Priya P.
Jul 27, 2026
Good, with caveats
Good overall, though it was busier than I expected. Still glad we went. Went with my partner and we both enjoyed it.
ReportInstant confirmationFlexible cancellation
Private guide in Chicago: the Old Town walk
A private guide who knows Chicago properly — a working lakefront, Prairie School architecture and a deep-dish argument. No coach, no rush, and the day bends to what you actually want to see.
4.5
12 reviewsMore photos on request
What you’ll do
- A guide who lives in the city, not a tour dispatcher
- Private — your group only, at your own pace
- A table reserved for lunch on request
- Hotel pickup and drop-off included
About this experience
Your guide is a historian or an architect who has lived in Chicago for years. The day is yours: they will show you what they would show a friend, skip the parts that are only worth a photograph, and find you a table for lunch somewhere locals eat. Because it is private, the pace is whatever suits you, and you can change the plan as the day goes on.
Pick your date
October 2026
Mon
Tue
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AvailableLimited availabilitySelected
Meeting point
the Skydeck lobby on Wacker Drive
233 S Wacker Dr, Chicago, IL 60606
Wheelchair accessibleIncluded
- Licensed private guide
- Hotel pickup and drop-off
- Museum and site entries
- Lunch reservation on request
Not included
- Meals
- Hotel accommodation
- Travel insurance
- Gratuities
Cancellation policy
Free cancellation up to 24 hours before the guide is confirmed, with no fee at any point.
Less than 24 hours before0% refund
24 hours – 3 days before90% refund
More than 3 days before100% refund
Good to know
Duration7 hours
Languagesenglish, en, zh, fr, de
CountryUS
Traveller reviews
4.5
12 reviews
1 star0%
2 star0%
3 star8%
4 star33%
5 star58%
Hannah H.
Jul 19, 2026
Would book again
Smooth from start to finish. No queues, no confusion, and the guide knew the area inside out. Went with my partner and we both enjoyed it.
26 found this helpful · ReportChloe C.
Jun 22, 2026
Highly recommend
One of the best experiences of our trip. Everything ran on time and the staff were genuinely helpful. Went as a group of four and everyone was happy.
16 found this helpful · ReportWei W.
Jun 10, 2026
Better than expected
The photos do not do it justice. We spent far longer here than we planned to. Travelled on my own and felt completely comfortable.
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