Podcasts about Chicago, Illinois

The loudest arguments in this feed are about the Bears, and the most revealing one is barely about football. In Podcast: What we learned about the Chicago Bears at the NFL's annual meetings, the hosts of Shaw Local's Bears Insider Podcast react to George McCaskey's comment about fans getting used to a move, and one of them reckons more people would be upset about Hammond. The hosts relay that Kevin Warren wants a stadium open in 2030 and that McCaskey said stadium borrowing would not affect roster building. A football show has turned into a discussion of where a city's institutions belong and who carries the cost.

Many of these shows return to the question of who pays: for property bills, for condo loans, for a shooting in a drive-thru, for a family's revolutionary past. The question has a backdrop. In September 2026 a projected 2027 city budget gap of $882.4 million was reported, and a market estimate that month put rents up nearly 5% year on year. By late September 2026 the Cubs and the White Sox were both in postseason baseball.

Sports talk is what you will hear. Keep listening and the feed widens into a business podcast, documentary reporting on violence, family history, a 1950s radio reporter and improvisers talking about crockpots.

What Chicago is

Chicago is in northeastern Illinois, on Lake Michigan's southwestern shore. The Census Bureau estimated the city's population at 2,731,585 as of July 1, 2025, a count of the city and not the metropolitan area. Its economy spans finance, commerce, industry and transportation, and its cultural identity includes architecture, jazz, blues and house music.

Game days and stadium geography

The Bears shows divide by temperament. Bear Report Radio Podcast: Chicago Bears and 2nd City Gridiron work like draft rooms. In The Halas Beat: Should the Chicago Bears trade for DT Dexter Lawrence? the hosts compare the price of the trade with what other defensive tackles have cost. On 2nd City Gridiron, Ari Temkin and Jacob Infante argue in Chicago Draft Room: Dexter Lawrence, Rueben Bain Jr & Why Day 2 Makes or Breaks the Bears that the second day is where this draft will be won. The Nicholas Moreano Show plays like a beat reporter's notebook. After a 19-16 loss to Detroit at Soldier Field, Moreano names the secondary's lack of speed as one of the defense's weaknesses.

Talk radio adds heat. Steve Rosenbloom hosts the Steve Rosenbloom Show, which he calls Saturday Suckage. In Jacob Infante of PFSN shares his Bears mock draft with us (Hour 2) he tells George McCaskey to take what Indiana is giving if the team is as short of money as Adam Schefter says. In Evan Altman on the Cubs young pitchers heading into Spring Training (Hour 2) he imagines season ticket holders from out west, or from Lake Forest, making the drive to northwest Indiana. That geography carries his argument: a stadium decision also decides whose game day gets longer. Score Evenings takes roster debates to callers in Herron: Ravens back out of their trade for Maxx Crosby (Hour 2).

The basketball shows run on fatigue. On Cash Considerations: A Chicago Bulls Pod, Ricky O'Donnell and Jason Patt use Bulls finally get the Blazers pick! to work through draft trade options. Bulls Bros slows down for history. In Sam Smith Talks All Things Bulls, Phil, 'Masters of the Game', Smith describes visiting Phil Jackson's house and finding almost no sports memorabilia on the walls. The hockey show catches the mood too: on CHGO Chicago Blackhawks Podcast, a host sighs, "my God, does Chicago need a basketball team that's not bad?"

The amateur level gets attention as well. On Hold My Beer Sports, Matt Scalzo talks with Neuqua Valley High School players about a 32-2 season in NVHS All State Basketball Players Cole Kelly and Mason Martin and NCAA Tournament Picks.

Property, taxes and the working day

Crain's Daily Gist, hosted by Amy Guth with Crain's reporters, explains how money moves through the city better than any other show here. In Cook County property tax hikes outpace inflation, the bill is broken down by district type, TIF districts included. The reporter also admits not knowing how appeals change the gap between taxes levied and taxes paid. In Landlords show cautious optimism after Hynes' assessor win, Danny Ecker explains why commercial landlords hoped for a fresh start, and the conversation recalls the old logic that "buildings don't vote." In 01/22/26: Illegitimate listing pops up for Frank Lloyd Wright house, Dennis Rodkin explains why he will not go beyond what he could verify: "as a reporter, you know, you only report what you know."

