Name: Challenge Mania Live: Hosted by DERRICK KOSINSKI & SCOTT YAGER
Start: 2026-07-18T17:00:00.000Z
End: 2026-07-18T20:00:00.000Z
Location: Main Stage, City Winery Chicago

City Winery Chicago Presents Challenge Mania Live: Hosted by DERRICK KOSINSKI & SCOTT YAGER live on Saturay, July 18th at 12:00pm!

Hosted by fan favorites Derrick Kosinski and Scott Yager of the hit Challenge Mania podcast, this live show features appearances from legendary competitors including C.T., Mark Long, Darrell Taylor, and more special guests to be announced. Expect behind-the-scenes stories, audience interaction, and plenty of surprises that capture the intensity and camaraderie of the series.

After the show, fans will have the opportunity to take part in an exclusive meet and greet, adding an extra layer to this unforgettable experience.

Join us for a special Saturday event packed with competition, community, and insider access. Secure your seats now and be part of the action.

🍽️  Brunch menu options will be available the day of the show. Please ask your server upon arrival and treat yourself to a delicious meal during the performance. Doors open at 10:30 AM, and service will continue until the end of the show.

🎶  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.

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Dine During the Show - Charcuterie & Cheese

Dine During the Show - Buffalo Chicken Sandwich

City Winery Chicago Main Stage

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Challenge Mania Live: Hosted by DERRICK KOSINSKI & SCOTT YAGER

City Winery Chicago Presents Challenge Mania Live: Hosted by DERRICK KOSINSKI & SCOTT YAGER live on Saturay, July 18th at 12:00pm!    Stars from popular reality competition series, MTV's The Challenge, appear in an interactive variety show, hosted by Derrick Kosinski & Scott Yager of the hit podcast, Challenge Mania. Join C.T, Mark Long, Darrell Taylor, and more Special Guests TBA. The live show starts at 12:00pm and ends at roughly 1:45pm. Ticket holders should arrive by 10:30AM as the doors will open for ALL SEATING promptly at 10:30AM. Please arrive by 10:30AM to get on line, regardless of your ticket type. The Meet N Greet will take place after the show.

Challenge Mania Live: Hosted by DERRICK KOSINSKI & SCOTT YAGER | City Winery Chicago

Stage Premier / Premium VIP Experience

Premier / Regular VIP Experience

Premier (Show Only)

Orchestra

Mezzanine Premier

Mezzanine

Seat Assigned at Venue

IMPORTANT NOTICE REGARDING ARBITRATION: YOU UNDERSTAND AND AGREE THAT THESE TERMS INCLUDE A MANDATORY ARBITRATION AGREEMENT AND CLASS ACTION WAIVER (SEE SECTION 12 BELOW) THAT REQUIRES INDIVIDUAL ARBITRATION OF ALL CLAIMS AS SET FORTH IN THE ARBITRATION AGREEMENT. You will be bound by this Arbitration Agreement, unless you opt out following the opt-out procedures set forth below. By entering this agreement, you expressly acknowledge that you have read and understand all of its terms and have taken time to consider the consequences of this important decision.

Please review our Terms and Conditions, which will govern purchases through the City Winery sites, including our refund and exchange policy. ALL TICKETS ARE NON-REFUNDABLE unless a show is canceled and store credit will be issued.

There is a $25 minimum food and beverage spend per person for all City Winery shows announced after January 15, 2025. All shows subject to the $25 minimum food and beverage spend per person clearly state this in the About section of the respective show page on citywinery.com.

No tickets, memberships, wine or other products purchased on City Winery's website are returnable or exchangeable for anything, including credit. All sales are final. Before purchasing tickets, it is your responsibility to carefully review your seat location, event, and performance date. When dining at our locations, all guests may be subject to a credit card pre-authorization. 

HOLDER VOLUNTARILY ASSUMES ALL RISKS, HAZARDS AND DANGERS arising from or relating in any way to the risk of contracting a communicable disease or illness (including exposure to COVID-19, a bacteria, virus, or other pathogen capable of causing a communicable disease or illness), whether occurring before, during, or after the event, however caused or contracted, and hereby waives all claims and potential claims against City Winery to such risks.

