Cultural Tours to Chicago

Highlights of Chicago

Millennium Park: Cloud Gate/The Bean, Crown Fountain, Jay Pritzker Pavilion

The Magnificent Mile • Morning views from Adler Planetarium

Chicago Riverwalk • Museum Campus


April 15 – 17, 2022

SPECIAL NOTE: All participants must be fully vaccinated as well as agree to abide by any current laws and restrictions in place at the time of the tour for social distancing, wearing masks, using hand sanitizer, etc.  By registering for this tour you’ll be agreeing to this.

April 15 – 17, 2022

Come join PhotoEnrichment Adventures Founder and Chicago native Ralph Velasco for a customized, small group tour of the Highlights of Chicago.

6 participants minimum to 10 maximum.

“Eventually, I think Chicago will be the most beautiful great city left in the world.”

~Frank Lloyd Wright


Chicago is a wonderful place to photograph and Ralph knows all the ins and outs of where the best places are to shoot – and eat and play – and so he’s put together a special small group tour.

This trip is limited to the first 10 people, with a 6 person minimum, so it’s going to be a small group with a great learning environment.

This will be a Photo Walking Tour of Chicago, for sure, but it’s not just about photography, although we will, of course, be photographing during each session.  As with all our tours, we want to provide an overall cultural experience of Chicago, and you won’t be disappointed.

The fee is just $399 total per person for all 3 days (made up of four 3-hour photography sessions), and this includes planning, guiding and photography instruction.  Please note that you’ll be responsible for your own transportation arrangements and other expenses, including any additional admissions, meals and hotels.

We’ll provide plenty of notice of where to meet and when, but the program starts at 5 pm CT on Friday, and we’ll meet on the east side of Cloud Gate (“the Bean”) in Millennium Park (more specifics to follow).  We’ll end the trip at approximately 11 am on Sunday morning by the Chicago River in the Loop.


Food Highlights (meals are optional and not included in your fee, and they will depend on each restaurant’s plans for opening): Billy Goat Tavern (“cheeborger, cheeborger“), Lou Malnati’s for Chicago-style Deep Dish Pizza, maybe even Portillo’s for a Chicago hot dog or famous Italian Beef.

Email me to register at



For out-of-towners, or locals looking for ultimate convenience, the group hotel will be the Club Quarters (75 E Wacker Dr, Chicago, IL 60601) where on last check rooms are typically around $190 per night via  You’re more than welcome to bring a spouse or friend, but only paid participants will be able to join us during each walking tour (non-photographers will love this tour, as well).

* Please note that accommodations are not included in your fee and you’ll be required to make your own reservations and it’s not mandatory to stay at this hotel.


“Club Quarters is where I’ve always tried to put our groups for the Chicago tour.  It’s a very conveniently-located boutique property right on Wacker Drive, just off Michigan Avenue, and it’s perfectly situated for all of our group activities on this tour.  I even recommend it to local Chicagoans joining the trip as it’s inexpensively priced and in the heart of it all.

I also recommend using the app SpotHero to find inexpensive parking nearby.”

~ Ralph Velasco

CEO, PhotoEnrichment Adventures


You will not regret visiting Chicago, it’s truly America’s least known great city!



The majority of this tour is over flat ground, but there are portions that may require us to negotiate a number of stairs or inclines, and we do a fair amount of walking each day (approximately 2 – 4 miles, on average, for each session).  So, if you’re at all sedentary, it’s recommended that you prepare with some physical activity leading up to the tour.

That said, a person of reasonable physical fitness should have no problem at all and as usual, you’re welcome to go at your own pace and catch up, if necessary, and for those not sure of their abilities, walking sticks are highly recommended.



The weather in Chicago can be somewhat unpredictable, so please be sure to check it right before heading out and I always recommend layering. Please also bring a rain shell if it looks like rain, as well as an umbrella and perhaps a plastic cover for your photo gear so it doesn’t get damaged.

We’ll have a number of indoor options available should the weather not cooperate but please know that some venues are still not open or operating normal hours, so we appreciate your being flexible and understanding if plans change or parts of this tour are cancelled or become unavailable.

  • “LOVED your presentation at The Refinery on Saturday!! You got me motivated to travel & I learned a lot!!  THANK YOU FOR YOUR TIME and for sharing your gift!!”

    Carole Haner-Brackett Photography Basics Meetup participant
  • “Thanks again for such an amazing trip…my photography interest and appetite has completely grown since the trip and I have come back so invigorated and inspired.  I’m excited to learn more and begin to take some higher quality pictures.”

