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Things to do in Chicago: 3 local trip ideas

3 ready-made day trips in Chicago, Illinois: cultural, family and foodie. Each one strings together a handful of stops in order.

CulturalFamilyFoodie
Cultural trip

Historic Loop Art

5 stops · about 7 hr 30 min of stops · ~$134 per person

Immerse yourself in Chicago's cultural history with a beautifully sequenced, completely walkable day through historic Loop theaters, galleries, and world-class museums.

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    Wildberry Pancakes & Cafe

    130 E Randolph St, Chicago, IL 60601, USA
    Wildberry Pancakes & Cafe, Chicago

    Try their signature specialty pancakes or flight of seasonal berries to kick off your day.

    ★ 4.5 on Google · about 1 hr 15 min · ~$22 per person · Directions
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    Chicago Cultural Center

    78 E Washington St, Chicago, IL 60602, USA
    Chicago Cultural Center, Chicago

    Look up to admire the world's largest Tiffany stained-glass dome in Preston Bradley Hall.

    ★ 4.7 on Google · about 1 hr · Free · Directions
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    The Gage

    24 S Michigan Ave, Chicago, IL 60603, USA
    The Gage, Chicago

    A historic, upscale-casual tavern serving great pub classics right across from the park.

    ★ 4.6 on Google · about 1 hr 15 min · ~$35 per person · Directions
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    The Art Institute of Chicago

    111 S Michigan Ave, Chicago, IL 60603, USA
    The Art Institute of Chicago, Chicago

    Head to the Impressionist wing to see iconic masterpieces like Seurat's A Sunday on La Grande Jatte.

    ★ 4.8 on Google · about 2 hr 30 min · ~$32 per person · Directions
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    Studebaker Theater

    410 South Michigan Avenue Fine Arts Building, Chicago, IL 60605, USA
    Studebaker Theater, Chicago

    Catch an evening performance or explore the country's oldest active art colony.

    ★ 4.8 on Google · about 1 hr 30 min · ~$45 per person · Directions
Family trip

Downtown Family Fun

4 stops · about 5 hr of stops · ~$115 per person

Enjoy a perfect, walkable family day in downtown Chicago, exploring scenic parks and iconic kid-friendly attractions paired with classic local dining.

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    Wildberry Pancakes & Cafe

    130 E Randolph St, Chicago, IL 60601, USA
    Wildberry Pancakes & Cafe, Chicago

    Arrive early or join the Yelp Waitlist online to secure a table for their famous fluffy pancakes.

    ★ 4.5 on Google · about 1 hr 15 min · ~$60 per person · Directions
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    Maggie Daley Park

    337 E Randolph St, Chicago, IL 60601, USA
    Maggie Daley Park, Chicago

    Let the kids burn off energy at the massive, whimsical play garden; entry is entirely free.

    ★ 4.7 on Google · about 1 hr 30 min · Free · Directions
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    201 E Randolph St

    201 E Randolph St, Chicago, IL 60602, USA
    201 E Randolph St, Chicago

    Walk across the BP Bridge to see 'The Bean' and splash in Crown Fountain's shallow reflecting pools.

    about 1 hr · Free · Directions
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    Giordano's

    130 E Randolph St, Chicago, IL 60601, USA
    Giordano's, Chicago

    Head back to Prudential Plaza to treat the family to iconic, cheese-pull-heavy Chicago stuffed deep dish.

    ★ 4.5 on Google · about 1 hr 15 min · ~$55 per person · Directions
Foodie trip

A Foodie Feast in Fulton Market

5 stops · about 6 hr 30 min of stops · ~$153 per person

Embark on a culinary journey through Chicago's legendary Fulton Market and West Loop, transitioning from world-class morning pastries to old-school Italian deli classics and trendy evening plates.

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    Good Ambler

    216 N Peoria St, Chicago, IL 60607, USA
    Good Ambler, Chicago

    Try their incredible laminated croissants or handmade chocolates alongside a pristine espresso.

    ★ 4.4 on Google · about 1 hr · ~$15 per person · Directions
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    Time Out Market Chicago

    916 W Fulton Market, Chicago, IL 60607, USA
    Time Out Market Chicago, Chicago

    Explore 50,000 square feet of curated local food stalls, and grab a drink on the rooftop terrace.

    ★ 4.5 on Google · about 1 hr 15 min · Directions
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    J.P. Graziano Grocery

    901 W Randolph St, Chicago, IL 60607, USA
    J.P. Graziano Grocery, Chicago

    Order the legendary 'Mr. G' sub and pick up a jar of their famous house-made giardiniera.

    ★ 4.7 on Google · about 45 min · ~$18 per person · Directions
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    The Aviary

    955 W Fulton Market, Chicago, IL 60607, USA
    The Aviary, Chicago

    Indulge in an interactive, multi-sensory cocktail experience from the minds behind Alinea.

    ★ 4.3 on Google · about 1 hr 30 min · ~$65 per person · Directions
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    Boqueria Fulton Market

    807 W Fulton Market, Chicago, IL 60607, USA
    Boqueria Fulton Market, Chicago

    Share authentic Barcelona-style tapas and a pan of fresh paella under the warm lights.

    ★ 4.6 on Google · about 2 hr · ~$55 per person · Directions

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