By Bobby Tanzilo Senior Editor/Writer Published Mar 01, 2009 at 8:14 AM

In lieu of grander vacations, my compact family has created something of a tradition of lightning-fast visits to the Windy City, based around hotel rate sales. Even 24 hours in downtown Chicago can be pricey, but with a little careful planning, an action-packed weekend down south doesn't have to break the bank.

Recently, our third such trip was built on a great rate -- less than $100 (not including parking) -- found online, at the historic Hilton, 720 S. Michigan Ave. A huge hotel -- the elevator bank boasts 14 cars! -- built in 1927, the Hilton is obviously feeling the pinch as one employee explained that the lobby bar was closed because the building was only at 14% capacity that weekend.

Arguably, our major expenses could end here since our toddler loves being in the hotel. The room in the Hilton offered views of construction and the El (as was the case on our previous visits at two other hotels, too), as well as the lake, Soldier Field, the Field Museum, the Shedd Aquarium and the Adler Planetarium (and Buddy Guy's Legends, too).

We also love that these little jaunts open new little worlds to our little one. One of the most successful and jaw-dropping examples for our kid was a quick ride on the State Street red line subway. But he also gets more and more practice being a courteous hotel guest and restaurant patron.

We opted to add a few sites and events to the agenda, too.

First up was a visit to the Hancock Observatory, 875 N. Michigan Ave. Adults are $15 but kids under 4 are free. Admission includes a multimedia "Sky Tour" that explains what you're looking at from 94 stories -- 1,000 feet -- above the Miracle Mile.

Because we visited Navy Pier during our summer visit and had talked up the Sears Tower, our child needed no help recognizing some of what could be seen. After a few minutes, hidden secrets of the city began to emerge and we delighted in spotting rooftop pools, the reflection of the Hancock tower on the waves of Lake Michigan and getting some fresh air in the fenced in open area (it was 60 degrees up there on that warm, sunny February day).

Dad was more than a little disappointed that the already award-winning Café Expression by Lavazza wasn't yet open on the observation deck, but we peeked in to try and get a glimpse.

"John Hancock Observatory not only has the best 360-degree views of Chicago," says general manager Daniel Thomas, "but now the experience is complete with new interactive and engaging features like the world’s highest Espression by Lavazza café, a free multi-media tour narrated by David Schwimmer and History Avenue.  Once the guests have finished at the Observatory, our complimentary concierge can help them plan their next Chicago adventure."

The observatory was a real hit and thanks to our having read about Curious George's trip across a downtown landscape attached to a bunch of balloons, we all knew what to expect the view to be like up there.

Afterward, we headed down the rapid-fire elevators for a quick lunch at the over-packed L'Appetito Café that served up delicious panini, espresso drinks, Italian cookies, gelato and also sells some packaged Italian specialty foods. Lunch for three, including cookies, was $20.

A perfectly timed e-mail alert from an Internet travel site clued us in to dirt-cheap tickets to see a Bob the Builder show at the Chicago Theatre that is skipping Milwaukee on its national tour. To stay within our budget and maximize our limited time, one of us accompanied our toddler to the show and the other met up with a friend who joined us for a post-show dinner.

To get to the theater, we walked a couple blocks to State Street, stopping off to check out the Water Tower and the horses attached to carriages on the western side of the square.

Then we descended beneath Chicago Avenue and rode the Red Line subway two stops to Lake. It was a short ride, but long enough for our train-loving toddler (I know, that's redundant, isn't it?) to experience what he's only seen in books. And at $4.50 for two adults -- again, kids are free (under 7) - it was one of the best bargains of the trip.

Meeting up after the show, we opted for an inexpensive dinner at the Artist's Café, 412 S. Michigan Ave., across from the Art Institute -- which we visited last time ‘round. The café -- a traditional diner -- opened in 1961 and is popular with Art Institute students, employees and patrons. There you can dine for around $10 per person, which in the heart of Chicago is a real bargain. There's also outdoor seating on Michigan Avenue when the weather is reliably warm.

While our toddler slept, we took turns chatting and having a drink in the hotel lobby with our friend before he caught his last train back out to the western suburbs. Babar and Celeste don't mind leaving their kids alone in hotel rooms, but we're more cautious that way.

