Ten Perfect Chicago Experiences

A friend of mine is moving.  He’s trying to choose which city to move his life, family, and business to.  For various reasons, the three finalists are Los Angeles, New York, and Chicago.

Listening to him talk about his decision-making process started me thinking about Chicago, and some of the — for lack of a better word — “perfect” Chicago experiences I’ve had, and try to occasionally recreate.

So, here’s my Top Ten Perfect Chicago Experiences.  A lot of them involve food, but I think that’s more about it adding two more senses to the equation than about gluttony.

1. Once Around The Loop

Jump on a Brown line train at Merchandise Mart, sit in the hobo corner, and just gaze at the architecture going by.  Get off at Clark and Lake.  You get a bonus view crossing the Chicago River on the upper deck of the Wells Street Bridge if you manage to get a seat on the left side.

(Price: $2.25)

2. Feed Me, Margie

Hop the Blue Line to the Western stop and skedaddle through some marginal territory to arrive at Margie’s Candies (1906 North Western Avenue).  Order the ice cream sundae of your dreams.  Until I started writing this article, I had no idea that both Al Capole and The Beatles sat in the same booths I have (thanks, Wikimopedia!)

(Price: About ten bucks)

3. Hot, Sweet, and Salty

Speaking of food, on one of those hot Summer days when the wind refuses to blow and the city is thick with tourists, here’s my advice: Take a deep breath, and dive into that hoarde at Navy Pier (600 East Grand Avenue).  Walk all the way to the end, then on your way back, stop for big plastic tumbler of freshly-squeezed, over-sugared lemonade, and a plastic tray of yellow corn chips and nacho cheese.  There’s hardly any places to sit and enjoy the Chicago skyline on Navy Pier, but you can usually score one of those horribly uncomfortable metal chairs outside the Haagen Dazs shop and watch the crowds go by.

(Price: Less than ten bucks)

4. Shopping in the Snow

The Drake Hotel at the top of Chicago's Magnificent Mile

On one of those evenings when the sun sets early and the snow is falling, bundle up more than you need to, stick chemical warmers in your gloves and pockets, and walk very slowly down Chicago’s main shopping drag.  Start at the Drake Hotel (140 East Walton Place), and window-shop your way down Michigan Avenue.  Duck in at The Apple Store, Burberry, or wherever catches your fancy for a quick warm-up.  At Wacker Drive, jog over to State Street, making your way southward.  Of course, you’re obligated to stop and spend 40 minutes lost in the animated windows at Marshall Field’s Macy’s (108 North State Street).  There’s no shame in that, and no shame in a man window shopping.  It’s even better if you do this with your significant other, because she’ll invariably drop hints about what she wants for Christmas.

(Price: Free)

5. Christkindlmarkt

After doing the State Street tour, blow through Block37 and end up at Christkindlmarkt.  This is a treasure that Chicago is lucky to have.  Every year, dozens of German companies come to Chicago to sell Christmas wares. Yes, you’ll spend more than you want to, but you’ll come away with gifts that you won’t easily find elsewhere, and a wonderful memory.  The market isn’t nearly as large as it used to be when it was across the street in the vacant lot that became Block37, but there must be 10,000 different types of Christmas tree ornaments, and 200 different kinds of wooden crafts thingies.  Though I’m not sure what the Peruvian stall has to do with a traditional European Christmas, their blanket hawkers have become a staple at the event. Be sure to have a hot schnitzel, a big soft pretzel (made by Chicago’s own Kim & Scott’s Pretzels), and a hot beverage served in an ornamental stocking.  Get a big bag of hot nuts and a box of chocolate cat’s tongues to bring home.

