Chicago weekend

Chicago, IL · Trip template

Weekend getaway9 places · 3 lists · 3-day itinerary

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Chicago weekend — Chicago, IL

Deep dish, architecture cruises, and rooftop season. This weekend getaway itinerary maps out 9 hand-picked places across Chicago, IL over 3 days — from the must-see landmarks to the local spots worth the detour. Preview the whole plan on the map, then duplicate it in Arriv to swap in your own picks, set your dates, and invite your crew.

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3-day Chicago itinerary

Day 1

  1. 19:30Girl & the Goat — Big first-night dinner
  2. 22:00The Violet Hour — Speakeasy nightcap

Day 2

  1. 10:00Chicago Architecture River Cruise — The best intro to the city
  2. 13:00Lou Malnati's Pizzeria — Deep dish — order when seated
  3. 15:00Millennium Park — The Bean photo op
  4. 17:30Cindy's — Golden-hour rooftop drinks
  5. 21:30Green Mill Cocktail Lounge — Late-set jazz

Day 3

  1. 11:30Portillo's — Italian beef before the airport
  2. 13:00Navy Pier

What's on this Chicago itinerary

9 places across 3 lists.

Deep dish & classics

  • Lou Malnati's Pizzeria
  • Portillo's — Chicago dogs and Italian beef.
  • Girl & the Goat — Book well ahead — Stephanie Izard's flagship.

Architecture & sights

  • Chicago Architecture River Cruise
  • Millennium Park — The Bean and Crown Fountain.
  • Navy Pier

Rooftops & bars

  • Cindy's — Rooftop in Chicago Athletic Association — park views.
  • The Violet Hour — Speakeasy cocktails in Wicker Park.
  • Green Mill Cocktail Lounge — Jazz club since 1907 — Al Capone's old haunt.

Chicago weekend getaway — FAQ

How many days do you need in Chicago?
This itinerary is built for 3 days and covers 9 spots across Chicago, IL. Once you duplicate it in Arriv you can stretch it out or trim it to fit your trip.
What are the must-do things in Chicago?
Highlights on this weekend getaway itinerary include Lou Malnati's Pizzeria, Portillo's, Girl & the Goat, plus 6 more places you can explore on the interactive map.
Is this Chicago itinerary free?
Yes. Preview the full itinerary and map for free, then duplicate it into your own Arriv trip to customize it, add reservations, and plan together with friends.
Can I customize this Chicago trip?
Absolutely. Tap "Use this trip" to get an editable copy — swap places, reorder the days, set your travel dates, and share it with your group.

Ready to plan your Chicago trip?

Duplicate this itinerary and make it yours — swap spots, set dates, and invite your crew.