CHICAGO - My Kind of Town (What to do there)

by sarahmfry, September 11, 2012
I get asked fairly often by friends who are planning a trip to Chicago...."What should we see? What can we do that's free or cheap?"  I was writing an email to some friends this morning to answer that question and it turned into a blog down memory lane.

On a date in Chicago. September 2008

You can spend a whole day doing the free stuff in Chicago:

Navy Pier.  It used to be the Navy base.   The main building has been turned into a sortof long mall with attractions.  There is lots of shopping, things to see, food to buy, and a nice walk outside along the water.  Outside there are rides, including a ferris wheel that is beautiful at night.  We often park at Navy Pier then ride the busses & subway around town (the busses stop right outside the Navy Pier main doors - to the right)

IMPORTANT PARKING/TRANSPORTATION NOTE:  Expect to pay at least $20-$30 for parking anywhere (driving around doesn't find you anything cheaper.  Many of the garages look cheaper because they post their "early bird" prices at the entrance.  But when you pull in you realize they're just as expensive.  And don't expect to find street parking.  Chicago is like a second (or third) home to us and I don't think we've EVER found street parking.  Seriously.  That is why we park one place and ride the bus or subway around for the day.  Besides, you wouldn't want to fight traffic driving around downtown and pay for re-parking.  The bus/subway (CTA) pass is great, because you can just hop on and off wherever you want.  And the drivers are helpful if you don't have a clue what you're doing.

You can get a CTA bus/subway pass at Osco or Walgreens drug stores.  There is a Walgreens very close to Navy Pier.  David walks there to buy the passes.  A 1-day CTA (Chicago Transit Authority) pass is $5.75 for unlimited rides on busses and subway all day.  They also have passes for more days if you're staying longer.  You can buy these online, but we usually don't plan that far in advance.  They can take up to 10 days to arrive in the mail.  If you are planning enough in advance for a trip, it would be very helpful to have your passes in advance.  Don't forget to pick up a bus schedule or subway map.  If you're overwhelmed at first, just ask someone for help.  There are people everywhere.

The busses were nearly empty on Christmas Eve!
We love the Subway

Clarification about the trains:  "Metra" is the train system that brings people in from the suburbs.  It only goes to Union Station. If you see "CTA" it refers to the busses and subway system downtown.  The subway is also referred to as the "L" - as in elevated subway.  This is still the CTA subway, it just goes above ground part of the time so they call it the "L".  Those terms were confusing to me for awhile.  If you're big-city-brave and want to experience something new, you can park in one of the free Metra stations somewhere in the suburbs and ride the double-decker train into the city. You would end up at Union Station.  Then you would purchase a CTA pass there to get around downtown.  We have enjoyed doing this for different reasons:  when we have stayed in a hotel in the suburbs, coming in from David's school is north of Chicago, and just to give the kids the experience of riding the double decker Metra train.  It's pretty cool.

Waiting at the train station for Metra to take us into the city. October 2008

Watching the view from the train - on the way into the city from the northern suburbs

Riding the double decker train into the city. September 2008

Enough about transportation.....On to more FREE STUFF:

Cloud Gate....affectionately known around the world as "The Bean"  (It's in Millenium park. Nothing major to do at the bean, but it is cool and a classic "Chicago" work of art.  It is definitely worth seeing and a great photo op.  (In the winter they have ice skating.)

David and Caiden bravely holding up the bean....with astounded stranger boy looking on in awe.

 Museum of Contemporary Art Chicago - Closed on Mondays.  "Suggested" admission of $12.   We went in free - don't know if they've changed that and make you pay now.  It's really a neat museum.  We laughed at a lot of what we saw ( I don't have a whole lot of respect for a lot of Contemporary art's ideas), but it was fun.

There is a beautiful farmer's sidewalk market right outside of the Museum of Contemporary Art
World's Tallest Church Building - The First United Methodist Church of Chicago.  Called the "skyscraper church."  Not the world's tallest church, mind you.  That church is in Ulm, Germany. (Not sure what the difference is between the world's tallest Church and the world's tallest Church Building.  But this one is tall.  I promise. 

