All destinations
Illinois, USA
Chicago
Deep-dish pizza, riverfront architecture, and killer museums.
Best time: May – October
Sample Itineraries
Three ways to see Chicago.
These are sample plans to spark ideas. Every trip is fully customized to your travel style, budget, and dates.
3-Day Chicago Weekend
A quick, high-impact weekend in Chicago.
Fly ORD/MDW · CTA · Walk
Day 1 — Arrival & city highlights
Places
- The Bean at Millennium Park
- Navy Pier
Sights & experiences
- Architecture river cruise
- Skydeck at Willis Tower
Food to try
- Deep-dish at Lou Malnati's
Day 2 — Neighborhoods & culture
Places
- Art Institute
- Wrigley Field
Sights & experiences
- Cubs game at Wrigley
- Art Institute afternoon
Food to try
- Chicago dog at Portillo's
Day 3 — Slow morning & signature moment
Places
- Willis Tower
- Lincoln Park
Sights & experiences
- Architecture river cruise
Food to try
- Italian beef sandwich
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