Purchasers are bound by the laws of the State of purchase, and City Winery reserves the right to pursue, to the fullest extent of the law, all penalties allowable for anyone caught counterfeiting, reproducing for sale, or altering tickets for unpaid or illegal entry into an event. We may also prohibit you from using the Site and revoke your Vinofile Membership privileges. Tickets unlawfully resold or attempted to be resold for profit, counterfeit or copied tickets may be seized and canceled without compensation. City Winery has the right to restrict or deny ticket purchasing privileges to anyone that we determine to be in violation of our policies. You agree not to sell for profit, reproduce for sale, alter, or counterfeit the ticket for any reason, and assume all financial liability for the copying of the user’s unique order number and ticket name. Unauthorized third party selling or bartering without consent of the artist or venue, is forbidden and can result in suspension or cancellation of Vinofile Membership and the right to purchase tickets for City Winery Events. Please contact the Local Box Office if you have any questions about transferring or reselling tickets or City Winery reserves the right to cancel your purchase without notice.

Mobile Ticketing/SMS is a free product and City Winery, City Vineyard or El Bar do not charge you to receive your tickets. Please keep in mind that your mobile service provider's standard rate for receiving text messages may apply. Upgrade opportunities, cancellations, wait-list ticket purchases, restaurant discounts and other details can be communicated through Email and Text messaging. Message frequency varies. You’re free to unsubscribe to any email and text communication in the future by texting STOP to opt-out.  Carriers are not liable for delayed or undelivered messages. If you have any questions about the rate, please contact your service provider for more information.

By opting into City Winery's SMS program, you consent to receive recurring marketing and promotional text messages (e.g., event announcements, exclusive offers, reminders) to the mobile number provided. Message frequency may vary.

● Consent: Participation requires you to opt in. Consent to receive SMS is not a condition of purchase. 

● Opt-Out: You may opt out at any time by replying STOP to any message. 

● Help: For assistance, reply HELP or contact us at guestservices@citywinery.com or call us at 646-751-6033. 

● Charges: Message and data rates may apply. Check with your mobile carrier. 

● Carriers: Wireless carriers are not liable for delayed or undelivered messages. 

● Eligibility: You must be at least 18 years old or have parental consent to participate.

Event staff reserves the right to refuse admission to, or eject, any person whose conduct the management deems to be disorderly or otherwise fails to comply with event rules. Breach of terms or rules will terminate your license to attend the event and will not result in a refund.

Opening acts may sometimes tour with headlining performers. City Winery is not always made aware of opening acts or the length of their performances. These opening acts are subject to change or cancelation at any time without notice. No refund will be given if an opening act is changed or canceled unless the venue or promoter approves it.You voluntarily assume all risks and dangers incidental to an Event, whether occurring before, during or after the Event, and you waive any claims for loss, damage, personal injury, illness or death against City Winery, the management of City Winery, any agent of City Winery, the performing artist(s), participants, and all of their respective parents, affiliated entities, agents, officers, directors, owners and employees on behalf of yourself and any minor accompanying you or for whom you purchased a Ticket.

City Winery always makes a best attempt possible to release tickets to Vinofile Members early. However, there are sometimes instances when an artist insists their tickets go on sale to everyone at the same time. Vinofile Membership Renewal: Membership is automatically renewed annually, until members request to cancel. Annual membership is renewed for one year by payment of the membership fee in full in advance on the anniversary of the initial purchase. Annual Membership can be canceled prior to renewal by emailing guestassistance@citywinery.com or contacting your local Box Office. Annual Membership refunds are available for up to 30 days after renewal. Vinofile Plus Membership is automatically renewed monthly, until members request to cancel after the first six months. Please note that Vinofile Plus membership requires a six month commitment. Cancellations within the first 6 months will incur a $150 cancellation fee. After the first six months, monthly membership is renewed for one month by payment of the membership fee in full in advance on the monthly anniversary of the initial purchase. Wine and other benefits not picked up or redeemed within six months are forfeited. All memberships must be paid in good standing and all past balances paid for any declined or expired credit card attempts.City Winery can not accept responsibility for damage to or loss of any personal property at an Event.

