Chicago DayCations

Be a tourist in your own city

Curated experience with fellow Chicagoans - no flight or luggage necessary!

  • A street scene viewed through a large archway, with an art market on the sidewalk featuring paintings and drawings, and historical buildings with balconies and shutters in the background.

    Classic Tour

    Saturday

    $85/ person

    Play tourist in your own city!

    Start with a relaxed stroll along the Chicago Riverwalk, coffee in hand, soaking in skyline views you probably rush past every day. Then hop on a guided Architecture boat tour to see the city from the water, hear the stories behind the buildings, and experience Chicago the way visitors do. Afterward, step inside the stunning Chicago Cultural Center: a hidden gem filled with mosaics, marble, and one of the world’s largest Tiffany domes. All while connecting with other locals doing the same thing: slowing down, exploring, and rediscovering what makes Chicago special

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  • A brick sidewalk lined with trees and residential buildings, with an American flag hanging outside one of the buildings, and fallen leaves on the ground.

    China Town Tour

    Saturday

    $115/ person

    Great food. Hidden gems. Real Chicago energy.

    Chicago's Chinatown has been here since the early 1900s and it's still one of the most vibrant, delicious, and underexplored neighborhoods in the entire city. Starting with a guided Food and walking tour: on foot, with locals, and with a very full stomach. Afterwards, we’ll continue exploring and discovering the neighborhood with a small group of fellow Chicagoans who love this city as much as you do.

    COMING SOON →
  • Split view of two scenes: on the left, an ornate classical marble fountain with sculptures, and on the right, a hillside of colorful buildings overlooking the sea.

    Ol' Chicago Town

    Saturday Night

    $55/ person

    Chicago, After Dark

    A Haunted History, Speakeasy & Live Music Night Out. Start the evening with a guided haunted history walking tour through the streets of old Chicago — gangsters, ghost stories, Prohibition secrets, and the real history behind the city's most notorious era. Your guide brings it all to life, block by block, after dark. From there, and close out the evening at a live music venue — blues, jazz, or soul, the way Chicago intended.

    COMING SOON →
  • A pink stucco house exterior with a dark wooden door, a decorative white angel face above the door, a lantern light fixture above the angel, shadows of palm leaves on the wall, two utility meters in a small recessed area, and a window with a black wrought iron railing.

    Be Well, Chicago

    Saturday

    $65/ person

    A vibrant journey through culture, color, and charm.
    Experience the best of Mexico with a thoughtfully curated adventure from dynamic Mexico City to the artistic heart of San Miguel de Allende. Enjoy private museum tours, artisan markets, and authentic culinary moments - all with boutique accommodations and seamless travel between cities. Bold, beautiful, and deeply inspiring.

    Coming Soon →