Chicago, IL, USA

Seeing Second City

2 Guests

2 Nights

1 Bedroom

1 Bathroom

Laugh out loud at Second City and dine at one of Chicago's top restaurants during a Chicago getaway filled with comedy, cuisine, and city charm.

1695 (2 Nights)

2195 (3 Nights)

Cost to Non-Profit

1695

Chicago Stay
Chicago, Illinois, 2-night stay for 2 at a four-star hotel in the Chicago area, offering convenient access to downtown neighborhoods, cultural landmarks, and the city’s lakefront.
Second City
Tickets for 2 to a live performance at The Second City in Chicago, featuring sketch comedy and improvisational performances from one of the city's most iconic comedy institutions.
Dining Choice
Dinner for 2 with a choice of Pequod’s Pizza, Rose Mary, or Obélix, highlighting Chicago’s diverse range of deep-dish, modern Italian, and contemporary French dining.
City Access
A location positioned for access to Chicago’s most recognized attractions, including Millennium Park, the Magnificent Mile, and the city’s surrounding neighborhoods.

Overview

Laugh your way through a Chicago getaway with a hilarious and heartfelt experience at the world-famous Second City comedy club. Known as the launchpad for comedic icons like Tina Fey, Steve Carell, Bill Murray, and Stephen Colbert, The Second City delivers an unforgettable night of improv, sketch comedy, and spontaneous brilliance. Whether you’re a lifelong fan of comedy or new to the scene, you’ll find yourself caught up in the infectious energy and wit that defines this legendary Chicago institution.

Your Windy City experience continues with a delicious dinner at one of Chicago’s top restaurants. Choose from deep-dish perfection at the iconic Pequod’s Pizza, the Croatian-Italian fusion delights at Rose Mary, or innovative French fare at Obélix, each offering a flavor of the city’s renowned culinary scene.

After a night of laughter and Chicago’s finest flavors, retreat to comfort at a four-star Chicago-area hotel. Whether you explore Millennium Park, stroll along the Magnificent Mile, or dive into the city’s vibrant neighborhoods, this package puts you at the center of the action.
Comedy, cuisine, and culture, Seeing Second City is your ticket to the ultimate Chicago experience.

Featured Amenities

Air Conditioning
Complimentary Wi-Fi
Prime Downtown Location
Walking Distance to Attractions

Terms of Use

Package Redemption

Trip winners will receive an email within 15 business days after the event containing their redemption certificate number and instructions for accessing our dedicated Trip Winner Portal. The portal includes everything needed to begin the trip planning process, including important information, next steps, and direct communication with their dedicated Booking Specialist. Reservations must be made at least 60 days before travel and are subject to availability and property inventory. Travel must be booked within 12 months of notification and completed within 24 months. Once confirmed, reservations are final. Packages are non-refundable and may not be transferred or resold. Blackout dates include the weeks of Thanksgiving, Christmas, and New Year’s.