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O-Town: 25th Anniversary of the Debut Album
City Winery LLC
O-Town: 25th Anniversary of the Debut Album

O-Town: 25th Anniversary of the Debut Album

08/30/2026
Sun 7:00 PM
Main Stage, City Winery Chicago
1200 W. Randolph St
Chicago 60607
United States
Sold out
Return later to check if tickets are available again.
(opens in a new tab)(opens in a new tab)City Winery Chicago Presents O-Town: 25th Anniversary of the Debut Album live on Sunday, August 30th at 7:00 PM!

O Town burst onto the music scene in 1999 as the breakout stars of Making the Band, the first major network musical reality series produced by ABC. Created in collaboration with Lou Pearlman, the mastermind behind the Backstreet Boys and *NSYNC, the show followed the formation and meteoric rise of O Town across three seasons on ABC and MTV.

The group made history as the first artists signed by Clive Davis to his J Records label and quickly found chart topping success. Their debut albums produced multiple hit singles including “Liquid Dreams” and the number one smash “All or Nothing,” which earned a Song of the Year nomination at the 2001 Radio Music Awards.

By 2003, shifts in the music industry, legal turmoil surrounding their former management, and restrictive contracts forced the group to step away. Though the chapter closed sooner than expected, the foundation had been laid for a future return on their own terms.

That return came in 2014 when Jacob Underwood, Trevor Penick, Dan Miller, and Erik Michael Estrada reunited as a four piece and released their third studio album Lines and Circles. The group launched their first national tour in over a decade and went on to perform alongside acts like 98 Degrees, Ryan Cabrera, Dream, New Kids on the Block, Boyz II Men, and Paula Abdul. They also made their acting debut in Nick Carter’s cult film Dead 7, which premiered on SyFy.

Fueled by years of touring and overwhelming fan support, O Town chose to independently fund their next chapter. A 2016 Kickstarter campaign surpassed its goal in just hours and nearly doubled by the end of the campaign, proving the enduring loyalty of their fanbase.

Now, O Town celebrates the 25th anniversary of their debut album with a special live show revisiting the music that defined an era while honoring the journey that brought them here. Expect nostalgia, harmonies, and the hits that made O Town a pop phenomenon.(opens in a new tab)


🍽️ We provide food and beverage service directly to your table in the venue. Or, for an expanded menu and more relaxed experience, arrive early and enjoy a meal in our restaurant before the show. When dining in the restaurant, reservations are encouraged and can be made via Resy starting one month before the show. View Our Concert Dining Menu.(opens in a new tab)


Reserve your preferred wine by filling out this form(opens in a new tab) and have a bottle waiting at your table when you arrive at your show. No more waiting for your first drink! We will save your wine preference and have a bottle at your table for all future shows. When you want to change your wine, come back to this form and update your preference.


2 Item Per Person Encouraged

🎶 While we do not require a two-item food or beverage minimum, we strongly encourage it. Most ticket revenue goes directly to the artist and production costs, so food and drink purchases help support the staff, service, and atmosphere that make these intimate shows possible.

The good news: we think you’ll love the food and wine just as much as the show.


🍷 Members get 48 hour early access to new shows, pay no ticket fees, and earn points to exchange for complimentary tickets. Vinofile Plus members also receive many wine benefits. Add a membership to your cart during checkout to start saving now. Already a member? Make sure you are signed in to access your benefits. Become a Vinofile Member and enjoy the benefits today.(opens in a new tab)

O-Town: 25th Anniversary of the Debut Album
Main Stage, City Winery Chicago
Sold out
Return later to check if tickets are available again.
08/30/2026
Sun 7:00 PM
Main Stage, City Winery Chicago
1200 W. Randolph St
Chicago 60607
United States