Best of Chicago

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

10 daysLocal gems

Trip length

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.

Sightseeing
Art Institute of Chicago
A world-class museum with iconic works like 'American Gothic' and 'A Sunday on La Grande Jatte'.
Sightseeing
Cloud Gate (The Bean)
Get that iconic reflection shot in Millennium Park.
Rest
Maggie Daley Park
Relax or play in this innovative park with a climbing wall and an ice-skating ribbon in winter.
Activity
Chicago Architecture Center River Cruise
The absolute best way to see and learn about the city's incredible architecture.

Sightseeing
Shedd Aquarium
Dive into aquatic wonders from around the globe, right on the lakefront.
Sightseeing
Field Museum
Come face-to-face with Sue the T. Rex and explore natural history.
Sightseeing
Adler Planetarium
Explore the cosmos with stunning sky shows and exhibits.
Rest
Northerly Island Park
Enjoy serene lakefront views and a peaceful escape from the city bustle.

Sightseeing
360 Chicago Observation Deck
Experience 'The Tilt' for exhilarating views from the former John Hancock Center.
Shopping
Shopping on the Magnificent Mile
Browse high-end boutiques and flagship stores along Michigan Avenue.
Shopping
Water Tower Place
An iconic vertical mall with a variety of shops and dining options.
Sightseeing
Historic Water Tower and Pumping Station
A resilient survivor of the Great Chicago Fire.
Rest
Oak Street Beach
Relax on the sand with stunning city skyline views.

Sightseeing
Lincoln Park Zoo
A free, historic zoo with diverse animals and beautiful grounds.
Sightseeing
Lincoln Park Conservatory
Wander through exotic plant collections in a Victorian-era glass house.
Shopping
Green City Market
A vibrant farmers market (seasonal) promoting local and sustainable food.
Activity
The Second City
Catch a hilarious improv show at this legendary comedy institution.

Shopping
Randolph Street Market
Trendy vintage, antique, and artisan market (seasonal, check dates).
Food
Fulton Market District
Explore Michelin-starred restaurants and trendy eateries.
Shopping
Wicker Park
Discover unique boutiques, record stores, and vibrant street art.
Shopping
Myopic Books
Get lost for hours in this massive, independent used bookstore.

Sightseeing
National Museum of Mexican Art
Discover incredible Mexican art and culture in the heart of Pilsen.
Sightseeing
Pilsen Murals
Stroll down 16th Street for vibrant, thought-provoking street art and murals.
Nightlife
Thalia Hall
Catch a show or grab a drink in this historic, beautifully restored landmark.
Sightseeing
Promontory Point
Enjoy stunning panoramic views of the Chicago skyline from this unique peninsula.

Sightseeing
Merchandise Mart
A massive wholesale design center, impressive from the outside and often has public art.
Nightlife
House of Blues Chicago
Enjoy live music and Southern-inspired cuisine in a vibrant setting.
Food
Eataly Chicago
Indulge in authentic Italian food, from fresh pasta to gourmet groceries.
Food
Portillo's (River North)
Savor classic Chicago hot dogs and Italian beef in a lively, themed setting.

Sightseeing
Museum of Science and Industry
Explore a U-505 submarine and a full-size 727 in this interactive museum.
Sightseeing
Frank Lloyd Wright's Robie House
Admire this Prairie Style masterpiece on the University of Chicago campus.
Sightseeing
University of Chicago Campus
Stroll through the stunning Gothic architecture of this prestigious university.
Rest
Osaka Garden (Garden of the Phoenix)
Find tranquility in this serene Japanese garden on an island in Jackson Park.

Activity
Wrigley Field Tour
Take a tour of the iconic ballpark, even on non-game days.
Sightseeing
Wrigleyville
Soak in the electric atmosphere around Wrigley Field, especially on game days.
Activity
Lakefront Trail (Lakeview stretch)
Bike or walk along the scenic lakefront with stunning city views.
Rest
Belmont Harbor
Watch boats come and go and enjoy the peaceful harbor ambiance.

Food
Margie's Candies (Western Ave)
Indulge in old-fashioned ice cream sundaes and handmade chocolates.
Sightseeing
Navy Pier
Take a ride on the Centennial Wheel for panoramic city and lake views (touristy but iconic).
Rest
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.