Chicago Events May 2027

Concerts, sports, comedy shows, Broadway performances, and live events across Chicago, IL.

Updated: November 5, 2026

Explore upcoming events in Chicago in May 2027, including concerts, sports events, comedy shows, Broadway performances, festivals, and live entertainment across the city and nearby areas. Browse events by date, venue, category, and neighborhood throughout the month.

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153 Upcoming Events
7 Event Categories

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Popular Events in May

Explore top concerts, sports events, comedy shows, and live performances happening this month.

Chicago Events by Date

Browse events happening each day during May 2027.

Chicago Events Schedule – May 2027

Browse concerts, sports, comedy shows, Broadway performances, festivals, and live events across Chicago.

Upcoming Confirmed Events 153

May 01, 2027, Time TBA — Professional (MLB), High Demand, Weekend Event: Chicago White Sox vs. Los Angeles Angels at Rate Field • 47754 seats, 333 West 35th Street, Chicago, IL 60616, US. From $52, Avg Ticket Price: ~ $203, Tickets Available: 242. Select Seats

May 01, 2027, 2:00 PM Sat — MUSICAL / PLAY, High Demand, Weekend Event: Hadestown at Auditorium Theatre - IL • 3901 seats, 50 East Congress Parkway, Chicago, IL 60605, US. From $84, Avg Ticket Price: ~ $227, Tickets Available: 450. Select Seats

May 01, 2027, 2:00 PM Sat — MUSICAL / PLAY, Weekend Event: Reunion in Bartersville at The Yard at Chicago Shakespeare Theatre, 800 East Grand Avenue, Chicago, IL 60611, US. From $77, Avg Ticket Price: ~ $134, Tickets Available: 50. Select Seats

May 01, 2027, 7:00 PM Sat — Professional (MLS), Best Value, Weekend Event: Chicago Fire FC vs. Toronto FC at Soldier Field • 61500 seats, 1410 S. Museum Campus Drive, Chicago, IL 60605, US. From $38, Avg Ticket Price: ~ $252, Tickets Available: 63. Select Seats

May 01, 2027, 7:00 PM Sat — POP / ROCK, Weekend Event: Palaye Royale at House Of Blues - Chicago • 1300 seats, 329 N Dearborn St, Chicago, IL 60654, US. From $45, Avg Ticket Price: ~ $71, 22 tickets remaining! Select Seats

May 01, 2027, 7:00 PM Sat — MUSICAL / PLAY, Weekend Event: Reunion in Bartersville at The Yard at Chicago Shakespeare Theatre, 800 East Grand Avenue, Chicago, IL 60611, US. From $77, Avg Ticket Price: ~ $143, Tickets Available: 70. Select Seats

May 01, 2027, 7:00 PM Sat — COMEDY, Weekend Event: Ian Bagg at Zanies Comedy Club - Chicago, 1548 North Wells Street, Chicago, IL 60610, US. From $91, Avg Ticket Price: ~ $121, 14 tickets remaining! Select Seats

May 01, 2027, 7:30 PM Sat — MUSICAL / PLAY, Best Value, Weekend Event: A Psalm for the Wild-Built at Lifeline Theatre, 6912 N. Glenwood, Chicago, IL 60626, US. From $41, Avg Ticket Price: ~ $54, Tickets Available: 45. Select Seats

May 01, 2027, 7:30 PM Sat — MUSICAL / PLAY, High Demand, Weekend Event: Hadestown at Auditorium Theatre - IL • 3901 seats, 50 East Congress Parkway, Chicago, IL 60605, US. From $84, Avg Ticket Price: ~ $219, Tickets Available: 468. Select Seats

May 01, 2027, 7:30 PM Sat — CLASSICAL, Weekend Event: Chicago Symphony Orchestra: Hisaishi Conducts Hisaishi at Orchestra Hall At Chicago Symphony Center • 2522 seats, 220 S. Michigan Ave., Chicago, IL 60604, US. From $93, Avg Ticket Price: ~ $222, Tickets Available: 1248. Select Seats

May 01, 2027, 7:30 PM Sat — MUSICAL / PLAY, Weekend Event: Disillusioned at City Lit Theater Company, 1020 West Bryn Mawr Avenue, Chicago, IL 60660, US. From $43, Avg Ticket Price: ~ $50, 24 tickets remaining! Select Seats

May 01, 2027, 7:30 PM Sat — POP / ROCK, Weekend Event, Pay Later Available: Idina Menzel at Lyric Opera House - IL • 3563 seats, 20 North Wacker Drive, Chicago, IL 60606, US. From $116, Avg Ticket Price: ~ $401, Tickets Available: 55. Select Seats

May 01, 2027, 8:00 PM Sat — BALLET, Weekend Event: Alonzo King Lines Ballet at Harris Theater, 205 E. Randolph, Chicago, IL 60601, US. From $50, Avg Ticket Price: ~ $94, Tickets Available: 108. Select Seats

May 01, 2027, 9:15 PM Sat — COMEDY, Weekend Event: Ian Bagg at Zanies Comedy Club - Chicago, 1548 North Wells Street, Chicago, IL 60610, US. From $91, Avg Ticket Price: ~ $121, 14 tickets remaining! Select Seats

