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Chicago Trips
Chicago, IL
Weekend trips to the Windy City never get old. Deep dish pizza, architecture boat tours, rooftop bars with skyline views, and endless neighborhoods to explore.
Itinerary
Day 1
- Deep dish at Lou Malnati's or Giordano's
- Walk the Magnificent Mile
- Rooftop bar with skyline views
Day 2
- Architecture boat tour on the Chicago River
- Explore Millennium Park and Cloud Gate (The Bean)
- Dinner in the West Loop
Favorite Spots
Lou Malnati's
FoodThe deep dish debate is real — but Lou's is the answer.
Architecture Boat Tour
AttractionThe best way to see Chicago — from the river.
Millennium Park
AttractionThe Bean, Crown Fountain, and people-watching at its finest.
West Loop
FoodChicago's best dining neighborhood — period.