Chicago & Great Lakes Week

Arrive in Chicago — Architecture and the Loop

The Chicago Architecture Foundation river cruise is the only correct first move. Book the 90-minute version. Then walk Millennium Park, eat in the South Loop, and plan the week.

Morning

Activity

Architecture Center river cruise

The best introductory tour of any city in the US. A docent narrates 50+ buildings from the river. Early morning and evening tours sell out first. Book ahead.

1h 30m~$45

Tip

The Ventra 7-day pass is the best value for transit

A 7-day unlimited pass costs $28 and covers every L train and CTA bus. Buy at any L station or the Ventra app. Beats Uber for every trip under 5 miles.

Full Day

Museum Campus full day

Art Institute, Field Museum, Shedd Aquarium, and Adler Planetarium are all within walking distance on the lakefront. Buy a CityPASS to cover 3 of them for $90 instead of $140+.

8h~$90

Pilsen, Wicker Park, and Lincoln Square

Three Chicago neighborhoods in one day. Pilsen for Mexican murals and food, Wicker Park for vintage and cocktail bars, Lincoln Square for the actual German-American neighborhood the city built.

Afternoon

Meal

Chicago deep dish at Lou Malnati's or Pequod's

Lou Malnati's is the classic. Pequod's in Lincoln Park has the caramelized crust edge that is genuinely different. Neither is fast food — budget 30 minutes to bake.

~$35

Indiana Dunes National Park day trip

Indiana Dunes is 60 miles from downtown. Mount Baldy is a 126-foot migrating sand dune right on Lake Michigan. The 3-Dune Challenge is a 1.5-mile scramble that takes 2 hours.

Milwaukee day trip via the North Shore

Milwaukee is 90 minutes north on I-94. Brewery tour at Miller or Lakefront Brewery, lunch in the Third Ward, and the Milwaukee Art Museum Calatrava wing. Easy day trip.

Afternoon

Activity

Milwaukee Art Museum

Calatrava's movable brise-soleil (the wings) opens and closes at noon. The permanent collection has a strong American art section. The building alone is worth the trip.

3h~$25

Chicago South Side music and food

Bronzeville, Hyde Park, and the South Side jazz and blues history. Buddy Guy's Legends in the South Loop for the best live blues club in the city. Jazz Showcase is the quieter, older option.

Logan Square brunch and departure

Logan Square has the best brunch scene in the city. Lula Cafe is the classic. Fat Rice for Portuguese-inspired food. Then the Blue Line straight to O'Hare from Logan Square station.