Best of Chicago
Lakefront miles, world-class museums, and mural-covered side streets.
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
- 1Art Institute of Chicago
A world-class museum with iconic works like 'American Gothic' and 'A Sunday on La Grande Jatte'.
- 2Cloud Gate (The Bean)
Get that iconic reflection shot in Millennium Park.
- 3Maggie Daley Park
Relax or play in this innovative park with a climbing wall and an ice-skating ribbon in winter.
- 4Chicago Architecture Center River Cruise
The absolute best way to see and learn about the city's incredible architecture.
Day 2 · Museum Campus & South Loop
- 1Shedd Aquarium
Dive into aquatic wonders from around the globe, right on the lakefront.
- 2Field Museum
Come face-to-face with Sue the T. Rex and explore natural history.
- 3Adler Planetarium
Explore the cosmos with stunning sky shows and exhibits.
- 4Northerly Island Park
Enjoy serene lakefront views and a peaceful escape from the city bustle.
Day 3 · Magnificent Mile & Gold Coast Glamour
- 1360 Chicago Observation Deck
Experience 'The Tilt' for exhilarating views from the former John Hancock Center.
- 2Shopping on the Magnificent Mile
Browse high-end boutiques and flagship stores along Michigan Avenue.
- 3Water Tower Place
An iconic vertical mall with a variety of shops and dining options.
- 4Historic Water Tower and Pumping Station
A resilient survivor of the Great Chicago Fire.
- 5Oak Street Beach
Relax on the sand with stunning city skyline views.
Day 4 · Lincoln Park & Old Town Charm
- 1Lincoln Park Zoo
A free, historic zoo with diverse animals and beautiful grounds.
- 2Lincoln Park Conservatory
Wander through exotic plant collections in a Victorian-era glass house.
- 3Green City Market
A vibrant farmers market (seasonal) promoting local and sustainable food.
- 4The Second City
Catch a hilarious improv show at this legendary comedy institution.
Day 5 · West Loop & Wicker Park's Hip Vibe
- 1Randolph Street Market
Trendy vintage, antique, and artisan market (seasonal, check dates).
- 2Fulton Market District
Explore Michelin-starred restaurants and trendy eateries.
- 3Wicker Park
Discover unique boutiques, record stores, and vibrant street art.
- 4Myopic Books
Get lost for hours in this massive, independent used bookstore.
Day 6 · Pilsen Murals & South Side History
- 1National Museum of Mexican Art
Discover incredible Mexican art and culture in the heart of Pilsen.
- 2Pilsen Murals
Stroll down 16th Street for vibrant, thought-provoking street art and murals.
- 3Thalia Hall
Catch a show or grab a drink in this historic, beautifully restored landmark.
- 4Promontory Point
Enjoy stunning panoramic views of the Chicago skyline from this unique peninsula.
Day 7 · River North Art & Entertainment
- 1Merchandise Mart
A massive wholesale design center, impressive from the outside and often has public art.
- 2House of Blues Chicago
Enjoy live music and Southern-inspired cuisine in a vibrant setting.
- 3Eataly Chicago
Indulge in authentic Italian food, from fresh pasta to gourmet groceries.
- 4Portillo's (River North)
Savor classic Chicago hot dogs and Italian beef in a lively, themed setting.
Day 8 · Hyde Park & University Charm
- 1Museum of Science and Industry
Explore a U-505 submarine and a full-size 727 in this interactive museum.
- 2Frank Lloyd Wright's Robie House
Admire this Prairie Style masterpiece on the University of Chicago campus.
- 3University of Chicago Campus
Stroll through the stunning Gothic architecture of this prestigious university.
- 4Osaka Garden (Garden of the Phoenix)
Find tranquility in this serene Japanese garden on an island in Jackson Park.
Day 9 · Wrigleyville & Lakeview Fun
- 1Wrigley Field Tour
Take a tour of the iconic ballpark, even on non-game days.
- 2Wrigleyville
Soak in the electric atmosphere around Wrigley Field, especially on game days.
- 3Lakefront Trail (Lakeview stretch)
Bike or walk along the scenic lakefront with stunning city views.
- 4Belmont Harbor
Watch boats come and go and enjoy the peaceful harbor ambiance.
Day 10 · Sweetfarewell & Lakefront Views
- 1Margie's Candies (Western Ave)
Indulge in old-fashioned ice cream sundaes and handmade chocolates.
- 2Navy Pier
Take a ride on the Centennial Wheel for panoramic city and lake views (touristy but iconic).
- 3Ohio 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.