Credit Card. During the enrollment process you will provide a credit card to be used as your form of payment for your recurring subscription (“Subscription Card”). You may change your Subscription Card at any time by contacting guestassistance@citywinery.com.

Recurring Subscription. By enrolling in Vinofile or Vinofile Plus you agree that until you cancel your subscription, we may charge your Subscription Card on a recurring basis according to the frequency you selected. We will never charge you for an amount greater than the Maximum Price, plus applicable sales tax. You may cancel your subscription at any time by contacting guestassistance@citywinery.com.

Representations. You represent that you will not use any credit card or other form of payment unless you have authorization to do so. We will not be liable in the event others acting with or without your permission use your credit card to make orders.

By completing this purchase I agree that I am over 21 years of age. Wine shipping is available for all states except AL, AR, KY, MI, MS, SD and UT. We cannot ship wine outside the United States. I agree that someone 21 years of age or older must be present to sign for the package at the destination. Our shipping company will not leave wine unattended and will return the product to City Winery after two attempts. Additional shipping fees will apply to re-ship the item.

No wine, memberships or other products purchased on City Winery's website are returnable or exchangeable. All sales are final. Virtual Wine Tasting Purchases

1. To ensure the best service in planning virtual wine tastings events, City Winery must receive a final delivery guarantee no later than five (10) business days prior to the Event date.

2. The final delivery guarantee may not fall below 90% of the contracted Guest Guarantee. If no delivery guarantee is given, the original estimated guarantee specified in the City Winery Event Agreement will be considered the delivery guarantee.

3. Payments. A Deposit equaling 50% of the Estimated Charges (which will be the Guaranteed Minimum Per Person times the Minimum Guest Count) is required at the time of booking. The 50% Deposit is nonrefundable once this Agreement is signed. Final payment is due at the time of shipping.

4. Cancellation. You may not cancel this Agreement once your custom order is produced. The option to reschedule an event is determined on a case-by-case basis, subject to availability, and not guaranteed.

5. Alcohol Service to Minors Someone over the age of 21 years of age must be home and able to provide identification prior to receiving the wines.

6. Taxes In addition to the Estimated Charges which includes the Administrative Fee, Client agrees to pay separately any and all federal, state, municipal or other taxes imposed on or applicable to your event. In the State of New York, Sales Tax is charged at a rate of 8.875%

7. Shipping City Winery will arrange for shipment on behalf of our customer, to an address in New York State. All wine deliveries must be signed for by an adult over the legal drinking age (21+). We cannot leave packages on your doorstep and we cannot ship to P.O. boxes. If a shipment is damaged or lost during transit it must be reported to City Winery within 5 business days of the expected delivery date. We will work with the appropriate courier to resolve the issue.

8. Inability to Perform. City Winery shall not be liable for its failure to perform or for limited or interfered performance or other cause beyond the reasonable control of the City Winery due to Acts of God, including, but not limited to, flood, tornado, earthquake, storm, lightning, fire, epidemic or war, national emergency, civil disturbance, riot, sabotage, terrorism, court order or machinery or equipment failure, labor troubles, disputes or strikes, government regulations, utility shortages, restrictions upon travel affecting transportation of foods, beverages or supplies; or any other cause, whether specifically enumerated herein or not, the same shall not constitute a breach of this Agreement by City Winery, and City Winery shall not be liable to Client for any loss as a result of a force majeure event. Client shall be responsible for all additional costs incurred to address any force majeure events impacting the staging of the Event. If, for example, an outdoor event is moved indoors due to rain (subject to space availability), You shall be responsible for all additional labor costs and any additional room rental charges (refer to Section 16. Inclement Weather Clause). Should any Act of God described in this section prevent City Winery from providing you with any services contracted herein, City Winery shall use reasonable efforts to provide you with a substitute date of commensurate value based on availability, and any amounts paid to City Winery shall be applied and credited to your payment obligations in connection with such substitute date.

