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Best of Chicago

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

10 daysLocal favorites
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 · Welcome to the Loop & Grant Park

  • 1
    Art Institute of Chicago

    A world-class museum with iconic works like 'American Gothic' and 'A Sunday on La Grande Jatte'.

  • 2
    Cloud Gate (The Bean)

    Get that iconic reflection shot in Millennium Park.

  • 3
    Maggie Daley Park

    Relax or play in this innovative park with a climbing wall and an ice-skating ribbon in winter.

  • 4
    Chicago Architecture Center River Cruise

    The absolute best way to see and learn about the city's incredible architecture.

Day 2 · Museum Campus & South Loop

  • 1
    Shedd Aquarium

    Dive into aquatic wonders from around the globe, right on the lakefront.

  • 2
    Field Museum

    Come face-to-face with Sue the T. Rex and explore natural history.

  • 3
    Adler Planetarium

    Explore the cosmos with stunning sky shows and exhibits.

  • 4
    Northerly Island Park

    Enjoy serene lakefront views and a peaceful escape from the city bustle.

Day 3 · Magnificent Mile & Gold Coast Glamour

  • 1
    360 Chicago Observation Deck

    Experience 'The Tilt' for exhilarating views from the former John Hancock Center.

  • 2
    Shopping on the Magnificent Mile

    Browse high-end boutiques and flagship stores along Michigan Avenue.

  • 3
    Water Tower Place

    An iconic vertical mall with a variety of shops and dining options.

  • 4
    Historic Water Tower and Pumping Station

    A resilient survivor of the Great Chicago Fire.

  • 5
    Oak Street Beach

    Relax on the sand with stunning city skyline views.

Day 4 · Lincoln Park & Old Town Charm

  • 1
    Lincoln Park Zoo

    A free, historic zoo with diverse animals and beautiful grounds.

  • 2
    Lincoln Park Conservatory

    Wander through exotic plant collections in a Victorian-era glass house.

  • 3
    Green City Market

    A vibrant farmers market (seasonal) promoting local and sustainable food.

  • 4
    The Second City

    Catch a hilarious improv show at this legendary comedy institution.

Day 5 · West Loop & Wicker Park's Hip Vibe

  • 1
    Randolph Street Market

    Trendy vintage, antique, and artisan market (seasonal, check dates).

  • 2
    Fulton Market District

    Explore Michelin-starred restaurants and trendy eateries.

  • 3
    Wicker Park

    Discover unique boutiques, record stores, and vibrant street art.

  • 4
    Myopic Books

    Get lost for hours in this massive, independent used bookstore.

Day 6 · Pilsen Murals & South Side History

  • 1
    National Museum of Mexican Art

    Discover incredible Mexican art and culture in the heart of Pilsen.

  • 2
    Pilsen Murals

    Stroll down 16th Street for vibrant, thought-provoking street art and murals.

  • 3
    Thalia Hall

    Catch a show or grab a drink in this historic, beautifully restored landmark.

  • 4
    Promontory Point

    Enjoy stunning panoramic views of the Chicago skyline from this unique peninsula.

Day 7 · River North Art & Entertainment

  • 1
    Merchandise Mart

    A massive wholesale design center, impressive from the outside and often has public art.

  • 2
    House of Blues Chicago

    Enjoy live music and Southern-inspired cuisine in a vibrant setting.

  • 3
    Eataly Chicago

    Indulge in authentic Italian food, from fresh pasta to gourmet groceries.

  • 4
    Portillo's (River North)

    Savor classic Chicago hot dogs and Italian beef in a lively, themed setting.

Day 8 · Hyde Park & University Charm

  • 1
    Museum of Science and Industry

    Explore a U-505 submarine and a full-size 727 in this interactive museum.

  • 2
    Frank Lloyd Wright's Robie House

    Admire this Prairie Style masterpiece on the University of Chicago campus.

  • 3
    University of Chicago Campus

    Stroll through the stunning Gothic architecture of this prestigious university.

  • 4
    Osaka Garden (Garden of the Phoenix)

    Find tranquility in this serene Japanese garden on an island in Jackson Park.

Day 9 · Wrigleyville & Lakeview Fun

  • 1
    Wrigley Field Tour

    Take a tour of the iconic ballpark, even on non-game days.

  • 2
    Wrigleyville

    Soak in the electric atmosphere around Wrigley Field, especially on game days.

  • 3
    Lakefront Trail (Lakeview stretch)

    Bike or walk along the scenic lakefront with stunning city views.

  • 4
    Belmont Harbor

    Watch boats come and go and enjoy the peaceful harbor ambiance.

Day 10 · Sweetfarewell & Lakefront Views

  • 1
    Margie's Candies (Western Ave)

    Indulge in old-fashioned ice cream sundaes and handmade chocolates.

  • 2
    Navy Pier

    Take a ride on the Centennial Wheel for panoramic city and lake views (touristy but iconic).

  • 3
    Ohio Street Beach

    A popular spot for swimming and sunbathing with great city views.

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