Best of Chicago

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 · Arrival & Architectural Wonders

1
Chicago Architecture Foundation Center River Cruise
A must-do to understand the city's iconic skyline from a unique perspective.
2
Millennium Park
Home to 'The Bean' (Cloud Gate) and other public art, great for photos and people-watching.
3
The Art Institute of Chicago
One of the oldest and largest art museums in the US, with an incredible collection.

Day 2 · Museum Campus & Lakefront

1
Field Museum
Explore natural history and see Sue, the most complete T-Rex skeleton.
2
Shedd Aquarium
A world-class aquarium with a diverse collection of aquatic life.
3
Adler Planetarium
America's first planetarium offers stunning views of the city skyline and space exhibits.
4
Museum Campus Trail
Walk or bike along the lakefront for incredible views of the city.

Day 3 · Navy Pier & Magnificent Mile

1
Navy Pier
Enjoy rides, dining, and unparalleled views of the skyline and Lake Michigan.
2
Ohio Street Beach
Relax on this popular city beach with great views.
3
Magnificent Mile
World-class shopping, dining, and iconic architecture.
4
360 CHICAGO Observation Deck
Experience the 'TILT' for a thrilling view of the city from the John Hancock Center.

Day 4 · Pilsen Murals & Deep Dish

1
Pilsen Historic District
Explore vibrant street art, colorful murals, and authentic Mexican culture.
2
National Museum of Mexican Art
Free admission and a fantastic collection of Mexican art and culture.
3
Lou Malnati's Pizzeria (Pilsen location)
Indulge in a classic Chicago deep-dish pizza in the heart of Pilsen.

Day 5 · Lincoln Park Charm & Zoo

1
Lincoln Park Zoo
One of the last free zoos in the country, a beautiful urban oasis.
2
Lincoln Park Conservatory
A stunning Victorian-era glass house with exotic plants.
3
North Avenue Beach
Enjoy stunning skyline views and relax on the sand.
4
Museum of Broadcast Communications
Explore the history of radio and television, and see the Chicago Television Walk of Fame.

Day 6 · Hyde Park & Promontory Point

1
Museum of Science and Industry
Housed in the former Palace of Fine Arts from the 1893 World's Columbian Exposition, with incredible hands-on exhibits.
2
Frank Lloyd Wright's Robie House
A prime example of Prairie Style architecture.
3
Promontory Point
A local gem with breathtaking panoramic views of the Chicago skyline, especially at sunset.

Day 7 · Sweet Treats & Wicker Park Vibes

1
Margie's Candies
An old-school ice cream parlor and candy shop, a true Chicago institution since 1921.
2
Wicker Park
Trendy neighborhood with independent boutiques, vintage shops, and cool cafes.
3
Myopic Books
A legendary independent bookstore in Wicker Park, perfect for browsing.
4
Empty Bottle
Catch live music at this iconic Wicker Park venue.

Day 8 · Leisurely Departure

1
Garfield Park Conservatory
One of the largest and most impressive conservatories in the world, a tranquil escape.
2
West Loop/Fulton Market District
Enjoy a leisurely brunch in this foodie paradise before heading to the airport.

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.