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Best Luxury vacations in Chicago
Mon, Jan 13 - Thu, Jan 16
William P. Hobby - O'Hare Intl.
$921
The price now is $591 per personFlight + Hotel
Fri, Dec 13 - Mon, Dec 16
Hartsfield-Jackson Atlanta Intl. - O'Hare Intl.
$532
The price now is $380 per personFlight + Hotel
Mon, Jan 13 - Thu, Jan 16
William P. Hobby - O'Hare Intl.
$363
The price now is $263 per personFlight + Hotel
Mon, Jan 13 - Thu, Jan 16
William P. Hobby - O'Hare Intl.
$351
The price now is $260 per personFlight + Hotel
Fri, Dec 13 - Mon, Dec 16
Hartsfield-Jackson Atlanta Intl. - O'Hare Intl.
$468
The price now is $359 per personFlight + Hotel
Mon, Jan 13 - Thu, Jan 16
William P. Hobby - O'Hare Intl.
$714
The price now is $600 per personFlight + Hotel
Thu, Jan 16 - Sun, Jan 19
Logan Intl. - O'Hare Intl.
$390
The price now is $328 per personFlight + Hotel
Sun, Dec 15 - Wed, Dec 18
Minneapolis - St. Paul Intl. - O'Hare Intl.
$355
The price now is $300 per personFlight + Hotel
Mon, Jan 13 - Thu, Jan 16
William P. Hobby - O'Hare Intl.
$281
The price now is $239 per personFlight + Hotel
Thu, Jan 16 - Sun, Jan 19
George Bush Intercontinental - O'Hare Intl.
$274
The price now is $234 per personFlight + Hotel
Fri, Dec 13 - Mon, Dec 16
Hartsfield-Jackson Atlanta Intl. - O'Hare Intl.
$424
The price now is $363 per personFlight + Hotel
Fri, Dec 13 - Mon, Dec 16
Hartsfield-Jackson Atlanta Intl. - O'Hare Intl.
$387
The price now is $334 per personFlight + Hotel
Mon, Jan 13 - Thu, Jan 16
William P. Hobby - O'Hare Intl.
$254
The price now is $220 per personFlight + Hotel
Fri, Dec 13 - Mon, Dec 16
Hartsfield-Jackson Atlanta Intl. - O'Hare Intl.
$691
The price now is $599 per personFlight + Hotel
Mon, Jan 13 - Thu, Jan 16
William P. Hobby - O'Hare Intl.
$409
The price now is $360 per personFlight + Hotel
Fri, Dec 13 - Mon, Dec 16
John F. Kennedy Intl. - O'Hare Intl.
$577
The price now is $509 per personFlight + Hotel
Luxury vacation packages for 3 nights
Mon, Jan 13 - Thu, Jan 16
William P. Hobby - O'Hare Intl.
$921
The price now is $591 per personFlight + Hotel
Thu, Feb 13 - Sun, Feb 16
Hartsfield-Jackson Atlanta Intl. - O'Hare Intl.
$714
The price now is $506 per personFlight + Hotel
Fri, Dec 13 - Mon, Dec 16
Hartsfield-Jackson Atlanta Intl. - O'Hare Intl.
$532
The price now is $380 per personFlight + Hotel
Mon, Jan 13 - Thu, Jan 16
William P. Hobby - O'Hare Intl.
$363
The price now is $263 per personFlight + Hotel
Mon, Jan 13 - Thu, Jan 16
William P. Hobby - O'Hare Intl.
$351
The price now is $260 per personFlight + Hotel
Fri, Dec 13 - Mon, Dec 16
Hartsfield-Jackson Atlanta Intl. - O'Hare Intl.
$468
The price now is $359 per personFlight + Hotel
Thu, Jan 16 - Sun, Jan 19
Logan Intl. - O'Hare Intl.
$460
The price now is $375 per personFlight + Hotel
Thu, Feb 13 - Sun, Feb 16
Hartsfield-Jackson Atlanta Intl. - O'Hare Intl.
$438
The price now is $364 per personFlight + Hotel
Thu, Feb 13 - Sun, Feb 16
Hartsfield-Jackson Atlanta Intl. - O'Hare Intl.
