Portraiture in the Age of Trump
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Jack Siegel is a Chicago-based photographer who traverses the streets of Chicago with camera in hand.  Jack's practice includes architectural photography and urban landscapes.

Archive

  • Architecture 174
  • Blues 17
  • CTA 12
  • Chicago 506
  • Chicago Tourism 127
  • Crime 13
  • Cubs 10
  • Demonstrations 284
  • Donald J. Trump 103
  • Festivals 103
  • Flowers 13
  • Food 9
  • Jazz 96
  • Maxwell 1
  • Musicians 146
  • Parades 39
  • Performance 287
  • Protest 253
  • Public Declarations 256
  • Sports 11
  • Street 111
  • Things to Do in Chicago 138
  • Urban Landscapes 199
  • Windows 11
  • June 2026 5
  • May 2026 9
  • April 2026 8
  • March 2026 11
  • February 2026 4
  • January 2026 11
  • December 2025 4
  • November 2025 6
  • October 2025 2
  • September 2025 8
  • August 2025 15
  • July 2025 4
  • June 2025 11
  • May 2025 12
  • April 2025 5
  • March 2025 16
  • February 2025 5
  • January 2025 4
  • November 2024 3
  • October 2024 12
  • September 2024 5
  • August 2024 14
  • July 2024 9
  • June 2024 5
  • May 2024 10
  • April 2024 9
  • March 2024 8
  • February 2024 7
  • January 2024 5
  • December 2023 11
  • November 2023 8
  • October 2023 12
  • September 2023 5
  • August 2023 7
  • July 2023 7
  • June 2023 8
  • May 2023 4
  • April 2023 7
  • March 2023 1
  • February 2023 3
  • January 2023 2
  • November 2022 2
  • October 2022 3
  • September 2022 8
  • August 2022 2
  • July 2022 8
  • June 2022 5
  • May 2022 4
  • April 2022 2
  • March 2022 2
  • February 2022 1
  • December 2021 2
  • November 2021 1
  • October 2021 3
  • September 2021 3
  • August 2021 5
  • March 2021 2
  • February 2021 1
  • December 2020 1
  • November 2020 1
  • October 2020 2
  • September 2020 2
  • August 2020 5
  • July 2020 2
  • June 2020 1
  • March 2020 2
  • February 2020 6
  • January 2020 2
  • December 2019 1
  • November 2019 2
  • October 2019 5
  • September 2019 10
  • August 2019 16
  • July 2019 4
  • June 2019 3
  • February 2019 3
  • November 2018 2
  • October 2018 8
  • September 2018 7
  • August 2018 4
  • July 2018 4
  • June 2018 12
  • May 2018 23
  • April 2018 9
  • March 2018 7
  • January 2018 7
  • December 2017 2
  • November 2017 3
  • October 2017 5
  • August 2017 12
  • July 2017 18
  • June 2017 20
  • May 2017 15
  • April 2017 15
  • March 2017 8
  • February 2017 19
  • January 2017 5
  • December 2016 2
  • November 2016 10
  • October 2016 4
  • September 2016 5
  • August 2016 1
  • July 2016 14
  • June 2016 15
  • May 2016 7
Show and Tell Jack B. Siegel's Photographs and Commentary
Juneteenth
Jun 20

Jun 20 Juneteenth

Jack Siegel
Demonstrations, Donald J. Trump, Performance, Protest, Public Declarations

On Saturday, June 20, 2026, some 70 people gathered in Chicago’s Federal Plaza to commemorate Juneteenth. Chicago Mayor Brandon Johnson was the most prominent speaker. Here are my thoughts about and images from the commemoration.

Albanians Reject Ivanka
Jun 14

Jun 14 Albanians Reject Ivanka

Jack Siegel
Chicago, Demonstrations, Donald J. Trump, Parades, Performance, Protest, Public Declarations

Today, Sunday June 14, 2026, members of Chicago’s Albanian community held a rally at Millennium Park, to protest Jared Kushner’s development plans for Sazan Island off the cost of Albania. Here are my thoughts about and images from the demonstration and subsequent march.

