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Chicago Itinerary- For a Perfect Weekend Trip

No matter where I go and no matter what I see, one thing always remains true –  I am mad, deeply and profoundly in love with New York City. 

On my 3 days travel, I have met many people who feel the same adoration that I do for NYC, about Chicago, the windy city.

Its broad and dangerous charm has to me, remained on movie screens and Broadway shows.  This Great American town, the home of  Al Capone, Roxy Hart, and of course the one and only Oprah is my next experience.

Although I remain convinced that I will never meet a city like New York, I must admit that Chicago has become a close second. 


Chicago’s Magnificent Mile


The first thing I have to say about Chicago is that its dangerous reputation is greatly exaggerated.

Contrary to what many believe about Chicago, I got the impression that it was safe and tame. 

Perhaps this was a false impression on my part but, it was one I could simply not shake off. 

Another feeling I could not shake off was curiosity as I was walking down the Chicago streets.

There is something special about its avenues that are broad and decidedly more mid-western than the European feel of NYC’s downtown. 

Thankfully, the streets are nowhere near as crowded as NYC, and the people demonstrate that mid-western, polite attitude.  

On my first day in Chicago, upon arrival at the hip and centrally located Cambria Magnificent Mile Chicago hotel, I dropped off my bags and walked right out onto the Magnificent Mile;  aptly named because no matter how the economy is doing, business here is booming. 

This street definitely reminds me of Fifth Avenue, a glitzy and glamorous place where all the top retailers compete for coveted tourist (and local) dollars.


My suite at the Cambria Hotel

 The Cambria Hotel is one of those few places that manage to host both a hip rooftop bar and perfectly quiet suites that fill you with a sense of peace and comfort.

The beds, custom made with the finest linens and unique styling make you sit up and take notice of this carefully crafted space. 

It’s the kind of place you can come to the party and relax, or, as I am, on business. 

Amazingly,  it does all this at a lower price than the other Miracle Mile hotels which is no small feat for this pricey Chicago prime real estate location.

Just know that no matter what you decide to do here, you will find the perfect place and a space to do it –  in style.  Be sure to check them out on your visit. 

Day 1 – Chicago

The Navy Pier features a Ferris wheel and gorgeous views.

After my walk down the Magnificent Mile, I made my way over to the famous Navy Pier.  Initially completed in 1916, the Navy Pier is the oldest Chicago public space. 

It eventually fell into a state of disrepair but was revived again during the start of the Urban Renaissance in the mid-1990s.  Today, it’s a family-friendly attraction with a huge Ferris wheel,  children’s museum, and plenty of restaurants and bars.

A bonus is the lovely view of downtown that you can take in as you stroll down its 3,300 feet.  I suggest coming here during sunset as the view of downtown is magnificent and I loved watching the sunset over the buildings. 


A performance at Shedd Aquarium.

If you’ve followed me for any length of time you probably already know I love to learn.  Getting to visit places where learning is a way of life is a privilege – I have toured museums, research centers, universities – and aquariums. 

The Shedd Aquarium in Chicago is a hundred year old institution steeped in research, rescue work – and fun.  I have been to dozens of aquariums around the world but, this is the first and only one that I have visited that is host to  a beluga rescue and research center. 

This alone made the visit worthwhile for me, but on top of that there is an incredible dolphin show (with rescue dolphins) and loads of other exhibits, almost too many to count. I have to say, this aquarium is a must see stop on your visit to Chicago. 

Travel Tip – if you are here in the summer, visit the aquarium on a late Wednesday afternoon for the weekly Jazz evening.  The crowd tends to be older and it’s a fun grown up adventure in one of the coolest places in Chicago.

Day 2 – Chicago

The Riverwalk in the fall is gorgeous.

On my second morning in Chicago I made my way over to the Riverwalk, Chicago’s huge public space,  that travels for miles along the Chicago river.  Here, you can wander aimlessly for hours surrounded by beautiful buildings on one side and water on the other. 

Seeing that the space is so large, it’s not crowded, as tourists are spread out over many miles of the river walk.  Chicago’s River, which just a hundred years ago was so full of waste that it was solid enough for small animals to walk on is now a peaceful and clean green space. 

I suggest taking a long stroll along the river with a cup of coffee (or an ice cream depending on the weather) for one of the best and free experiences in Chicago. 