Laricy LIVE speaks from inside the trade. Host Matt Laricy is a working agent, and his show reflects a broker's interests. In Rate Update with Ben Cohen | Laricy LIVE E181, Cohen explains how a condo building can appear on a lender's do-not-lend list after the loan work is done, which can kill a sale. Straight Up Chicago Investor's 36th Ward: Future of Chicago with Alderman Gil Villegas gives an alderman's own account of rallying colleagues against a budget he did not support. He describes enlisting long-serving council chairwomen for credibility. Take it as his version of events.

After the shooting

Motive (WBEZ) is the most demanding listen on the page. It includes descriptions of gun violence, the killing of a child and beatings in prison. 4: Getting In And Getting Out covers the killing of seven-year-old Jaslyn Adams at a McDonald's drive-thru in Lawndale and the blame that fell on her father, Jonte Adams. He tells friends who want revenge to go be with their kids. Host Patrick Smith records two anti-violence workers, Fats and his supervisor Vernell, disagreeing over whether Adams deserved the blame. Smith then traces Fats's own exit from gang life back to a used car. 6: Aftermath follows Ceci, who works on gang conflicts in Little Village, after her neighbor Nikki's car is shot up during a trip for tamales. The series stays with people after the news moves on. The episodes discussed here date from 2022 and 2023, so treat them as documentary and not as current reporting.

1: The Blind Spot moves to Western Illinois Correctional Center in Mount Sterling. The reporter fought the state for more than a year to obtain security footage, and says plainly, "None of them deserve to be beaten." Listeners who want more on the state can go to the Illinois page.

The long memory

Mother Country Radicals is Zayd Dohrn's history of his parents' Weather Underground years, a series whose Chapter 10: Inheritance is dated July 2022. Chapter 2: Days of Rage places Bernardine Dohrn's office a few blocks from Fred Hampton's on the West Side. In the same chapter Dohrn asks his father about violence, and describes the four days of protest and Mayor Daley asking, "What right has anyone to walk down the street with a chain in their hand?" The story extends well beyond the city, and readers following that thread can turn to the United States page.

Chicago History Podcast's FROM THE ARCHIVES - Sundown Towns of Chicago with Ernest Crim III tells how Oak Park met the chemist Percy Julian in 1950. The water commissioner refused to turn on his water until Julian threatened legal action. Night Beat Presented by the Great Detectives of Old Time Radio comes from far outside the city: Adam Graham presents it from Boise, Idaho. He brings back Randy Stone of the Chicago Star, who notes in Night Beat: Five Days Off For Christmas that a missing child's mother "lived only three blocks from my smug little tower."

Culture in its own words

AirGo, hosted by Damon A. Williams and Daniel Kisslinger, makes its politics plain. Its stated aim is liberation, and its conversations are warm and searching. In Ep 389 - Heavy Crownz Breaks Down New Album Trench Baby Turned Farmer, the artist reclaims his album's title: "during war, the trench is your safe space." A host adds that North Side teenagers he worked with could all name their neighborhood. Crooks and Nannies offers easier company. Erin's Okra Yield drifts from a corned beef crockpot to gazpacho to a seventh-inning stretch. The newest Radio One Chicago episodes date from 2020. In Live From The Lair | Dr. Lopez, its guest recalls wandering into what was then Loop College while window shopping and enrolling two hours later. City Cast Chicago's Jacoby Cochran and producer Michelle Navarro trade late-night picks in Chicago's 24-Hour Restaurant Guide.

Where to start

• If you want the city's finances explained: Crain's Daily Gist, Cook County property tax hikes outpace inflation.
• For reporting that stays after the headlines: Motive (WBEZ), 4: Getting In And Getting Out. Listen for how blame gets assigned and who pushes back.
• For history with a family stake: Mother Country Radicals, Chapter 2: Days of Rage.
• For stadium talk that is really about home: Shaw Local's Bears Insider Podcast, Podcast: What we learned about the Chicago Bears at the NFL's annual meetings.
• For an old-time radio evening: Night Beat Presented by the Great Detectives of Old Time Radio, Night Beat: The Man with the Red Hair.

The Chicago feed on this page plays clips from these shows.