Title: Chicago Luxury Vacations 2026 | Expedia.com ![](https://images.trvl-media.com/place/178248/e6aa83ce-7ad8-43a5-9d1d-b055eefa7e78.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Chicago Luxury Vacations ## Book a Luxury Hotel + Flight or Car together to unlock savings ## 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. ![Kimpton Gray Hotel by IHG](https://images.trvl-media.com/lodging/14000000/13360000/13351500/13351499/14bf852a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Kimpton Gray Hotel by IHG Downtown Chicago $439 per person Apr 3 - Apr 5 found 16 hours ago Roundtrip flight included Atlanta (ATL) to Chicago (ORD) 9.2/10 Wonderful! (1,003 reviews) Wonderful hotel to stay at. Located right downtown and a close walk to everything. Loved the complimentary cocktail hour too! Reviewed on Feb 23, 2026 ![Fairmont Chicago at Millennium Park](https://images.trvl-media.com/lodging/1000000/20000/16000/15937/8bd99f5f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Fairmont Chicago at Millennium Park Downtown Chicago Save 100% on your flight $539 per person May 5 - May 7 found 2 hours ago Roundtrip flight included Columbus (CMH) to Chicago (ORD) 8.6/10 Excellent! (2,070 reviews) Very nice & clean hotel and near the Bean and shops are walkable. Reviewed on Mar 3, 2026 ![DoubleTree by Hilton Chicago - Magnificent Mile](https://images.trvl-media.com/lodging/1000000/30000/21200/21152/757dbd3e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### DoubleTree by Hilton Chicago - Magnificent Mile Downtown Chicago $716 per person May 4 - May 8 found 1 day ago Roundtrip flight included Omaha (OMA) to Chicago (ORD) 8.8/10 Excellent! (2,332 reviews) Clean but not room service Reviewed on Mar 2, 2026 ![Waldorf Astoria Chicago](https://images.trvl-media.com/lodging/3000000/2720000/2717600/2717582/1ede47da_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Waldorf Astoria Chicago Downtown Chicago $1,262 per person May 5 - May 9 found 1 day ago Roundtrip flight included Atlanta (ATL) to Chicago (ORD) 9.4/10 Exceptional! (1,001 reviews) Nice bellmen, nice front staff, rooms were cozy and well kept. Everyone was very friendly and helpful. We would stay again. Reviewed on Mar 1, 2026 ![Trump International Hotel & Tower Chicago](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/209f8cff_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Trump International Hotel & Tower Chicago Downtown Chicago Save 100% on your flight $741 per person May 4 - May 6 found 2 hours ago Roundtrip flight included Columbus (CMH) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) Above the beyond. My back went out. Had wheelchair Asap took me uop and helprd mre get into bed. Reviewed on Mar 3, 2026 Don't see what you're looking for? See all available trips from Columbus to Chicago [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-04-04/2026-04-11/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* Luxury vacations in Chicago Price found within the past 48 hours. Click for updated prices. ![Park Hyatt Chicago](https://images.trvl-media.com/lodging/1000000/30000/20700/20695/c8149674_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Park Hyatt Chicago Downtown Chicago $655 per person Apr 3 - Apr 5 found 22 hours ago Roundtrip flight included New York (NYC) to Chicago (ORD) 9.6/10 Exceptional! (1,001 reviews) The room was a little dated. I was surprised that you didn’t have CNBC as a TV choice, I thought the gym was dated and the WiFi was inadequate Reviewed on Feb 28, 2026 ![Waldorf Astoria Chicago](https://images.trvl-media.com/lodging/3000000/2720000/2717600/2717582/1ede47da_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Waldorf Astoria Chicago Downtown Chicago $1,262 per person May 5 - May 9 found 1 day ago Roundtrip flight included Atlanta (ATL) to Chicago (ORD) 9.4/10 Exceptional! (1,001 reviews) Nice bellmen, nice front staff, rooms were cozy and well kept. Everyone was very friendly and helpful. We would stay again. Reviewed on Mar 1, 2026 ![Trump International Hotel & Tower Chicago](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/209f8cff_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Trump International Hotel & Tower Chicago Downtown Chicago Save 100% on your flight $741 per person May 4 - May 6 found 2 hours ago Roundtrip flight included Columbus (CMH) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) Above the beyond. My back went out. Had wheelchair Asap took me uop and helprd mre get into bed. Reviewed on Mar 3, 2026 Don't see what you're looking for? See all available trips from Columbus to Chicago [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-04-04/2026-04-11/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night Luxury vacations in Chicago Price found within the past 48 hours. Click for updated prices. ![DoubleTree by Hilton Chicago - Magnificent Mile](https://images.trvl-media.com/lodging/1000000/30000/21200/21152/757dbd3e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### DoubleTree by Hilton Chicago - Magnificent Mile Downtown Chicago $427 per person May 6 - May 9 found 1 day ago Roundtrip flight included Memphis (MEM) to Chicago (ORD) 8.8/10 Excellent! (2,332 reviews) Clean but not room service Reviewed on Mar 2, 2026 ![Fairmont Chicago at Millennium Park](https://images.trvl-media.com/lodging/1000000/20000/16000/15937/8bd99f5f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Fairmont Chicago at Millennium Park Downtown Chicago $719 per person May 6 - May 9 just found Roundtrip flight included Lincoln (LNK) to Chicago (ORD) 8.6/10 Excellent! (2,070 reviews) Very nice & clean hotel and near the Bean and shops are walkable. Reviewed on Mar 3, 2026 ![Thompson Chicago, by Hyatt](https://images.trvl-media.com/lodging/1000000/30000/26100/26076/w3837h2557x3y3-ef0f356b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Thompson Chicago, by Hyatt Downtown Chicago $773 per person May 6 - May 9 just found Roundtrip flight included Lincoln (LNK) to Chicago (ORD) 9.2/10 Wonderful! (1,323 reviews) We loved are stay at the Thompson hotel. It's very clean, and is close to our favorite shops and restaurants. Reviewed on Mar 2, 2026 Don't see what you're looking for? See all available trips from Columbus to Chicago [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-04-04/2026-04-11/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night Luxury vacations in Chicago Price found within the past 48 hours. Click for updated prices. ![Thompson Chicago, by Hyatt](https://images.trvl-media.com/lodging/1000000/30000/26100/26076/w3837h2557x3y3-ef0f356b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Thompson Chicago, by Hyatt Downtown Chicago Save 100% on your flight $670 per person May 4 - May 8 found 15 hours ago Roundtrip flight included Denver (DEN) to Chicago (ORD) 9.2/10 Wonderful! (1,323 reviews) We loved are stay at the Thompson hotel. It's very clean, and is close to our favorite shops and restaurants. Reviewed on Mar 2, 2026 ![LondonHouse Chicago, Curio Collection by Hilton](https://images.trvl-media.com/lodging/13000000/12790000/12786700/12786616/7aab5ae1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### LondonHouse Chicago, Curio Collection by Hilton Downtown Chicago Save 100% on your flight $877 per person May 4 - May 8 found 15 hours ago Roundtrip flight included Denver (DEN) to Chicago (ORD) 9.4/10 Exceptional! (3,595 reviews) Loved the view! Everything was beautiful Reviewed on Mar 4, 2026 ![Fairmont Chicago at Millennium Park](https://images.trvl-media.com/lodging/1000000/20000/16000/15937/8bd99f5f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Fairmont Chicago at Millennium Park Downtown Chicago Save 100% on your flight $977 per person May 4 - May 8 found 15 hours ago Roundtrip flight included Denver (DEN) to Chicago (ORD) 8.6/10 Excellent! (2,070 reviews) Very nice & clean hotel and near the Bean and shops are walkable. Reviewed on Mar 3, 2026 Don't see what you're looking for? See all available trips from Columbus to Chicago [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-04-04/2026-04-11/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 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](https://www.expedia.com/welcome-one-key) 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](https://www.expedia.com/Downtown-Chicago.d6350699.Destination-Travel-Guides):** 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](https://www.expedia.com/Near-North-Side.d137043.Destination-Travel-Guides):** 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](https://www.expedia.com/The-Loop.d800024.Destination-Travel-Guides):** 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](https://www.expedia.com/Woodfield-Mall-Chicago.d6064089.Vacation-Attraction)**: 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](https://www.expedia.com/LEGOLAND-Discovery-Center-Chicago.d6169680.Vacation-Attraction)**: 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](https://www.expedia.com/Wintrust-Arena-South-Loop.d553248634328853320.Vacation-Attraction)**: 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. | **Month![](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/calendar.png)** | **Temperature (Fahrenheit)![](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__hot.png)** | **Rainfall (mm)![](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__rain.png)** | | ----------------------------------------------------------------------------------------------- | ---------------------------------------------------------------------------------------------------------------------- | ------------------------------------------------------------------------------------------------------------ | | January | 24.8 | 52.3 | | February | 28.8 | 49.3 | | March | 38.8 | 69.1 | | April | 50.5 | 92.5 | | May | 61.0 | 104.9 | | June | 71.1 | 103.1 | | July | 75.9 | 101.9 | | August | 74.1 | 101.3 | | September | 66.4 | 84.1 | | October | 54.3 | 82.3 | | November | 41.5 | 86.9 | | December | 28.9 | 65.3 | ## 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 $427\. 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](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/209f8cff_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### 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 ... 9.4/10 Exceptional! (1,844 reviews) Above the beyond. My back went out. Had wheelchair Asap took me uop and helprd mre get into bed. Reviewed on Mar 3, 2026 [](https://expedia.com/Chicago-Hotels-Trump-International-Hotel-Tower-Chicago.h1723215.Hotel-Information) ![The Langham, Chicago](https://images.trvl-media.com/lodging/7000000/6310000/6309400/6309326/a75a4abb_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### 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 ... 9.8/10 Exceptional! (1,003 reviews) Staff was very friendly and helpful. Generous amenities as well. Reviewed on Feb 27, 2026 [](https://expedia.com/Chicago-Hotels-The-Langham.h6309326.Hotel-Information) ![The Peninsula Chicago](https://images.trvl-media.com/lodging/1000000/590000/581300/581213/e294b3a4_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### 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 ... 9.8/10 Exceptional! (1,003 reviews) Room was amazing. Staff was fantastic. Best Hotel we have ever stayed at Reviewed on Feb 26, 2026 [](https://expedia.com/Chicago-Hotels-The-Peninsula-Chicago.h581213.Hotel-Information) [See all 5,616 properties in Chicago](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package®ionId=178248) 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. ## More vacations you might like ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.com/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.com/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Kid Friendly Vacations [](https://expedia.com/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Kid_Friendly%20Vacations.click) 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