(Price: Free to browse, listen, and smell, but you can spend anywhere from $3 to $300 on a gift)

6. I Can See Forever

Willis Tower rises above the clouds, and everything else, in Chicago

The most common question I get from visitors to Chicago is “Should I visit Willis Tower, or the Hancock Center?”  My answer is simple: Both.  Each tower offers a different experience, different views, and different reasons to go.  Willis Tower (nee Sears Tower, 233 South Wacker Drive) has the cache of being the taller of the two, and the one that is better known.  Plus it’s right in the business district so you get a lot of good views of other skyscrapes.  But it’s a little off the usual tourist track, unless you arrived in Chicago by train.  The John Hancock Center (875 North Michigan Avenue, of which I am a proud former resident) has the better view, so if you have to do only one, Big John is it.  Not only does it have epic views, but those views include the Willis Tower.  And what’s a photograph of the Chicago skyline without its most famous building in it, right?  Still, the Hancock Center is the king of gimmicks and sideshows, with its Christmas train display, its cafe in the sky, skating rink, restaurant, bar, and more.  But in my experience, all of that pales in comparison with the primal fear and thrill one gets from walking on The Ledge at Willis Tower.

(Price: Willis Tower: $16, $21 for the Hancock)

7. The Big Ragu

Carmine's on Rush

Chicago is peppered with old school eateries.  I’m not taking about the Berghoff, and other places that have been in the tourbooks for decades.  I’m talking about ones that fly under the radar because they’re so good, they don’t need publicity.  One of my favorites is Carmine’s (1043 North Rush Street).  I’ve been here a few times for lunch, and took a group of visitors from Houston and Washington here one night.  Each time has been better than the last.  The atmosphere is old school Chicago, but not the tacky, manufactured type that tries to make fake links to Al Capone.  I’m talking about Richard J. Daley-era Chicago.  I’m talking about back when this area was strip clubs and underground gambling halls, instead of high end boutique shopping.  A time when out-of-town businessmen came to Rush Street to have a “good time,” but often ended up getting a “clip job.”  Carmine’s is comfortable, but mercifully not informal.  It clearly has its regulars, and part of the fun of going there is the people watching.  But it can sometimes be hard to get in.  If you can’t, have a gelatto from the Mariano Park Pavilion (1031 North State Street) across the street, sit on a bench, and watch the beautiful people go by.

(Price: About $35 at Carmine’s, around $5 for a snack across the street, people watching in the park is always free.)

8. Slow Boat To China

Chicagoans undervalue the city’s Chinatown.  It’s really quite good compared the ones in other cities.  As immigrant Chinese have become more assimilated into American culture, Chinatowns across the country have shifted, changed, and in many places, evaporated.  Chicago’s is still holding on, and is much better than the ones in Seattle, Los Angeles, or even Vancouver’s famed Chinatown, which claims (possibly falsely) to be the largest outside San Francisco.

The way to make your Chinatown day trip even more memorable, is to arrive by boat.  Just hop on a water taxi at the Michigan Avenue bridge.  You get to see the same sights as the $35 architecture boat tours, but at a fraction of the price, because your a commuter, not a tourist.  A short aquatic ride later, you’re deposited at Ping Tom Park (300 West 19th Street).  From there, it’s a quick stroll through the real Chinatown to the heart of things.

That stroll is very educational.  Most Midwesterners’ notions of Chinatown are about as accurate as their images of China.  This journey shows that immigrant Chinese live in townhouses with tiny lawns and high fences, just like most of the rest of Chicago.  You’ll spot the occasional sign of Oriental heritage — a tiny pagoda here, red curtains there, Chinese characters on the wrought-iron fences.  It’s a snapshot of assimilation in progress. The big exception is 1908 South Louis Parkway, which we did an article about a couple of years ago.  It’s worth a quick detour to peer down an alley and glimpse the back of it.