The real German U-boat captured in WW2 at the museum of Industry and Science.

After the Riverwalk I made my way into the Museum of Science and Industry. Just a short Uber ride away (Uber and its competitors is the easiest and fastest way to get around Chicago with surprisingly low fares) from Michigan avenue, is this sprawling museum that reminded me of the Museum of Natural History in New York City and the Smithsonian in D.C. 

The museum features exhibits oriented towards both children and adults as well as a great set of in depth special exhibitions.  One of my personal favorites was the simulated tornado, something I have never seen in another museum. 

Of particular interest to any history buff is the U505 exhibit – the well told true story of an American warship that captured a Nazi submarine boat and helped turned the tide of war.

The exhibit ends dramatically at the foot of the actual captured U boat. If interested, an onboard tour is available for an additional price, and I strongly suggest purchasing the special attraction ticket online as they do sell out.  


Taken at dusk during the River Cruise with the Chicago Architecture Foundation.

One of the most highly reviewed attractions in Chicago is the Chicago Architecture Foundation River Cruise. There are many imitators, but the tour I link to is the only one done by the not-for-profit foundation working to preserve and beautify Chicago. 

The Architecture Foundation cruise is the only one conducted by qualified docents – volunteers who do this out of love, not money, and won’t even accept tips. Your guide’s affection for and knowledge of Chicago’s architecture is both evident and contagious.

It’s a rare and always valuable privilege to be guided by someone who is truly excited about the subject, and this makes this tour a particularly enjoyable venture. You will learn a bit about Chicago’s history and a lot about the buildings that surround you on this 90-minute tour. 

Be prepared to walk away, as I did, with a new appreciation for the architecture that surrounds you every day.  This experience was probably my favorite in Chicago and is an absolute must not miss. 

To grab the tour walk down to Riverwalk on the corner of Michigan Avenue.  Dusk is the most popular time and advanced tickets are highly recommended.  


Day 3 – Chicago.

Riverwalk – a selfie of a different kind.

Today was my day to do very little, and so I didn’t get out of the Cambria hotel until after 12.  I took a slow stroll down the Riverwalk and stopped by City Winery. 

They offer a great mix of wines and an even better location to enjoy them.  If you are in the area be sure to try the Riverwalk White, a dry California mix. 

This place is amazing for people watching and I found myself almost unwilling to move on to my next location as I sat by the water, a glass of good white in hand.  These are the days I feel pretty damned lucky. 


The view from the Skydeck at the Willis (formerly Sears) tower.

As I walked over to the Willis Tower (formerly the Sears Tower) I was struck with excitement to be visiting such an amazing structure.

I have already visited the Eiffel Tower in Paris, the CN tower in Toronto and of course the Empire State Building.  In my experience, the line may be long but always worth it. 

Once you get to the top of those other attractions, you have plenty of opportunities to take pictures, relax and take in the views or, have a nice meal and drink ( champagne in the Eiffel tower). 

That is not the case here and I have to say I am pretty disappointed with my visit to the Skydeck and I now consider this experience to be a bit of a tourist trap. 

It took me about an hour to get up, even though I had prearranged my tickets (make sure you get the will call, the line to get the tickets would have been another hour at least). 

After I finally got up I was surprised and disappointed to notice that all windows had a large bar running across them, preventing visitors from getting too close and forcing them to lean over to get closer to the window to take a picture. 

Another disappointment was that there was nowhere to sit down and take in the view. 

No benches other than by the bathroom, no restaurant, no place to get a drink.  In general,  the entire place seemed designed to get you in and out as quickly as possible and not to let you enjoy the view. 

Only one window with no bar was available, and you guessed it – there was a line to get to it. 

There was also the “walk out” a few feet from the building feature on plexiglass, but I just didn’t have it in me to wait another hour.

This is still a great tourist experience that’s worth the wait if you go on a weekday and you know what to expect – and haven’t been to the previously mentioned great buildings. 

If you have visited many similar landmarks I’d skip this one in favor of another stroll down the Riverwalk or Michigan Avenue. 


The Windy city at Sunset.

That’s all for my weekend trip to Chicago.  This is a gorgeous city with plenty to do and I will definitely be back. 

If you found this article helpful, please let me know in comments.  Thank you for joining me!  My next trip is to Cooperstown NY, a hidden upstate NY gem for a true Americana fall experience.

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