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Chicago

Holiday ideas to Chicago

Introduction

The holiday ideas listed below are designed to give you a flavour of the things to do in Chicago. We specialise in tailoring all aspects of your holiday to meet your precise needs. To start planning your trip, just call one of our destination specialists on 020 7590 0636.

List of itineraries

3 available
M/V Victory I in Georgian Bay

Splendour of the Great Lakes - Chicago to Toronto

12-day tailor-made cruise from £5,495 pp incl. flights

The awe-inspiring Great Lakes make up one fifth of the world's fresh surface water. Discover this spectacular region in elegant style with fine dining and enrichment activities onboard the Victory I or Victory II.

Historic Route 66

Historic Route 66 – Great American Road Trip

18-day tailor-made self-drive from £2,145 pp incl. flights

Take a trip along Route 66, America’s most celebrated highway. inspired countless films, books and songs, from Jack Kerouac’s On the Road to Woody Guthrie’s 'The Ballad of Tom Joad' and Bobby Troup’s classic '(Get Your Kicks On) Route 66'.

Lake Michigan, USA

Highlights of the Great Lakes

14-day tailor-made self-drive from £2,265 pp incl. flights

Watch as sweeping shorelines, architectural icons and powerhouse cities combine.

Why book with Wexas Travel?

At Wexas, we specialise in bespoke travel experiences. Our itineraries are just samples of what we can arrange, and can be changed depending on your precise needs, finances and ideas by our experienced destination specialists.

Contact one of our consultants on 020 7590 0636 to discuss how we can tailor your holiday.

Learn why Wexas is the leader in creating luxury holidays. What is tailor-made travel?

Expert advice & support

Visit us in our London office

Let our travel specialists curate the perfect holiday:

  • Inspirational ideas based on experience
  • Established for over 45 years
  • Tailor a holiday to your precise requirements
  • Personalised quotes and documentation
  • In-depth Wexas travel guides

Every step of the way

Every step of the way

Our services are with you from start to finish:

  • Dedicated personal consultants
  • Wexas Travel App
  • Free airport lounges on qualifying bookings
  • Care and guidance pre, post and during holiday
  • Full financial security: ABTA & ATOL protected