9. Indemnification. To the extent permitted by law, you agree to indemnify, defend and hold harmless City Winery, and all of its officers, employees, directors, partners, and agents against all claims, losses or damages to persons or property, governmental charges or fines, and costs (including reasonable attorney's fees) (“Claims”), arising out of or connected with your function, except those claims arising out of the negligence or willful misconduct of City Winery. You further indemnify City Winery form all Claims related to a breach by you of this Agreement and you represent and warrant that your activities conducted at City Winery and in connection with the Event shall not infringe the patent, copyright or trademark rights or violate rights of privacy or publicity of any third party.

10. Promotional Considerations. We have the right to review and approve any advertisements or promotional materials in connection with your function which specifically reference the City Winery intellectual property, including but not limited to our name or logo. City Winery reserves the right to refuse approval of any material bearing its name, likeness or logo for any reason, in its sole discretion. 11. Attorney’s Fees. The parties agree that in the event that any dispute arises in any way relating to or arising out of this Agreement, the prevailing party in any arbitration or court proceeding will be entitled to recover an award of its reasonable attorney's fees and costs, plus pre and post judgment interest, as may be finally determined and awarded by the trier of fact.

12. ARBITRATION AGREEMENT, CLASS ACTION/JURY TRIAL WAIVER, AND DISPUTE RESOLUTION PROCEDURES (THE “ARBITRATION AGREEMENT”)

The law of the State of New York shall govern these Terms, without reference to its choice of law rules.

Class action/JURY TRIAL waiver: YOU AND CITY WINERY AGREE THAT EACH MAY BRING claims against the other only on an individual basis and not as a plaintiff or clASS member in any PURPORTED class, AGGREGATE, MASS, COLLECTIVE, or representative action or proceeding, AND THAT EACH ARE WAIVING THE RIGHT TO A TRIAL BY JURY. If any court or arbitrator determines that this Class Action/Jury Trial Waiver is void or unenforceable for any reason or that an arbitration can proceed on a class basis, then the Arbitration Agreement shall be deemed null and void in its entirety, and you and City Winery shall be deemed not to have agreed to arbitrate Covered Disputes (as that term is defined below). To the extent any claims are allowed to proceed on a class, collective, consolidated, or representative basis, such claims must be litigated in a federal or state court of competent jurisdiction in New York City, New York, and the parties agree that the litigation of those claims shall be stayed pending the outcome of any individual claims in arbitration.

MANDATORY BINDING ARBITRATION OF DISPUTES: YOU AND CITY WINERY AGREE THAT ALL COVERED DISPUTES WILL BE RESOLVED BY BINDING INDIVIDUAL ARBITRATION IN THE MANNER SPECIFIED IN THIS SECTION AND THAT YOU AND CITY WINERY WAIVE ANY RIGHT TO BRING SUCH CLAIMS BEFORE ANY COURT OF LAW. RIGHTS THAT YOU WOULD HAVE IF YOU WENT TO COURT, SUCH AS ACCESS TO DISCOVERY, MAY BE UNAVAILABLE OR LIMITED IN ARBITRATION.

Any controversy or claim arising under or related to the Services, related in any way to your relationship with City Winery with respect to the Services, these Terms and their interpretation or the breach, termination or validity thereof, the relationships which result from these Terms, including disputes about the formation, breach, termination, interpretation, validity, scope, applicability, or enforceability of the Terms and this Arbitration Agreement and/or questions of the arbitrability of any controversy or claim brought by you or City Winery (collectively, “Covered Disputes”), whether such Covered Disputes arose before, on, or subsequent to you entering these Terms, shall be settled by binding arbitration if not resolved through the informal dispute resolution procedure set forth below. The arbitrator shall also be responsible for determining all threshold arbitrability issues, including issues relating to whether these Terms are unconscionable or illusory, in whole or in part, and any defense to arbitration, including waiver, delay, laches, or estoppel. Covered Disputes are subject to this Arbitration Agreement whether based in contract, statute, regulation, ordinance, tort (including, but not limited to, fraud, misrepresentation, fraudulent inducement, negligence, gross negligence or reckless behavior), or any other legal or equitable theory. Covered Disputes shall be arbitrated on an individual basis, and shall not be consolidated in any arbitration with any claim or controversy of any other party.