    Sarah Radka Cuba tour participant
  • “Thanks for a great trip.  All went smoothly and I had a great time.  I return a better photographer for certain and have a new perspective on what I see.  You offer a great product – smart itineraries, hotels and food choices…I look forward to another trip.”

    David Wild Morocco tour participant
  • “The fun, adventure and friendship with you means everything to us, along with a great photo or two along the way!”

    Brandon and Shea Mayberry Morocco and Spain tours participant
  • “Ralph, Morocco truly is magical!  Thanks for a beautiful two weeks!”

    Leslie Talley Morocco, Turkey and Cambodia tours participant
  • “Our tour leader Ralph was one of the most knowledgeable trip leaders I have experienced over the past 40 years. He is a very experienced photographer and generously shared his knowledge, talents and experience with us.  I think I learned more composition skills and believe I am a better photographer.”

    Larry Ehemann Central Europe, Cuba East and Romania tour participant
  • “I really liked the [small] size of the tour. It felt like traveling with friends from very early on, and continued to feel that way. That last hotel we stayed in, the one in Budapest, was such a treat! Those views were fabulous, and it ended the trip in style. Ralph is a good trip leader… He wasn’t hovering, but he did stop and give tips and I felt well-tended. The local guides were all outstanding!”

    Heather Hellier Central Europe tour participant
  • “Ralph is an engaging and knowledgeable photographer that puts his world class experience in your hands. This trip has been off the charts.”

    Steve Grove Travel photography class, Cambodia and Vietnam tour participant
  • “The photo critique alone [at the Photography Boot Camp] is worth the price of admission.”

    Shaune Kelly Photography Boot Camp, Cuba and Tuscany tour participant
  • “Great examples clearly demonstrated the points Ralph made.  His teaching methods made many things much simpler to understand.  I thoroughly enjoyed this class!”

    Brenda Hatcher Photography Boot Camp participant


April 15 – 17, 2022



Friday: 5 – 8 pm

Saturday: 8:15 – 11:15 am & 5 – 8 pm

Sunday: 8:15 – 11:15 am


$399 for all 3 days (includes four 3-hour sessions)*

$119 for each individual 3-hour session

* Priority will first be given to those who can commit to all 3 days, and we have to work on a first come, first served basis.


Please request the details of this trip, including complete itinerary, by contacting us at This Link.

To register, you can pay with a credit card via PayPal (Click This Link to request invoice) or deposit a check directly into the PhotoEnrichment Programs, Inc. bank account at any Bank of America branch.

We’ll send you all the payment details if you’ll contact us above.


Program includes:

  • All planning and anywhere from 3 to 6 hours per day of photography instruction and guidance with Ralph Velasco.


Program does not include:

  • Airfare to and from Chicago (ORD) from your home airport, if applicable.
  • Accommodations, although we’ll make recommendations.
  • Meals are not included, although we may meet as a group for particular meals and then each person will be expected to pay their own way.
  • Cost of necessary transportation to and from the airport and to/from the starting point of certain activities, although most everything will be within walking distance.
  • Items of a personal nature.
Tentative Schedule
Friday: 5 – 8 pm – Millennium Park in early evening, optional night shoot of Wrigley Building along the Chicago River after eating at Billy Goat Tavern (you’ll have to decide if you want to bring tripod and carry it until then). Before the night shoot, those who are interested can go for a “cheeborger” at the infamous Billy Goat Tavern on Lower Michigan Avenue, assuming it’s open. 
Flights arriving by 2 pm or earlier today at O’Hare Airport should allow plenty of time to meet us at 5 pm for the start of the tour.
Saturday: 8:15 am – 11:15 am – Meet at the Bean again in Millennium Park so we can shoot it in the morning with different light, no crowds and get some very unique photo ops. We’ll then slowly make our way to the Art Institute and out Adams Street, see the Calder sculpture and take a peek inside the Rookery Building on LaSalle Street.  Then we’ll head north, see the Picasso sculpture, State of Illinois building (from outside only) and then out the Chicago River Walk and end at an optional lunch at Lou Malnati’s for deep dish pizza.
This afternoon is free so that you can explore on your own or get some rest.
Saturday: 5 – 8 pm – Meet at the Chicago Riverwalk sign on the NW corner of Wacker Drive and Michigan Avenue, aka the Magnificent Mile, then we’ll walk north, make some secret stops on the way, then we’ll go up to the top of the John Hancock tower to the Signature Room on the 96th floor (assuming it’s safe and open, may require each participant to purchase one drink) for amazing views over the city around sunset. If not open we’ll see how we’re doing on time and adjust if necessary.  Those who are interested should then head back to the corner of Wells and Wacker to witness “Art on the Mart,” a very cool art installation held there (time of year varies).
Sunday: 8:15 – 11:15 am – We’ll meet out at the Adler Planetarium for some morning shots of the city skyline (you’ll probably want to take a taxi or Uber and know that it can be windy out there, so layer up!), then we’ll slowly walk our way through the Museum Campus and west out Roosevelt Road and up Clark Street to Printer’s Row, an interesting neighborhood, then further north and back to the area of the hotel where we’ll end our tour at around 11:15 am.
Arranging airline departures after 3 pm on Sunday should allow plenty of time to comfortably make your flights.
This schedule was created so that, if necessary, you can fly in earlier on Friday and leave early afternoon on Sunday and still be able to participate in all aspects of this program in just 3 days.  Certainly feel free to extend your stay to see more of our wonderful city.

