USA · Midwest
Chicago
Architecture, deep dish, and blues on Lake Michigan
Chicago is America's most underrated big city — a walkable lakefront, an extraordinary skyline, some of the world's best food, and a cultural scene that punches far above its size. The free Chicago Riverwalk and miles of lakefront trail make it surprisingly easy to have an excellent time here without spending much at all.
Budget/day
$120–$200
Best time
May, June, July, August +2 more
Currency
USD
US Visa
Visa required
Top things to do in Chicago
- Take the Chicago Architecture Foundation river cruise — the best way to see the skyline
- Visit Millennium Park, home to Cloud Gate (the Bean) and free summer concerts
- Eat deep-dish at Lou Malnati's or thin-crust at Vito & Nick's for the full debate
- Explore the Art Institute of Chicago, home to Seurat's A Sunday Afternoon
- Walk the lakefront trail from the Museum Campus to Navy Pier
What a Chicago trip actually costs
Estimates for a 7-night trip for 2 people from a major US hub, all-in.
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Chicago travel tips for US visitors
Visa: Domestic — no travel documents required.
- 1O'Hare (ORD) and Midway (MDW) both serve Chicago — compare flights to both.
- 2The CTA Blue Line from O'Hare to downtown costs $5 vs $60+ for a taxi.
- 3July 4th weekend and St. Patrick's Day are wildly expensive — avoid.
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