Winter Activities near Chicago, IL

18 places

Discover a winter wonderland near Chicago, where seasonal activities blend outdoor fun and cozy retreats, making for memorable experiences amid stunning backdrops.

Maggie Daley Park photo

Maggie Daley Park

Open until

Skating here is unforgettable, with a scenic quarter-mile ribbon and stunning skyline views, all while enjoying hot chocolate after a fun skate.

GALLERY

Hopemark Health Millennium Park

Open until

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4.0

Celebrate the festive spirit at Millennium Park, with its stunning Cloud Gate sculpture, holiday market, seasonal tree, and winter activities.

Creamsicle orchid

Lincoln Park Conservatory

Opens at

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4.5

Oasis: I appreciate the stunning array of tropical plants from around the world, making it a warm, colorful retreat in the winter.

LOGO

The Godfrey Hotel Chicago

Open until

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3.0

Enchantment captures the rooftop lounge's charm, featuring cozy heated igloos, fire pits, and seasonal delights amidst stunning skyline views.

Garfield Park Conservatory photo

Garfield Park Conservatory

Opens at

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5.0

Serenity surrounds me in this vast glass haven, where vibrant tropical plants and tranquil koi ponds create a peaceful winter retreat.

Photo by Management

Chicago Electric Boat Company

Opens at

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5.0

Adventure awaits with heated hot tub boats on the Chicago River, offering a cozy, BYOB experience amidst winter sightseeing.

LOGO

The Morton Arboretum

Open until

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4.5

Discovery awaits at the Morton Arboretum with its stunning light displays, winter trails, and family-friendly seasonal activities.

Art Institute of Chicago photo

Art Institute of Chicago

Open until

Marveling at the intricate detail in the miniature rooms offers a fascinating glimpse into craftsmanship and art history unique to this museum.

Photo by viajaconlu

Soundings at Shedd Aquarium

Open until

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3.5

Underwater, I find joy in vibrant marine life, engaging with beluga whales and feeding stingrays at this unforgettable Chicago gem.

Second City Works Inc photo

Second City Works Inc

Opens at

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4.5

Laughter thrives here, where iconic improv and sketch comedy create unforgettable moments, often featuring surprise celebrity guests.

Curtain call for the young Tommy actors, age 4 and age 10.  7-06-2023 matinee performance.

Goodman Theatre

Opens at

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4.0

Culture thrives at the Goodman Theatre, where I can experience critically acclaimed productions and captivating Broadway classics in a historic setting.

Wild mushroom ravioli

Kennedy Rooftop

Opens at

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4.0

Elevating my evenings, Kennedy Rooftop’s cozy igloos and stunning city views wrapped in winter charm make it a unique urban retreat.

Bacon app

Kaiser Tiger

Opens at

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3.5

Gathering at Kaiser Tiger is special with summer bocce and cozy winter curling, creating unforgettable seasonal experiences for everyone.

Tea time

The Peninsula Chicago

Open until

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4.5

Indulgence defines The Peninsula Chicago with its luxury spa and the unique rooftop ice skating rink offering stunning city views.

The Magnificent Mile

The Magnificent Mile

Opens at

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4.5

Buzzing with energy, the Magnificent Mile features stunning holiday lights, vibrant shopping, and festive events that create a lively downtown atmosphere.

Apple strudel

Christkindlmarket Chicago

Opens at

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4.0

Whimsy fills Christkindlmarket, an original German holiday market where I savor festive foods, mulled wine, and charming gifts.

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AIRE Ancient Baths - Chicago

Open until

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4.0

Tranquility enveloped me at AIRE Ancient Baths, where luxury meets relaxation through seven thermal baths, salt scrubs, and soothing red wine soaks.

07.03.25 Navy Pier Store

Navy Pier

Opens at

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3.5

Radiating with charm, Navy Pier offers stunning views of Lake Michigan, festive light displays, and indoor experiences perfect for any season.