The next morning, we walked three blocks to the Eleven City Diner, a Brooklyn-style Kosher deli and diner, with a bit of a hipster vibe, where I was happy to share my egg cream with my son, for his first taste of this childhood favorite of mine.

Eleven City Diner, 1112 S. Wabash Ave., was not only staffed with just about the nicest people we encountered all weekend (and that's saying something since darn near everyone was sweet as pie), it was also affordable and, oddly, packed with Wisconsinites, from our Milwaukee-native waiter to the table of New Berliners next to us.

We decided against the lox and I went for the completely over the top Tom Waits 2 a.m. Breakfast 1987, which for $10.95 got me two eggs, two huge pancakes, two delicious and slightly tangy sausages, house potatoes and two slices of toast.

Next, we zipped down Lake Shore Drive to Obama's Hyde Park neighborhood to check out some of the many, many charms of the Museum of Science and Industry, 57th Street and Lake Shore Drive, which has so much to see and do that we dubbed it the Louvre of Family Museums.

The Idea Factory is a science-focused Brinn-style room with some really engaging hands-on stuff for the kids and it was an instant hit. We stopped here first and momentarily thought we'd never make it any deeper into the museum.

But then our toddler saw a real John Deere tractor and combine that you could climb into and we were off. That led us up to the insanely huge model railroad layout -- called The Great Train Story -- that's in a hall with real steam engines, trolley cars, jet-propelled cars and a Boeing 727 suspended from the ceiling. The experience of seeing them all in the same space is awe inspiring.

"ToyMaker 3000: An Adventure in Automation" was a really interesting look into engineering and the manufacturing process, but we popped in only briefly, bagging once we realized that it's meant for much older children.

Although "Yesterday's Main Street" is much smaller than the "Streets of Old Milwaukee" it was a hit and so was "Colleen Moore's Fairy Castle," a model of a turreted castle complete with improbably huge dining room and towers.

As we walked around the outside of the gorgeous Silver Streak Pioneer Zephyr, our little one was yawning nearly non-stop and we knew that even though there was a real submarine and lots more to see, it was time to go.

Admission is $13 for adults, $9 for kids 3-11. Parking is $16 although we quickly realized that parking in Hyde Park on a Sunday morning is easy, free and almost restriction-free. We found a spot a 5-minute walk from the door.

And 23 hours after we hit the Loop, we were headed back to Milwaukee, with some solid memories blowing around in our heads.

If you're looking for guidebooks to Chicago, Time Out offers a thorough general guide ($19.95) and an annual "Eating & Drinking" guide ($11.99), too.

The main book is in its fourth edition and the 2009 food guide is the second edition.

The general guidebook -- which also has a short section on day trips to Milwaukee, Madison and The Dells -- is perfect for planning short and longer visits to the city. The "Children" section of the guidebook has five pages of suggestions perfect for little ones, including restaurants. But, remember much of what's discussed in the book's other 330-odd pages is also fun with kids.

Bobby Tanzilo Senior Editor/Writer

Born in Brooklyn, N.Y., where he lived until he was 17, Bobby received his BA-Mass Communications from UWM in 1989 and has lived in Walker's Point, Bay View, Enderis Park, South Milwaukee and on the East Side.

He has published three non-fiction books in Italy – including one about an event in Milwaukee history, which was published in the U.S. in autumn 2010. Four more books, all about Milwaukee, have been published by The History Press.

With his most recent band, The Yell Leaders, Bobby released four LPs and had a songs featured in episodes of TV's "Party of Five" and "Dawson's Creek," and films in Japan, South America and the U.S. The Yell Leaders were named the best unsigned band in their region by VH-1 as part of its Rock Across America 1998 Tour. Most recently, the band contributed tracks to a UK vinyl/CD tribute to the Redskins and collaborated on a track with Italian novelist Enrico Remmert.

He's produced three installments of the "OMCD" series of local music compilations for OnMilwaukee.com and in 2007 produced a CD of Italian music and poetry.

In 2005, he was awarded the City of Asti's (Italy) Journalism Prize for his work focusing on that area. He has also won awards from the Milwaukee Press Club.

He can be heard weekly on 88Nine Radio Milwaukee talking about his "Urban Spelunking" series of stories.