The Magnificent Mile - It's not quite as defined as it sounds...You probably won't stop and say "Oh!  This must be the magnificent mile!"   It's basically a long stretch of expensively wonderful window shopping along Michigan Avenue.  It is truly a beautiful sight at Christmas with all the lights.  We prefer to focus our attention around the Water Tower area.

Water Tower Place - This is one of the central places downtown. The Water Tower itself is actually just a tower in the middle of the road, but the stores and restaurants around it are great.   There is also great shopping (window shopping, for us!) in the Water Tower Place mall.

Inside Water Place, you will find the American Girl Place and the Lego Store  This is a regular small-but-cool Lego store - and not to be confused with the larger Legoland Discovery Center

An example of the amazing Lego creations at the Lego Store @ Water Tower Place. Mind-boggling!

American Girl Place 2008.  There is an expensive tea room, but it's out of our league. : ) We usually share a low-dollar treat from the treat shop right outside the tea room.

Palmer House Hotel - This may not mean anything to you unless you enjoy Fry Family history and fancy hotels. : )  This is the hotel where Grandpa Fry was  bellboy when he left home and went to Chicago to get a job at about 15 years of age.  It's just a gorgeously elegant place - worth seeing.


Lincoln Park Zoo - It's open and FREE 365 days a year!  It's not an earth-shattering zoo, but it is very nice and sort of like taking a stroll through the park.  We really enjoy it.  We also love Brookfield Zoo and are members there this year, but you don't want to go to Brookfield unless that is your only plan for the day.  It's massive. And not free.
Lincoln Park Zoo - March 2010

Walk along the lakefront - "Few if any other cities in the United States can boast a 26 mile lakefront with 33 beaches, 19 miles of bicycling paths, walking trails, driving ranges and golf courses, volleyball and soccer games, harbors and nature areas like bird and wildlife sanctuaries – all free and open to the public. These fabulous amenities share the lakefront with renowned museums, a world-famous fountain, a unique historic theater, cultural centers and other popular attractions."

We have enjoyed just taking a picnic to one of the (non-beach) parks along the lake.  Watching the sail boats, looking across the water to the skyline, enjoying the sea gulls and the breeze.  Can't beat that for free.  : )


There is plenty of fast food on the streets downtown if you don't care about dining experiences.  But I will warn you, if you just decide to grab a bite in the food court at the mall, you can easily spend as much as you would if you actually went to a restaurant and had a nice Chicago Dining experience.   The prices at these Chicago food courts will make you gulp. (Pack a sandwich or grab a sandwich from a dollar menu and eat by the lake!)

A few of our favorites for a special time:

Giordanos - You can't leave Chicago without trying real Chicago-style pizza at least once.  Giordianos is our favorite.  This is some serious pizza.  The sauce is on top of the cheese, and the crust is hard to have to experience it.  But expect to wait about 45 minutes for them to create such deliciousness.  (Go after you've been walking for awhile and are ready to sit for a bit.) If you're trying to decide what size to order for the stuffed pizza, you may want to order one size smaller than you would order for normal pizza.  It's seriously thick.  A small stuffed cheese is $13.50.  We go to the location at the corner of  Rush Street and Superior street.  It is close to the Water Tower square - an easy walk.  Just ask anyone you see to point you in the right direction.  Gino's is also a very famous Chicago pizza stop.  We prefer both the pizza and the atmosphere at Giordanos - it's a little more classy.  Ginos is a little more pub-ish.  But many, many famous people have eaten at Gino's East and left their mark.  And it is pretty cool that everyone signs the walls.

Great feeling - relaxing at Giordano's after a long day of walking the city.  October 2008
Celebrating Karissa's 6th Birthday at Giordanos in Chicago.  July 2010
Christmas Eve with David's family.  2010

Ralph Lauren Restaurant - Classy and delicious for a very special occasion.  Go at lunch to save. (You'll still pay at least $10.00 per person.)  Their fries are truly amazing.  We went alone on a date....You probably won't want to take tired kids in there after a day of sightseeing.  Giordanos' atmosphere handles that much better.

