Book Chicago Luxury Vacations
Best Luxury vacations in Chicago
Palmer House a Hilton Hotel
Theatre District
Price was $1,036, price is now $721 per person
$721
per person
Aug 22 - Aug 27
Roundtrip flight included
Orlando (MCO) to Chicago (ORD)
Stay at this 4-star spa hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast. Our guests praise the helpful staff in our reviews. Popular attractions Art Institute of Chicago and Millennium Park are located nearby. Discover genuine guest reviews for Palmer House a Hilton Hotel, in Downtown Chicago neighborhood, along with the latest prices and availability – book now.
I love the 1920's feel of this hotel Such a beautiful public areas, dining rooms. Feels like a step back into 1920's glamour. The walk down long hallways to many rooms is long for anyone with difficulty waking. Many rooms on Wacker st side are on the EL so noisy at night. Rooms are good size for city hotel. Could use another chair and small table.
I will always stay there in downtown Chicago. Convenient to many theaters, restaurants and Lakefront, museums.
Reviewed on Mar 8, 2022
The Langham, Chicago
River North
Save 100% on your flightPrice was $1,314, price is now $956 per person
$956
per person
Sep 22 - Sep 25
Roundtrip flight included
Baltimore (BWI) to Chicago (ORD)
Stay at this 5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast. Our guests praise the helpful staff and the comfy rooms in our reviews. Popular attractions Chicago Riverwalk and Chicago Theatre are located nearby. Discover genuine guest reviews for The Langham, Chicago, in Downtown Chicago neighborhood, along with the latest prices and availability – book now.
Our experience at The Langham was excellent, the hotel is beautiful, the service was wonderful and the location was perfect with walkable shopping, restaurants and great sights to see. My first trip to Chicago in 30 years and it was amazing. Love the city, love the hotel!
Reviewed on Aug 17, 2021
Fairmont Chicago at Millennium Park
The Loop
Price was $982, price is now $719 per person
$719
per person
Sep 22 - Sep 25
Roundtrip flight included
Baltimore (BWI) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, breakfast, and a 24-hour fitness center. Our guests praise the helpful staff and the comfy rooms in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby. Discover genuine guest reviews for Fairmont Chicago at Millennium Park, in Downtown Chicago neighborhood, along with the latest prices and availability – book now.
Paying Extra for Fairmont Gold was not worth it.
Reviewed on Jul 24, 2022
Luxury vacation packages for 4 nights
The Langham, Chicago
River North
Save 100% on your flightPrice was $1,413, price is now $961 per person
$961
per person
Sep 22 - Sep 26
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Stay at this 5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast. Our guests praise the helpful staff and the comfy rooms in our reviews. Popular attractions Chicago Riverwalk and Chicago Theatre are located nearby. Discover genuine guest reviews for The Langham, Chicago, in Downtown Chicago neighborhood, along with the latest prices and availability – book now.
Our experience at The Langham was excellent, the hotel is beautiful, the service was wonderful and the location was perfect with walkable shopping, restaurants and great sights to see. My first trip to Chicago in 30 years and it was amazing. Love the city, love the hotel!
Reviewed on Aug 17, 2021
InterContinental Chicago Magnificent Mile, an IHG Hotel
Magnificent Mile
Save 100% on your flightPrice was $924, price is now $649 per person
$649
per person
Sep 22 - Sep 26
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby. Discover genuine guest reviews for InterContinental Chicago Magnificent Mile, an IHG Hotel, in Downtown Chicago neighborhood, along with the latest prices and availability – book now.
AFTER check in we were informed hot water would be turned off from 11pm to 6am. Also the windows would be cleaned in the AM so keep your curtains closed. This should have been disclosed before check in to give us an opportunity to stay elsewhere for $400 a night. Unacceptable.
Reviewed on Jun 6, 2022
The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago
River North
Save 100% on your flightPrice was $1,333, price is now $976 per person
$976
per person
Nov 3 - Nov 7
Roundtrip flight included
Orlando (MCO) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, 2 restaurants, and a rooftop terrace. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby. Discover genuine guest reviews for The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago, in Downtown Chicago neighborhood, along with the latest prices and availability – book now.
