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First time trip-itinerary and meals suggestions needed

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wayne pa
posts: 267
reviews: 22
First time trip-itinerary and meals suggestions needed

We are traveling with 10(D) and 12(S) year old who have a variety of interests but are not fancy eaters so I'm not looking for fine dining options. I have not chosen a hotel looking at hotels near Grant or Millennium Parks Still checking sites for a good deal but think I’ll end up at The Essex Inn.

Here is a draft itinerary. Just trying to get everything to fit but I’m up for any changes to itinerary since nothing is set in stone except baseball games (one of the main reasons for our trip).

Also, if anyone has suggestions on places to eat.

Thank you!

Saturday, August 23rd

flight into O'Hare arrive at 11

check in hotel or drop bags


Lincoln Park (zoo, pond for boat ride and Chicago History Museum)

Oak street beach


Navy Pier for the evening of amusements and fireworks @10:15

does anyone know anything about the Cirque show on the pier?

are my children too old for the Children’s Museum?

Sunday, August 24th

Breakfast: near hotel

9am Wrigley tour

Lunch: (somewhere near Wrigley)

1:20 game (will take Metro) (ends around 5)

Back to hotel for swim


Millennium Park (Bean/Jay Pritzker Park/Crown Fountain)

Monday, August 25th

Breakfast: Yolk

Shedd (be there by 9am)

Lunch: at aquarium

Finish aquarium

Back to hotel for swim

Dinner: Ed Debevic’s

Tuesday, August 26th


Willis Tower (opens at 9 am)

Wendella combined lake and river tour (90 minutes)

Lunch: pizza place

Walk Magnificent mile

Back to hotel


7:10 White Sox Game

Wednesday, August 27th


Museum of Industry and Science (uboat and coal mine)

Lunch: in museum

Finish up museum


Grant Park (Buckingham Fountain-water show top of hour)

Thursday, August 28th


One more stroll in the park

Flight leaves O’Hare at 1:45

21 replies to this topic
Houston, Texas
posts: 8,596
reviews: 306
11. Re: First time trip-itinerary and meals suggestions needed

Also the Field Museum is an excellent choice if you can fit it in.

Giordanos, Lou Malnati's, Gino's East are great places for you to get pizza from.

Rensselaer, Indiana
posts: 4,702
12. Re: First time trip-itinerary and meals suggestions needed

Day 1: You've just got too much scheduled on this day. If your flight gets in at 11 a.m., you probably won't get down to the Essex Inn until at least 12:30 p.m. if you are flying into O'Hare. When you allow at least 1/2 hour for check in, etc. and about 45 minutes travel time up to the Lincoln Park Zoo area, it's going to be mid-afternoon. That is, unless you are willing to spring for cab rides everywhere.

Are you speaking of the swan boats at Lincoln Park? They haven't had those for a few years now, ever since the Nature Boardwalk was constructed. You can cross that off your list. Your children may wish to take a ride on the Endangered Species Carousel at the Zoo - but, if not, at least take a look at it. Just lovely.

Not to state the obvious, but the Cirque show at Navy Pier is not Cirque du Soleil. I mention this only because I remember that last year someone posted a critique where they didn't realize it was different.

Just remember that any tour will recommend that you to be there a certain amount of time prior to the commencement of it (usually 1/2 hour). That means Wrigley - and you'll have to find a place open quite early for breakfast on a Sunday. An 8 a.m. opening would not give you enough time to eat and travel up to Wrigley Field for a 9 a.m. tour, even taking the Red Line.

I don't think you'll have enough time for both the Willis Tower and the Wendella tour in a single morning, unless you mean a very late lunch. You'd really have to zoom through Willis to make that time frame. Remember, again, you'll have to show up early for the boarding of the tour (recommended 1/2 hour is pretty much standard), the tour itself is 90 minutes and then you have to allow for disembarking (another 10-15 minutes). So that 90 minute tour ends up actually being around 2 hours - not including travel time to get to the boarding area.

Chicago, Illinois
posts: 216
reviews: 188
13. Re: First time trip-itinerary and meals suggestions needed

The Childrens Museum is geared toward younger kids. As for restaurants, if you want something really "Chicago", go to a Chicago pizza place such as Giordano's or Uno's. There will be a wait, so make sure you place your pizza order while you wait.

wayne pa
posts: 267
reviews: 22
14. Re: First time trip-itinerary and meals suggestions needed

Thank you ChiTownFriend for all your suggestions re: timing of activities as well as the fact that the Navy pier show is not Cirque. I will be reworking my schedule accordingly. I really wish some of the museums I'm considering had evening hours. (Only the Field appears to have "evening hours" which only means staying open until 6 rather than 5 during most of our stay) I'll be able to rework better once I really decide on a hotel.

