Title: Illinois Luxury Vacations 2026 | Expedia.com ![](https://images.trvl-media.com/place/215/aa920d34-e093-4af5-87ef-8a5ae8eefcac.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Illinois Luxury Vacations ## Book a Luxury Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to $1,045 when you book a flight and hotel together\* - ### Find the right fit With over 300,000 hotels worldwide, it's easy to create a perfect package - ### Rest easy Plan, book, and manage your trip all in one place ## Top Luxury vacation packages in Illinois Price found within the past 48 hours. Click for updated prices. ![The Westin Chicago Lombard](https://images.trvl-media.com/lodging/2000000/1700000/1690600/1690548/ef211bfd_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Westin Chicago Lombard $271 per person May 7 - May 10 found 1 day ago Roundtrip flight included Atlanta (ATL) to Chicago (ORD) 9/10 Wonderful! (1,204 reviews) The pool was big and nice Reviewed on Mar 5, 2026 ![Kimpton Gray Hotel by IHG](https://images.trvl-media.com/lodging/14000000/13360000/13351500/13351499/9bf8883a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Kimpton Gray Hotel by IHG Downtown Chicago Save 100% on your flight $958 per person May 8 - May 13 found 4 hours ago Roundtrip flight included Atlanta (ATL) to Chicago (ORD) 9.2/10 Wonderful! (1,000 reviews) Amazing hotel, amazing location Reviewed on Mar 6, 2026 ![Trump International Hotel & Tower Chicago](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/4465cc02_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Trump International Hotel & Tower Chicago Downtown Chicago $570 per person Apr 6 - Apr 8 found 23 hours ago Roundtrip flight included Charlotte (CLT) to Chicago (ORD) 9.4/10 Exceptional! (1,839 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 ![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 $436 per person May 7 - May 9 found 1 day 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 ![Hotel Arista](https://images.trvl-media.com/lodging/3000000/2150000/2141800/2141763/a6c36a1d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Arista Save 100% on your flight $487 per person May 7 - May 11 found 8 hours ago Roundtrip flight included Dallas (DFW) to Chicago (ORD) 9.4/10 Exceptional! (1,002 reviews) Room was clean, staff was friendly and parking was really easy. Very comfortable stay. Reviewed on Mar 5, 2026 Don't see what you're looking for? See all available trips from Columbus to Illinois [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-04-07/2026-04-14/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* Luxury vacations in Illinois Price found within the past 48 hours. Click for updated prices. ![Trump International Hotel & Tower Chicago](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/4465cc02_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Trump International Hotel & Tower Chicago Downtown Chicago $570 per person Apr 6 - Apr 8 found 23 hours ago Roundtrip flight included Charlotte (CLT) to Chicago (ORD) 9.4/10 Exceptional! (1,839 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 ![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 Save 100% on your flight $921 per person Apr 8 - Apr 11 found 1 day ago Roundtrip flight included Boston (BOS) 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 ![The Peninsula Chicago](https://images.trvl-media.com/lodging/1000000/590000/581300/581213/e294b3a4_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Peninsula Chicago Downtown Chicago Save 100% on your flight $1,297 per person May 7 - May 10 found 24 hours ago Roundtrip flight included Boston (BOS) to Chicago (ORD) 9.8/10 Exceptional! (1,000 reviews) Great location (very walkable), well equipped gym, very good restaurant Reviewed on Mar 5, 2026 Don't see what you're looking for? See all available trips from Columbus to Illinois [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-04-07/2026-04-14/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night Luxury vacations in Illinois Price found within the past 48 hours. Click for updated prices. ![Hilton Chicago](https://images.trvl-media.com/lodging/1000000/20000/12600/12570/274f52b9_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hilton Chicago Downtown Chicago Save 100% on your flight $274 per person May 7 - May 10 found 1 day ago Roundtrip flight included Atlanta (ATL) to Chicago (ORD) 8.6/10 Excellent! (2,658 reviews) Hotel was really nice and super clean. Staff were amazing. Reviewed on Mar 3, 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 $332 per person May 7 - May 10 found 1 day ago Roundtrip flight included Atlanta (ATL) 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 ![Palmer House a Hilton Hotel](https://images.trvl-media.com/lodging/1000000/10000/8100/8079/9d783fbd_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Palmer House a Hilton Hotel Downtown Chicago Save 100% on your flight $330 per person May 7 - May 10 found 1 day ago Roundtrip flight included Atlanta (ATL) to Chicago (ORD) 8.6/10 Excellent! (2,310 reviews) The