If you’re in Chicago for just one day—maybe passing through on your way somewhere else like I often do—I’ve got a few go-to spots to make the most of it. Over the years, I’ve found myself with just enough time to catch one iconic sight or settle in for a great local meal, and I’ve learned that even a short visit can feel special in this city.
Whether you want to snap a photo at a classic landmark or simply relax and enjoy the food scene, here are a few ideas I’ve tried and loved. You can pack in just enough Chicago charm to make it memorable without feeling rushed.
Unique One Day Ideas in Chicago:
Bike, Blade, or Stroll the Chicago Lakefront Trail
The The Chicago Lakefront Trail is a shared-use walking and cycling path spanning along Chicago's Lake Michigan coastline, stretching for 18.5 miles past the city's Lincoln, Grant, Burnham, and Jackson Parks and a number of seasonal public beaches. The trail, which was designated in 1963 as the city's first official bicycle path, was recently renovated in 2018 in an effort to reduce congestion. Major attractions accessible via the trail include the city's Museum of Science and Industry, McCormick Place, Navy Pier, and Belmont and Monroe Harbors. Several dog parks are also accessible via the trail, along with the city's 31st Street, Grant Park, and Wilson Avenue skate parks. The Chicago Lakefront Trail users looking to avoid crowds can take the Navy Pier Flyover, which avoids congestion at the intersections of Grand Avenue and Illinois Street.
Step Into Gilded Glamour at The Driehaus Museum
The Driehaus Museum is a living history museum in Chicago's Near North Side neighborhood, converting the 1883 Samuel M. Nickerson House into a recreation of the splendor of the American Gilded Age. The National Register of Historic Places-listed museum has been open to the public since 2008, showcasing the architecture and interior design of the Gilded Age with pieces sourced from the personal fine and decorative arts collection of Chicago philanthropist Richard H. Driehaus.
Works on display include pieces from Belle Epoque artists such as Édouard Colonna and the Herter Brothers, along with one of the world's most noted collections of Tiffany decorative works and stained glass pieces. Visitors can enjoy guided and self-guided tours daily at the museum, including an audio tour using Acoustiguide technology. Public programming includes an annual turn-of-the-century-themed murder mystery dinner event and a quarterly jazz concert series.
Address: The Driehaus Museum, 40 E Erie St, Chicago, IL 60611, Phone: 312-482-8933
Get Lost in Green at the Garfield Park Conservatory
Garfield Park Conservatory is one of the largest conservatory and botanical garden parks in the United States, originally created in 1907 by landscape architect Jens Jensen. The facility, which was designed as an attempt to create the world's largest publicly-owned botanical conservatory, spans more than 4.5 acres today in Chicago's Garfield Park, presenting eight indoor garden displays showcasing a wide variety of exotic and native plant species. It has been named today as one of the American Institute of Architects' 200 Great Places in Illinois and has won significant international museum awards, including the prestigious National Medal for Museum and Library Services. Visitors can enter the conservatory for free daily and view notable plant holdings, including a collection of bicentennially-aged cycads and an expansive palm tree collection.
Address: 300 N Central Park Ave, Chicago, IL 60624, Phone: 312-746-5100
Play, Eat, and Wander at Chicago’s Navy Pier
Chicago's Navy Pier is one of the American Midwest's most popular tourist attractions, overlooking Chicago's gorgeous Lake Michigan shoreline for a six-block stretch within the city's Streeterville neighborhood. The venue, which was originally developed as the city's Municipal Pier in 1915, was renovated into a retail and entertainment center in 1995 and attracts over nine million visitors each year today. 50 acres of retail, dining, and family attractions are offered at the pier, including the newly-added Centennial Wheel, a beautiful 200-foot observation wheel overlooking the waterfront. Other attractions include the family-friendly Pier Park amusement park, the Amazing Chicago's Funhouse Maze, the Chicago Shakespeare Theater, and the Chicago Children's Museum.
600 E Grand Ave, Chicago, IL 60611, Phone: 312-595-7437
Celebrate the Written Word at The American Writers Museum
The American Writer's Museum is a new museum in Chicago celebrating the history and legacy of America's greatest writers, opened to the public in May of 2017. The museum, which was modeled after the Dublin Writer's Museum, is the home of the Wintrust Chicago Gallery, which honors seminal figures in the city's literary community, with a focus on how the city's authors have pushed social boundaries and served as positive agents of social change in America. At the museum's Children's Literature Gallery, young visitors can enjoy interactive exhibitions, including tabletop reading screens. Other exhibitions include the Nation of Writers literary timeline and the Mind of a Writer gallery, which offers wordplay activities and other games to help young writers hone their creative and literary skills.
Address: The American Writer's Museum, 180 N Michigan Ave, Chicago, IL 60601, Phone: 312-374-8790
Discover Local Talent at Dreambox Gallery and Studio
Stop by Dreambox Gallery and Studio, one of Chicago's hottest contemporary art galleries.
Address: Dreambox Gallery and Studio, 2415 W North Ave, Chicago, IL 60647, Phone: 773-292-0419
Chicago for Couples:
See the City Through Local Eyes with Chicago for Chicagoans
Chicago for Chicagoans offers a unique perspective on Chicago's eclectic and lively neighborhoods, operating pay-what-you-can walking tours throughout the year. The nonprofit, which was founded by Patti Swanson in 2016, is focused around giving local Chicago residents an opportunity to showcase their unique neighborhoods and cultural histories. Tours focus on a different Chicago neighborhood each month, lasting approximately two hours and ending at a local independent restaurant for a group meal. Past tour themes have included a Chicago History 101 tour series, urban planning tours, Jewish history tours, and tours focusing on the city's feminist and LGBTQ heroes. Though participants with financial limitations are absolutely encouraged to attend tours for free, donations are welcomed for those able to pay to help sustain continued business operations.
Grab a Pint with History at Monk’s Pub Chicago
Have a fun meal at Monk's Pub Chicago, an Old World-style pub and bar in Chicago's vibrant Loop district.
Address: Monk's Pub Chicago, 205 W Lake St, Chicago, IL 60606, Phone: 312-357-6665
Treasure Hunt at the Randolph Street Market
The Randolph Street Market is an indoor-outdoor seasonal market held within Chicago's Beaux Arts Plumbers Hall, open to the public year-round inside the hall and showcasing outdoor vendors between May and September. The market, which has been acclaimed by international publications such as The New York Times, Travel and Leisure, and Lucky Magazine, is home to the internationally-renowned Chicago Antique Market, frequently described as a "mecca of cool" for perusing for the city's hippest and hottest market finds. More than 100 vendors are featured on site, including vendors selling as part of the Indie Designer Market and Modern Vintage Chicago. The family-friendly market also features a children's play area and activities for young visitors, including market treasure maps.
Address: The Randolph Street Market, 1341 W Randolph St, Chicago, IL 60607, Phone: 312-666-1200
Jump to a Spot...
- • Bike, Blade, or Stroll the Chicago Lakefront Trail
- • Step Into Gilded Glamour at The Driehaus Museum
- • Get Lost in Green at the Garfield Park Conservatory
- • Play, Eat, and Wander at Chicago’s Navy Pier
- • Celebrate the Written Word at The American Writers Museum
- • Discover Local Talent at Dreambox Gallery and Studio
- • See the City Through Local Eyes with Chicago for Chicagoans
- • Grab a Pint with History at Monk’s Pub Chicago
- • Treasure Hunt at the Randolph Street Market