Diego D.
Aug 23, 2026
Below expectations
Not what was advertised. The description promised more than the experience delivered. Travelled on my own and felt completely comfortable.
12 found this helpful · ReportInstant confirmationFlexible cancellation
Private guide in Chicago: the Upper Quarter 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.
4.0
14 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
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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
4.0
14 reviews
1 star7%
2 star0%
3 star21%
4 star29%
5 star43%
Ingrid I.
Aug 12, 2026
Would book again
Smooth from start to finish. No queues, no confusion, and the guide knew the area inside out. Squeezed it in around a work trip and it was worth the time.
36 found this helpful · ReportRavi R.
Jul 24, 2026
Highly recommend
A highlight of the trip. I have already recommended it to two friends who are visiting next month. Went as a group of four and everyone was happy.
17 found this helpful · ReportWei W.
May 5, 2026
Better than expected
The photos do not do it justice. We spent far longer here than we planned to. Went as a group of four and everyone was happy.
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