Upcoming Chicago Events

Name: Chicago Skyline Sail – Escape the City Hustle
Start: 2025-09-26T15:00:00-05:00
End: 2025-09-26T16:15:00-05:00
Location: Tall Ship Windy

Check out what's happening all around Chicago.

September 23, 2025: Sep23
Tours & Attractions
Chicago Skyline Sail – Escape the City Hustle
Experience Chicago’s Stunning Skyline from the Water! AVAILABLE NOW SAIL DAILY May 16, THROUGH Sept 28! Leave the hustle and bustle behind! Explore Chicago’s shores with…
Event details
Tuesday, September 23rd
1:00 p.m. – 2:15 p.m.
See all events in series
Tall Ship Windy
600 East Grand Avenue Navy Pier
Sep23
Tours & Attractions
Chicago Skyline Sail – Escape the City Hustle
Experience Chicago’s Stunning Skyline from the Water! AVAILABLE NOW SAIL DAILY May 16, THROUGH Sept 28! Leave the hustle and bustle behind! Explore Chicago’s shores with…
Event details
Tuesday, September 23rd
3:00 p.m. – 4:15 p.m.
See all events in series
Tall Ship Windy
600 East Grand Avenue Navy Pier
Sep23
Tours & Attractions
90 Minute Architecture River Tour in Chicago
Experience Chicago’s Best 90-Min Architecture Boat Tour starting May 3, 2025! Led by expert tour guides, this is perfect for all ages. Explore the city’s…
Event details
Tuesday, September 23rd
5:00 p.m. – 7:00 p.m.
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Summer Of George, 900 South Wells Street, Chicago, United States
Summer Of George, 900 South Wells Street, Chicago, United States
Sep23
Tours & Attractions
Big Bus Tours’ Sunset Live Tour
Big Bus Tours, the global leader in open-top bus sightseeing, invites visitors to experience the enhanced Sunset Live Tour in Chicago. Available May 8 through…
Event details
Tuesday, September 23rd
7:30 p.m. – 9:15 p.m.
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618 N Clark St.
618 N. Clark St
September 24, 2025: Sep24
Museums, Galleries & Exhibitions, Tours & Attractions
Franz West: Millennium Park
Franz West” Millennium Park features two monumental installations by West: Stonehenge (2011) and Dorit (2002), set against the iconic backdrop of Millennium Park. Stonehenge, with…
Loop
Event details
Wednesday, September 24th
Millennium Park
201 E Randolph St
Sep24
Tours & Attractions
Homeschool Days at PEPPA PIG World of Play Chicago
Join us for Homeschool Days at Peppa Pig World of Play Chicago, where preschool families can enjoy an OINKTASTIC discount! Experience the magic of Peppa…
Event details
Wednesday, September 24th
10:00 a.m. – 5:00 p.m.
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Peppa Pig World of Play Chicago
5 Woodfield Mall
Sep24
Tours & Attractions
Chicago Skyline Sail – Escape the City Hustle
Experience Chicago’s Stunning Skyline from the Water! AVAILABLE NOW SAIL DAILY May 16, THROUGH Sept 28! Leave the hustle and bustle behind! Explore Chicago’s shores with…
Event details
Wednesday, September 24th
1:00 p.m. – 2:15 p.m.
See all events in series
Tall Ship Windy
600 East Grand Avenue Navy Pier
Sep24
Tours & Attractions
Chicago Skyline Sail – Escape the City Hustle
Experience Chicago’s Stunning Skyline from the Water! AVAILABLE NOW SAIL DAILY May 16, THROUGH Sept 28! Leave the hustle and bustle behind! Explore Chicago’s shores with…
Event details
Wednesday, September 24th
3:00 p.m. – 4:15 p.m.
See all events in series
Tall Ship Windy
600 East Grand Avenue Navy Pier
Sep24
Tours & Attractions
90 Minute Architecture River Tour in Chicago
Experience Chicago’s Best 90-Min Architecture Boat Tour starting May 3, 2025! Led by expert tour guides, this is perfect for all ages. Explore the city’s…
Event details
Wednesday, September 24th
5:00 p.m. – 7:00 p.m.
See all events in series
Summer Of George, 900 South Wells Street, Chicago, United States
Summer Of George, 900 South Wells Street, Chicago, United States
Sep24
Tours & Attractions
Tropical Wednesdays
Immerge yourself in a cultural experience as Latin dances come alive on Taylor street – Salsa, Bachata, Cumbia, and Cha Cha Cha with margarita!
Event details
Wednesday, September 24th
6:00 p.m. – 8:00 p.m.
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Vintage Bar Chicago
1449 W. Taylor St.
Sep24
Tours & Attractions
Big Bus Tours’ Sunset Live Tour
Big Bus Tours, the global leader in open-top bus sightseeing, invites visitors to experience the enhanced Sunset Live Tour in Chicago. Available May 8 through…
Event details
Wednesday, September 24th
7:30 p.m. – 9:15 p.m.
See all events in series
618 N Clark St.
618 N. Clark St
September 25, 2025: Sep25
Museums, Galleries & Exhibitions, Tours & Attractions
Franz West: Millennium Park
