Chicago Luxury Vacations

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Indulge in opulence and culture on a luxurious Chicago getaway

Chicago is renowned for its urban allure, towering skyscrapers, vibrant theater scene, stunning architecture, world-class museums, captivating art, iconic monuments, endless entertainment options, breathtaking scenery, and unparalleled shopping experiences. This bustling city offers a perfect blend of cosmopolitan charm and natural beauty, with its picturesque lakefront, scenic riverwalks, and lush parks. Visitors can indulge in the diverse culinary scene, explore the cultural richness, immerse themselves in the city's history, and revel in the lively atmosphere. Chicago truly offers something for every luxury traveler seeking an unforgettable vacation.

Top Luxury vacation packages in Chicago

Price found within the past 48 hours. Click for updated prices.
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

Downtown Chicago
$681
per person
Nov 16 - Nov 19
found 1 day ago
Roundtrip non-stop flight included
Jackson (JAN) to Chicago (ORD)
8.8/10 Excellent! (2,334 reviews)
Music in restaurant was very annoying. Upon arrival to room on the surface it looked clean but under better inspection much dust was very evident on phone & nightstand, & above the air vent where you can adjust temperature & fan there was dark dirt & what looked like black mold. Molding around floor in bathroom looked like it hadn’t been cleaned in months.

Reviewed on Sep 15, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
Save 100% on your flight
$857
per person
Nov 16 - Nov 19
found 1 day ago
Roundtrip non-stop flight included
Jackson (JAN) to Chicago (ORD)
9.6/10 Exceptional! (1,995 reviews)
InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

Downtown Chicago
Save 100% on your flight
$1,317
per person
Nov 16 - Nov 21
found 1 day ago
Roundtrip non-stop flight included
St. Louis (STL) to Chicago (ORD)
9.2/10 Wonderful! (3,269 reviews)
Comfortable and aesthetic! Enjoyed our stay a lot.

Reviewed on Sep 16, 2026

Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

Downtown Chicago
Save 100% on your flight
$839
per person
Nov 16 - Nov 19
found 1 day ago
Roundtrip non-stop flight included
Jackson (JAN) to Chicago (ORD)
9.4/10 Exceptional! (1,010 reviews)
Clean room, nice location

Reviewed on Sep 15, 2026

The Peninsula Chicago

The Peninsula Chicago

Downtown Chicago
Save 100% on your flight
$1,129
per person
Nov 16 - Nov 19
found 1 day ago
Roundtrip non-stop flight included
Jackson (JAN) to Chicago (ORD)
9.8/10 Exceptional! (1,001 reviews)
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5* Luxury vacations in Chicago

Price found within the past 48 hours. Click for updated prices.
Park Hyatt Chicago

Park Hyatt Chicago

Downtown Chicago
$731
per person
Nov 17 - Nov 19
found 8 hours ago
Roundtrip flight included
Norfolk (ORF) to Chicago (ORD)
9.6/10 Exceptional! (1,006 reviews)
Amazing

Reviewed on Sep 8, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
Save 100% on your flight
$857
per person
Nov 16 - Nov 19
found 1 day ago
Roundtrip non-stop flight included
Jackson (JAN) to Chicago (ORD)
9.6/10 Exceptional! (1,995 reviews)
The Peninsula Chicago

The Peninsula Chicago

Downtown Chicago
Save 100% on your flight
$1,129
per person
Nov 16 - Nov 19
found 1 day ago
Roundtrip non-stop flight included
Jackson (JAN) to Chicago (ORD)
9.8/10 Exceptional! (1,001 reviews)
Don't see what you're looking for?
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3 Night Luxury vacations in Chicago

Price found within the past 48 hours. Click for updated prices.
Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

Downtown Chicago
Save 100% on your flight
$839
per person
Nov 16 - Nov 19
found 1 day ago
Roundtrip non-stop flight included
Jackson (JAN) to Chicago (ORD)
9.4/10 Exceptional! (1,010 reviews)
Clean room, nice location

Reviewed on Sep 15, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
Save 100% on your flight
$857
per person
Nov 16 - Nov 19
found 1 day ago
Roundtrip non-stop flight included
Jackson (JAN) to Chicago (ORD)
9.6/10 Exceptional! (1,995 reviews)
Park Hyatt Chicago

Park Hyatt Chicago

Downtown Chicago
Save 100% on your flight
$962
per person
Nov 19 - Nov 22
found 1 day ago
Roundtrip flight included
Houston (IAH) to Chicago (ORD)
9.6/10 Exceptional! (1,006 reviews)
Amazing

Reviewed on Sep 8, 2026

Don't see what you're looking for?
See all available trips from Singapore to Chicago
View all trips

4 Night Luxury vacations in Chicago

Price found within the past 48 hours. Click for updated prices.
Park Hyatt Chicago

Park Hyatt Chicago

Downtown Chicago
Save 100% on your flight
$1,176
per person
Nov 21 - Nov 25
found 1 day ago
Roundtrip flight included
Wichita (ICT) to Chicago (ORD)
9.6/10 Exceptional! (1,006 reviews)
Amazing

