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Chicago – Windy City

Celebrate Chicago

Many songs and movies have been based on or in Chicago.  For years my husband and I have wanted to travel there. In May we finally had the chance.  I wasn’t sure what to expect especially since most of the news you hear about Chicago involves violence.  However, from the airport to the city streets we were quite pleased.

We stayed in the historic hotel called Raffaelo (201 E Delaware Pl, Chicago, IL 60611)  The hotel is wonderfully located on the Magnificent Mile and within walking distance of the shops, great restaurants, and the John Hancock center.  The hotel also boasts a donut and coffee shop as well as a quaint rooftop bar.  Huge props to the hotel for allowing early check-in.  We arrived at 11am and for a $50 fee they said we could go ahead and check into our room.    Yes- please!

The only negatives about the hotel are the elevators.  They are extremely small and sometimes only 1 elevator would be working at a time.  However, we are not averse to taking stairs so it wasn’t a huge deal for us.  Who would we recommend staying here?

  • Yes- couples, business travel, and single tourists
  • Maybe – families/young kids – the only drawback to families staying here is it is an older hotel so the elevator might not fit a stroller and all your belongings. Also since there is a bar on the top of the hotel there are some interesting folks that wandering in the lobby in the later hours.  *They do have security working the lobby in the evenings and you do have to have a key card to get the elevators to work so that adds an extra peace of mind*

Some of the fun things we did in Chicago included the Gray Line Hop On/Off Trolley.  (website link )  We bought a 72 hour pass which allowed us to see every “touristy” stop along their tour routes.  We love that the Trolley allows for stops in order to explore more of a destination spot.  My husband and I often walked and would use the Trolley for transport.  It was super convenient.  We also loved the different drivers and what they would tell us about each location.  Every driver was different some stressed history and architecture; others were more movies and arts.  It is also something we highly recommend.  We try to take these tours in every city we can.

CTA –Highlights:

Chicago is CLEAN unlike New York where you see trash on the streets, sidewalks, everywhere.   Chicago was built with an underground road and alleyways.  This is where the trash accumulates so you don’t see it while walking the streets.  What a great idea!

We loved all the parks in Chicago.  They are incredibly clean and family friendly.  We literally walked for hours exploring the Millennium Park, Buckingham Fountain, the river front & the lake front.  We also took the challenge (totally self-imposed) to walk the entire Magnificent Mile.  There are some of the tallest buildings in the world located along this stretch of road.  Some of these include Trump Tower, John Hancock building, and Water Tower Place.

We were able to explore the John Hancock Building’s observatory on the 94th floor.  (go here for the link to tickets and more info  We went at night and had the most amazing views of the ocean and Chicago city streets.  Since this observatory is less busy than the Willis Tower we were able to spend over an hour taking pictures and watching the sunset.

NOTE: Photography pros & novices set up their cameras on the western side of the observatory in the hopes of capturing the “perfect” sunset.  If you want to capture the sunset arrive early afternoon and get your spot.  We were still able to get some amazing pictures because there really isn’t a bad location.  The John Hancock observatory also boasts the Tilt which is an extra fee.  It allows the occupant to be slowly tilted toward the street for an even better view.  Neither my husband nor I chose to do this but it looked fun.

Now on to the Willis Tower (link here – known as the Sears Tower when we were growing up.  We stopped during late afternoon hoping to be able to arrive in time for the sunset.  It was packed but crowds move quickly.  We were able to imagine we were in the scene of Ferris Bueller’s Day off and leaned against the windows alongside the mannequins posed as Sloan and Cameron.  We got to walk out onto the glass floor to see the street below.  I wish they had this option all around the observation deck since the better views were not on that side of the building but it was fun and super freaky.

Another fun adventure was a boat tour on the Tall Ship Windy.  (Website is here They sail out of Navy Pier so we decided to grab dinner and then hop on the sailboat.  It is a family run business with friendly staff that caters to making your experience a memorable one.  They even offer blankets which I needed because even in May the lake breeze was cold.

Blues music flourishes here with some of the best blues around.  We stopped one night in Blues Chicago.  It is a small local joint that features local and big time artists.  We had a blast and the bouncer was hilarious.  We highly recommend going.  We also stopped in Buddy Guys Legends.  While the music was good the food service was terrible.  We sat for over an hour waiting to be served.  We never got a waitress and finally left.  It’s too bad because the artists sounded great.

When in Chicago there are some things you must eat one item is the Chicago Dog.  We ate at Portillo’s Hot Dogs (100 W Ontario St, Chicago, IL 60610).  It is a great place with 2 floors, covered outdoor patio seating and more to choose from than just hot dogs.  It really had such yummy hot dogs and French fries.

I heard they also sell a cake shake.  They literally take a huge slice of cake, blend it up, add ice cream, and make a milkshake with a straw the size of your finger!  I mean WHAT?!  YUMMY!  Unfortunately I am lactose intolerant but my husband wishes he had tried it while there.

All in all we absolutely loved our visit to Chicago.

We felt safe the entire time and it is a lovely city with beautiful sights!





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