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My Itinerary for my upcoming Chicago trip

Yellowsnow51

Yellowsnow51

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Son is graduating boot camp at Great Lakes Navy facility so we are heading up a few days before to the Windy City. Never been. Pumped.

iPad 2 fully charged.



Chicago Itinerary (Subject to change)

Day 1
Drop bags at hotel

10:30 AM
Walk Riverwalk.

11:30 AM
Lunch at Portillo's.

Checking off:
  • Italian Beef
  • Chicago Dog
  • Cake Shake
1:30 PM
Architecture Cruise

3:30 PM
Navy Pier

5:00 PM
Hotel check-in and rest

6:15 PM
Garrett Popcorn snack

8:00 PM
360 Chicago

Late Dinner at
Francesca’s on Chestnut

Day 2
9AM Millenium Park

10 AM
Cindy’s Rooftop brunch

11:00 AM
Art Institute

2:00 PM
Rental car

Head to
Great Lakes graduation Ticket Pickup

The Silo for early Dinner

Home Alone House/ Area in way back

Water taxi to Fulton Market
  • The Publican for Charcuterie
Rainbow Cone or Venchi Chocolate on way back

Day 3

6:15am
Departure for graduation

9am-
Graduation begins

Noon-
Chicago Botanical Garden on way back
Drop rental car.

Manny’s Deli or Pizza somewhere for lunch

NEED TO FILL IN THIS SPOT

Dinner at Gene and Georgetti’s for late dinner

What am I missing? Doing wrong?
 
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AlexanderUrinis

AlexanderUrinis

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Not sure if you drink, but there are some good breweries in Chicago. I did a mini beer trip several years ago and had a blast.

Hope you enjoy your time!
 
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Yellowsnow51

Yellowsnow51

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The_Joker13_rivals said:
Corner bar in Bucktown

******* Christ, get some Chicago pizza. Gino’s east gets **** for being touristy, but it’s fvckin good.
Click to expand...
I have it on there. Probably not gonna do Manny’s. I also will be leaving the wife and kid after putting them to bed and going to the casino to play blackjack for a bit. So pizza will probably happen sometime around there as well.
 
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5

52317Hawk

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Go to Obama's library on the near south side. Drive down and park 4 blocks away and walk down. See the "culture".
 
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fatpiggy

fatpiggy

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Aug 18, 2002
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Yellowsnow51 said:
Son is graduating boot camp at Great Lakes Navy facility so we are heading up a few days before to the Windy City. Never been. Pumped.

iPad 2 fully charged.



Chicago Itinerary (Subject to change)

Day 1
Drop bags at hotel

10:30 AM
Walk Riverwalk.

11:30 AM
Lunch at Portillo's.

Checking off:
  • Italian Beef
  • Chicago Dog
  • Cake Shake
1:30 PM
Architecture Cruise

3:30 PM
Navy Pier

5:00 PM
Hotel check-in and rest

6:15 PM
Garrett Popcorn snack

8:00 PM
360 Chicago

Late Dinner at
Francesca’s on Chestnut

Day 2
9AM Millenium Park

10 AM
Cindy’s Rooftop brunch

11:00 AM
Art Institute

2:00 PM
Rental car

Head to
Great Lakes graduation Ticket Pickup

The Silo for early Dinner

Home Alone House/ Area in way back

Water taxi to Fulton Market
  • The Publican for Charcuterie
Rainbow Cone or Venchi Chocolate on way back

Day 3

6:15am
Departure for graduation

9am-
Graduation begins

Noon-
Chicago Botanical Garden on way back
Drop rental car.

Manny’s Deli or Pizza somewhere for lunch

NEED TO FILL IN THIS SPOT

Dinner at Gene and Georgetti’s for late dinner

What am I missing? Doing wrong?
Click to expand...
The one thing I dont see on your list is biking the lake front path. You can rent those blue divvy bikes from almost any corner and make your way to the lakefront. Make sure to go into the wind first. Best way to see the city imo.
 
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A

Aardvark86

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Oct 12, 2021
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Yellowsnow51 said:
Son is graduating boot camp at Great Lakes Navy facility so we are heading up a few days before to the Windy City. Never been. Pumped.

iPad 2 fully charged.



Chicago Itinerary (Subject to change)

Day 1
Drop bags at hotel

10:30 AM
Walk Riverwalk.

11:30 AM
Lunch at Portillo's.