Reviewed on Sep 8, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
Save 100% on your flight
$1,555
per person
Oct 16 - Oct 20
found 11 hours ago
Roundtrip flight included
Birmingham (BHM) to Chicago (ORD)
9.6/10 Exceptional! (1,995 reviews)
Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

Downtown Chicago
$1,201
per person
Nov 16 - Nov 20
found 17 hours ago
Roundtrip non-stop flight included
San José (SJO) to Chicago (ORD)
9.4/10 Exceptional! (1,010 reviews)
Clean room, nice location

Reviewed on Sep 15, 2026

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See all available trips from Singapore to Chicago
View all trips

Top reasons for your vacation to Chicago

  • Urban allure and stunning architecture: Chicago is renowned for its towering skyscrapers and captivating architecture, offering a perfect blend of cosmopolitan charm and natural beauty.
  • World-class museums and art galleries: Visitors can immerse themselves in the city's rich cultural scene, exploring top-notch museums and captivating art galleries.
  • Culinary scene and lively atmosphere: Indulge in the diverse culinary scene, experience the lively atmosphere, and immerse yourself in the city's history and entertainment options.
  • Luxurious shopping experiences: Chicago boasts a range of high-end shopping options, making it a haven for luxury travelers seeking retail therapy.
  • Breathtaking scenery and picturesque lakefront: Take in the stunning scenery along the lakefront, explore lush parks, and enjoy the breathtaking views of Chicago's natural beauty.

Book a Package and Save Money on Your Chicago Vacation

A travel package combines flights and hotels or flights and car rental, making it convenient to book everything in one place. It can save you money and time by eliminating the need to search for separate deals. With a variety of options available, you can customize your package to suit your preferences and budget. Expedia's price and theme filters ensure you find a great deal.

Indulge in a luxurious vacation in Chicago , where you can marvel at stunning skyscrapers, immerse yourself in world-class theater and art, and explore fascinating museums. Experience the city's rich architecture and vibrant entertainment scene, all while enjoying upscale shopping and breathtaking scenery. Book your package now for the perfect luxury vacation.

How to Save Money on a Vacation to Chicago

  • Take advantage of public transportation options in Chicago, such as the CTA buses and trains, to save money on local transport.
  • Consider purchasing a Chicago CityPASS, which offers discounted admission to popular attractions like the Art Institute of Chicago and Shedd Aquarium.
  • Explore free attractions in Chicago, including Millennium Park and the Lincoln Park Zoo.
  • Save on dining expenses by trying out local food trucks and affordable yet delicious Chicago-style deep dish pizza.
  • Book your luxury accommodations through Expedia's OneKey program to earn rewards and save money on your stay.
  • Take advantage of discounts and deals offered by Expedia's OneKey program for activities and sightseeing in Chicago.
  • Consider visiting Chicago during the off-peak season, typically from November to March, for lower hotel rates and fewer crowds.
  • Utilize ride-sharing services like Uber or Lyft for convenient and cost-effective transportation within the city.
  • Take advantage of free walking tours in Chicago, such as the Chicago Greeter program, to explore the city and learn about its history without spending money.
  • Save on shopping expenses by visiting outlet malls like the Fashion Outlets of Chicago, where you can find luxury brands at discounted prices.

Where to Stay in Chicago

Chicago offers a variety of luxurious neighborhoods for a memorable vacation. Magnificent Mile is known for its upscale shopping, while Gold Coast boasts elegant mansions and fine dining. River North is an art lover's paradise, with its galleries and trendy restaurants. For a sophisticated experience, head to the Loop, home to iconic skyscrapers and theaters.

  • Downtown Chicago: Experience the awe-inspiring skyscrapers, urban vibe, and stunning architecture. Explore world-class museums, enjoy scenic views of the river, catch a theater performance, and immerse yourself in the vibrant art and entertainment scene. Don't miss the iconic monuments that add to the grandeur of this area.
  • Near North Side: Indulge in the luxury of towering skyscrapers, urban charm, and remarkable architecture. Discover art at museums, admire the scenic river, indulge in shopping at upscale boutiques, and savor exquisite dining options. With the picturesque lake as a backdrop, this area offers a truly lavish experience.
  • The Loop: Immerse yourself in the urban charm and architectural wonders of this area. Explore renowned museums, marvel at iconic skyscrapers, catch a theater show, and indulge in shopping and dining experiences that cater to refined tastes. The Loop's monuments add a touch of historical significance to this luxurious destination.

Explore the best places to visit in Chicago

Chicago (and vicinity) offers a luxurious experience for vacationers. With its impressive skyline and iconic architecture, the city is a haven for urban enthusiasts. Explore world-class museums and art galleries, indulge in theater shows, and marvel at historic monuments. Enjoy the vibrant nightlife and entertainment scene, or simply take in the stunning scenery along the lakefront. And for those seeking retail therapy, Chicago boasts a range of high-end shopping options. Immerse yourself in luxury and sophistication during your stay in the Windy City.

