6 Best Private & Custom City Tours In Chicago

Chicago, City Tours, Private, Private & Custom City Tours, Sightseeing & City Tours, Tour Reviews, Tours

Chicago Private Custom City Tour with Hotel Pick Up

/ June 4, 2026

1.Chicago Private Custom City Tour with Hotel Pick Up

Chicago private custom city tour with hotel pickup. See Millennium Park, Loop, Lincoln Park, Hyde Park and Wrigley Field in 3–4 hours.

Chicago Premium Driving Tour with River Boat Cruise and Sky Deck

/ June 4, 2026

2.Chicago Premium Driving Tour with River Boat Cruise and Sky Deck

A half-day small-group Chicago combo with a narrated drive, Cloud Gate and skyline stops, plus an included architecture river cruise.

★ 4.5

“This was a fantastic way to “do” Chicago! Jack was very personable and accommodating. It is obvious that he loves his city, and he is very knowledgeable in the things that make Chicago great. The activities included in this tour really set it apart as well. The tour company chose the best and took care…”

165 reviews4 hours (approx.)by See Sight Tours USA

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Chicago, City Tours, Private, Private & Custom City Tours, Sightseeing & City Tours, Tour Reviews, Tours

Best of Chicago: Architecture & Highlights City Private Tour

/ June 4, 2026

3.Best of Chicago: Architecture & Highlights City Private Tour

Private 2-hour downtown architecture walk from Chicago Theatre to Cloud Gate, with Pedway tunnels, river views, Picasso, and included snacks.

★ 5.0

“Our guide was very informative. We learned a lot of fun facts too! Seeing the inside of some historical buildings was amazing.”

94 reviewsFrom $245.00by WeVenture

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Chicago, Guided, Private, Private & Custom City Tours, Tour Reviews, Tours

Chicago: Private custom tour with a local guide

/ June 12, 2026

4.Chicago: Private custom tour with a local guide

A private custom walking tour of Chicago with a local guide, flexible route, museum exteriors focus, and practical city advice for your day.

★ 4.4

“Service sublime notre guide Bart nous a bien expliqué l’histoire de Chicago le tout dans un français parfait :) une visite à faire on aurait du prendre davantage de temps que 2h je recommande vivement cette visite en français de l’histoire de Chicago”

28 reviews2 - 8 hoursFrom $129by Guydeez

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Chicago, Cruises & Boat Tours, Evening Experiences, Private & Custom City Tours, Skydeck & Observation Decks, Tour Reviews, Tours

Chicago Night Driving Tour with Skydeck and River Cruise

/ June 13, 2026

5.Chicago Night Driving Tour with Skydeck and River Cruise

Chicago night driving with Willis Tower Skydeck, Cloud Gate, and a post-dark Chicago River cruise. Small group, $189, about 3.5 hours.

★ 4.5

“By the description and price of this excursion, I ASSUMED we would be going into more than one tall building, with a tour guide. The ad also seems to suggest that the night boat tour was a small group. It was not. It was aboard a larger vessel that was oversold, therefore we had to…”

26 reviews3 hours 30 minutes (approx.)From $189.00by See Sight Tours USA

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