Checking off:
  • Italian Beef
  • Chicago Dog
  • Cake Shake
1:30 PM
Architecture Cruise

3:30 PM
Navy Pier

5:00 PM
Hotel check-in and rest

6:15 PM
Garrett Popcorn snack

8:00 PM
360 Chicago

Late Dinner at
Francesca’s on Chestnut

Day 2
9AM Millenium Park

10 AM
Cindy’s Rooftop brunch

11:00 AM
Art Institute

2:00 PM
Rental car

Head to
Great Lakes graduation Ticket Pickup

The Silo for early Dinner

Home Alone House/ Area in way back

Water taxi to Fulton Market
  • The Publican for Charcuterie
Rainbow Cone or Venchi Chocolate on way back

Day 3

6:15am
Departure for graduation

9am-
Graduation begins

Noon-
Chicago Botanical Garden on way back
Drop rental car.

Manny’s Deli or Pizza somewhere for lunch

NEED TO FILL IN THIS SPOT

Dinner at Gene and Georgetti’s for late dinner

What am I missing? Doing wrong?
Click to expand...
Consider popping into the dreihaus museum if you are located downtown with a smallish window. Wonderful Victorian mansion and usually an interesting side exhibit that changes. If you like that sort of thing.

If you want to see a cool church off the beaten path, check out St. John cantius - amazing preservation story and restoration.

I could spend all day at the art institute, but it’s right sized that you can bite off as much as you want depending on what you like.

also: for breakfast, wild berry by millennium park
 
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hawkeyetraveler

hawkeyetraveler

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Aug 10, 2010
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Yellowsnow51 said:
Son is graduating boot camp at Great Lakes Navy facility so we are heading up a few days before to the Windy City. Never been. Pumped.

iPad 2 fully charged.



Chicago Itinerary (Subject to change)

Day 1
Drop bags at hotel

10:30 AM
Walk Riverwalk.

11:30 AM
Lunch at Portillo's.

Checking off:
  • Italian Beef
  • Chicago Dog
  • Cake Shake
1:30 PM
Architecture Cruise

3:30 PM
Navy Pier

5:00 PM
Hotel check-in and rest

6:15 PM
Garrett Popcorn snack

8:00 PM
360 Chicago

Late Dinner at
Francesca’s on Chestnut

Day 2
9AM Millenium Park

10 AM
Cindy’s Rooftop brunch

11:00 AM
Art Institute

2:00 PM
Rental car

Head to
Great Lakes graduation Ticket Pickup

The Silo for early Dinner

Home Alone House/ Area in way back

Water taxi to Fulton Market
  • The Publican for Charcuterie
Rainbow Cone or Venchi Chocolate on way back

Day 3

6:15am
Departure for graduation

9am-
Graduation begins

Noon-
Chicago Botanical Garden on way back
Drop rental car.

Manny’s Deli or Pizza somewhere for lunch

NEED TO FILL IN THIS SPOT

Dinner at Gene and Georgetti’s for late dinner

What am I missing? Doing wrong?
Click to expand...
Solid itinerary. You are packing a ton in and I guess you will be exhausted at the end of the trip!

Couple pointers:
  • I personally find Navy Pier to be meh if you don’t have young kids, but the views of the city are pretty cool from there.
  • I haven’t done 360 Chicago. There used to be a bar called the Signature Lounge up there which was an old school romantic spot for the sunset and drinks. Went a few times and every time someone around us proposed to their future wife. Great views!
  • 3 hours at the Art Institute won’t be much time. Seeing as you are CLEARLY a planner I would make sure to figure out what you want to see and focus on those areas. Also check for any special exhibits - they get all the world class traveling exhibits.
  • There will be a bit of walking for you. Example: The Publican is at least 1/2 mile from the water taxi drop off. If anyone in your group has mobility issues just be aware. Ubers will be easy to get in a pinch.
  • Publican has a world class beer list. Don’t just get the charcuterie (which is exceptional) get some frites (with the egg) and some mussels with a good trippel. They have the best mussels I have ever had and I have had plenty in France and Belgium. The no pic works in the office building kitty-corner to Publican so I have been many a time and never had a bad meal. Absolutely exceptional restaurant.
  • If you go for pizza I personally prefer the Chicago tavern style to deep dish, but if you haven’t had a Chicago style deep dish then I suppose that is kind of a mandatory tourist thing over Manny’s.
For your open afternoon:
  • there are tons of other museums, although a little more kid centric like The Field Museum, the Planetarium, The Acquarium and Science and Industry. Three of those are right by Soldier Field along the lake. Even if you don’t go in walking along the lake (edit: or biking as @fatpiggy suggests) in summer is usually great.
  • The Obama library is right by science and industry and close to the University of Chicago campus. I’m sure it is sold out already, but you could take pictures of the crazy architecture and spin up hours of HROT shItposts from both sides. You aren’t opposed to a good trolling thread after all.
  • Is there a Cubs or Sox game the open afternoon? If So that would be a good time. Even if not, grabbing a photo and beer while wandering around Wrigley is a tourist mainstay.
 
