Three Signature 3-day Chicago itineraries


I was born and raised in Chicago.  After 48 years with an airline, I've wandered the streets of Paris, sampled street food in Southeast Asia, and explored countless other destinations.  I always come home convinced that Chicago is the greatest city in the United States, and possibly in the world.  


Its architecure rivals Europe.  Its culinary scene is world class.  Its lakefront is breathtaking.  And it remains a city of neighborhoods, each telling its own story.


Come see for yourself.

Classic Chicago

Day 1 - Iconic Chicago

  • Architecture river cruise 

  • Explore Millennium Park and take in the skyline

  • Visit the renowned Art Institute of Chicago with its wonderful Impressionist collection

  • Riverfront walk and cocktails

Day 2 - Food and the Lakefront

  • West Loop culinary tour

  • Wicker Park boutiques & cafés

  • Lakefront walk or bike ride

  • Sunset cruise the lake

  • Improv show at the world famous Second City

Day 3 - Explore a neighborhoood

  • You should absoluely see all the iconic sights, but Chicago is truly a city of neighborhoods, and you haven’t fully experienced it until you’ve explored at least one. My personal favorite is Andersonville on the city’s north side. Originally settled by Swedish immigrants, it now features a vibrant mix of independently owned shops, art galleries, restaurants, and bars. But of course we'll discuss your interests and travel style and choose the neighborhood that's the best fit for you.



Chicago with Kids

Day 1 - Lakefront and Icons

  • Navy Pier, Chicago Children's Museum, ferris wheel

  • After lunch - Millenium Park, the Bean, Crown Fountain

  • Maggie Daley Park (playground)

Day 2 - Choose your Adventure

  • Field Museum: dinosaurs and native environments

  • Adler Planetarium: hands-on space fun

  • Shedd Aquarium - whales and colphins

  • Museum of Science and Industry - U-boat, coal mine

  • After lunch (maybe a picnic), beach time or a bike ride or walk on the Lakefront Trail

Day 3 - Zoo

  • Lincoln Park Zoo, carousel, kids train

  • Lunch

  • ten minutes to the dock by Uber or taxi (or 20 minutes by bus) - take a boat ride - Wendella architecture tour or water taxi to Chinatown

Luxury in Chicago

Day 1 - Art and a Park

  • Visit Millennium Park

  • Chicago Architecture River Cruise

  • After lunch - 

  • Art Institute Guided Tour with an Expert

  • Rooftop cocktails

  • Dinner

Day 2 - Choose your Activity

  • Helicopter tour

  • Private tour of downtown Chicago TV and movie sites

  • Local fashion designers private tour with a stylist

  • Private tour of Lincoln Park Zoo

  • Food tour

  • Before dinner - Ultimate Couples Bath at Aire Ancient Baths

Day 3 - Choose a Chicago Neighborhood

  • Explore the neighborhood that best suites your taste and interests with a private guide.

  • Sunset tour on a private boat

Chicago has a plethora of Michelin and other fine dining, as well as wonderful neighborhood restaurants. We'll choose those that best suit your taste.

 

Possible additions to this itinerary:

  • Sporting event - baseball/basketball/football/hockey

  • Theater tickets/ballet/concert

  • Second City improv show

These itineraries are just starting points for your completely customized experience.


You can research Chicago on your own.


But if you’re ready for an experience that is curated, effortless and uniquely yours, I would be honored to design it for you. With more than 50 years of global travel experience, I’ve learned to design trips that are seamlessly organized and elevated yet relaxed. I’ll handle all the details and make all the reservations, so that you can just relax and experience the best of my beloved hometown.