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Best of Chicago

Lakefront miles, world-class museums, and mural-covered side streets.

5 daysLocal gems
Trip length
3-day5-day7-day10-day
Best time to visit: May to October

Late spring through early fall is warm and lively along the lakefront, with patios and festivals in full swing. Winters are long and bitterly cold.

Day 1·Lakefront & Parks

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  1. Sightseeing

    Millennium Park

    Iconic 'Bean' sculpture and beautiful gardens.

  2. Sightseeing

    Art Institute of Chicago

    World-class collection, plan to spend a few hours.

  3. Rest

    Maggie Daley Park

    A fun, active park for all ages, with skyline views.

Day 2·Architectural Marvels & River Views

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  1. Activity

    Chicago Architecture Foundation Center River Cruise

    The best way to see the city's famous architecture.

  2. Shopping

    The Magnificent Mile

    Stroll and admire the historic buildings and upscale shops.

  3. Food

    Giordano's

    Experience classic Chicago deep-dish pizza.

  4. Sightseeing

    360 Chicago Observation Deck

    Breathtaking panoramic views, especially at sunset.

Day 3·Museum Campus & Pilsen

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  1. Sightseeing

    Field Museum

    Home to Sue, the most complete T-Rex skeleton.

  2. Sightseeing

    Shedd Aquarium

    One of the oldest and largest aquariums in the world.

  3. Sightseeing

    Pilsen Murals

    Explore vibrant street art and rich Chicano culture.

  4. Sightseeing

    National Museum of Mexican Art

    Free admission and a fantastic collection of Mexican art.

Day 4·Lincoln Park & Sweets

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  1. Sightseeing

    Lincoln Park Zoo

    Free zoo with a wide variety of animals and a beautiful setting.

  2. Sightseeing

    Lincoln Park Conservatory

    Historic Victorian glass house with stunning plant collections.

  3. Food

    Margie's Candies

    Old-school ice cream parlor serving legendary sundaes since 1921.

  4. Nightlife

    Kingston Mines

    Two stages of live blues music, a true Chicago experience.

Day 5·Hyde Park & Promontory Views

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  1. Sightseeing

    Museum of Science and Industry, Chicago

    Interactive exhibits, including a German U-boat.

  2. Sightseeing

    University of Chicago

    Explore the beautiful Gothic architecture of this prestigious university.

  3. Rest

    Promontory Point

    Relaxing spot with incredible skyline views, especially at sunrise or sunset.

Make it your own

Start from this curated plan — Runes copies it into your trips so you can tweak dates, budget, pace, and stops. Personalized to your style soon.

Or plan your own Chicago trip