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PIPS PLACES TO SEE · DAYTIME IN THE CITY

Chicago

Lakefront skylines, world-class museums, and soulful streets

Chicago wears its daytime beauty on Lake Michigan's edge, where gleaming skyscrapers meet green parkland and grand museum steps. Spend a day drifting from the shimmer of the Bean to the jazz-soaked history of Bronzeville, and you'll feel why this city is the heart of the Midwest. Everything here rewards a slow, stylish wander.

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Washington Park
Black-Owned

DuSable Black History Museum

740 E 56th Pl, Chicago, IL 60637
Tue–Sun 10am–5pm

The nation's oldest independent Black history museum honors the African American journey with art, artifacts, and living memory.

Pip’s Tip Tuesday to Sunday, 10 to 5. The nation's oldest independent Black history museum, in Washington Park.

Bronzeville
Black-Owned

Monument to the Great Northern Migration

2600 S Dr Martin Luther King Jr Dr, Chicago, IL 60616
Open daily, 24 hours

A striding bronze traveler honors the millions who journeyed north to build Chicago's storied Black metropolis.

Pip’s Tip Open 24 hours, free, in Bronzeville. A striding bronze traveler honoring the Great Migration.

Auburn Gresham · tour
Black-Owned

Chicago Mahogany Tours

8530 S Racine Ave, Chicago, IL 60620
Tours by reservation

Black-owned tour company running deep-dive neighborhood tours of Bronzeville, Englewood, Pullman and Chatham, told through the people who built Chicago's Black Metropolis.

Pip’s Tip By reservation only. Black-owned company running deep-dive Bronzeville and South Side neighborhood tours.

Millennium Park / Loop

Cloud Gate (The Bean)

201 E Randolph St, Chicago, IL 60602
Daily 6am–11pm

Chicago's mirror-polished icon reflects the whole skyline in one dreamy, selfie-perfect curve.

West Loop

Skydeck Chicago at Willis Tower

233 S Wacker Dr, Chicago, IL 60606
Daily 9am–10pm

Step onto The Ledge's glass box 1,353 feet up and float above the city on a clear day.

Grant Park / Loop

Art Institute of Chicago

111 S Michigan Ave, Chicago, IL 60603
Thu–Mon 11am–5pm

Guarded by bronze lions, this legendary museum holds Hopper, Seurat, and one of the world's great Impressionist collections.

Streeterville

Navy Pier

600 E Grand Ave, Chicago, IL 60611
Daily 10am–8pm

Ride the Centennial Wheel over the lake and let the breeze, boats, and carnival colors carry the afternoon.

Museum Campus

Field Museum of Natural History

1400 S Lake Shore Dr, Chicago, IL 60605
Daily 9am–5pm

Meet SUE the T. rex and wander halls of ancient Egypt, gems, and wonders from every corner of Earth.

Museum Campus

Shedd Aquarium

1200 S DuSable Lake Shore Dr, Chicago, IL 60605
Daily 9am–5pm

Beluga whales, sea otters, and a Caribbean reef unfold against a postcard view of the skyline.

Museum Campus

Adler Planetarium

1300 S DuSable Lake Shore Dr, Chicago, IL 60605
Wed–Sun 9am–4pm

America's first planetarium offers immersive sky shows and the single best lakefront view of the downtown skyline.

Hyde Park

Museum of Science and Industry

5700 S DuSable Lake Shore Dr, Chicago, IL 60637
Daily 9:30am–4pm

Explore a real U-505 submarine, a coal mine, and hands-on marvels inside a grand Beaux-Arts palace.

Lincoln Park

Lincoln Park Zoo

2001 N Clark St, Chicago, IL 60614
Daily 10am–5pm

One of the last free zoos in America, set in leafy parkland with lions, gorillas, and a gentle stroll to the lakefront.

