Green Door Tavern

Tucked away on a side street in River North sits one of the oldest bars in Chicago. The unassuming Green Door Tavern first opened its doors in 1872, making it one of the few remaining ties to Chicago’s past before the Great Fire of 1871. Step inside this low-key tavern and you’ll feel transported back in time thanks to the well-preserved historic decor, artifacts from famous visitors, and rare Prohibition-era tilework behind the bar. Despite its dive bar appearance, the Green Door Tavern serves upscale fusion bar bites like green chile cheese fries and Korean barbecue tacos along with one of the city’s most revered burgers.

678 N Orleans St, Chicago, IL 60654
(312) 664-5496

Honey Pie

Craving delicious homemade pies in a cozy, retro setting? Look no further than Honey Pie on North Clark Street. The delightful throwback diner slings delectable sweet and savory pies perfect for sharing with your pie-loving travel companions. Come hungry and sample a few different slices or order an entire pie to enjoy back home—the kitchen offers fruit, cream, custard, pot pies, and seasonal specialties. Honey Pie’s decor transports diners back to the 1940s with vintage woodwork, pastel colors, and a classic diner counter. You’ll feel like you stepped out of a time machine!

1638 N Clark St, Chicago, IL 60614
(773) 234-7175

Ping Tom Memorial Park

One of Chicago’s best kept secrets is this gorgeous 18-acre public park modeled after classical Chinese gardens. Tucked away in the heart of Chinatown, Ping Tom Memorial Park boasts serene walking paths, carefully curated gardens and flowers, a field house with exhibits, and panoramic city views along the Chicago River. Rent a kayak or stand up paddleboard from the on-site boathouse during warmer months or pack a picnic to enjoy in the open green space with the Chicago skyline as your backdrop. Ping Tom Memorial Park is also known for its unique public art installations and summer music concert series.

300 W 19th St, Chicago, IL 60616
(312) 746-5962

Room 1520

For one-of-a-kind rooftop views of Chicago, head to Room 1520, named after its perch 152 floors above downtown. This lively indoor and outdoor bar sits on the corner of the luxury Fairmont Chicago hotel on North Michigan Avenue. Come for the sunset views over the Chicago River, Lake Michigan, and Millennium Park then stay for the photogenic interiors and creative cocktails like the cucumber gimlet and the spice-filled Dunes cocktail. Room 1520 strikes the perfect balance between sleek hotel bar and relaxed neighborhood hangout. Stop by in the warmer months and snag a coveted seat on their rooftop patio.

200 N Columbus Dr, Chicago, IL 60601
(312) 573-1520

The 606

What was once an abandoned rail line is now one of Chicago’s most unique city parks. The 606, also known as the Bloomingdale Trail, is a 2.7-mile recreational trail and linear park that runs through the Bucktown, Wicker Park, Logan Square, and Humboldt Park neighborhoods. Go for a walk, jog, or bike ride on The 606’s paved trail and take in public art displays, lush gardens, and sweeping skyline views from a new perspective. Multiple access points with stairs and ramps lead up to the elevated trail and several neighborhood parks connect for the ultimate urban outdoor experience.

1809 N Ridgeway Ave, Chicago, IL 60647
(312) 742-4622

Float Room

Looking for the ultimate urban relaxation? Chicago’s Float Room in the West Loop offers an oasis of calm through flotation therapy sessions. Float effortlessly in a private FloatPod filled with body-temperature water and infused with Epsom salt in a zero-gravity environment. The sensory deprivation experience leaves guests feeling mentally clarity, creativity, and deep relaxation. Float Rooms are popping up in major cities across the US as the benefits of floating become more well-known. Each session lasts an hour but can feel like you spent hours meditating.

807 W Washington Blvd, Chicago, IL 60607
(312) 243-4041

Garfield Park Conservatory

Escape the concrete jungle without leaving the city at Garfield Park Conservatory. The immaculate botanical haven houses stunning plant life from around the world across it’s 4.5 acres of greenhouses. See cacao and vanilla orchid vines, take in the aroma of citrus trees, and marvel at rare water lilies in bloom. Beyond the greenhouses, Garfield Park itself serves as a lovely urban oasis with sprawling lawns, nature areas, and sports facilities. Visit on a weekday morning and you’ll feel like you have the gardens all to yourself. The conservatory also hosts seasonal flower shows from orchids in the winter to spring bulb displays.

300 N Central Park Ave, Chicago, IL 60624
(312) 746-5100


For amazing views of Chicago’s skyline without the hassle of crowds, head to Skylark in the trendy Pilsen neighborhood. This laid-back rooftop bar offers stunning views of the Loop across Chinatown and U.S. Cellular Field. Relax with a drink from their extensive menu and take in one of the best sunset views in the city. Skylark attracts a friendly and unpretentious crowd for affordable drinks in one of Chicago’s hippest neighborhoods. The indoor area also has a full menu of global bites like vegan bibimbap and Szechuan ribs if you get hungry. It’s the perfect neighborhood spot to experience Chicago like a local.

2149 S Halsted St, Chicago, IL 60608
(312) 666-2200

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