How many days do you need in Chicago?
Three days. That is the length of the itinerary we built for Chicago.
Here is what each day holds. Every stop below carries its time, and every gap says how to get to the next stop, with the walk or drive time wherever both stops are mapped.
Chicago · 3 days United States
Best time: June to September is lakefront season.
The Loop and the riverDay 1
📍9:00 AMCloud Gate (the Bean)
Millennium Park before the crowds, then Lurie Garden next door.
🚶 ~10 min · 🚗 ~1 min · 0.4 mi
⛴️11:00 AMArchitecture river cruise
Ninety minutes of skyline history from the water.
🚶 ~54 min · 🚗 ~7 min · 2.0 mi
📍6:30 PMItalian beef, dipped
Al’s or Johnnie’s; lean forward, elbows out, no shame.
Museum Campus and the lakeDay 2
📍11:00 AMArt Institute
Doors open at 11 (closed Tuesdays): American Gothic, Nighthawks, and the Thorne miniature rooms.
🚶 ~34 min · 🚗 ~4 min · 1.3 mi
🌳3:00 PMLakefront trail walk or bike
South to the Museum Campus peninsula for the skyline photo.
🚗 ~8 min · 2.2 mi
🍽️7:00 PMDeep dish dinner
Lou Malnati’s or Pequod’s caramelized crust; order when seated, it takes 45 minutes.
NeighborhoodsDay 3
🌳10:00 AMWicker Park and Logan Square
Record shops, murals, and third-wave coffee along Milwaukee Avenue.
🚗 ~10 min · 2.9 mi
📍2:00 PMWrigleyville or Pilsen
Catch a Cubs day game in season, or Pilsen’s mural district and mole.
🚶 ~39 min · 🚗 ~5 min · 1.5 mi
📍8:00 PMGreen Mill jazz
Capone’s old booth is still there; the late set is the real one.
This is how Petrel lays out a trip. Upload your own confirmations and it builds this for your dates: flights and hotels included, with live flight status and the travel time between stops.
This is one of 126 free itineraries. Open it, change anything you want, and it becomes your trip.