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Yellowsnow51

Yellowsnow51

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hawkeyetraveler said:
Solid itinerary. You are packing a ton in and I guess you will be exhausted at the end of the trip!

Couple pointers:
  • I personally find Navy Pier to be meh if you don’t have young kids, but the views of the city are pretty cool from there.
  • I haven’t done 360 Chicago. There used to be a bar called the Signature Loungeup there which was an old school romantic spot for the sunset and drinks. Went a few times and every time someone around us proposed to their future wife. Great views!
  • 3 hours at the Art Institute won’t be much time. Seeing as you are CLEARLY a planner I would make sure to figure out what you want to see snd focus on those areas. Also check for any special exhibits - they get all the world class traveling exhibits.
  • There will be a bit of walking for you. Example: The Publican is at least 1/2 mile from the water taxi drop off. If anyone in your group has mobility issues just be aware. Ubers will be easy to get in a pinch.
  • Publican has a world class beer list. Don’t just get the charcuterie (which is exceptional) get some frites (with the egg) and some mussels with a good trippel. They have the best mussels I have ever had and I have had plenty in France and Belgium. The no pic works in the office building kitty-corner to Publican so I have been many a time and never had a bad meal. Absolutely exceptional restaurant.
  • If you go for pizza I personally prefer the Chicago tavern style to deep dish, but if you haven’t had a Chicago style deep dish then I suppose that is kind of a mandatory tourist thing over Manny’s.
For your open afternoon:
  • there are tons of other museums, although a little more kid centric like The Field Museum, the Planetarium, The Acquarium and Science and Industry. Three of those are right by Soldier Field along the lake. Even if you don’t go in walking along the lake in summer is usually great.
  • The Obama library is right by science and industry and close to the University of Chicago campus. I’m sure it is sold out already, but you could take pictures of the crazy architecture and spin up hours of HROT shItposts from both sides.
  • Is there a Cubs or Sox game the open afternoon? If So that would be a good time. Even if not, grabbing a photo and beer while wandering around Wrigley is a tourist mainstay.
Click to expand...
Good stuff. The architecture tour departs from navy pier so that will just a lap around it.

I will have beer everywhere I go.

I can pickup the car whenever so we will get that after we are done at art institute.

We all can walk fine so distance is no problem.

No games in town.

I will get whatever pizza I see that I like. Don’t really care if it’s deep dish or not.
 
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fatpiggy

fatpiggy

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fatpiggy said:
The one thing I dont see on your list is biking the lake front path. You can rent those blue divvy bikes from almost any corner and make your way to the lakefront. Make sure to go into the wind first. Best way to see the city imo.
Click to expand...
Well ****, maybe not. lol

 
hawkeyetraveler

hawkeyetraveler

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Yellowsnow51 said:
Good stuff. The architecture tour departs from navy pier so that will just a lap around it.

I will have beer everywhere I go.

I can pickup the car whenever so we will get that after we are done at art institute.

We all can walk fine so distance is no problem.

No games in town.

I will get whatever pizza I see that I like. Don’t really care if it’s deep dish or not.
Click to expand...
Sounds like you have your sh*t squared away, it will be a great trip. One thing I forgot to say, there are special events in the city basically every weekend in the summer. When are you coming this way again?
 
Yellowsnow51

Yellowsnow51

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Mid
hawkeyetraveler said:
Sounds like you have your sh*t squared away, it will be a great trip. One thing I forgot to say, there are special events in the city basically every weekend in the summer. When are you coming this way again?
Click to expand...
Middle of July. Only thing I saw was Nick Offerman doing something. The only thing I’d be interested in is catching some live music somewhere.
 
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hawkeyetraveler

hawkeyetraveler

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fatpiggy said:
Lincoln Ave Street Festival is the weekend of July 25th . Good time
Click to expand...
It seems like there is a festival like this every weekend of the summer. They are all usually fun for some live music and beers.

I just looked it up, in mid July they also have:

Windy City Smokeout which is a country fest by the United Center with major headliners. Not my scene, but if you like country music and BBQ that seems interesting.

Also many smaller neighborhood fests:
Square roots fest in oldtown
West fest
Wicker Park fest

And more.

Chicago is one of the best cities on the planet in summer (just stay East and north) and one of the worst cities in winter.
 
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AFM22

AFM22

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2-2.5 hours at the art institute isn't enough.

You could spend 10 hours in there and not see everything.

You will likely be able to cover the hits, though.

There's also the field museum nearby.
 
hawkeyetraveler

hawkeyetraveler

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AFM22 said:
I once saw a beluga take a huge green shid at Shedd.
Click to expand...
Belugas are the Hoss of the ocean. Change my mind.