  • Woodfield Mall: Experience a luxurious shopping spree at Woodfield Mall, featuring a wide range of stores. Indulge in delicious dining options, explore the beautiful forests and lakes nearby, and immerse yourself in nature. Enjoy friendly interactions with locals and engage in activities like kayaking and biking.
  • LEGOLAND¬Æ Discovery Center: Visit this unique store where you can immerse yourself in a world of LEGO. Explore the stunning forests and lakes surrounding the center, engage in sports and outdoor activities, and delight in nature's beauty. Enjoy dining options and interact with friendly people while indulging in shopping and engaging in activities like kayaking and biking.
  • Wintrust Arena: Immerse yourself in the vibrant urban atmosphere of Wintrust Arena. Marvel at the impressive skyscrapers and architectural wonders surrounding the arena. Discover the rich art and theater scene, explore museums, and enjoy the serene views of the nearby lake. Engage with friendly people and appreciate the presence of monuments that add to the charm of Chicago.

Best months to visit Chicago

Chicago boasts a year-around average temperature of 51.3°F, peaking at 75.9°F in July, its warmest month, and dipping to an average low of 24.8°F in January, the coolest. Rainfall averages at 82.8mm annually, with May seeing the heaviest showers and February being the driest month.

MonthTemperature (Fahrenheit)Rainfall (mm)
January24.852.3
February28.849.3
March38.869.1
April50.592.5
May61.0104.9
June71.1103.1
July75.9101.9
August74.1101.3
September66.484.1
October54.382.3
November41.586.9
December28.965.3

All you need to know about luxury vacations in Chicago

What can I expect from a luxury Chicago vacation?

Luxury means the very finest of the things you enjoy most. Indulge your every waking moment—and restful night—with a luxury Chicago vacation. Sip handcrafted cocktails by an infinity pool, sink into bliss at a full-service spa with a massage cabana on the beach, and chat, cheers, and laugh through exquisite breakfasts, lunches, and dinners with spectacular views. 

How can I find all-inclusive luxury vacation packages in Chicago?

By refining your filters, the most opulent all-inclusive vacation packages will appear before your eyes. Check the 5* filter to find truly sensational stays. You barely need to lift a finger. 

Can I book a cheap Chicago luxury vacation?

Affordable luxury is only ever a few clicks away. Enter your travel dates and sort the grandiose getaways on offer by price to see the most fiscally friendly retreats first. Filter by budget, too, to find your perfect balance of luxury. Right now, luxury vacations start at $681. Prices and availability are subject to change. Additional terms may apply.

How can I book a luxury family vacation in Chicago?

Tailor your luxury family escape by checking the filters that set the whole family’s hearts a-flutter. Whether that’s wet and wild water parks, heavenly hot tubs, or the kid-quieting magic of free Wi-Fi. 

Can I book a package in Chicago with a luxury vacation home?

A private paradise is true luxury! Filter by property type for houses, villas, and apartments. For an amazingly affordable all-in-one luxury experience, book your accommodation, airfare, and car rental as a package.   

How can I find the best luxury vacation deals in Chicago?

Find absolute delight in the dropdown! Simply sort your tempting search results by deals to find that lean-budget luxury. For a budget conscious stay, consider booking a stay away from big cities or outside the peak months.

Can I book a luxury holiday in Chicago with free cancellation and/or flexible dates?

Freedom and flexibility are the greatest luxuries of all. Get both when you filter by payment option and book a trip with free cancellation or on a buy now, pay later plan. 

Why should I book my luxury trip to Chicago with Expedia?

A luxurious trip follows a stress-free booking experience. Find, build, and book the most glorious of getaways in seconds—with ATOL protection for added peace of mind.

Top Luxury Chicago Hotels

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

401 N Wabash Ave Chicago IL
  • 10 min drive from Wrigley Field
Trump International Hotel & Tower Chicago is a lush 5-star boutique property where you can be treated to deep soaking bathtubs and pillowtop beds. The spa, indoor ...
Trump International Hotel & Tower Chicago
The Langham, Chicago

The Langham, Chicago

330 North Wabash Avenue Chicago IL
  • 10 min drive from Wrigley Field
Enjoy a posh stay at The Langham, Chicago, where you'll find deep soaking bathtubs and a champagne service. Deluxe amenities at this hotel include a spa, an ...
The Langham, Chicago
The Peninsula Chicago

The Peninsula Chicago

108 East Superior Street Chicago IL
  • 9 min drive from Wrigley Field
Treat yourself to some luxurious accommodations at The Peninsula Chicago, where you can enjoy amenities like pillowtop beds, designer toiletries, and more. Deluxe ...
The Peninsula Chicago
See all 5,410 properties in Chicago
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

$27
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Willis Tower Skydeck and The Ledge Ticket

Chicago: Willis Tower Skydeck and The Ledge Ticket

$47
per adult
88% of travellers recommend
Chicago: Willis Tower Skydeck and The Ledge Ticket
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

$25
per adult
90% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
See all activities in Chicago

More vacations you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.