For what we want to do the Essex Inn seems pretty well located so I'm still focusing in on that hotel. Although, we do like to stay at Embassy Suites for the convenient and delicious buffet breakfast which enables us to get up and out to see the sites quickly. However, the Embassy suite prices in Chicago are a bit high ~even considering breakfast is included and it doesn't appear the hotels are found much on hotwire.

Rensselaer, Indiana
posts: 4,702
15. Re: First time trip-itinerary and meals suggestions needed

You're welcome. Sometimes people don't realize how the little things, such as travel times, boarding/wait times for tours, fully affect their entire schedule for the day.

Before I go into this, did you purchase City Passes or some other pass? If so, this suggestion will not come about under their terms.

Inasfar as late hours, the Shedd has their Jazzin' at the Shedd on Wednesdays 5-10 p.m. Family-friendly and there is late entry (look at the website for full details). Maybe switch your Monday & Wednesday schedules? Except, of course, for the swim. To be honest, you'd probably more appreciate it after the MSI, instead of going to Buckingham Fountain, then.

I should also mention that when you take the Wendella cruise, some appreciable time will be spent in the locks. Only mentioning this, in case your kids get kind of impatient, but at their ages shouldn't be so much of a problem.

Edited: 12:44 pm, June 20, 2014
wayne pa
posts: 267
reviews: 22
16. Re: First time trip-itinerary and meals suggestions needed

ChiTownFriend thank you again for your helpful advice!!

No, I did not purchase the City Pass yet but was looking into it.

That is great news about Jazzin at the Shedd! I recently saw the event on groupon and read the description, or I guess I should say misread it. I thought it was just a music concert on the aquarium outside grounds and did not realize the event allowed you into the aquarium itself. That sounds like a lot of fun and would be something we would definitely enjoy and it would take care of many itinerary issues and concerns. Now, if I can only find that groupon....

I'm not happy with my first day itinerary. I think I might just forget Lincoln park on this trip and just think about doing lunch, Wendella and Navy pier that 1st day. However, I am worried about flight delays and Wendella reservations.. obliviously still tweaking the entire itinerary with the Jazzin at the Shedd news.

It would be most helpful if I could just decide on a hotel. The Essex Inn seems pretty good based on our needs and budget but I'm wondering if it's a bit far South of most attractions we're interested in-should we be closer to Millennium Park?

Thanks again for your help. I just love TA!!!

Chicago, Illinois
posts: 18
17. Re: First time trip-itinerary and meals suggestions needed

Except for the first day, I think your itinerary is quite reasonable. On the first day, I would find getting to Lincoln Park a hassle after having just dealt with airports, airlines, and hotel check-ins. It might be more relaxing to do the beach. Just as someone else suggested above, I also would suggest Ohio Street beach, as it is closer to the area you are thinking about staying. It's also right next to Navy Pier. If you wanted to get your Chicago pizza experience in on that day, there is a Giordano's near that area as well--just a few blocks south of the river.

On the day you are at Wrigley Field, there is a diner called Salt and Pepper that might be fun for the kids--just south of the ballpark on Clark. However, there is a lot around that area--won't be hard to find a place for lunch.

It looks like after the game you are heading to Millennium Park. There is a restaurant there called Park Grill. You will probably want a reservation there. Assuming the game ends at 5:00, a 7:00 reservation should give you enough time to get back downtown on the el. If you get there early, you can kill time seeing some of the Park while you are waiting.

If you decide to do the evening Shedd visit, you might move the visit to Willis Tower to Monday morning (where you originally have the Shedd scheduled), so that your Tuesday morning is not so hectic.

Enjoy the city!

Chicago, Illinois
posts: 12
reviews: 6
18. Re: First time trip-itinerary and meals suggestions needed

Check this out for a hotel guide: makeitbetter.net/entertainment/outings-a-tra…

I would recommend the Aloft for your family!

wayne pa
posts: 267
reviews: 22
19. Re: First time trip-itinerary and meals suggestions needed

Thank you Flaneurette21. So many hotel choices!

I have switched around our itinerary based on TA recommendations.


Lunch near hotel

Wendella (river/lake tour)

Willis Tower (Wednesday if it doesn’t work here)

North Beach

Dinner near pier

Navy Pier (Fireworks 10:15)


Wrigley tour 9:30

Lunch in or around ballpark

Cubs game 1:20

Grant Park

Dinner: Lou Malnati's

Summerdance 7:30-9:30 (Grant Park)


MIS (all day lunch in museum)

Dinner: Ed Debevic's

Millennium Park in evening


Breakfast: Yolk (on way to museum)

Field Museum

7:10 White sox game (dinner at ballpark)


Lincoln Park or Art Institute

5:00-10:00 Jazzin at the Shedd


One last look around

1:45 flight home

Destination Expert
for Chicago, Illinois
posts: 33,623
reviews: 66
20. Re: First time trip-itinerary and meals suggestions needed

You might want to consider dinner in Chinatown on the way to the Sox game. It's on the way.

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