 
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baltimorened

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Yellowsnow51 said:
Son is graduating boot camp at Great Lakes Navy facility so we are heading up a few days before to the Windy City. Never been. Pumped.

iPad 2 fully charged.



Chicago Itinerary (Subject to change)

Day 1
Drop bags at hotel

10:30 AM
Walk Riverwalk.

11:30 AM
Lunch at Portillo's.

Checking off:
  • Italian Beef
  • Chicago Dog
  • Cake Shake
1:30 PM
Architecture Cruise

3:30 PM
Navy Pier

5:00 PM
Hotel check-in and rest

6:15 PM
Garrett Popcorn snack

8:00 PM
360 Chicago

Late Dinner at
Francesca’s on Chestnut

Day 2
9AM Millenium Park

10 AM
Cindy’s Rooftop brunch

11:00 AM
Art Institute

2:00 PM
Rental car

Head to
Great Lakes graduation Ticket Pickup

The Silo for early Dinner

Home Alone House/ Area in way back

Water taxi to Fulton Market
  • The Publican for Charcuterie
Rainbow Cone or Venchi Chocolate on way back

Day 3

6:15am
Departure for graduation

9am-
Graduation begins

Noon-
Chicago Botanical Garden on way back
Drop rental car.

Manny’s Deli or Pizza somewhere for lunch

NEED TO FILL IN THIS SPOT

Dinner at Gene and Georgetti’s for late dinner

What am I missing? Doing wrong?
Click to expand...
congratulations on your son's graduation....the NAVY is a great way to begin life in the adult world.
 
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rchawk

rchawk

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Oct 27, 2001
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hawkeyetraveler said:
Son is graduating boot camp at Great Lakes Navy facility so we are heading up a few days before to the Windy City. Never been. Pumped.

iPad 2 fully charged.



Chicago Itinerary (Subject to change)

Day 1
Drop bags at hotel

10:30 AM
Walk Riverwalk.

11:30 AM
Lunch at Portillo's.

Checking off:
  • Italian Beef
  • Chicago Dog
  • Cake Shake
1:30 PM
Architecture Cruise

3:30 PM
Navy Pier

5:00 PM
Hotel check-in and rest

6:15 PM
Garrett Popcorn snack

8:00 PM
360 Chicago

Late Dinner at
Francesca’s on Chestnut

Day 2
9AM Millenium Park

10 AM
Cindy’s Rooftop brunch

11:00 AM
Art Institute

2:00 PM
Rental car

Head to
Great Lakes graduation Ticket Pickup

The Silo for early Dinner

Home Alone House/ Area in way back

Water taxi to Fulton Market
  • The Publican for Charcuterie
Rainbow Cone or Venchi Chocolate on way back

Day 3

6:15am
Departure for graduation

9am-
Graduation begins

Noon-
Chicago Botanical Garden on way back
Drop rental car.

Manny’s Deli or Pizza somewhere for lunch

NEED TO FILL IN THIS SPOT

Dinner at Gene and Georgetti’s for late dinner

What am I missing? Doing wrong?
Click to expand...
Yellow I lived in the city, not the suburbs, for thirty years 1993-2023. You are doing everything right for the most part. Good call on Gene and Gergetti's in the Loop and Manny's Deli. Navy Pier is more fun for kids than adults, never been to the bontanical garden. Garrett's popcorn is good but not worth the long wait in line.

If you ask ten different Chicagoans where to get the best pizza you might get ten different answers. My favorite is Lou Malnati's but you may feel different.

If you don't mind walking you may not need the car so much. The Loop, River North, you can hoof it if you are healthy enough. Seriously the traffic is no fun, take a cab if you have to.

And very importantly, congratulations to your son, you must be a proud Dad.
 
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baltimorened

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Yellowsnow51 said:
He’s got a full ride to VMI on a ROTC scholarship so that’s nice. They send him there for two weeks before he starts in VA in August.
Click to expand...
now that's a smart young man...ROTC is one of the best ways to get a college education and get paid for it....congratulations to you..
 
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Aardvark86

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Yellowsnow51 said:
He’s got a full ride to VMI on a ROTC scholarship so that’s nice. They send him there for two weeks before he starts in VA in August.
Click to expand...
Dude. I walk my dogs past vmi campus every morning. They produce exceptionally fine young men and women who grow into balanced and engaged adult citizens. Though the va public universities are currently the rope in a game of political tug of war, the students see them through.

When you’re in town next, or if you/he ever need anything here in big lex, ping me. (We’ve also got a slightly primitive carriage house that is walking distance to everything if you ever have a problem finding a place on big weekends here).
 
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