$504
The price now is $421 per personFlight + Hotel
Mon, Jan 13 - Thu, Jan 16
William P. Hobby - O'Hare Intl.
$714
The price now is $600 per personFlight + Hotel
Thu, Jan 16 - Sun, Jan 19
Logan Intl. - O'Hare Intl.
$390
The price now is $328 per personFlight + Hotel
Sun, Dec 15 - Wed, Dec 18
Minneapolis - St. Paul Intl. - O'Hare Intl.
$355
The price now is $300 per personFlight + Hotel
Thu, Jan 16 - Sun, Jan 19
George Bush Intercontinental - O'Hare Intl.
$274
The price now is $234 per personFlight + Hotel
Fri, Dec 13 - Mon, Dec 16
Hartsfield-Jackson Atlanta Intl. - O'Hare Intl.
$424
The price now is $363 per personFlight + Hotel
Fri, Dec 13 - Mon, Dec 16
Hartsfield-Jackson Atlanta Intl. - O'Hare Intl.
$387
The price now is $334 per personFlight + Hotel
Fri, Dec 13 - Mon, Dec 16
Hartsfield-Jackson Atlanta Intl. - O'Hare Intl.
$691
The price now is $599 per personFlight + Hotel
Luxury vacation packages for 4 nights
Thu, Feb 13 - Mon, Feb 17
Dallas-Fort Worth Intl. - O'Hare Intl.
$906
The price now is $652 per personFlight + Hotel
Thu, Jan 16 - Mon, Jan 20
Orlando Intl. - O'Hare Intl.
$421
The price now is $312 per personFlight + Hotel
Thu, Feb 13 - Mon, Feb 17
Dallas-Fort Worth Intl. - O'Hare Intl.
$590
The price now is $469 per personFlight + Hotel
Thu, Jan 16 - Mon, Jan 20
Orlando Intl. - O'Hare Intl.
$357
The price now is $303 per personFlight + Hotel
Thu, Jan 16 - Mon, Jan 20
Miami Intl. - O'Hare Intl.
$275
The price now is $239 per personFlight + Hotel
Thu, Feb 13 - Mon, Feb 17
Dallas-Fort Worth Intl. - O'Hare Intl.
$712
The price now is $620 per personFlight + Hotel
Fri, Dec 13 - Tue, Dec 17
Miami Intl. - O'Hare Intl.
$458
The price now is $400 per personFlight + Hotel
Fri, Dec 13 - Tue, Dec 17
John F. Kennedy Intl. - O'Hare Intl.
$620
The price now is $541 per personFlight + Hotel
Thu, Feb 13 - Mon, Feb 17
Dallas-Fort Worth Intl. - O'Hare Intl.
$509
The price now is $446 per personFlight + Hotel
Fri, Dec 13 - Tue, Dec 17
John F. Kennedy Intl. - O'Hare Intl.
$661
The price now is $580 per personFlight + Hotel
Thu, Feb 13 - Mon, Feb 17
Dallas-Fort Worth Intl. - O'Hare Intl.
$375
The price now is $329 per personFlight + Hotel
Thu, Feb 13 - Mon, Feb 17
Dallas-Fort Worth Intl. - O'Hare Intl.
$789
The price now is $693 per personFlight + Hotel
Wed, Dec 18 - Sun, Dec 22
Mobile Regional - O'Hare Intl.
$1,673
The price now is $1,476 per personFlight + Hotel
Fri, Dec 13 - Tue, Dec 17
John F. Kennedy Intl. - O'Hare Intl.
$991
The price now is $878 per personFlight + Hotel
Fri, Feb 7 - Tue, Feb 11
Miami Intl. - O'Hare Intl.
$785
The price now is $696 per personFlight + Hotel
Mon, Dec 16 - Fri, Dec 20
Los Angeles Intl. - O'Hare Intl.
$685
The price now is $610 per personFlight + Hotel
Luxury vacation packages for 5 nights
Tue, Jan 14 - Sun, Jan 19
Fort Lauderdale - Hollywood Intl. - O'Hare Intl.
$600
The price now is $398 per personFlight + Hotel
Tue, Jan 14 - Sun, Jan 19
Fort Lauderdale - Hollywood Intl. - O'Hare Intl.
