This weekend itinerary offers a dynamic mix of Chicago's most anticipated festivals, a major Broadway show, iconic museum exhibitions, and a classic White Sox game, culminating in a celebration of the city's rich musical heritage. Curated for residents, it highlights diverse and immersive experiences easily accessible via public transit, ensuring a memorable rediscovery of the city.
Kick off your weekend at the annual Taste of Greektown, a vibrant street festival celebrating Greek culture with authentic food, live music, and family-friendly entertainment.
This festival transforms the streets of the historic Greektown neighborhood into a lively block party.
Expect a festive atmosphere with delicious Greek culinary delights from local restaurants, traditional dance performances, and live bands. It's a great way to experience a unique cultural facet of Chicago. Entry to the festival is typically free, with food and drink available for purchase.
Accessible via CTA Blue Line (UIC-Halsted stop) or various CTA bus routes, including the #8 Halsted bus.
Experience the Tony-winning new musical, MJ The Musical, delving into the life and career of Michael Jackson.
This electrifying production features a plethora of his iconic hits, exploring his stratospheric rise to fame.
A must-see for theater enthusiasts and Michael Jackson fans, MJ The Musical offers a high-energy performance with incredible choreography and music. It's a Broadway in Chicago production, known for drawing large crowds and critical acclaim. Running time is approximately 2 hours and 30 minutes, including an intermission.
Located in the heart of the Loop. Easily accessible by CTA Brown, Orange, Pink, Purple, and Green Lines (State/Lake or Clark/Lake stops) or Red Line (Lake or Monroe stops). Numerous bus routes also stop nearby.
Immerse yourself in local creativity at the Bucktown Arts Fest, a free, volunteer-run, and highly respected arts festival featuring over 200 artists, live music, spoken word, and a dedicated kids' stage.
This long-standing neighborhood tradition offers a fantastic opportunity to discover unique art, enjoy diverse performances, and support local talent. It's known for its community-focused vibe and high-quality artwork. Perfect for a relaxed morning stroll.
Take the CTA Blue Line to Damen or Western, then a short walk. Various local bus routes also serve the Bucktown area.
Explore the latest contemporary art exhibitions at the Museum of Contemporary Art Chicago (MCA).
On view are 'Paul Pfeiffer: Prologue to the Story of the Birth of Freedom', 'Pipilotti Rist: Supersubjektiv', 'Wafaa Bilal: Indulge Me', and 'City in a Garden: Queer Art and Activism in Chicago', among others.
The MCA is a vital institution for modern and contemporary art, offering thought-provoking and innovative works. These exhibitions showcase a range of media and perspectives, providing a deep dive into current artistic discourse. Allow at least 2-3 hours to explore multiple galleries.
Accessible via CTA Red Line (Chicago stop) or the #3, #10, #26, #66, #146, #147, #151 bus routes.
Savor a variety of tacos from some of Chicago’s most beloved eateries at the Lakeview Taco Fest.
This popular street festival features live music, wrestling, and an impressive selection of taco vendors.
A quintessential Chicago street festival experience, perfect for foodies and those looking for a lively atmosphere. Sample unique taco creations and enjoy the energetic vibe of the Lakeview neighborhood. Come hungry!
Take the CTA Brown Line to the Southport stop, which is just steps away from the festival. The #152 Addison bus also provides close access.
Cheer on the Chicago White Sox as they face off against the Minnesota Twins at Guaranteed Rate Field.
This Saturday game also features a special giveaway for attendees.
Experience America's pastime with a local flair at a White Sox game. The atmosphere on the South Side is electric, especially with a giveaway day, making it a fun outing for sports fans. Expect classic ballpark food and enthusiastic fans.
Directly accessible via the CTA Red Line (Sox-35th stop), located across the street from the ballpark. Limited parking is available but public transit is highly recommended.
Conclude your weekend by celebrating Chicago’s deep roots in house music at the Chicago House Music Festival.
While the full conference may span several days, Sunday often features free public performances and dance parties in Millennium Park.
A truly authentic Chicago experience, highlighting a genre born in the city. Expect a diverse lineup of DJs and live performers, creating a vibrant, dance-filled atmosphere. It’s a fantastic way to enjoy a Sunday afternoon outdoors with a uniquely Chicago soundtrack. Schedule details for specific performances will be announced closer to the date.
Millennium Park is centrally located in the Loop, easily accessible via multiple CTA train lines (Brown, Green, Orange, Pink, Purple to Randolph/Wabash or Blue Line to Monroe, then a short walk) and numerous bus routes.
Delve into world-class art at the Art Institute of Chicago.
Explore ongoing exhibitions such as 'Gustave Caillebotte: Painting His World', 'Pixy Liao: Relationship Material', and 'Charles Gaines: Night/Crimes'. Consider joining a free gallery tour for an insightful overview.
As one of the oldest and largest art museums in the United States, the Art Institute offers a vast and diverse collection. The special exhibitions provide a fresh perspective for even seasoned locals. Free gallery tours (typically 1:00 PM) offer a curated experience of highlights or specific themes.
Located in the heart of the Loop. Easily accessible by CTA Brown, Green, Orange, Pink, Purple Lines (Adams/Wabash or State/Lake stops) or Red Line (Monroe or Adams stops). Many bus routes also serve Michigan Avenue.
Test your cinematic knowledge at Music Box Theatre's Movie Trivia event, part of their engaging weekend programming.
A perfect relaxed cap to your weekend, this event at the beloved independent Music Box Theatre offers a unique opportunity to engage with film culture in a fun, competitive setting. It’s a local favorite, known for its charming ambiance and diverse programming. Enjoy a drink at their lounge before or after. Confirm specific trivia themes closer to the date.
Take the CTA Brown Line to the Southport stop, then walk a few blocks north on Southport Avenue. The #9 Ashland bus and #22 Clark bus also connect to the area.
This weekend itinerary for Chicago can be customized using our AI travel planner. Chat with our AI assistant to modify activities, adjust timings, add personal preferences, and get recommendations for restaurants, hotels, and transportation.