Gorgeous lobby and outdoor fire pit sitting area plus complimentary strong hot coffee at bar; as our room did not have a city view which we had paid up for, we were promptly moved to a floor with a view and treated like royalty - thank you to Michael for the welcoming treatment and swift switch as we were only there one night… I am also impressed that the item I left in room is already located and could be either picked up or delivered, such attention to service details!!
Parking validation was also a huge plus and we were so close to Michigan Ave it was a perfect little getaway for myself and daughter for us to celebrate her birthday! No wonder it’s tops on the best of 2021 list of best hotels in the world!!
Reviewed on Jan 1, 2022
Luxury vacation packages for 5 nights
Palmer House a Hilton Hotel
Theatre District
Price was $1,036, price is now $721 per person
$721
per person
Aug 22 - Aug 27
Roundtrip flight included
Orlando (MCO) to Chicago (ORD)
Stay at this 4-star spa hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast. Our guests praise the helpful staff in our reviews. Popular attractions Art Institute of Chicago and Millennium Park are located nearby. Discover genuine guest reviews for Palmer House a Hilton Hotel, in Downtown Chicago neighborhood, along with the latest prices and availability – book now.
I love the 1920's feel of this hotel Such a beautiful public areas, dining rooms. Feels like a step back into 1920's glamour. The walk down long hallways to many rooms is long for anyone with difficulty waking. Many rooms on Wacker st side are on the EL so noisy at night. Rooms are good size for city hotel. Could use another chair and small table.
I will always stay there in downtown Chicago. Convenient to many theaters, restaurants and Lakefront, museums.
Reviewed on Mar 8, 2022
Fairmont Chicago at Millennium Park
The Loop
Save 100% on your flightPrice was $1,269, price is now $893 per person
$893
per person
Aug 22 - Aug 27
Roundtrip non-stop flight included
Boston (BOS) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, breakfast, and a 24-hour fitness center. Our guests praise the helpful staff and the comfy rooms in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby. Discover genuine guest reviews for Fairmont Chicago at Millennium Park, in Downtown Chicago neighborhood, along with the latest prices and availability – book now.
Paying Extra for Fairmont Gold was not worth it.
Reviewed on Jul 24, 2022
The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago
River North
Save 100% on your flightPrice was $1,940, price is now $1,415 per person
$1,415
per person
Oct 8 - Oct 13
Roundtrip flight included
Sioux Falls (FSD) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, 2 restaurants, and a rooftop terrace. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby. Discover genuine guest reviews for The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago, in Downtown Chicago neighborhood, along with the latest prices and availability – book now.
Gorgeous lobby and outdoor fire pit sitting area plus complimentary strong hot coffee at bar; as our room did not have a city view which we had paid up for, we were promptly moved to a floor with a view and treated like royalty - thank you to Michael for the welcoming treatment and swift switch as we were only there one night… I am also impressed that the item I left in room is already located and could be either picked up or delivered, such attention to service details!!
Parking validation was also a huge plus and we were so close to Michigan Ave it was a perfect little getaway for myself and daughter for us to celebrate her birthday! No wonder it’s tops on the best of 2021 list of best hotels in the world!!
Reviewed on Jan 1, 2022
Luxury vacation packages for 6-7 nights
InterContinental Chicago Magnificent Mile, an IHG Hotel
Magnificent Mile
Price was $1,597, price is now $1,151 per person
$1,151
per person
Nov 1 - Nov 7
Roundtrip non-stop flight included
Rome (ROM) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby. Discover genuine guest reviews for InterContinental Chicago Magnificent Mile, an IHG Hotel, in Downtown Chicago neighborhood, along with the latest prices and availability – book now.
AFTER check in we were informed hot water would be turned off from 11pm to 6am. Also the windows would be cleaned in the AM so keep your curtains closed. This should have been disclosed before check in to give us an opportunity to stay elsewhere for $400 a night. Unacceptable.