Rules & Governing Law: In the event of a Covered Dispute, you and City Winery each agree to send the other party a written notice of the Covered Dispute stating the name, address, and contact information of the party giving notice; the facts giving rise to the Covered Dispute; and the relief requested (“Notice of Dispute”). You must send any Notice of Dispute by mail at City Winery, PO Box 30083, New York, NY 10011. We will send any Notice of Dispute to you at the email address or mailing address we have for you, if any. You and City Winery agree to attempt to resolve in good faith the Covered Dispute through informal negotiation within 30 days after the Notice of Dispute is received. After the end of that 30-day period and not before, you or City Winery may commence an arbitration proceeding as set forth in this Arbitration Agreement. Notwithstanding the foregoing, your right and City Winery’s right to bring an individual action in small claims court shall not require an attempt to first resolve the Covered Dispute through informal negotiation.

If the parties cannot resolve the Covered Dispute informally, you and City Winery each agree that the Covered Dispute shall be resolved exclusively through final and binding individual arbitration, rather than in court. All Covered Disputes shall be submitted to ADR Services, Inc. (“ADR Services”) for arbitration in the county in which you reside, by remote means, or another mutually agreeable location, and judgment on the arbitration award may be entered by any court of competent jurisdiction. The arbitration will be administered by ADR Services in accordance with its rules and procedures, including any supplementary rules and fee schedules then in effect (the “Rules”), except as modified by this Arbitration Agreement. ADR Services’ Rules are available at https://www.adrservices.com/services-2/arbitration-rules/. For information on how to commence an arbitration proceeding, you can contact ADR Services at www.adrservices.com. Notwithstanding the foregoing, either you or City Winery may seek any interim or preliminary relief from a court of competent jurisdiction in New York City, New York, necessary to protect the intellectual property rights of you or City Winery pending the completion of arbitration.

City Winery LLC

City Winery complies with the privacy laws and regulations of the United States of America. This privacy notice describes the privacy policy associated with the City Winery website and app. Except as set forth in this privacy notice, City Winery will not share personal information about you with anyone. City Winery will not sell your SMS opt-in to third parties, nor will it share it with third parties to allow such third parties or affiliates to use it for their own marketing purposes. By interacting with the City Winery website and app, you agree to accept the practices described in this privacy notice.

A. Information You Give Us: City Winery receives and stores any information you choose to enter on the City Winery website, or provide us in any other way, such as by telephone or by electronic mail. This information may include your name, address, e-mail address, and/or telephone number. We also collect from you certain information such as your credit card number and billing address when you order products through the City Winery web site.

B. Automatic Information: Certain applications in City Winery website invoke a standard feature found in web browser software called cache.

C. In addition to the information described above, we may collect your mobile phone number if you choose to opt in to receive SMS text messages from City Winery.

A. Electronic Mail: If you bought a ticket, you will be added to certain mailings by City Winery for future concerts and events.

I. General: If we request demographic information, we will not share information about you as an individual with any other entity. If we do share demographic information with third parties, we will give them aggregate information only.

II. Agents and Service Providers : City Winery engages other companies and individuals to perform services on our behalf. Examples of these services include processing credit card payments, providing order fulfillment and customer services, sending postal mail and e-mail to you, and analyzing data. While these agents and service providers may have access to your personal information in connection with the performance of services for City Winery, they may not use such information for any purpose other than providing such services to City Winery.

