Luxury Illinois Holidays 2026/27 | Luxury Hotels In Illinois
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Holidays to Illinois with If Only

From the iconic skyline of Chicago to the scenic banks of the Mississippi River, Illinois offers a diverse mix of urban attractions, historic landmarks and natural beauty. Explore the vibrant culture, architecture and dining scene of the 'Windy City', follow stretches of legendary Route 66, discover charming small towns and delve into the legacy of Abraham Lincoln.

Whether cruising along the Mississippi River or enjoying world-class museums and entertainment, combining vibrant city life, fascinating history and scenic landscapes, Illinois offers plenty to discover beyond Chicago.

 

We currently feature 6 luxury properties in Illinois

 
Chicago Athletic Association Hotel

Chicago Athletic Association Hotel

Chicago, Illinois, The United States

star star star star

Old-world Chicago style blends with modern day luxuries in the Chicago Athletic Association Hotel, located overlooking Chicago's Millennium Park.

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Fairmont Chicago, Millennium Park

Fairmont Chicago, Millennium Park

Chicago, Illinois, The United States

star star star star star

Discover Fairmont Chicago, Millennium Park, where contemporary elegance blends seamlessly with a classic approach to luxury service.

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Loews Chicago Hotel

Loews Chicago Hotel

Chicago, Illinois, The United States

star star star star

Loews Chicago Hotel is a dramatic steel and glass tower offering luxurious accommodation and affording guests spectacular views of the city skyline and the immensity of Lake Michigan.

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Palmer House, a Hilton Hotel

Palmer House, a Hilton Hotel

Chicago, Illinois, The United States

star star star star

Steeped in tradition and integral to the history of this bustling metropolis, Palmer House Hilton is a luxurious escape from the hubbub of downtown Chicago.

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Pendry Chicago

Pendry Chicago

Chicago, Illinois, The United States

star star star star

The ideal mix of Art Déco glamour, sophistication and state-of-the art modernity.

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Viceroy Chicago

Viceroy Chicago

Chicago, Illinois, The United States

star star star star

A cool and chic urban retreat in Chicago’s historic Gold Coast district.

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Showing 6 out of 6 luxury properties

Highlights

From city sights to outdoor pursuits, there’s plenty on the menu in Illinois.

Shop on the Magnificent Mile

Chicago's Magnificent Mile is one of the city's premier shopping destinations. Stroll along its elegant, tree-lined avenues, browse luxury boutiques and flagship stores, or visit Water Tower Place, one of the world's pioneering vertical malls. Shopping is only part of the appeal, however.

Take in panoramic city views from 360 Chicago on the 94th floor of the former John Hancock Centre, explore the nearby Museum of Contemporary Art, or embark on a Chicago Architecture River Cruise, one of the city's most popular experiences for a fascinating perspective on Chicago's iconic skyline and landmark buildings from the Chicago River.

Shop on the Magnificent Mile
Head off the beaten track

Head off the beaten track

Illinois combines urban attractions with outstanding outdoor experiences. Explore the scenic trails and wineries of Shawnee National Forest, discover the waterfalls and canyons of Starved Rock State Park, or enjoy boating and fishing on the state's rivers and lakes. From forested landscapes to iconic waterways, Illinois offers plenty of opportunities to get outdoors and explore.

Shop, eat and play at Navy Pier

Set on the shores of Lake Michigan, Navy Pier is one of Chicago's most popular attractions. This vibrant lakefront destination features restaurants, shops, parks, entertainment and experiences for all ages. Take a ride on the iconic Centennial Wheel for spectacular views of the city skyline, explore the Chicago Children's Museum, enjoy a sightseeing cruise, or relax by the waterfront.

During the summer months, regular fireworks displays illuminate the sky, making Navy Pier a memorable destination for families and visitors alike.

Shop, eat and play at Navy Pier

Luxury Tours in Illinois

Climate

Average sun hours per day
Average monthly rainfall (mm)
Average daily temp (c)
  January
3
43
-6
  February
3
38
-4
  March
6
67
3
  April
7
97
10
  May
9
88
15
  June
10
99
21
  July
12
100
23
  August
11
96
22
  September
9
90
18
  October
7
68
12
  November
6
74
5
  December
3
63
-3