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Day-by-day itinerary

7 Days in Chicago

Every stop below is a real, bookable experience — planned morning to evening and grouped by neighbourhood so you spend the day exploring, not commuting.

Days

7

Experiences

21

Total from

1265 USD

Walking

5.6 km

How long are you staying?1 day2 days3 days4 days5 days6 days7 days
Plan around a theme:All experiencesFamily tripFood & drinkHistory & cultureBudget

Day 1

Chicago

  1. Go City Chicago Explorer Pass: Choose from 39 Attractions
    Go City Chicago Explorer Pass: Choose from 39 AttractionsMorning · 09:00 · museumFrom 84 USD
  2. Big Bus: Chicago Hop-on Hop-off Bus Tour
    Big Bus: Chicago Hop-on Hop-off Bus TourAfternoon · 14:00 · Chicago · attractionFrom 49 USD
  3. Chicago Skyline Pass
    Chicago Skyline PassEvening · 19:30 · theatreFrom 103 USD

Day 2

Chicago

  1. Go City Chicago All-Inclusive Pass: Choose from 39 Attractions
    Go City Chicago All-Inclusive Pass: Choose from 39 AttractionsMorning · 09:00 · museumFrom 149 USD
  2. Chicago Explorer Pass: 2 to 7 Attractions including 360 Chicago
    Chicago Explorer Pass: 2 to 7 Attractions including 360 ChicagoAfternoon · 14:00 · attractionFrom 84 USD
  3. Chicago Top 3 Attractions Pass
    Chicago Top 3 Attractions PassEvening · 19:30 · theatreFrom 104 USD

Day 3

Chicago

0.6 km on foot

  1. Skydeck Chicago Tickets
    Skydeck Chicago TicketsMorning · 09:00 · Skydeck Chicago · museumFrom 42.33 USD
  2. Color Factory Chicago: Entry Ticket
    Color Factory Chicago: Entry TicketAfternoon · 14:00 · Color Factory Chicago · attractionFrom 34 USD
  3. Chicago: Underground Pedway & the Loop Guided Walking Tour
    Chicago: Underground Pedway & the Loop Guided Walking TourEvening · 19:30 · theatreFrom 35 USD

Day 4

Chicago

1.2 km on foot

  1. The Art Institute of Chicago: Fast Pass
    The Art Institute of Chicago: Fast PassMorning · 09:00 · Art Institute of Chicago · museumFrom 40 USD
  2. 90-min Chicago River and Lake Michigan Architecture Cruise by Wendella
    90-min Chicago River and Lake Michigan Architecture Cruise by WendellaAfternoon · 14:00 · Wendella Tours & Cruises · attractionFrom 45 USD
  3. Chicago Architecture: A Walk Through Time
    Chicago Architecture: A Walk Through TimeEvening · 19:30 · theatreFrom 30 USD

Day 5

Chicago

1.8 km on foot

  1. Chicago C3® CityPASS®: 3 Attractions of your choice
    Chicago C3® CityPASS®: 3 Attractions of your choiceMorning · 09:00 · museumFrom 109 USD
  2. 90-min Scenic Sunset Lake Michigan Cruise by Wendella
    90-min Scenic Sunset Lake Michigan Cruise by WendellaAfternoon · 14:00 · Wendella Tours & Cruises · attractionFrom 45 USD
  3. The Chicago Theatre Tour Experience
    The Chicago Theatre Tour ExperienceEvening · 19:30 · Chicago Theatre · theatreFrom 30 USD

Day 6

Chicago

1.4 km on foot

  1. Museum of Illusions Chicago: Entry Ticket
    Museum of Illusions Chicago: Entry TicketMorning · 09:00 · Museum of Illusions Chicago · museumFrom 43 USD
  2. Chicago Architecture Evening Cruise by Shoreline
    Chicago Architecture Evening Cruise by ShorelineAfternoon · 14:00 · Equitable Building · attractionFrom 46 USD
  3. Tiffany in Chicago: Guided Tour
    Tiffany in Chicago: Guided TourEvening · 19:30 · theatreFrom 30 USD

Day 7

Chicago

0.6 km on foot

  1. Medieval Torture Museum: Entry Ticket
    Medieval Torture Museum: Entry TicketMorning · 09:00 · Medieval Torture Museum · museumFrom 35.83 USD
  2. Chicago: Canine Cruise
    Chicago: Canine CruiseAfternoon · 14:00 · attractionFrom 46 USD
  3. Chicago: Guided Gangsters & Food Walking Tour
    Chicago: Guided Gangsters & Food Walking TourEvening · 19:30 · theatreFrom 80.89 USD

Every stop is bookable

Prices and availability are live — open any stop to pick a date and book it in minutes.

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