Chicago Bluesfest--Day Whee
Jun 7

Jun 7 Chicago Bluesfest--Day Whee

Jack Siegel
Blues, Chicago, Chicago Tourism, Festivals, Musicians, Performance, Things to Do in Chicago

Today, June 7, 2026, saw the Chicago Blues Festival charge into Day 3 of its annual run. The day included performances by Melody Angel, Chris Cain, Katherine Davis, Deitra Farr, Sue Foley, Lee Kanehira, Lynne Jordan, Mary Lane, Taj Mahal, and Nora Jean Wallace. Here are my thoughts about and images from the day.

Chicago Bluesfest--Day 2
Jun 6

Jun 6 Chicago Bluesfest--Day 2

Jack Siegel
Blues, Chicago, Chicago Tourism, Festivals, Jazz, Musicians, Performance, Things to Do in Chicago

Today, June 6, 2026, saw the Chicago Blues Festival charge into Day 2 of its annual run. The day included performances by Billy Branch and the Sons of the Blues, Ronnie Baker Brooks, Nick Moss, Ruthie Foster, Shakura S’Aida, Dylan Triplett, and Dexter Allen. Here are my thoughts about and images from the day.

Chicago Bluesfest--Day 1
Jun 5

Jun 5 Chicago Bluesfest--Day 1

Jack Siegel
Blues, Chicago, Chicago Tourism, Festivals, Jazz, Musicians, Performance, Things to Do in Chicago

Today, June 5, 2026, saw the annual Chicago Blues Festival kickoff. The day included Charlie Musselwhite and Elvin Bishop performing as a duo, as well as guitar slingers Ronnie Baker Brooks, Torozon Cannon, Tinsley Ellis, Lil’ Ed and Nick Moss challenging each other in the battle of the axes. Here are my thoughts about and images from the day.

Anti-War on Memorial Day
May 25

May 25 Anti-War on Memorial Day

Jack Siegel
Chicago, Demonstrations, Donald J. Trump, Parades, Performance, Protest, Public Declarations

Veterans held a Memorial Day demonstration at Chicago’s Vietnam War Memorial along the Riverwalk. Here are my thoughts about and images from the demonstration.

Iranians Condemn Regime
May 24

May 24 Iranians Condemn Regime

Jack Siegel
Demonstrations, Donald J. Trump, Performance, Public Declarations, Protest

Members of Chicago’s Iranian community gathered outside the Wrigley Building on Sunday, may 24, 2026 demanding that the Iranian theocratic regime stop executing Iranian protesters. Here are my thoughts about and images from the demonstration.

Remembering
May 23

May 23 Remembering

Jack Siegel
Chicago, Demonstrations, Parades, Performance, Public Declarations

On Saturday, May 23, 2026, the City of Chicago celebrated Memorial Day with a commemorative ceremony followed by a parade. Here are my thoughts about and images from the event.

Tax the Rich
May 20

May 20 Tax the Rich

Jack Siegel
Chicago, CTA, Demonstrations, Donald J. Trump, Parades, Performance, Protest, Public Declarations

On Thursday, May 21, 2026, 75 people demonstrated outside of State Representative Margaret Croke’s office demanding that the State of Illinois raise $4 Billion in Additional Tax Revenue to fund social services. Here are my thoughts about and images from the demonstration

Snelling Speaks
May 20

May 20 Snelling Speaks

Jack Siegel
Chicago, Crime, Demonstrations, Donald J. Trump, Performance, Protest, Public Declarations

Five or six people held a protest outside of Maggiano’s in River North while Chicago Police Superintendent Larry Snelling delivered a lunchtime address. Here are my thoughts about and images from the protest.

Flag Raising
May 16

May 16 Flag Raising

Jack Siegel
Chicago, Demonstrations, Donald J. Trump, Parades, Performance, Public Declarations, Things to Do in Chicago

Chicago’s Palestinian Community gathered in Daley Plaza today for the community’s annual flag raising ceremony. Here are my thoughts about and images from the joyous event.

Chicago Flips Red
May 12

May 12 Chicago Flips Red

Jack Siegel
Chicago, Demonstrations, Donald J. Trump, Performance, Protest, Public Declarations

Mayoral candidate Danielle Carter-Walters spoke during a Chicago Flips Red rally in Daley Plaza on Tuesday, May 12, 2026. Here are my thoughts about and images from the rally.

May Day
May 2

May 2 May Day

Jack Siegel
Demonstrations, Donald J. Trump, Parades, Performance, Protest, Public Declarations

Today is International Workers’ Day, a day set aside each year to celebrate labor. In Chicago, over two dozen organizations gathered together in Union Park for a march through the streets of Chicago to Daley Plaza. Here are my thoughts about and images from the march.

