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Chicago 3-Day Itinerary
The perfect long weekend in Chicago. Three days of must-see attractions, local favorites, and insider tips — from $75 to $450 per day.
Trip Overview
Duration
3 Days
Best Time
May to June, September to October
Budget Cost
$225
Mid-Range
$525
1
Day 1
Millennium Park
Millennium Park, Chicago Riverwalk architecture tour, deep-dish at Lou Malnati's
Estimated cost: $175 (mid-range)
2
Day 2
Art Institute of Chicago
Art Institute of Chicago, Michigan Avenue, Navy Pier at sunset
Estimated cost: $175 (mid-range)
3
Day 3
Field Museum
Field Museum, Museum of Science and Industry, Hyde Park, blues club on Halsted
Estimated cost: $175 (mid-range)
Total 3-Day Cost Estimate
Budget
$225
$75/day x 3 days
Mid-Range
$525
$175/day x 3 days
Luxury
$1350
$450/day x 3 days
Insider Tips
- ✓Get a Chicago Card or use Ventra — CTA trains and buses cover nearly everything including O'Hare
- ✓Deep-dish is a tourist ritual but locals eat thin-crust tavern-style: try Vito & Nick's or Pat's
- ✓The Chicago Riverwalk is free and stunning — join an architecture boat tour departing from it
- ✓Museum Campus groups the Field Museum, Shedd Aquarium, and Adler Planetarium — buy a CityPASS to save 40%
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