Reviewed on Jun 6, 2022
Fairmont Chicago at Millennium Park
The Loop
Price was $1,621, price is now $1,172 per person
$1,172
per person
Nov 1 - Nov 7
Roundtrip non-stop flight included
Rome (ROM) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, breakfast, and a 24-hour fitness center. Our guests praise the helpful staff and the comfy rooms in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby. Discover genuine guest reviews for Fairmont Chicago at Millennium Park, in Downtown Chicago neighborhood, along with the latest prices and availability – book now.
Paying Extra for Fairmont Gold was not worth it.
Reviewed on Jul 24, 2022
Chicago Athletic Association, a Hyatt Hotel
Theatre District
Price was $1,630, price is now $1,217 per person
$1,217
per person
Nov 1 - Nov 7
Roundtrip non-stop flight included
Rome (ROM) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 3 bars/lounges. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Millennium Park and Art Institute of Chicago are located nearby. Discover genuine guest reviews for Chicago Athletic Association, a Hyatt Hotel, in Downtown Chicago neighborhood, along with the latest prices and availability – book now.
Gorgeous facility and exceptionally helpful, kind staff. Great dining options. Loved the gym.
Reviewed on Mar 21, 2022
Luxury hotels in Chicago
Trump International Hotel & Tower Chicago
401 N Wabash Ave, Chicago, IL, 60611
Free Cancellation
Reserve now, pay when you stay
At Trump International Hotel & Tower Chicago, guests enjoy a full-service spa, an indoor pool, and a gym. Parking is available for USD 62 per night (USD 78 per night for valet parking), and there's also limo/town car service. The front desk has multilingual staff on hand 24/7 to help with securing valuables, dry cleaning/laundry, and luggage storage. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Other amenities at this luxury hotel include a sauna, free WiFi in public areas, and conference space.
The Langham, Chicago
330 North Wabash Avenue, Chicago, IL, 60611
Free Cancellation
Reserve now, pay when you stay
At The Langham, Chicago, guests enjoy a full-service spa, an indoor pool, and a gym. Valet parking is available for USD 78 per night, and there's also limo/town car service. The front desk has multilingual staff on hand 24/7 to help with concierge services, luggage storage, and dry cleaning/laundry. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Other amenities at this luxury hotel include a sauna, free WiFi in public areas, and a spa tub.
The Peninsula Chicago
108 East Superior Street, Chicago, IL, 60611
Free Cancellation
Reserve now, pay when you stay
At The Peninsula Chicago, guests enjoy a full-service spa, an indoor pool, and a gym. Valet parking is available for USD 76.00 per night, and there's also limo/town car service. Multilingual staff at the front desk are standing by 24/7 to help with dry cleaning/laundry, tours or tickets, and luggage storage. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Other amenities at this luxury hotel include a rooftop terrace, free WiFi in public areas, and express check-in.
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.
Book Chicago luxury vacations
You want the best of everything in life, and that includes when you travel. Get the full treatment on your next trip, with five-star service, delicious dining and tons of extra amenities to pamper you like royalty. With luxury Chicago vacations, “living the dream” isn’t just a saying. You really can make your dreams a reality—and then dream even bigger. You’ll never look at vacations the same way again.
Experience the ultimate luxury
With silky soft sheets and plush pillows, you’ve never slept better than you will in your luxury hotel room. But when the sun peeks through the curtains, you’ll jump out of bed. That’s because in Chicago, real life is even better than dreams. Grab yourself a gourmet coffee and get to the first task of the day—even if that just means a leisurely brunch, or getting to your spa appointment. On luxury vacations in Chicago, the day is yours. We’re just here to help you have your perfect 5-star getaway.
- Live a life of luxury: We have tons of highly rated hotels, where you’ll find all the upscale amenities you want. You could find splendid spas, ritzy restaurants, deluxe bath products and more.
- Bundles for your budget: You don’t have to be a big spender to find luxury vacation packages—but you can be if you want to. When you bundle your flight and hotel with Orbitz, you know you’re getting a great deal.
Your luxury vacation starts now. Booking on Orbitz is so easy, you’ll feel like you have a personal assistant…and once you’re in Chicago, you just might. The only problem in your future: You won’t want to go home!
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