Northwest Chicago Luxury Vacations

Book a Luxury Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to ¥109,000 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 Northwest Chicago

Price found within the past 48 hours. Click for updated prices.
Eaglewood Resort and Spa

Eaglewood Resort and Spa

¥229,944
per person
Oct 5 - Oct 7
found 6 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.8/10 Excellent! (1,249 reviews)
I came here to relax, play golf and listen to the great bands for my 52nd bday. My cousin and I had a great time. We are planning to return for a relaxing staycation.

Reviewed on Aug 18, 2026

The Westin Chicago Northwest

The Westin Chicago Northwest

¥237,659
per person
Oct 5 - Oct 7
found 6 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.8/10 Excellent! (1,015 reviews)
Don't see what you're looking for?
See all available trips from Tokyo to Northwest Chicago
View all trips

3 Night Luxury vacations in Northwest Chicago

Price found within the past 48 hours. Click for updated prices.
Eaglewood Resort and Spa

Eaglewood Resort and Spa

¥389,870
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip flight included
Kitakyushu (KKJ) to Chicago (ORD)
8.8/10 Excellent! (1,249 reviews)
I came here to relax, play golf and listen to the great bands for my 52nd bday. My cousin and I had a great time. We are planning to return for a relaxing staycation.

Reviewed on Aug 18, 2026

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

4 Night Luxury vacations in Northwest Chicago

Price found within the past 48 hours. Click for updated prices.
Motel 6 Elk Grove Village, IL

Motel 6 Elk Grove Village, IL

¥312,151
per person
Sep 19 - Sep 23
found 23 hours ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
8.4/10 Very Good! (1,269 reviews)
Hyatt Place Itasca

Hyatt Place Itasca

¥312,900
per person
Sep 20 - Sep 24
found 5 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.8/10 Excellent! (1,236 reviews)
the room is clean and spacious, but the air conditioner is a bit noisy; the breakfast is great!

Reviewed on Aug 16, 2026

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

Top Luxury Northwest Chicago Hotels

Holiday Inn Chicago - Schaumburg by IHG

Holiday Inn Chicago - Schaumburg by IHG

1998 North Roselle Road Schaumburg IL
  • 4 min drive from Woodfield Mall
Visit Holiday Inn Chicago - Schaumburg by IHG for a relaxing stay in Schaumburg. Sought-after amenities at this hotel include an indoor pool, a restaurant, and ...
Holiday Inn Chicago - Schaumburg by IHG
Renaissance Schaumburg Convention Center Hotel

Renaissance Schaumburg Convention Center Hotel

1551 Thoreau Dr N Schaumburg IL
  • 20 min walk from Woodfield Mall
Treat yourself to a luxury stay at Renaissance Schaumburg Convention Center Hotel, where you can enjoy amenities like pillowtop beds, designer toiletries, and ...
Renaissance Schaumburg Convention Center Hotel
Hyatt Regency Schaumburg Chicago

Hyatt Regency Schaumburg Chicago

1800 East Golf Rd Schaumburg IL
  • 9 min walk from Woodfield Mall
Treat yourself to some luxurious accommodations at Hyatt Regency Schaumburg Chicago, where you can enjoy amenities like pillowtop beds, rainfall showers, and ...
8.6/10 Excellent! (1,412 reviews)
"Love the market they have, the sandwiches and salads are good. Thanks to Peter for securing my paintings I had left behind. The staff is very friendly and helpful. The room I had this time needed some remodeling. The bathroom door is just odd, needs to be a sliding pocket door. Also, I wish you humans ..."

Reviewed on Aug 17, 2026

Hyatt Regency Schaumburg Chicago
See all 3,904 properties in Northwest 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

¥4,309
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

¥3,920
per adult
90% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Chicago: Willis Tower Skydeck and The Ledge Ticket

Chicago: Willis Tower Skydeck and The Ledge Ticket

¥7,518
per adult
88% of travellers recommend
Chicago: Willis Tower Skydeck and The Ledge Ticket
See all activities in Northwest Chicago
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.