III. Protection of City Winery and Others: We release account and other personal information when we believe release is appropriate to comply with law; enforce or apply our User Agreement; or protect the rights, property, or safety of City Winery, our users, or others. This includes exchanging information with other companies and organizations for fraud protection and credit risk reduction.

IV. Business Transfers: As we continue to develop our business, we might sell all or certain of our assets. In such transactions, your personal information may be one of the transferred business assets.

V. City Winery App: City Winery collects location information in the app to send push notifications when a user is near one of our City Winery locations. This collection of location data is optional and can be accepted or declined by the user within the app.

VI. How We Use Information: We use your mobile number to send you transactional and marketing text messages, including event updates, special offers, and reminders.

VII. Sharing of Information We may share your mobile phone number with trusted third-party service providers (such as SMS platforms, carriers, and aggregators) solely for the purpose of delivering text messages. We do not sell or rent your phone number to third parties.

VIII. Your Choices You may opt out of receiving SMS text messages at any time by replying STOP to a message or contacting us directly at guestservices@citywinery.com or call us at 646-751-6033. Standard message and data rates may apply.

City Winery works to protect the security of your information during transmission by using Secure Sockets Layer ("SSL") software, which encrypts information you input. If you make a purchase via the City Winery web site, we will use your credit card number only to process your payment and will not use it for marketing purposes. For reasons of security, credit card information is not stored on our Web Server. We will retain order information for our records, but this information is never shared with third parties.

City Winery is committed to protecting your privacy; however, this privacy notice applies only to the information collected via the City Winery web site. If you came to the City Winery web site from any other web site, or if you link to another site from the City Winery web site (you can check where you are by checking the URL in the location bar on your browser), please be sure that you review the privacy policy of that site, as it may differ from ours.

The ticket processing fee and all other fees charged on this event are for the administration, operations, and other expenses associated with this event (including but not limited to the ticketing and sales platforms), and will be retained by City Winery.

We do not knowingly collect personal information from any children under 13. Any portion of the City Winery web site intended for children under 13 will not request any personal information.

7. Conditions of Use, Notices, and Revisions

If you choose to interact with the City Winery web site, your visit and any dispute over privacy is subject to this privacy notice. Our business changes constantly. Accordingly, this notice may change, and use of information that we gather now is subject to the privacy notice in effect at the time of use. You should check the City Winery web site periodically to see recent changes.

8. CALIFORNIA PRIVACY POLICY & EU GDPR & FULL PRIVACY POLICY DETAILS

If you have any questions about this Privacy Policy or our information-handling practices, or if you would like to request information about our disclosure of personal information to third parties for their direct marketing purposes, please contact us by e-mail or postal mail as found on our Contact Us page.

City Winery will not sell your SMS Opt-In to third parties, nor will it share with third parties to allow such third parties or affiliates to use it for their own marketing purposes. No mobile information will be shared with third parties / affiliates for marketing / promotional purposes. All the above categories exclude text messaging originator opt-in data and consent; this information will not be shared with any third parties.

Upon messaging opt-in, the end user agrees to receive messages from City Winery regarding order updates or account notifications. End users can opt-out by replying STOP or request more information by replying HELP. Message frequency varies. Message and data rates may apply. If you need assistance or have questions about our SMS service, reply with "HELP" to any SMS message you receive, or contact our customer support team at guestservices@citywinery.com

By purchasing seats marked as ADA Accessible, you acknowledge that you require the ADA compliant features of these seats.

Privacy Officer c/o Legal Department/City Winery

New York - 25 11th Avenue, New York, NY, 10011 | (646)-751-6033

Chicago - 1200 W Randolph St, Chicago IL, 60607 | (312)-733-9463

Nashville - 609 Lafayette Street, Nashville, TN , 37203 | (615)

Atlanta - 650 North Avenue, Ponce City Market, Atlanta, GA, 30308 | 404-946-3791 

Boston - 80 Beverly Street, Boston, MA, 02114 | 617-933-8047

Challenge Mania Live: Hosted by DERRICK KOSINSKI & SCOTT YAGER

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City Winery LLC