Small Group Tours with Travel Photographer Ralph Velasco

Tour some of Chicago’s most photogenic highlights with experienced tour organizer, professional travel photographer and local Chicagoan Ralph Velasco

  • Early evening walk in Millennium Park, including Cloud Gate/The Bean, Crown Fountain and Jay Pritkzer Pavilion (designed by Canadian-American architect Frank Gehry), BP Bridge and Lurie Garden
  • Optional evening shoot on the Chicago River of the Wrigley Building after having a “cheeborger” at Billy Goat Tavern on Lower Michigan Avenue
  • Morning walk through Millennium Park to see it in different light and without tourists, then walk west into the Loop and up to the Chicago Riverwalk and an optional lunch at Lou Malnati’s for deep dish Chicago-style pizza
  • Walk on Chicago’s Magnificent Mile (Michigan Avenue) making several stops to see and photograph some hidden gems
  • Visit the top of the John Hancock Center for incredible views of the city, assuming it’s open and safe (purchasing a drink is required and not included)
  • Stunning panoramas of the city skyline from the Adler Planetarium in the morning
  • Walk west out Roosevelt Road to Clark Street and into Printer’s Row
  • Walk along the Chicago Riverwalk where Ralph’s PhotoWalkingTours were originally born


There are a number of optional activities you might like to arrange for your free time (check first that they are open):


This is an insider’s look at Chicago, “the Second City.”

All activities and timing subject to change as local conditions and rules dictate.


Ralph Velasco with Camera by Michelle Kate LaVigne

Ralph Velasco is a U.S.-based travel photography instructor, author and international guide who has organized and led over 100 international tours and more than 100 domestic tours in the United States.  His international trips have included Armenia & the Republic of Georgia, Egypt, Morocco, the Adriatic, Central Europe, Iceland, Bhutan & Nepal, Vietnam, Cambodia, India, Spain, Portugal, Tuscany, Romania, Mexico’s Copper Canyon, Turkey and other locations.

Ralph is an award-winning travel photography blogger, podcast host and public speaker, and for more than 12 years he’s been the Founder and CEO (Chief Experience Officer) of PhotoEnrichment Adventures.  Recently he created a new travel brand called Alla Campagna Experiences where the focus is less on photography in each destination and even more about the culture, people, food, drink and other unique activities and experiences they have to offer, all while staying in unforgettable properties, such as private castles, wine estates, one-of-a-kind boutique hotels, villas and converted mansions, mostly in and around the Mediterranean.

Subscribe to Ralph’s new YouTube channel, The Continental DRIFTER, as well as visit its accompanying travel blog at this link.  At The Continental DRIFTER you can expect travel advice, interesting stories, expert interviews and easy-to-use photography tips for Baby Boomers and Gen X travelers.

Now, invest in yourself…get out and travel!


Here are testimonials from actual past Chicago tour participants:

“Just wanted to thank you for the Chicago Photowalk. Every time I go out shooting with you, I say that I come back with the best photos I’ve ever taken, and this trip is no exception! Thanks so much for helping me get to the next level!”

~ Denise C. (Chicago and Southern California tour participant)


“Always wanted to visit the Windy City. What a perfect way to go—Ralph is not only a very helpful and knowledgeable photographer, but he knows the city like the back of his hand. I recommend his walking tour whether you are a beginner or experienced shooter. A great weekend with many, many photo ops.”

~ Lowell D. (Chicago and Cuba tour participant)


“I found Chicago a fascinating town!  It is full of photo opportunities, from the beautiful, simple park scenes to the grand architecture.  There is something for everyone, including great food! I’m looking forward to returning.” 

~ Wendy H. (Chicago and Central Europe tour participant)

All activities and itinerary details are subject to change, but rest assured we’ll make every effort to provide a comparable alternative in the unlikely event changes to our schedule need to be made.

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