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Chicago in 3 days with friends

Itineraries · Chicago, IL · 3 days

A 3-day Chicago plan for a group: the Bean and the Art Institute, an architecture river cruise, deep dish two ways, Lincoln Park and Wrigley Field, and the Skydeck to finish.

Chicago rewards a plan that follows the river and the lake. Day 1 stays in the Loop, Day 2 heads north along the lakefront, and Day 3 pairs a big museum with the view from Willis Tower. There's deep dish on two nights so the group can settle the Lou's versus Pequod's debate.

Where
Chicago, IL
How long
3 days, 13 stops
Good for
First trips to Chicago, summer weekends, groups of 2 to 8
Best time
May to October, when the river cruises run and the lakefront is busy
Updated
October 15, 2026

Plan it together in Freya

Every stop goes on your trip with its place from Apple Maps, so the group gets directions, drive times and the weather. Then swap things out, vote and split the costs.

Add to Freya

Not on an iPhone? Copy the plan for the group chat, or open it in the builder.

Day 1: The Loop and the river

If we have time

  • Any time360 ChicagoDo875 N Michigan Ave, Chicago, IL · Map of 360 ChicagoNight views from the 94th floor

Day 2: Lincoln Park and the lakefront

  • 10:00 AMLincoln Park ZooDo2001 N Clark St, Chicago, IL · Map of Lincoln Park ZooFree
  • 11:30 AMNorth Avenue BeachDo1600 N Lake Shore Dr, Chicago, IL · Map of North Avenue BeachWalk out to the end for the skyline
  • 1:00 PMPequod's PizzaEat2207 N Clybourn Ave, Chicago, IL · Map of Pequod's PizzaPan pizza with the caramelized crust; expect a wait
  • 3:00 PMWrigley FieldDo1060 W Addison St, Chicago, IL · Map of Wrigley FieldCatch a Cubs game, or take a ballpark tour on off days
  • 7:30 PMAu ChevalEat800 W Randolph St, Chicago, IL · Map of Au ChevalBurgers on the West Loop's Restaurant Row

If we have time

Day 3: A big museum and the view

If we have time

  • Any timeNavy PierDo600 E Grand Ave, Chicago, IL · Map of Navy PierThe Centennial Wheel and lake views

Tips

  • Tap a contactless card or phone at CTA train turnstiles and on buses; you don't need to buy a Ventra card first.
  • Book the architecture river cruise ahead on summer weekends, and sit on the top deck.
  • Deep dish takes 30 to 45 minutes to bake. Order as soon as you sit down, or call ahead.
  • It's often cooler by the lake than inland. Bring a layer for the cruise and the beach.

Plan it together in Freya

Every stop goes on your trip with its place from Apple Maps, so the group gets directions, drive times and the weather. Then swap things out, vote and split the costs.

Add to Freya

Questions

Is 3 days enough for Chicago?

For a first visit, yes. This plan fits 13 stops into 3 days (Day 1: The Loop and the river; Day 2: Lincoln Park and the lakefront; Day 3: A big museum and the view). Add a day if your group likes a slower pace.

When is the best time to go to Chicago?

May to October, when the river cruises run and the lakefront is busy.

Where should a group eat in Chicago?

This plan stops at Portillo's, Lou Malnati's Pizzeria, Pequod's Pizza, Au Cheval and Billy Goat Tavern. Vote on dinner in Freya if the group can't agree.

What if the group wants to split up?

The ideas under “If we have time” (360 Chicago, The Second City and Navy Pier) are optional. In Freya, set who's going on a stop so everyone knows where to meet back up.

How do we use this plan as a group?

Tap Add to Freya on an iPhone. Every stop goes on a shared trip with its place from Apple Maps, so the group gets directions, drive times and the weather. Friends join from a link with just their first name, then swap stops, vote on plans and split the costs.

More itineraries

Have your own plan in a Google Doc or an AI chat? Paste it into Freya, or share it to Freya from any app. Here’s how. Or make your own version of this plan in the builder.