Magnificent Mile

360 Chicago Observation Deck

875 N Michigan Ave, Chicago, IL 60611
Daily 10am–9pm

Perched atop the old Hancock, tilt out over Michigan Avenue on TILT for a heart-in-throat downtown panorama.

East Garfield Park

Garfield Park Conservatory

300 N Central Park Ave, Chicago, IL 60624
Wed–Mon 9am–5pm

One of the largest glasshouse gardens in the country, a lush free escape into palms, ferns, and desert blooms.

Grant Park

Buckingham Fountain

301 S Columbus Dr, Chicago, IL 60605
Daily 8am–11pm (seasonal)

This grand rococo fountain erupts in soaring water displays every hour against the open sweep of the lake.

Porter, IN · out of town

Indiana Dunes National Park

1215 N State Rd 49, Porter, IN 46304
Daily, dawn to dusk

Just an hour southeast, golden dunes and Lake Michigan beaches offer a wild, windswept counterpoint to the city.

SW Michigan · wine country

Round Barn Winery & Estate

10983 Hills Rd, Baroda, MI 49101
Daily (seasonal; reduced in winter)

The flagship SW Michigan destination, winery, distillery and brewery on a landmark round-barn estate with estate vineyards and a weekend 'Jammin' in the Vineyard' music series, under 2 hours from Chicago.

SW Michigan · wine country

Domaine Berrien Cellars

398 E Lemon Creek Rd, Berrien Springs, MI 49103
Daily 12–6p (summer)

A serious estate winery with a tasting room nestled among its own vineyards in the Lake Michigan Shore AVA, known for dry, varietal-driven wines and picnicking on the deck.

SW Michigan · wine country

Fenn Valley Vineyards

6130 122nd Ave, Fennville, MI 49408
Daily 11a–5p (year-round)

One of Michigan's oldest and most respected family estates, surrounded by its own vineyards near Saugatuck, with reserved tastings, tours and wine by the glass, a classic Lake Michigan wine day.

The Loop · tour

Chicago Architecture Center River Cruise

112 E Wacker Dr, Chicago, IL 60601
Daily cruises mid-March–late November

Ninety minutes on the Chicago River with a trained volunteer docent explaining more than fifty buildings, from Gothic revival towers to glass giants overhead.

Streeterville · tour

Bobby's Bike Hike

540 N Lake Shore Dr, Chicago, IL 60611
Daily 8:30am–6:30pm in summer

Small-group bike tours along the lakefront and through Old Town and Bronzeville, plus a well-loved evening ride pairing pizza, hot dogs and city history.

Lincoln Park · beach

North Avenue Beach

1601 N Jean-Baptiste Pointe DuSable Lake Shore Dr, Chicago, IL 60611
Daily 6am–11pm

Chicago's busiest lakefront beach, with a ship-shaped beach house, dozens of volleyball courts and a straight-on view of the downtown skyline.

Gold Coast · beach

Oak Street Beach

1000 N Jean-Baptiste Pointe DuSable Lake Shore Dr, Chicago, IL 60611
Daily 6am–11pm

Crescent of sand at the foot of the Gold Coast, minutes from Michigan Avenue shopping, with a lakefront path, cafe and skyscrapers rising behind you.

Jackson Park · beach

63rd Street Beach

6300 S Jean-Baptiste Pointe DuSable Lake Shore Dr, Chicago, IL 60649
Daily 6am–11pm

Historic South Side beach in Jackson Park with a restored 1919 beach house, courtyard fountain and wide quiet sand that draws family cookouts all summer.

Featured Trip

A
This month's Sunday drive

Chicago Architecture River Cruise

Ninety minutes on the river that explains the whole skyline.

Upcoming in Chicago

TBASoon

PIPS Sunday Drive: Chicago

A family caravan and a picnic at the overlook. Members hear first.

Details

City Sponsor

Make it a weekend.

Day trips are one chapter of Pip's Lifestyle, find the stays, brunch spots, lounges and the Domino Club below.