Experience Chicago with Private, Customizable City Tours

Key facts

What's included

Itinerary

A flexible, private tour covering Chicago’s top sights and hidden gems, tailored to your interests.

1. Stop 1

   Holy Name Cathedral, built in 1875, is a historic Gothic Revival church and a city landmark, rebuilt after the Great Chicago Fire.

   10 minutes

2. Stop 2

   Visit the 94th-floor observation deck for panoramic views of Chicago and Lake Michigan, with interactive displays, the TILT experience, and great photo spots.

   45 minutes

3. Stop 3

   Explore Michigan Avenue's shopping district, lined with luxury boutiques, historic sites, and renowned restaurants.

   1 minute

4. Stop 4

   Enjoy scenic views of the Chicago River, walk or bike along the water, or rent kayaks for a water-based adventure. The area features public art, outdoor dining, and lively events.

   20 minutes

5. Stop 5

   Visit the LondonHouse Rooftop for stunning city skyline views and photo opportunities from a chic rooftop bar.

   15 minutes

6. Stop 6

   Stop at a historic venue hosting concerts and events in a beautifully preserved setting.

   1 minute

7. Stop 7

   Discover a stunning architectural landmark hosting free art exhibitions and performances.

   10 minutes

8. Stop 8

   See Cloud Gate ('The Bean'), Crown Fountain, Jay Pritzker Pavilion, and Lurie Garden, with plenty of photo ops and cultural experiences.

   25 minutes

9. Stop 9

   Visit one of the largest and oldest art museums in the U.S., home to diverse collections spanning centuries.

   1 minute

10. Stop 10

    Tour the historic Blackstone Hotel, rebuilt after the Great Chicago Fire, symbolizing resilience and luxury.

    1 minute

11. Stop 11

    See the Marquette Building, a prime example of early skyscraper design and Chicago’s architectural heritage.

    10 minutes

12. Stop 12

    Explore the Rookery Building, a cherished piece of Chicago architecture reflecting the city’s innovative spirit.

    1 minute

13. Stop 13

    Visit the Chicago Board of Trade Building, an Art Deco landmark symbolizing Chicago’s financial history, topped with Ceres, the Roman goddess of agriculture.

    5 minutes

14. Stop 14

    Stop at the Federal Reserve Bank’s Money Museum to learn about money, banking, and the U.S. economy, including a display of $1 million in cash.

    15 minutes

15. Stop 15

    Ascend to the 103rd floor of Willis Tower for breathtaking views, the glass Ledge, and interactive exhibits about Chicago’s architecture.

    45 minutes

16. Stop 16

    Visit Chicago Union Station, a historic transportation hub blending functionality with architectural beauty.

    10 minutes

17. Stop 17

    Experience Chicago’s Chinatown, known for its traditional Chinese architecture, authentic cuisine, and vibrant street life.

    15 minutes

18. Stop 18

    Relax at a historic park on the South Side, home to the Museum of Science and Industry and scenic lagoons.

    1 minute

19. Stop 19 Pass by

    Visit the Obama Presidential Center in Jackson Park, a future landmark celebrating civic engagement and Chicago’s South Side history.

20. Stop 20

    See a Frank Lloyd Wright-designed building in Hyde Park, showcasing Prairie School architecture.

    1 minute

21. Stop 21

    Tour the University of Chicago campus, featuring Gothic architecture, the Rockefeller Memorial Chapel, Harper Library, and Robie House.

    10 minutes

22. Stop 22

    Explore the lakefront area with the Field Museum, Shedd Aquarium, and Adler Planetarium, offering exhibits on natural history, marine life, and astronomy.

    1 minute

23. Stop 23

    Visit the Field Museum’s exhibits, including Sue the T. rex, fossils, and cultural artifacts. Engage with interactive displays suitable for all ages.

    40 minutes

24. Stop 24

    See Buckingham Fountain, one of Chicago’s most iconic landmarks, with impressive water displays set against the city skyline.

    10 minutes

25. Stop 25

    Experience Navy Pier, a lively entertainment hub with a Ferris wheel, theaters, shops, and seasonal events, attracting millions each year.

    1 minute

26. Stop 26

    Relax at the Lincoln Park Conservatory, a historic glass greenhouse filled with tropical plants, orchids, and seasonal flowers.

    20 minutes

27. Stop 27

    Visit Lincoln Park Zoo and Conservatory, offering free wildlife encounters, lush gardens, and family-friendly activities.

    40 minutes

28. Stop 28

    See the Elks National Memorial, a grand monument honoring WWI veterans, with a massive dome and intricate interiors.

    10 minutes

29. Stop 29

    Tour Wrigley Field, one of the oldest ballparks in the U.S., and learn about the Chicago Cubs’ storied history.

    20 minutes

30. Stop 30

    End your tour at the riverfront area by the Trump International Hotel & Tower, offering outdoor dining and great city views.

    10 minutes

Meeting point & pickup

Hotel pickup included for all travelers

I offer flexible pickup locations to make your experience as convenient as possible. Whether you're staying in downtown Chicago, a vibrant neighborhood, or even have a layover at O'Hare Airport, I can arrange a pickup that works for you. If you're at O'Hare, I'll customize a quick tour to help you make the most of your time, ensuring you get back to your flight stress-free. Just let me know where you’re located, and I’ll ensure a smooth, memorable start to your tour!

How to get there

Pickup is available from 678 listed hotels. Exact pickup time is confirmed after booking.

Cancellation & confirmation