$1,258
The price now is $875 per personFlight + Hotel
Tue, Jan 14 - Sun, Jan 19
Fort Lauderdale - Hollywood Intl. - O'Hare Intl.
$1,102
The price now is $771 per personFlight + Hotel
Tue, Jan 14 - Sun, Jan 19
Fort Lauderdale - Hollywood Intl. - O'Hare Intl.
$1,037
The price now is $726 per personFlight + Hotel
Mon, Feb 17 - Sat, Feb 22
WAS-All Airports - O'Hare Intl.
$616
The price now is $469 per personFlight + Hotel
Tue, Jan 14 - Sun, Jan 19
Fort Lauderdale - Hollywood Intl. - O'Hare Intl.
$435
The price now is $344 per personFlight + Hotel
Thu, Feb 13 - Tue, Feb 18
Jacksonville Intl. - O'Hare Intl.
$639
The price now is $516 per personFlight + Hotel
Thu, Feb 13 - Tue, Feb 18
Jacksonville Intl. - O'Hare Intl.
$782
The price now is $642 per personFlight + Hotel
Tue, Jan 14 - Sun, Jan 19
Fort Lauderdale - Hollywood Intl. - O'Hare Intl.
$699
The price now is $580 per personFlight + Hotel
Mon, Feb 17 - Sat, Feb 22
WAS-All Airports - O'Hare Intl.
$1,087
The price now is $903 per personFlight + Hotel
Tue, Jan 14 - Sun, Jan 19
Fort Lauderdale - Hollywood Intl. - O'Hare Intl.
$457
The price now is $392 per personFlight + Hotel
Thu, Feb 13 - Tue, Feb 18
Jacksonville Intl. - O'Hare Intl.
$420
The price now is $366 per personFlight + Hotel
Thu, Feb 13 - Tue, Feb 18
Jacksonville Intl. - O'Hare Intl.
$554
The price now is $484 per personFlight + Hotel
Mon, Feb 17 - Sat, Feb 22
WAS-All Airports - O'Hare Intl.
$1,408
The price now is $1,245 per personFlight + Hotel
Tue, Dec 24 - Sun, Dec 29
NYC-All Airports - O'Hare Intl.
$1,330
The price now is $1,179 per personFlight + Hotel
Tue, Jan 14 - Sun, Jan 19
Fort Lauderdale - Hollywood Intl. - O'Hare Intl.
$389
The price now is $346 per personFlight + Hotel
Luxury vacation packages for 6-7 nights
Sat, Feb 15 - Sat, Feb 22
Bradley Intl. - CHI-All Airports
$3,004
The price now is $2,135 per personFlight + Hotel
Fri, Dec 13 - Thu, Dec 19
Seattle - Tacoma Intl. - O'Hare Intl.
$1,574
The price now is $1,173 per personFlight + Hotel
Mon, Feb 17 - Sun, Feb 23
WAS-All Airports - O'Hare Intl.
$731
The price now is $556 per personFlight + Hotel
Sun, Feb 23 - Sat, Feb 29
QLA-All Airports - O'Hare Intl.
$696
The price now is $535 per personFlight + Hotel
Sun, Dec 15 - Sat, Dec 21
NYC-All Airports - O'Hare Intl.
$915
The price now is $727 per personFlight + Hotel
Mon, Feb 17 - Sun, Feb 23
WAS-All Airports - O'Hare Intl.
$513
The price now is $414 per personFlight + Hotel
Fri, Dec 13 - Thu, Dec 19
Seattle - Tacoma Intl. - O'Hare Intl.
$815
The price now is $659 per personFlight + Hotel
Mon, Feb 17 - Sun, Feb 23
WAS-All Airports - O'Hare Intl.
$1,297
The price now is $1,076 per personFlight + Hotel
Fri, Dec 13 - Thu, Dec 19
Seattle - Tacoma Intl. - O'Hare Intl.
$1,721
The price now is $1,474 per personFlight + Hotel
Mon, Dec 16 - Sun, Dec 22
George Bush Intercontinental - O'Hare Intl.
