kinda been worried about is that our flight doesn't land at O'Hare until about 9:30pm. Do I need to worry about the crowd on the subway to Downtown that late at night? Just don't want to get caught in a bad place with our luggage and get it "confiscated" while we are walking to/from the subway to the hotel.

I live here and at that time of night on the weekend, I wound just take a taxi into the city. Is it more expensive? Of course!

The $ spent will be worth being driven straight to your hotel and not walking around downtown with all your luggage screaming I'm a tourist, look at me, come steal my luggage. It sucks but better than the alternative!!

Heismenberg said:

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Also, one thing that I've kinda been worried about is that our flight doesn't land at O'Hare until about 9:30pm. Do I need to worry about the crowd on the subway to Downtown that late at night? Just don't want to get caught in a bad place with our luggage and get it "confiscated" while we are walking to/from the subway to the hotel.

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My wife and I's first trip to Chicago was a delayed flight into Midway that landed about that time. We had the same concern as you and just took a cab. I have been on the blue line going out towards O'Hare at like 1:30 am and it really wasn't as bad as I thought it would be, but I wasn't carrying luggage either.

As mentioned: Portillo's for Italian Beef and a proper Chicago deep dish pizza will take at least 45 minutes to make.
I like Pizzeria Due - https://www.pizzeriaunodue.com/
If you want a nice steak - Gibson's on Rush Yes, I'm sure there are better steaks out there but... this is one of those venues you just must go to.

And for some fun, go upstairs at Ditka's to where they have the bar and the cigar bar. I met the coach there one night and a kid who looks remarkably like Ditka sang Sinatra songs. Good times. Plenty of Ditka's Dallas Cowboys memorabilia lines the hallways leading to the men's room.

Heismenberg said:

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Thanks for all the feedback. Can't wait to go. Guess I'll have to wear an Aggie hat while I'm there just to see if I get any Gig Em's or Howdy's. I heard the water taxi is the same route as the Architectural boat tours but 1/4 the price because they don't narrate the ride. Is this true?

Also, one thing that I've kinda been worried about is that our flight doesn't land at O'Hare until about 9:30pm. Do I need to worry about the crowd on the subway to Downtown that late at night? Just don't want to get caught in a bad place with our luggage and get it "confiscated" while we are walking to/from the subway to the hotel.

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Just get an Uber or a cab. Don't mess with the subway

You are with your wife so don't do this, but if you are traveling alone you can take the blue line a few stops away from ORD, hop off and get an uber for half the cost of having them pick you up at the airport.

So it looks like we can take the blue line and get off at Washington, which would be 1/3 mile or about a 6-7 minute walk. I've heard lots of people in the downtown area can be seen hauling luggage. We will probably each just take a carry on, so I wouldn't think it would be too big of a deal unless everyone thinks it's too risky/dangerous.

Chicago seems to be the Uber/lift capital of the world. They are everywhere.

One of the cool things about Chicago is that the "El Train" goes to the airport (both ORD and MDW).

I would figure out where your hotel is and figure out whatever stops you need to change trains at once you reach the "Inner Loop" and you shouldn't need to walk more than about 4-5 blocks once you get to a stop close to your hotel. Especially if you're staying near Michigan Avenue and the Chicago River.

I've done this numerous times but... in fairness, the most recent time was in 2007. I'm sure everything has changed since then

Just like any big city, you need to pay attention to what's going on around you and don't act like a tourist.

The "El Train" is super cheap and pretty much goes everywhere you'd actually want to go - except for the walking you'll do around Navy Pier, etc.

Back in 2003, I had a computer systems installation I did near the intersection of Michigan and Ontario. I traveled from Denver to Chicago 8 weeks in a row during the summer. The food was so good, I think I gained at least 10+ lbs that summer.

Enjoy!

Garrett's popcorn. Chicago mix

Purple Pig for sure. It's in the area you're staying.

If you drink and want to go to a really cool tiki bar, try 3 Dots and Dash. Make a reservation the day before.

Architectural boat tour is an absolute must. We did the river/Lake Michigan one. Super cool to go out on the lake and see the skyline from there. Don't miss it.

