STAYPINEAPPLE CHICAGO SETS THE STAGE AS THE PERFECT HOTEL NEAR THE CHICAGO THEATER DISTRICT
Staypineapple Chicago, An Iconic Hotel
Staypineapple Chicago, a hotel near the Chicago Theater District, is the best ticket in town to experience world-class entertainment inside some of the country’s most renowned theaters.
A perfect choice for theater enthusiasts and cultural explorers alike, our hotel close to the Chicago Theater District puts you in the epicenter of Chicago's rich performing arts scene. We’re ideally situated a short walking distance from the city’s most celebrated theaters, including:
The Chicago Theatre: Known for its stunning architecture and iconic marquee that can be seen right outside of the windows of many of our comfortable guest rooms, this historic venue hosts a diverse range of performances from Broadway shows to live concerts. Check out these upcoming events:
- May 31-June 1: Nikki Glaser
- June 7: Alison Kraus
- June 13: Trevor Wallace
- July 2: Jeff Goldblum
- July 22-23: Yeah Yeah Yeahs
- August 5-6: Death Cab for Cutie
- September 9: Bonnie Raitt
The Goodman Theatre: Renowned for its innovative productions and captivating plays, the Goodman Theatre is a cultural gem and Chicago’s oldest and largest not-for-profit theater, located a short walk away from our Chicago Theater District hotel. Check out these upcoming events:
- June 21-July 27: The Color Purple
The Cadillac Palace Theatre: Our hotel near the Cadillac Palace, where you can experience popular productions and Broadway hits, is an elegant theater known for its ornate interiors that were inspired by the Palace of Versailles. Check out these upcoming events:
- June 3-8: Tina - The Tina Turner Musical
- June 10-22: Kimberly Akimbo
- July 9-August 2: Disney’s Beauty and the Beast
The CIBC Theatre: This iconic venue, close to our Chicago Theater District hotel, which became a popular destination for vaudeville acts when it first opened, hosts a range of performances from dazzling Broadway hits to innovative new works. Check out these upcoming events:
- May 6-18: Hadestown
- October 14-19: The Book of Mormon
The James M. Nederlander Theatre: A beacon for theatrical excellence and celebrated for its beautiful art deco design, not unlike the interiors of Staypineapple Chicago, features blockbuster Broadway musicals and top-tier performances. Check out these upcoming events:
- August 12-31: MJ
- October 21-November 2: The Sound of Music
- November 11-30: Hell’s Kitchen
The Harris Theater: As Chicago’s home for music and dance showcasing world-renowned and emerging talent, this theater is located along the northern edge of Millenium Park, which you can marvel at from our Millenium Park View Suite at our hotel near the Harris Theater. Check out these upcoming events:
- May 10: Balanchine + Beyond
- July 19-20: BFDI & Inanimate Insanity 2025 Tour
- September 9: Whose Live Anyway?
While you’re staying at Staypineapple Chicago, our hotel near the Chicago Theater District in the heart of the bustling Loop neighborhood, plan the perfect night of dinner and a show by enjoying premier dining at our on-site restaurant, Atwood.
Beyond the Chicago Theater District, you'll find a variety of events to enjoy year-round — from summer festivals to holiday magic — all just steps from our hotel.
In Grant Park, just a 7-minute drive or 20-minute walk away, catch the Grant Park Music Festival in June, Lollapalooza in August, and the NASCAR Chicago Street Race in July. October brings the Chicago Marathon, starting and ending in the park.
Those celebrating Chicago Pride in June can take a short 20-minute car ride or 30 minutes on the L to get to the starting point of the Chicago Pride Parade.
The Chicago Jazz Festival lights up Millennium Park in August — just a 5-minute walk.
In September and October, the internationally acclaimed event series, Sundays on State, transforms Chicago’s iconic State Street — happening right next to Staypineapple Chicago.
Also in October, don’t miss the Chicago International Film Festival happening citywide.
The Chicago Thanksgiving Parade in November marches down State Street — right next to our hotel! Some rooms have perfect views, and we offer cozy packages so you can watch in comfort (just like this Staypineapple guest’s festive CORE Memory).
And just 4 minutes away by foot, the Christkindlmarket in Daley Plaza brings holiday cheer all season long — with a surprise gift for guests who book direct with our special Christkindlmarket offer.
Once the New Year is in full swing, February brings the most exciting time of the year for theater lovers — Chicago Theatre Week. Over 100 performances across the city offer value-priced tickets, many at theaters just a few short minutes’ walk from Staypineapple Chicago.
Book your stay at Staypineapple Chicago today and immerse yourself in the magic of the city’s theater scene. We can’t wait to welcome you to the best seats in town!