$1,245
The price now is $1,067 per personFlight + Hotel
Mon, Feb 17 - Sun, Feb 23
WAS-All Airports - O'Hare Intl.
$572
The price now is $494 per personFlight + Hotel
Wed, Jan 15 - Wed, Jan 22
LON-All Airports - O'Hare Intl.
$1,122
The price now is $982 per personFlight + Hotel
Mon, Feb 17 - Sun, Feb 23
WAS-All Airports - O'Hare Intl.
$511
The price now is $449 per personFlight + Hotel
Mon, Feb 17 - Sun, Feb 23
WAS-All Airports - O'Hare Intl.
$503
The price now is $445 per personFlight + Hotel
Sun, Feb 23 - Sat, Feb 29
QLA-All Airports - O'Hare Intl.
$1,191
The price now is $1,056 per personFlight + Hotel
Mon, Dec 16 - Sun, Dec 22
George Bush Intercontinental - O'Hare Intl.
$625
The price now is $554 per personFlight + Hotel
Luxury hotels in Chicago
Price for 1 night 2 adults*
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!
Luxury hotels with recent reviews
Recently booked Luxury hotels
Embassy Suites Chicago Downtown Magnificent Mile 4.0 out of 5.0
Crowne Plaza Hotel Chicago O'Hare 3.5 out of 5.0
Residence Inn Chicago Downtown/Loop 3.5 out of 5.0
Hampton Inn Chicago - Gurnee 2.5 out of 5.0
Four Points by Sheraton Chicago O'Hare Airport 3.0 out of 5.0
Chicago Marriott Downtown Magnificent Mile 4.0 out of 5.0
How much does it cost to fly to Chicago?
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Hartsfield-Jackson Atlanta Intl. (ATL)
O'Hare Intl. (ORD)
Minneapolis - St. Paul Intl. (MSP)
O'Hare Intl. (ORD)
LaGuardia (LGA)
O'Hare Intl. (ORD)
Minneapolis - St. Paul Intl. (MSP)
Midway Intl. (MDW)
Hartsfield-Jackson Atlanta Intl. (ATL)
Midway Intl. (MDW)
Liberty Intl. (EWR)
O'Hare Intl. (ORD)
LaGuardia (LGA)
O'Hare Intl. (ORD)
Liberty Intl. (EWR)
Midway Intl. (MDW)
John F. Kennedy Intl. (JFK)
Midway Intl. (MDW)
John F. Kennedy Intl. (JFK)
O'Hare Intl. (ORD)
Mexico City Intl. (MEX)
O'Hare Intl. (ORD)
LaGuardia (LGA)
Midway Intl. (MDW)
Mexico City Intl. (MEX)
Midway Intl. (MDW)
Minneapolis - St. Paul Intl. (MSP)
Greater Rockford (RFD)
Minneapolis - St. Paul Intl. (MSP)
O'Hare Intl. (ORD)
Minneapolis - St. Paul Intl. (MSP)
Midway Intl. (MDW)
Minneapolis - St. Paul Intl. (MSP)
Greater Rockford (RFD)
LaGuardia (LGA)
O'Hare Intl. (ORD)
Liberty Intl. (EWR)
O'Hare Intl. (ORD)
Liberty Intl. (EWR)
Midway Intl. (MDW)
John F. Kennedy Intl. (JFK)
O'Hare Intl. (ORD)
LaGuardia (LGA)
Midway Intl. (MDW)
Hartsfield-Jackson Atlanta Intl. (ATL)
O'Hare Intl. (ORD)
Hartsfield-Jackson Atlanta Intl. (ATL)
Midway Intl. (MDW)
LaGuardia (LGA)
O'Hare Intl. (ORD)
John F. Kennedy Intl. (JFK)
Midway Intl. (MDW)
Mexico City Intl. (MEX)
O'Hare Intl. (ORD)
Mexico City Intl. (MEX)
Midway Intl. (MDW)
Other Luxury destinations
More to explore for Chicago
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Chicago Hotels
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Chicago Car Rentals
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Chicago Vacations
Save more by combining flights, hotels and cars
^Savings based on all package bookings with Flight + Hotel made on Orbitz.com from January 1, 2018 to December 31, 2018 as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.