May 02, 2027, Time TBA — Professional (MLB), Best Value, High Demand, Weekend Event: Chicago White Sox vs. Los Angeles Angels at Rate Field • 47754 seats, 333 West 35th Street, Chicago, IL 60616, US. From $38, Avg Ticket Price: ~ $234, Tickets Available: 241. Select Seats

May 02, 2027, 1:00 PM Sun — MUSICAL / PLAY, High Demand, Weekend Event: Hadestown at Auditorium Theatre - IL • 3901 seats, 50 East Congress Parkway, Chicago, IL 60605, US. From $84, Avg Ticket Price: ~ $227, Tickets Available: 473. Select Seats

May 02, 2027, 2:00 PM Sun — MUSICAL / PLAY, Weekend Event, Pay Later Available: Reunion in Bartersville at The Yard at Chicago Shakespeare Theatre, 800 East Grand Avenue, Chicago, IL 60611, US. From $111, Avg Ticket Price: ~ $178, Tickets Available: 35. Select Seats

May 02, 2027, 2:00 PM Sun — BALLET, Weekend Event: Alonzo King Lines Ballet at Harris Theater, 205 E. Randolph, Chicago, IL 60601, US. From $49, Avg Ticket Price: ~ $96, Tickets Available: 169. Select Seats

May 02, 2027, 2:00 PM Sun — CLASSICAL, High Demand, Weekend Event: Sondra Radvanovsky & SeokJong Baek at Lyric Opera House - IL • 3563 seats, 20 North Wacker Drive, Chicago, IL 60606, US. From $86, Avg Ticket Price: ~ $352, Tickets Available: 492. Select Seats

May 02, 2027, 2:30 PM Sun — MUSICAL / PLAY, Best Value, Weekend Event: A Psalm for the Wild-Built at Lifeline Theatre, 6912 N. Glenwood, Chicago, IL 60626, US. From $41, Avg Ticket Price: ~ $52, Tickets Available: 41. Select Seats

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About Events in Chicago During May 2027

May 2027 features concerts, sports games, comedy shows, Broadway performances, festivals, and live entertainment across Chicago and nearby IL areas. Major arenas, theaters, clubs, and entertainment venues continue to update their schedules throughout the month.

Browse All Events in May

Browse concerts, sports events, comedy shows, Broadway performances, festivals, and live entertainment happening this month.

Chicago White Sox

333 West 35th Street, Chicago, IL 60616

Event Dates 187

May 01, 2027 Time TBA

Hadestown

50 East Congress Parkway, Chicago, IL 60605

Event Dates 414

May 01, 2027 2:00 PM

Reunion in Bartersville

800 East Grand Avenue, Chicago, IL 60611

Event Dates 31

May 01, 2027 2:00 PM

Chicago Fire FC

1410 S. Museum Campus Drive, Chicago, IL 60605

Event Dates 15

May 01, 2027 7:00 PM

Ian Bagg

1548 North Wells Street, Chicago, IL 60610

Event Dates 52

May 01, 2027 7:00 PM

Palaye Royale

329 N Dearborn St, Chicago, IL 60654

Event Dates 14

May 01, 2027 7:00 PM

Chicago Symphony Orchestra

220 S. Michigan Ave., Chicago, IL 60604

Event Dates 106

May 01, 2027 7:30 PM

Idina Menzel

20 North Wacker Drive, Chicago, IL 60606

Event Dates 3

May 01, 2027 7:30 PM

Disillusioned

1020 West Bryn Mawr Avenue, Chicago, IL 60660

Event Dates 20

May 01, 2027 7:30 PM

A Psalm for the Wild-Built

6912 N. Glenwood, Chicago, IL 60626

Event Dates 28

May 01, 2027 7:30 PM

Alonzo King Lines Ballet

205 E. Randolph, Chicago, IL 60601

Event Dates 11

May 01, 2027 8:00 PM

Sondra Radvanovsky

20 North Wacker Drive, Chicago, IL 60606

Event Dates 3

May 02, 2027 2:00 PM

Calvin Harris

1901 West Madison Street, Chicago, IL 60612

Event Dates 37

May 02, 2027 7:30 PM

The Wombats

4746 North Racine Avenue, Chicago, IL 60640

Event Dates 11

May 04, 2027 7:30 PM

Henge

1001 W Washington Blvd, Chicago, IL 60607

Event Dates 16

May 04, 2027 8:00 PM

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Frequently Asked Questions

Quick answers about Chicago events, venues, schedules, and live entertainment.

What events are happening in Chicago during May 2027?

Chicago hosts concerts, sports games, comedy shows, Broadway performances, festivals, and live entertainment throughout May 2027.

Where can I find Chicago events by date?

Use the monthly event calendar and date filters to browse concerts, sports events, comedy shows, and live performances happening across Chicago.

Are concerts happening in Chicago during May 2027?

Yes. Concert schedules include touring artists, arena shows, local performances, music festivals, and live entertainment events throughout Chicago and nearby IL areas.