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Chicago by Old Town: a small-group day

One well-chosen day in Chicago: a working lakefront, Prairie School architecture and a deep-dish argument. Six guests at most, two specialists, and a private version if you would rather have it to yourselves.

4.8
10 reviews
Chicago River ferry b — Chicago
More photos on request
Instant confirmationFlexible cancellationMobile ticket acceptedSecure payment

What you’ll do

  • Six guests maximum — a genuinely small group
  • Two local specialists, both licensed and fluent in English
  • Hotel pickup and drop-off included
  • A private departure available for your party only

About this experience

Most days in Chicago are spent deciding what to do. This one is already decided: a small group of six, two specialists who know the city, and a day built around the things worth doing rather than the things worth photographing. It finishes with a long lunch somewhere you would not find on your own.

Pick your date

October 2026
Mon
Tue
Wed
Thu
Fri
Sat
Sun
AvailableLimited availabilitySelected

Meeting point

the Skydeck lobby on Wacker Drive

233 S Wacker Dr, Chicago, IL 60606

Wheelchair accessible

Included

  • Hotel transfers
  • All entries and permits
  • Reserved lunch
  • English-speaking specialists

Not included

  • Travel insurance
  • Personal shopping
  • Gratuities
  • Alcoholic drinks beyond lunch

Cancellation policy

Free cancellation up to 24 hours before, then a 20% administration fee.

Less than 24 hours before0% refund
24 hours – 3 days before80% refund
More than 3 days before100% refund

Good to know

Duration8 hours
Languagesenglish, en, zh
CountryUS

Traveller reviews

4.8
10 reviews
1 star
0%
2 star
0%
3 star
0%
4 star
20%
5 star
80%

Hannah H.
Sep 28, 2026

A real highlight

Beautiful setting and very well run. The timing gave us plenty of room to explore at our own pace. The children loved it, which is the real test.

5 found this helpful · Report
Marco M.
Sep 12, 2026

A real highlight

Beautiful setting and very well run. The timing gave us plenty of room to explore at our own pace. Squeezed it in around a work trip and it was worth the time.

10 found this helpful · Report
Chloe C.
Jul 15, 2026

Superb

Booked this for our anniversary and it exceeded expectations. Would do it again without hesitation. Travelled on my own and felt completely comfortable.

28 found this helpful · Report
Wei W.
Jul 1, 2026

Superb

The photos do not do it justice. We spent far longer here than we planned to. The children loved it, which is the real test.

21 found this helpful · Report

Reviews are only accepted from guests who completed a booking with EasyTrip.

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