Share with your friends!Share on Facebook
Pin on Pinterest
Tweet about this on Twitter

In this segment of “3 Perfect Days”, we are going to cover one of the most storied yet beautiful cities in the world…Chicago.  First, let’s start with a fun fact.  By now, most adult human beings know that Chicago has a long-standing nickname of “The Windy City”.  One step out onto Michigan Ave. and you may agree with this designation as the swirling winds gusts through Chicago’s famous corridors and sometimes give its inhabitants a jolt.  That said, “The Windy City” reference did not come from some clever meteorologist.  Instead, it came from Charles A. Dana, once the editor of the New York Sun—a paper published between 1833 and 1950—who wrote an editorial that said Chicago was windy because of its full-of-hot-air politicians.  Over a century later, you likely will not find an inhabitant of Chicago who does not agree with that assertion still.  

Where to Stay

There are so many great hotels in Chicago, it is impossible to pick one, and that fact is that many readers already have their favorite chains due to points programs.  So, I would suggest the area that you target is the popular River North area of Chicago.  It has close walking proximity to Lake Michigan, The Chicago River, Millennium Park, Michigan Avenue Shopping, Theatre, public transportation, and some of the best local dining in the world.  

When to Go

Chicago is a Summer City.  Period.  Late Spring and early Fall are beautiful as well, but to make the most of the city, go between Memorial Day and Labor Day.  May through September, Chicago will rank as one of the best cities in the world.

Your Itinerary

Day One.

Breakfast-Yolk in River North.  If you took our suggestion to stay in the River North neighborhood, you will be able to walk here.  They have a little something for everyone.

Shedd Aquarium and Adler Planetarium.  Chicago has some of the best museums in the world including the Field Museum, Chicago Institute of Art and the Museum of Science and Industry.  We recommend double dipping at the ‘Museum Campus” where the Field Museum, Adler Planetarium, and Shedd Aquarium all reside.  Skip the Field Museum until the kids are old enough to appreciate old fossils and artifacts that teach how the world was created.  Instead, hit the Shedd in the Morning, grab a snack at the Shedd café, and then hit the Planetarium.  or

DinnerGinos or Lou Malnatis.  Your family has been talking about it for days leading up to the trip, so get it done.  Pizza!  There are plenty of good pizza spots in Chicago.  Probably the two most popular are Ginos or Lous.  You cannot go wrong with either, and both are in the River North neighborhood. or

Day Two.

Breakfast-Lou Mitchells.  This Greek diner in the southwest loop area is on the National Register of Historic Places.  Many Presidents, politicians, actors and otherwise famous people love the ambiance of this place.  You may want to take a cab or Uber here as it is a bit of a walk.

Morning-Willis Tower Skydeck.  This place is walkable from Lou’s and a “must do” while in Chicago.  There are not many places in the world where you can stand out on a glass deck at over 1,300 feet in the air with breathtaking views of the City.

Lunch- Park Grill.  This location is right where you want to be to for the second half of your day.  Eat inside at the Grill which is a bit fancier and more expensive, but has air conditioning on a hot day.  Or, sit out on the plaza for an excellent view of the park and Michigan Ave.

Afternoon-Millennium Park.  See “The Bean” and some of the world-famous sculptures and artwork.  Play in Maggie Daily Park, and be sure to pack some dry clothes for the little ones as they have a chance to play in one of the fountains.  A must see here is Buckingham Fountain, and the Bean.

Dinner- Frontera Grill.  This is one of celebrity chef Rick Bayless spots that celebrates all things Mexico and the Southwest.  They have outdoor and indoor seating.

Day Three.

Breakfast-Corner Bakery Café. Go to the one at Michigan and Wacker.

Morning-Chicago Architecture Boat Tour.  Tour Chicago by boat as it travels up and down the Chicago River.  Learn about the city and some of the important architecture that city is world famous for.

Lunch-Billy Goat Tavern. As made famous by the skit on Saturday Night Live, this iconic Chicago landmark was once a hangout of all of the Chicago writers and reporters.  Get a double!

Afternoon-Michigan Avenue.  Walk, shop, play.  

Dinner-Volare’.  Volare’ is an Italian Restaurant in River East.  It is easily one of the best in the City with excellent service, great wine list, and phenomenal food that isn’t overpriced.

After dinner activities for all three nights include free concerts in Millennium Park, Bowling at 10 Pin, or a nice walk on the brand-new riverfront walkway.  Whatever you do, enjoy one of the most beautiful cities in the world.