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Chicago

Visit Chicago

Introduction

The 'windy city' of Chicago got its nickname from its unique politics, not the weather, so you can expect a laid back city built for all seasons, with world-class museums, miles of lakefront vistas, award-winning restaurants and luxury hotels. The 'Magnificent Mile' of Michigan Avenue has plenty to keep you entertained with lots of shops, as will the 250 local designers to be found in neighbourhood boutiques.

As the home of the legendary blues, expect free downtown and neighbourhood festivals with some of the world's best musicians. Chicago is the city where the skyscraper was born and you can take a tour to discover the architecture of Chicago's buildings and historical hotels or take advantage of plenty of free tourist attractions.

 

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Special offers in Chicago

M/V Victory I in Georgian Bay

Splendour of the Great Lakes

12-day tailor-made cruise from £4,730 pp incl. flights

Special
cruise offer

Cruise discount – Save up to £560 pp
Book by: 30 November 2019

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.

Top itineraries in Chicago

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 £2,300 pp incl. flights

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

Top places to stay in Chicago

The Knickerbocker

Chicago Millennium - The Knickerbocker, Illinois

Contemporary hotel

The Millennium Knickerbocker Hotel offers sleek and stylish accommodation in a great location, at the start of the Magnificent Mile with its endless shopping, dining and entertainment. Attractions such as the Museum of Contemporary Art, Art Institute of Chicago and 360 Chicago (formerly the John Han

The Thompson

The Thompson, Chicago

Contemporary hotel

This boutique hotel is set in one of Chicago’s hippest neighbourhoods, having won several Condé Nast awards.

Peninsula

The Peninsula, Chicago

Designer hotel

One of the city’s best-regarded hotels, the Peninsula has consistently been awarded the Forbes Five Star and AAA Five Diamond awards year on year.

Park Hyatt Chicago

Park Hyatt, Chicago

Contemporary hotel

Bringing residential living and gorgeous city views to guests, this hotel is centred around many of the city’s best attractions.

Chicago articles

Chicago Skyline

Illinois: The ultimate introduction to Route 66

Home to the most Route 66 national historic sites of any other state, learn why Illinois is the perfect introduction to the Mother Road.

Pontiac Route 66 Mural, Illinois

A holiday on Route 66

With nearly 2,500 miles to choose from, we’ve put together the must-see stops along Route 66 – America’s original road trip. Along with the big-city highlights, there’s plenty of off-the-beaten-track intrigue, including national parks and forgotten railroad towns.

Meet our Chicago experts

Speak to a tailor-made specialist on 020 7590 0636

Meet the team

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