Once in the center of Chinatown, the things to do are eat, and shop.  Start doing both at the double-decker strip mall called Chinatown Square, on the north corner of South Princeton Avenue and South Archer Avenue.  You’ll be greeted by strange looking and smelling herbs, oddly shaped dried fish bits, untraceable pre-paid cell phones, counterfeit contact lenses, grey market cosmetics, K-Pop VCDs, and more waving cat statues than you can shake a red lantern at.  Once you’re done mingling with the locals, head to the tourist drag on South Wentworth.  You can buy fortune cookies fresh from the factory, but be warned — every cookie in the bag will have the same fortune in it.  They’re meant to be bought in bulk by restaurants and mixed together.

Don’t bother with the boat on the way back — just hop on the Red Line train.  It’s cheaper, faster, and yet another true Chicago experience under your belt.

(Price: $4 for the water taxi, $2.25 for the subway back, lunch runs $5-$20, souvenirs from $1 to $400)

9. Astor After Dark

Chicago has many great historic districts.  One that is near the center of it all, yet often overlooked, is the Astor Street District.  It’s always fun to listen to tourists try to pronounce “Goethe” for the first time while trying to tell the driver of the 151 bus where they want to get off.

Start at North Astor Street and East Division Street, and walk north to Lincoln Park.  Make a U-ey around Cardninal George’s house and wander south on State Parkway.  If you’pre the sort of person who watches period dramas on PBS or reads Agatha Christie books, you’ll feel right at home.  Otherwise, it’s like a living museum of life in an earlier age.

There are three “best” times to go:

  1. On a warm Summer evening, when the living rooms are all lit up, and you can count the grand pianos in the parlors of people with more money than you.
  2. Just before Halloween, when many of the homes and even apartment buildings go all out with scarecrows, spray-on spider webs, and some remarkable, yet traditional, jack-o-lantern displays.
  3. Just before Christmas, when everyone has had time to put up their lights, trees, and garland.  The neighborhood is positively Dickensian (in a good way).  If you’re lucky you’ll end up there during a light snowfall at dusk when a horse-and-carriage full of tourists clip-clomps by.  Holy wayback machine, Batman!
(Price: Free)

10. Smoke on the Water,  A Fire in the Sky

Free fireworks over Navy Pier

This last experience is great because you have so many chances to experience it.  Independent of the city celebrations, Navy Pier puts on its own fireworks shows several times a week in the summer, and deep deep into the cold weather.  Check the Navy Pier web site for a full schedule.  One summer I made an effort to see every single Navy Pier fireworks show.  I saw about 90% of them, and the remarkable thing is that each one was different and spectacular.

How you choose to augment the light show is up to you.  You can do it from one of the nearby beaches, from friend’s boat, from one of the dinner cruises, from a friend’s condo roof, on a blanket with your sweetie on a grassy slope along the lakefront, or a hundred other places.  My only recommendation is that you don’t see it from Navy Pier, itself.  As noted earlier, there’s almost nowhere to sit on Navy Pier, and if you chose to see the fireworks from the pier, there is always going to be someone taller than you blocking the view.

(Price: Free)

What about you?

So, these are my top ten, though I could probably go on for another ten.  But I’d like to hear from you, what your favorite Chicago experiences are. Input from both locals and visitors is welcome.


Author: Editor

Editor founded the Chicago Architecture Blog in 2003, after a long career in journalism. He can be reached at chicagoarchitectureinfo@gmail.com.

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  1. Chicago is my favorite city in the United States.I’ve been to Los Angeles, New York,San Francisco and Washington.And my favourite is by far , Chicago, my friends agree with me.
    I’m from Barcelona, and I love living in Barcelona, but if I had to live in America, I would definitely go to Chicago because it offers everything a big city can offer, culturally speaking, and being near lake michigan would remember me to Barcelona, and my walks along the sea or with my bike, and I could be doing that perfectly in Chicago.

    Well, my top tens are :

    1) The John Hancock Center . The building itself is a marvel;It is truly the most international symbol to can have chicago.If I lived in Chicago, I am sure I would be a regular customer of the signature room , the restaurant located at the 95th floor , it is great no only for the fantastic views, also because it offers exquisite food and a great , and sytlish atmosphere .

