Chicago Holidays

Take to the Chicago River and paddle between some of the city’s best-known buildings, with the skyline rising on both sides. Guided daytime, sunset and even fireworks tours make this one of the most memorable ways to experience Chicago from a completely different angle.

Set off along the Lakefront Trail and ride beside Lake Michigan, passing beaches, harbours, parks and skyline viewpoints along the way. It is one of Chicago’s classic outdoor experiences, giving visitors an active way to see a large stretch of the city. 

Put your head for heights to the test at Maggie Daley Park’s climbing wall, where routes suit both beginners and more confident climbers. With Downtown’s towers all around you, it feels far removed from a standard indoor climbing session and gives the experience a distinctly Chicago setting.

Head out onto Lake Michigan by jet ski and enjoy a more adrenaline-fuelled side of Chicago’s waterfront. With the skyline behind you and open water ahead, it is a thrilling way to experience the city, especially on a warm day during the summer season.

For a faster-paced adventure, board the Seadog Extreme Thrill Ride from Navy Pier and brace yourself for high-speed turns, sudden spins and wave-skimming fun on Lake Michigan. It is a short but exhilarating experience, especially for visitors looking to add something more energetic to their trip.

Explore Chicago’s past at the Chicago History Museum, founded in 1856. Exhibitions trace the city from Indigenous homelands and the Great Chicago Fire to immigration and everyday life, using historic objects, photographs and personal stories to bring different eras into focus.

Walk through Pullman National Historical Park, one of America’s earliest planned industrial communities. The district preserves the Pullman factory area and workers’ neighbourhood, while exhibits explain company-town life, the 1894 Pullman Strike and Chicago’s wider connections with labour and railway history.

Visit the Jane Addams Hull-House Museum, where Jane Addams and Ellen Gates Starr founded their settlement in 1889. Exhibitions explore immigration, labour, women’s rights and social reform, showing how Hull-House became an influential centre for progressive activism in Chicago and beyond.

Stand beneath the Chicago Water Tower, completed before the Great Chicago Fire and one of the few public buildings in the devastated area to survive 1871. Its castellated Gothic Revival design later became a powerful symbol of Chicago’s determination to rebuild.

Step inside Glessner House on historic Prairie Avenue, completed in 1887 for industrialist John Glessner and his family. H. H. Richardson’s fortress-like design broke with Victorian convention, while original interiors reveal how Chicago’s wealthy families lived during the city’s Gilded Age.

Walk through Pilsen to see huge murals and mosaics reflecting Mexican identity, migration and community life. The 16th Street corridor is especially striking, while nearby galleries, panaderías and the National Museum of Mexican Art add more layers to the neighbourhood’s creative culture.

Experience Chicago’s Black creative culture through the Bronzeville Art District, where galleries spotlight African American and African diaspora artists. Seasonal art tours connect spaces including Gallery Guichard and Faie African Art Gallery, while public artworks continue the neighbourhood’s strong artistic tradition. 

Step beneath Chinatown’s gateway and explore Wentworth Avenue, lined with Chinese restaurants, bakeries, speciality shops and traditional architectural details. Visitors can also enter the Chinese-American Museum of Chicago, where exhibitions share stories of Chinese migration, family life and community in the Midwest.

Walk between the enormous Puerto Rican flag gateways marking Paseo Boricua in Humboldt Park. This stretch of Division Street is filled with murals, Puerto Rican-owned businesses and cultural spaces, including La Casita de Don Pedro, where bomba dance and drumming workshops take place.

Explore Devon Avenue in West Ridge, the heart of Chicago’s Indian and Pakistani communities. Saree shops, jewellery stores, international grocers, bakeries and restaurants line the street, giving visitors an everyday glimpse into the South Asian traditions woven into modern Chicago.

Watch one of Chicago’s most distinctive traditions as the river turns bright green for St Patrick’s Day. The annual dyeing, introduced in 1962, is followed by the downtown parade, while Irish celebrations continue across neighbourhoods, pubs and cultural venues throughout the city.

Spend a summer day at Millennium Park listening to the sound Chicago helped shape. First held in 1984, the Chicago Blues Festival brings established names and emerging musicians to multiple stages, with performances also reaching historic blues neighbourhoods and venues. 

Come hungry to Grant Park for Taste of Chicago, where restaurants and food vendors serve everything from deep-dish pizza to dishes reflecting the city’s international communities. Live music, dance sessions and family activities turn the long-running food festival into a wider celebration.

Find a spot along the lakefront and watch aircraft perform high-speed manoeuvres above Lake Michigan during the Chicago Air and Water Show. Held annually since 1959, the free summer spectacle draws huge crowds, with North Avenue Beach serving as its main viewing area.

Join music fans in Grant Park as Lollapalooza transforms the lakefront into a multi-stage festival each summer. The four-day event brings major international artists, emerging acts and a wide mix of genres together, with Chicago’s skyline forming the backdrop to the performances.

Spend an evening at The Second City in Old Town, where original sketch comedy and improvised performances have filled the stage for decades. The venue helped launch performers including Bill Murray, Tina Fey and Steve Carell, and continues to host regular live shows.

Step into one of Chicago’s classic jazz venues at the Green Mill in Uptown. Dating back to 1907, the former speakeasy still hosts live jazz, from big band to bebop, with curved booths and an atmosphere that nods to its Prohibition-era past.

Settle in for a late night of Chicago blues at Kingston Mines, a Lincoln Park institution with two stages and near-continuous live performances. Musicians have included Koko Taylor and Junior Wells, while Southern-style food adds to the relaxed, energetic atmosphere.

Catch a concert, comedy show or touring performance beneath the famous Chicago Theatre marquee on State Street. The programme regularly brings major artists to the city, while the grand lobby, sweeping staircase and ornate auditorium make the venue part of the experience.

See a live show inside the former Morton Salt complex beside the Chicago River. The Salt Shed combines indoor and seasonal outdoor stages, with programmes spanning contemporary music and touring artists, while summer performances add riverfront views and the city skyline to the evening.