Oops! How did THAT get in here?  Anthropologie is very near the RL restaurant at Water Tower.  I'd never been there, so I had to go in and see what all the fuss was about this store.  I found a coffee mug I could afford for $6!  Glad I got THAT out of my system.  Saved the bag to prove it.  lol  (March 2012)

Ghirirdelli  Ice Cream and Chocolate Shop. This is an adorable soda-fountain-type ice cream place.  It's right around the Water Tower (across from the Hershey store, no less!)  They have treats big enough to share.

It was David's idea on this date to go to Ghirirdelli and share a brownie sundae treat.  Is it any wonder I love this man?

If you 're up for spending a little more money:
Legoland Discovery Center, which is in Schaumburg.  It looks like quite a place....Admission is $15-18. We haven't been there yet.  (Ask Angie Davis if you want to know details about the Legoland experience.) Public transportation from downtown Chicago to Legoland: Take the CTA Blue Line to the Rosemont Station. Transfer to the Route 606 Pace bus. Exit at Woodfield Mall. LEGOLAND Discovery Center is located directly across the street.
The Skydeck Chicago at Willis Tower (formerly Sears Tower).   Tickets are $17.50.  But if you're the standing-on-a-glass-balcony-103-floors-up type of gal, go for it!  We haven't actually gone up since they changed things around and added the glass balconies.  But the view is spectacular from 103 floors up -any way you look at it.

Shedd Aquarium We went on free day one year.  It was okay, but I don't remember it being the most amazing aquarium ever.
Pausing the triple stroller in a quiet hall during our visit at Shedd Aquarium for an asthma treatment.  2008

Outside Shedd Aquarium.  October 2008

Field Museum I haven't been there yet but my parents and sister love it.

Museum of Science and Industry  My personal favorite.  Amazing place.  We made the trip up there with our school for a field trip.  Very kid and adult friendly.  Actually well worth the $15 admission.
Amazing model train display at the museum

If  you're taking a serious vacation to Chicago, want to see multiple sights, and have a hefty budget, you will want to consider the CityPASS, which gets you into 5 of the main attractions for $84. I know that's supposed to really be a great deal, but it's never sounded very cheap to us.  lol   It's only a good deal if you were planning on spending the money for most of those attractions anyway (and if you don't have a dozen kids.)

About hotels:  We think it's worth it to get a hotel downtown with Priceline name-your-own-price.  There's something great about being able to walk out of your hotel and right into the city life.  We suggest naming your own price of about $60-70 for a 3 star hotel downtown (you can click which areas you're willing to stay). But if you stay downtown, be sure to check on how much the hotel parking is for that hotel.  It is usually at least $30.00 per day.  But remember - you're going to pay that to park anywhere!

Enjoying a Priceline Hyatt in the suburbs 2008
  If you name your own price in the suburbs, you can get hotels even cheaper.  David used to do it every single week for school in the Chicago suburbs and regularly got an extended-stay-type hotel for about $25-30.  It was cheaper than using campus housing.  Obviously, hotel choice is very much a matter of personal opinion.  But we are willing to live on the edge and take a gamble in order to save some money through priceline.  We have gotten a few doozies in some cities (and had some great laughs), but we have used priceline for years.  And Priceline has made it possible for some pretty wonderful  stays within our budget.

 skyline - 2011
A note about weather:  It's not called the Windy City for nothing.  Expect it to be colder than you expect. The breezes off the lake are delicious as you walk the streets on a warm evening (take a little scarf or sweater in autumn or early spring).  But in the winter - it will bite through any coat you could muster.  Come to think of it, we are probably one of the few strange families who like to walk city streets in the dead of winter.  But it's worth mentioning.  Take hats and gloves and scarves and a good attitude.

Caiden Catching Chicago snowflakes on his tongue - Christmas Eve
Kayla eats a hot schnitzel at Christkindlmarket,  December 2011

Water Tower Place - Dec. 2010

It's been a fun trip down memory lane.  Chicago's my kind of town. : )


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