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 • Union Station

The Riverwalk • Buckingham Fountain • Night Shoot


Makeup Dates to Be Announced

Due to the extension of the Stay at Home Order by the Governor of the State of Illinois through April 30, 2020, this tour has been postponed until a future date which is yet to be determined and will later be announced.


Thank you, stay home and please be well.

Dates to Be Determined

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 11 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 for this April, when the weather should be great and it’s off season and so the city and sites will be less crowded.

This trip is limited to the first 11 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 shooting each day.  As with our tours, we want to provide an overall cultural experience of Chicago, and you won’t be disappointed.

The fee is just $349 total per person for all 4 days, and this includes planning, guiding and photography instruction services.  You’ll be responsible for your own flight arrangements and other expenses, including any additional admissions, meals and hotels.

We’ll provide an itinerary of where to meet and when, but the program starts at 5 pm CT on Thursday, April 23rd, and we’ll meet at The Bean in Millennium Park (specifics to follow).  We’ll end the trip at approximately 11 am on Sunday morning at Michigan Avenue and Wacker Drive.


Food Highlights (meals are optional and not included in fee): Billy Goat Tavern (“cheeborger, cheeborger“), Lou Malnati’s for Chicago-style Deep Dish Pizza, Portillo’s for a Chicago hot dog or famous Italian Beef.


Thursday: 5 – 9 pm – Millennium Park in early evening, night shoot of Wrigley Building along the Chicago River.  After those who are interested can go for a “cheeborger” at the infamous Billy Goat Tavern on Lower Michigan Avenue.  
Flights arriving by 2 pm today should allow plenty of time to meet us at 5 pm for the start of the tour.
Friday: 7 – 11 am – Millennium Park in the morning with different light, no crowds and some very unique photo ops. We’ll then make our way out the Chicago River Walk and end at an optional lunch at Lou Malnati’s deep dish pizza.
This afternoon and evening are free so that you can explore on your own.
Saturday: 5 – 9 pm – Walk up Michigan Avenue, aka the Magnificent Mile, make some secret stops on the way, then we’ll go up to the top of the John Hancock tower for amazing views over the city around sundown. Time permitting we’ll head to Buckingham Fountain for a night shoot.
Please note that Saturday is open until we meet at 5 pm so know that you can arrange other activities on your own.
Sunday: 7 – 11 am – We’ll meet out at the Adler Planetarium for some morning shots of the city skyline, the walk our way out the Museum Campus and west out Roosevelt Road and up Canal Street to Union Station where there are some nice interior photo ops. Finally, we’ll take an included water taxi ride up the Chicago River to Michigan Avenue and Wacker Drive to end our tour around 11 am.  
Arranging airline departures after 3 pm should allow plenty of time to comfortably make your flights.
This schedule was created so that, if necessary, you can fly in earlier on Thursday and leave early afternoon on Sunday and still be able to participate in all aspects of this program in just 4 days.
Email me to register at



Ideas for well-located hotel options will be provided, and 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.

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 can require us to negotiate a number of stairs or inclines, and we do a fair amount of walking each day, 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 go at your own pace and catch up, if necessary.

  • “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


Dates to Be Determined



Thursday: 5 – 9 pm

Friday: 7 – 11 am

Saturday: 5 – 9 pm

Sunday: 7 – 11 am


$349 for all 4 days*

$99 for individual days

* Priority will first be given to those who can commit to all 4 days.


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:

  • Up to 4 hours per day of photography instruction and guidance with Ralph Velasco
  • Fee for water taxi on Sunday

Program does not include:

  • Airfare to and from Chicago (ORD) from your home airport.
  • 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.

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 Chicago native 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
  • Evening shoot on the Chicago River of the Wrigley Building then those that are interested can have a “cheeborger” at Billy Goat Tavern on Lower Michigan Avenue
  • Morning walk through Millennium Park to see it in different light and without other tourists, then walk west out the Riverwalk and to lunch at Lou Malnati’s
  • 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 tower for incredible views of the city (purchasing a drink is required and not included)
  • Time permitting, optional evening shoot of Buckingham Fountain and the city skyline
  • Stunning panoramas of the city skyline from the Adler Planetarium in the morning
  • Walk west out Roosevelt Road to Canal Street and on to Union Station
  • 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:


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


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 and the Republic of Georgia, Egypt, Morocco, the Adriatic, Central Europe, Iceland, Bhutan and Nepal, Vietnam, Cambodia, India, Spain, Portugal, Tuscany, Romania, Mexico’s Copper Canyon, Turkey, Cuba and other locations

Ralph is an award-winning travel photography blogger, podcast host and public speaker, and for more than 10 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, in and around the Mediterranean.

He’s also Creator of Tour Organizer Training, a free webinar and online course series designed to teach everyday people, step-by-step, how to organize and lead their own special interest trips, whether around the world or around the corner.  Click here to join the next free webinar.

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.

Start typing and press Enter to search