Isaiah Collier
May 1

May 1 Isaiah Collier

Jack Siegel
Blues, Demonstrations, Donald J. Trump, Festivals, Jazz, Musicians, Performance

Isaiah Collier brought his saxophones and the Chosen Few to the Reva and David Logan Center for the Arts on Friday, May 1, 2026 to close out International Jazz Day week with a tribute to John Coltrane. Here are my thoughts about and images from the concert.

International Jazz Day
Apr 30

Apr 30 International Jazz Day

Jack Siegel
Blues, Chicago, Festivals, Jazz, Musicians, Performance

I had the opportunity to photograph the 15th International Jazz Day Thursday night, which was held at Chicago’s Lyric Opera House. Here are my thoughts about and images from the gala concert.

Herbie in Conversation
Apr 29

Apr 29 Herbie in Conversation

Jack Siegel
Blues, Festivals, Jazz, Musicians, Performance

In honor of International Jazz Day, Kris Bowers, Marcus Miller, and Herbie Hancock sat down for a panel discussion at the Chicago Cultural Center. Here are my thoughts about and images from the afternoon gathering.

Sketches of Spain
Apr 27

Apr 27 Sketches of Spain

Jack Siegel
Blues, Festivals, Jazz, Musicians, Performance

Orbert Davis reimagines Miles Davis’s seminal work, Sketches of Spain, four days before the 15th Annual Jazz Day celebration in the host city of Chicago. Here are my thoughts about and images from the concert.

Anti-Amazon Rally
Apr 13

Apr 13 Anti-Amazon Rally

Jack Siegel
Chicago, Demonstrations, Donald J. Trump, Performance, Protest, Public Declarations

On Monday, April 13, 2026, somewhere between 75 to 100 demonstrators rallied outside of Amazon’s Chicago officers demanding that Amazon and billionaires pay their fair share, whatever that might be. Here are my thoughts about and images from the rally.

Fantastic Negrito
Apr 11

Apr 11 Fantastic Negrito

Jack Siegel
Blues, Festivals, Jazz, Musicians, Performance

Vocalist and guitarist Fantastic Negrito brought his contemporary Blues and Soul to the Reva and David Logan Center for the Arts on Saturday April 11, 2026 for an exuberant concert. Here are my thoughts about and images from Negrito’s performance.

Iranian Monarchists
Apr 11

Apr 11 Iranian Monarchists

Jack Siegel
Chicago, Demonstrations, Donald J. Trump, Performance, Protest, Public Declarations

On Saturday, April 11, 2026, a group from Chicago’s Iranian community held a demonstration in Chicago calling for a free and democratic Iran. Here are my thoughts about and images from the rally.

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Chicago Journal (Experiences In Chicago)

  • Architecture 174
  • Blues 17
  • CTA 12
  • Chicago 506
  • Chicago Tourism 127
  • Crime 13
  • Cubs 10
  • Demonstrations 284
  • Donald J. Trump 103
  • Festivals 103
  • Flowers 13
  • Food 9
  • Jazz 96
  • Maxwell 1
  • Musicians 146
  • Parades 39
  • Performance 287
  • Protest 253
  • Public Declarations 256
  • Sports 11
  • Street 111
  • Things to Do in Chicago 138
  • Urban Landscapes 199
  • Windows 11
Archive By Year
  • 2016 58
  • 2017 122
  • 2018 83
  • 2019 44
  • 2020 24
  • 2021 17
  • 2022 37
  • 2023 75
  • 2024 87
  • 2025 92
  • 2026 48

Detours Journal (Experiences Elsewhere)

  • Architecture 49
  • Cityscapes 52
  • Demonstrations 26
  • Donald Trump 37
  • Gardens 10
  • Jazz Musicians 8
  • New York City 41
  • Oslo and Copenhagen 4
  • Performances 21
  • Portugal 13
  • Protest 28
  • Public Declarations 40
  • Signs and Posters 19
  • Street Musician 13
  • The Age of Trump 40
  • Travel 62
Archive By Year
  • 2016 48
  • 2017 14
  • 2018 10
  • 2019 5
  • 2021 4
  • 2022 9
  • 2023 13
  • 2024 9
  • 2025 18
  • 2026 3
 
 
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