United States Itinerary
The Perfect 5-Day Chicago Itinerary
Chicago 🇺🇸 · Built from 8 real traveler plans · 39 spots
Chicago is one of the most-planned destinations on Triply. We took 8 real traveler itineraries and distilled them into this 5-day plan — built around the 39+ places people actually saved, ranked by how often they show up. No filler, no tourist traps nobody bookmarks: just the spots real travelers keep choosing for Chicago.
5-Day Chicago Itinerary
Day 1
Day 2
Day 3
Day 4
Day 5
Top Things to Do in Chicago
- Chicago Riverwalk — ★ 4.6 (saved by 7 travelers)
- Shedd Aquarium — ★ 3.7 (saved by 6 travelers)
- Cloud Gate — ★ 4.7 (saved by 5 travelers)
- Adler Planetarium — ★ 4.5 (saved by 5 travelers)
- Field Museum — ★ 4.7 (saved by 4 travelers)
- North Avenue Beach — ★ 4.6 (saved by 4 travelers)
- Art Institute of Chicago — ★ 4.8 (saved by 3 travelers)
- Millennium Park — ★ 4.6 (saved by 3 travelers)
Where to Eat in Chicago
- Lou Malnati's Pizzeria — ★ 4.4
- Giordano's — ★ 4.5
- Portillo's Hot Dogs — ★ 4.4
- Green Street Smoked Meats — ★ 4.7
Chicago Travel FAQ
How many days do you need in Chicago?
Most travelers planning Chicago on Triply spend about 5 days there. That's enough to cover the top sights — Chicago Riverwalk, Shedd Aquarium, Cloud Gate — without rushing.
What are the top things to do in Chicago?
Based on 8 real Chicago itineraries, the most-saved spots are Chicago Riverwalk, Shedd Aquarium, Cloud Gate, Adler Planetarium, Field Museum, North Avenue Beach.
Where should I eat in Chicago?
The most-saved places to eat in Chicago are Lou Malnati's Pizzeria, Giordano's, Portillo's Hot Dogs, Green Street Smoked Meats.
Is Chicago worth visiting?
Chicago is one of the most-planned destinations on Triply, with 8 traveler itineraries covering 39+ spots — so yes, there's plenty to fill a 5-day trip.
Build your own Chicago trip
Get this itinerary route-optimized with your own saved spots, free in the Triply app.