    2) Willis tower. Though I love the view from the Hancock, I really prefer the one from the Willis tower, as I adore to see the in perspective my other favorite buildings,the Trump Tower, for example.Another great experience is to go by sunset to the top of the tower or at night and see how they lights of neighboring counties to Chicago are becoming smaller, an experience that only Chicago can offer.

    3) The Chicago Symphony Orchestra.
    Whenever I travel I do my best to find time and attend a concert by the fabulous and magnificent symphony orchestra of Chicago. I consider it one of the best in the world;
    it is a real privilege to attend a concert. if I lived in Chicago, I would go every week¡¡¡

    4)Lyric Opera of Chicago. As I am a great lover of Lyric, I can not live without Opera.Chicago offers one of the best opera companies in the world, all performances are of the highest artistic level, and attend a performance is a real pleasure.

    5)The Art Institute of Chicago. I can spend hours and hours into this wonder that is called The Art institute of Chicago, a real pleasure for the senses.
    It’s curious but many of my favorite works are exactly in this museum.a funny thing happened to me several years ago in relation to the art institute of chicago.
    Just back from Chicago to Barcelona, I had that go to Paris, while in Paris,I wanted to go see a painting by Gustave Moreau,named Cleopatra, I went to his house-museum, and not finding it,I finally asked at the information desk, where is the famous painting Cleopatra ??? and they said: It is being exhibited during these weeks at the art institute of Chicago¡¡¡
    Another major attractions of this magnificent museum is that it offers temporary exhibitions of great interest.

    6)One of the things I love about Chicago is its shops, bookstores and department stores. I I found all I need, and in turn,it makes me feel like I’m in Barcelona, as I can wander the streets, to see storefronts and shop windows and always being on the street without having to go into malls,that I do not like much, as may occur in other cities; for me the famous Madison Avenue reminds me a lot at Paseo de Gracia Avenue in Barcelona or Champs Elysées Avenue in Paris,in the way that you can go shopping and enjoy the walk while on the street. Especially in spring stroll through the shops of Madison Avenue is for me the best of Chicago, that shopping avenue has an European air and I love it.

    7) The Grant Park Music Festival.
    Few cities in the world can be proud as Chicago, to have a classical music festival of such prestige and that it reaches so many people, both residents of Chicago, and to those that visit the city, like me, it is a real pleasure to attend the concerts surrounded by a breathtaking view of the fabulous architecture of this unique city in the world.I love it¡¡¡

    8)Downtown Theater District.It is a marvel to attend the many shows offered in the different theaters. this is one of the things I miss so much when I’m in Barcelona, the fabulous musicals that I can only see while in Chicago.

    9)Chicago Lake and river cruise boat tour. I think the most fabulous experience for an architecture lover like me, and I think for any visitor to Chicago, is a ride by the river on boats that show you the fabulous architecture from the water. is a unique spectacle in the world.it is fabulous, I never get tired of it.

    10) The Buckingham fountain reminds me a lot the one I have in Barcelona. and the museum campus has the faboulous Adler Planetarium, the great great Shedd Aquarium, and the Field Museum of Natural History, a must to visit¡¡¡¡

    Well, and these are my top ten¡¡¡ I have many more though, Chicago is so great, that I definitely would choose Chicago as my city.;-)
    Greetings from Barcelona¡¡

    Post a Reply
    • Editor

      Great list, Santi. Funny how your list revolves around the arts, and mine around food!

      Post a Reply
  2. :-) . yes , It is funny.
    I could talk a lot about the food , as Chicago has great places , specially restaurants from a lot of countries, that I adore to discover,maybe in another post,and with more time.it took me some time to write all my favourite things of chicago and in English¡¡¡, but well, I enjoyed it, as while I was writing I was recalling my great time in your fantastic city¡¡¡.so it was a pleasure anyway.
    Congratulations for your blog¡¡¡ I hope you like mine:http://highhigherhighest.blogspot.com/

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