property is friendly. Awesome location and lobby. Reviewed on Mar 6, 2026 Don't see what you're looking for? See all available trips from Columbus to Illinois [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-04-07/2026-04-14/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night Luxury vacations in Illinois Price found within the past 48 hours. Click for updated prices. ![Hilton Chicago](https://images.trvl-media.com/lodging/1000000/20000/12600/12570/274f52b9_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hilton Chicago Downtown Chicago Save 100% on your flight $427 per person May 7 - May 11 found 9 hours ago Roundtrip flight included Austin (AUS) to Chicago (ORD) 8.6/10 Excellent! (2,658 reviews) Hotel was really nice and super clean. Staff were amazing. Reviewed on Mar 3, 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 $533 per person May 7 - May 11 found 1 day ago Roundtrip non-stop 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 ![Palmer House a Hilton Hotel](https://images.trvl-media.com/lodging/1000000/10000/8100/8079/9d783fbd_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Palmer House a Hilton Hotel Downtown Chicago Save 100% on your flight $468 per person May 7 - May 11 found 9 hours ago Roundtrip flight included Austin (AUS) to Chicago (ORD) 8.6/10 Excellent! (2,310 reviews) The property is friendly. Awesome location and lobby. Reviewed on Mar 6, 2026 Don't see what you're looking for? See all available trips from Columbus to Illinois [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-04-07/2026-04-14/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.com/deals?rfrr=THVAD_SPRING_PROMO_215) ## All you need to know about luxury vacations in Illinois #### What can I expect from a luxury Illinois vacation? Luxury means the very finest of the things you enjoy most. Indulge your every waking moment—and restful night—with a luxury Illinois 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 Illinois? 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 Illinois 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 $271\. Prices and availability are subject to change. Additional terms may apply. #### How can I book a luxury family vacation in Illinois? 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 Illinois 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 Illinois? 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 Illinois 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 Illinois 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 Illinois Hotels ![Trump International Hotel & Tower Chicago](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/4465cc02_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 $371 nightly $436 total Mar 15 - Mar 16 Total with taxes and fees 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 $435 nightly $511 total Apr 5 - Apr 6 Total with taxes and fees 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! (1,004 reviews) Did not use spa. Lots of restaurants, shops and experiences in the area. Reviewed on Mar 6, 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 $525 nightly $616 total Mar 8 - Mar 9 Total with taxes and fees 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! (1,004 reviews) Great location (very walkable), well equipped gym, very good restaurant Reviewed on Mar 5, 2026 [](https://expedia.com/Chicago-Hotels-The-Peninsula-Chicago.h581213.Hotel-Information) [See all 10,524 properties in Illinois](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package®ionId=215) 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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[Luxury Vacations in Greece ](https://www.expedia.com/lp/theme-vacations/luxury-vacations/67/Greece) > - [Luxury Vacations in New York ](https://www.expedia.com/lp/theme-vacations/luxury-vacations/178293/New-York) > - [Luxury Vacations in Bora Bora ](https://www.expedia.com/lp/theme-vacations/luxury-vacations/602861/Bora-Bora) > - [Luxury Vacations in Florida ](https://www.expedia.com/lp/theme-vacations/luxury-vacations/211/Florida) > - [Luxury Vacations in London ](https://www.expedia.com/lp/theme-vacations/luxury-vacations/178279/London) > - [Luxury Vacations in Arizona ](https://www.expedia.com/lp/theme-vacations/luxury-vacations/204/Arizona) ## More Vacation Ideas [Illinois Flights ](https://expedia.com/Destinations-In-Illinois.d215.Flight-Destinations)[ Illinois Hotels ](https://expedia.com/Destinations-In-Illinois.d215.Hotel-Destinations)[ Vacation Rentals in Illinois ](https://expedia.com/Destinations-In-Illinois.d215.Vacation-Rental-Destinations)[ Car Rentals in Illinois ](https://expedia.com/Destinations-In-Illinois.d215.Car-Rental-Destinations)[ Illinois Vacations ](https://expedia.com/Illinois.d215.Destination-Travel-Guides)[ Things to do in Illinois ](https://expedia.com/Things-To-Do-In-Illinois.d215.Travel-Guide-Activities) \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save even more - get up to 20% on select hotels when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app