If you like musicals/theater, Hamilton plays there year round. And it's a really cool experience inside an old historic theater.

If you like Kemah Boardwalk, then you'll love Navy Pier (i.e. don't go)

So we fly out this Thursday. Really looking forward to it. Think we're going to just take the train from O'Hare to the Clark/Lake station. From there it's about a 10 minute walk to the St. Jane hotel on North Michigan Avenue. If you guys think this is too risky of a walk with a rolling carry on around 10-11pm on a Thursday night I guess we could Uber.

Speaking of which, will Uber or Lyft even bother picking me up for less than a mile ride?

Since the Cubs are not in town, take a tour of Wrigley Field. I liked that as much as I liked going to a game. Maybe more.

Five guys, including myself, found ourselves walking in downtown Chicago late one night after returning from a White Sox game. We felt a little uneasy. With it being just you and your wife, please catch uber from the airport. It is the wise thing to do.

I, too, like walking around college campus'. DePaul is in a neat,old area of town. If yall are in to gangster history, John Dillinger was killed by the FBI just a block or 2 off the DePaul campus. Outside the Biograph Theater.

Looks like the ride from the airport to the hotel on Uber is less than $30. Guess I'll do that just to be in the safe side.

For sure. Do it in big cities

I realize this may be late... but I'll chime in on some things:

Uber from the airport. Not particularly from a safety standpoint, but from time. It's roughly a 30-45min el trip from ORD to loop. While I'm cheep and when traveling to visit my wife I would take the train to Logan Square then the bus to our apartment, it would be about 1-1.5hr trip due to all the stops.

Friday my wife and I are going to the free concert in millennium park. http://www.grantparkmusicfestival.com/2019-season/beethoven-symphony-no-8

There is a lot to do and see here.
Have fun.

Question about the Hancock Center. Is the 2 drink minimum deal at The Signature Room or is there another bar? Will jeans and polo shirt be acceptable during the day or do I need to wear nice pants?

Do we have to have reservations or can we just go in?

I've gone several times and not once has anyone on staff mentioned a 2 drink minimum so I wouldn't fret about it.

And jeans and a polo are fine!! There really isn't a dress code. And no rezzies. If the elevator line is long, you'll just have to wait!

I usually take people earlier in the day and I've never had to wait. Just walk on and up, drank, check out the view while we drank and head back down.

Make sure your wife goes to the bathroom. Thebest view is in the women's restroom IMO.

Wendella Boats architecture tour. There is a bar on the boat. Great way to spend an afternoon.

Just got back home. We had a freakin blast. Didn't get to do everything we wanted to do but we only had 2 full days to explore. Spent Saturday traveling to a wedding out of town but got back in time to go eat some spectacular sushi (Hot Wok Cool Sushi). Got a quick breakfast this morning and headed to the airport.

Took the Water Taxi up and down the river. Went to Chinatown and got some appetizers from one of the restaurants that were pretty tasty. Chinatown was kinda dirty, but a cool experience nonetheless. Also went to Navy Pier and took the lake tour which may have been my favorite part of the trip. Beautiful view of the skyline. It was also the only day we could see the skyline with the rain/fog.

Wrigley was awesome but they weren't offering tours yesterday. Walked around Wrigleyville and drank some Beers at Bernie's. Took the trane back towards the loop and got off at Sedgwick to walk to the zoo. The zoo sucked and there weren't many animals on display.

Only thing I really didn't get to do was experience Willis Tower or the Hancock Building. Didn't have time to fit that in on Friday and the rest of the time it was so foggy/low clouds and you couldn't even see the top half of the buildings. Didn't want to waste time to see clouds out a window. Also didn't get a chance to do the Museum district or see Soldier Field.

My favorite food was Labriola's and Portillo's. Damn good deep dish and hotdogs/beef sandwiches. And good lord that Chocolate cake shake. Wildberry Cafe was probably the best breakfast, but Nutella Cafe was pretty good too.

All in all, I would go back to Chicago in a second. I've never been to NYC, but from what I've heard, I don't think it can top Chicago. The people there were very nice as well.

I travel to Chi 3 times a year, NYC blows chi town outta the water! just my .02

Go see Jussie Smollet and all the crooked Obama's.