Franz West” Millennium Park features two monumental installations by West: Stonehenge (2011) and Dorit (2002), set against the iconic backdrop of Millennium Park. Stonehenge, with…
Loop
Event details
Thursday, September 25th
Millennium Park
201 E Randolph St
Sep25
Tours & Attractions
Homeschool Days at PEPPA PIG World of Play Chicago
Join us for Homeschool Days at Peppa Pig World of Play Chicago, where preschool families can enjoy an OINKTASTIC discount! Experience the magic of Peppa…
Event details
Thursday, September 25th
10:00 a.m. – 5:00 p.m.
See all events in series
Peppa Pig World of Play Chicago
5 Woodfield Mall
Sep25
Tours & Attractions
The World Within: Chicago’s Original & Best Architecture Interiors Tour
“Everything has beauty, but not everyone sees it.” (Confucius) Everyone does a boat tour when they visit Chicago. But as fun as that is, it’s…
Event details
Thursday, September 25th
11:00 a.m. – 1:00 p.m.
See all events in series
Chicago Loop & River North
Sep25
Tours & Attractions
Chicago Skyline Sail – Escape the City Hustle
Experience Chicago’s Stunning Skyline from the Water! AVAILABLE NOW SAIL DAILY May 16, THROUGH Sept 28! Leave the hustle and bustle behind! Explore Chicago’s shores with…
Event details
Thursday, September 25th
1:00 p.m. – 2:15 p.m.
See all events in series
Tall Ship Windy
600 East Grand Avenue Navy Pier
Sep25
Tours & Attractions
Chicago Skyline Sail – Escape the City Hustle
Experience Chicago’s Stunning Skyline from the Water! AVAILABLE NOW SAIL DAILY May 16, THROUGH Sept 28! Leave the hustle and bustle behind! Explore Chicago’s shores with…
Event details
Thursday, September 25th
3:00 p.m. – 4:15 p.m.
See all events in series
Tall Ship Windy
600 East Grand Avenue Navy Pier
Sep25
Tours & Attractions
90 Minute Architecture River Tour in Chicago
Experience Chicago’s Best 90-Min Architecture Boat Tour starting May 3, 2025! Led by expert tour guides, this is perfect for all ages. Explore the city’s…
Event details
Thursday, September 25th
5:00 p.m. – 7:00 p.m.
See all events in series
Summer Of George, 900 South Wells Street, Chicago, United States
Summer Of George, 900 South Wells Street, Chicago, United States
Sep25
Tours & Attractions
Big Bus Tours’ Sunset Live Tour
Big Bus Tours, the global leader in open-top bus sightseeing, invites visitors to experience the enhanced Sunset Live Tour in Chicago. Available May 8 through…
Event details
Thursday, September 25th
7:30 p.m. – 9:15 p.m.
See all events in series
618 N Clark St.
618 N. Clark St
September 26, 2025: Sep26
Museums, Galleries & Exhibitions, Tours & Attractions
Franz West: Millennium Park
Franz West” Millennium Park features two monumental installations by West: Stonehenge (2011) and Dorit (2002), set against the iconic backdrop of Millennium Park. Stonehenge, with…
Loop
Event details
Friday, September 26th
Millennium Park
201 E Randolph St
Sep26
Tours & Attractions
Homeschool Days at PEPPA PIG World of Play Chicago
Join us for Homeschool Days at Peppa Pig World of Play Chicago, where preschool families can enjoy an OINKTASTIC discount! Experience the magic of Peppa…
Event details
Friday, September 26th
10:00 a.m. – 5:00 p.m.
See all events in series
Peppa Pig World of Play Chicago
5 Woodfield Mall
Sep26
Tours & Attractions
The World Within: Chicago’s Original & Best Architecture Interiors Tour
“Everything has beauty, but not everyone sees it.” (Confucius) Everyone does a boat tour when they visit Chicago. But as fun as that is, it’s…
Event details
Friday, September 26th
11:00 a.m. – 1:00 p.m.
See all events in series
Chicago Loop & River North
Sep26
Tours & Attractions
Chicago Skyline Sail – Escape the City Hustle
Experience Chicago’s Stunning Skyline from the Water! AVAILABLE NOW SAIL DAILY May 16, THROUGH Sept 28! Leave the hustle and bustle behind! Explore Chicago’s shores with…
Event details
Friday, September 26th
1:00 p.m. – 2:15 p.m.
See all events in series
Tall Ship Windy
600 East Grand Avenue Navy Pier
Sep26
Tours & Attractions
The World Within: Chicago’s Original & Best Architecture Interiors Tour
“Everything has beauty, but not everyone sees it.” (Confucius) Everyone does a boat tour when they visit Chicago. But as fun as that is, it’s…
Event details
Friday, September 26th
1:00 p.m. – 3:00 p.m.
Chicago Loop & River North
Sep26
Tours & Attractions
Chicago Skyline Sail – Escape the City Hustle
Experience Chicago’s Stunning Skyline from the Water! AVAILABLE NOW SAIL DAILY May 16, THROUGH Sept 28! Leave the hustle and bustle behind! Explore Chicago’s shores with…
Event details
Friday, September 26th
3:00 p.m. – 4:15 p.m.
See all events in series
Tall Ship Windy
600 East Grand Avenue Navy Pier