ShoreTrips logo Shore Excursions - City Tours - Day Activities


Private Tour for up to 2 (Not a per person rate) $353 USD
Private Tour for up to 4 (Not a per person rate) $401 USD
Private Tour for up to 6 (Not a per person rate) $428 USD
*Selections and optional choices will be made during checkout


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ShoreTrips says...

Why suffer through the anxiety of 'missing' something when you can have an expert advise you in advance?

Often the arrival into a new city seems easy - until you get there. In a city like Chicago, where there is so much to see and do, we suggest sitting down with a local 'expert', meaning a passionate local, and getting the lay of the land. There are neighborhoods full of the culture developed long ago with the settling of immigrants. There are shopping areas for every age and taste - and among those neighborhoods might be a restaurant or small museum you would hate to miss. You can find a museum to satisfy any special interest - and the parks and great walking neighborhoods - overwhelming!

To avoid both confusion and disappointment, we suggest you sit down with one of our expert local guides. We will meet at a convenient location for you, whether it be your hotel lobby or apartment, and your Chicago docent will explain the layout of the city and how it relates to the location of your lodging. Using a map, we will show you the nearest transportation options which include the Metra to the "L". Tips on local customs, dining suggestions based on your tastes, events that may interest you as well as shopping, festivals, etc. will be part of your introduction.

You will have a chance to ask more direct questions based on your interests as well. Then...we will take you on a stroll through your neighborhood. This is particularly wonderful as you learn the area's history and have a chance to comfortably absorb the neighborhood ambiance with the guidance of a seasoned Chicagoan.

Depending on your location, we can stop occasionally to talk about historic buildings and monuments or show you how to purchase transit tickets. Your guide will know the best markets nearby as well as cafes and restaurants.

And finally, we will leave you with maps, a lot of knowledge, and a comfort level to allow you to enjoy every minute of your stay in the Windy City!

  • This Tour Includes:
  • Local English-speaking Chicago docent
  • Introduction to the city, the layout, major transportation options, and some must-see destinations
  • A short stroll in the neighborhood of your lodging
  • Additional maps

Days of Operation

Mon - yes
Tue - yes
Wed - yes
Thu - yes
Fri - yes
Sat - yes
Sun - yes

Departures (local time)

  • 1:00 PM (2 hrs)
  • 3:00 PM (2 hrs)
  • 5:00 PM (2 hrs)

Transfer / Meeting Instructions

No Taxi Required Specific pick up or taxi instructions will appear on your voucher after you purchase your trip.

Special Instructions

• It is imperative to include the address of your stay. If you are at a hotel with multiple locations, we must have the address.
• Best to have some questions ready in advance of your meeting.
• If you prefer, we can suggest a local coffee shop nearby but it is essential that we stay in the area so we can advise more properly.


• Please contact ShoreTrips if there are more than 6 in your party.