Northwest Side Cheap Vacations
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Top Cheap vacation packages in Northwest Side
Price found within the past 48 hours. Click for updated prices.
Le Méridien Essex Chicago
Downtown Chicago
Price was ￥343,526, price is now ￥309,246 per person
￥309,246
per person
Sep 19 - Sep 22
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9/10 Wonderful! (1,004 reviews)
Very clean and great view to the park. Staffs are helpful and respectful.
Reviewed on Jun 20, 2026
Level Chicago Fulton Market
Downtown Chicago
Price was ￥1,200,320, price is now ￥837,176 per person
￥837,176
per person
Aug 8 - Aug 13
found 3 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.2/10 Wonderful! (504 reviews)
Upscale amazing stay in trendy neighborhood in Chcago. Walking distance to coffee shops, great restaurants. The amenities were beyond what I expected/ great lap pool, hot tubs, sauna steam room and amazing gym with enough equipment to do a full strength training workout. We will stay here again!
Reviewed on Jun 25, 2026
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was ￥1,093,078, price is now ￥764,910 per person
￥764,910
per person
Aug 8 - Aug 13
found 3 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
8.2/10 Very Good! (2,767 reviews)
Clean rooms and comfortable beds but the windows were a little thin that you could hear everything outside.
Reviewed on Jun 27, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥666,224, price is now ￥548,055 per person
￥548,055
per person
Aug 8 - Aug 14
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (1,893 reviews)
Great location, wonderful staff.
Reviewed on Jun 26, 2026
Fairmont Chicago at Millennium Park
Downtown Chicago
Price was ￥382,568, price is now ￥339,412 per person
￥339,412
per person
Sep 19 - Sep 22
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
8.8/10 Excellent! (2,201 reviews)
Dated hotel with modest upgrades. Spacious room. Nice "grab and go" breakfast bar. Restaurant TORO served good food (branzino and brocolini). However, the hostess had a truly hostile attitude. We complained to the manager but it left us feeling disrespected. The St. Regis was dramatically better.
Reviewed on Jun 27, 2026
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View all trips5* Cheap vacations in Northwest Side
Price found within the past 48 hours. Click for updated prices.
The Peninsula Chicago
Downtown Chicago
Price was ￥498,167, price is now ￥449,412 per person
￥449,412
per person
Sep 19 - Sep 22
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.8/10 Exceptional! (1,009 reviews)
Amazing the staff was so friendly. The hotel is just I can’t believe I never stayed at this hotel. This is by far my top five hotels I will definitely be returning. Thank you so much for such a wonderful stay
Kimberly Chardukian
Reviewed on Jun 26, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥666,224, price is now ￥548,055 per person
￥548,055
per person
Aug 8 - Aug 14
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (1,893 reviews)
Great location, wonderful staff.
Reviewed on Jun 26, 2026
Four Seasons Hotel Chicago
Downtown Chicago
Price was ￥463,062, price is now ￥457,214 per person
￥457,214
per person
Sep 9 - Sep 13
found 11 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
We had a lovely 2 night stay in Chicago and the room with lake view was superb with lovely touches by the cleaning staff who made the stay very special
Reviewed on Jun 1, 2026
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See all available trips from Tokyo to Northwest Side
View all trips3 Night Cheap vacations in Northwest Side
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was ￥352,949, price is now ￥302,538 per person
￥302,538
per person
Sep 19 - Sep 22
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
8.2/10 Very Good! (2,767 reviews)
Clean rooms and comfortable beds but the windows were a little thin that you could hear everything outside.
Reviewed on Jun 27, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥378,586, price is now ￥322,070 per person
￥322,070
per person
Sep 19 - Sep 22
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (4,518 reviews)
The Hotel is well located. The staff is friendly and helpfull.Very clean facility, nice roof top bar/restaurant. Breakfast is oustanding. Overall great experience.
Reviewed on Jun 27, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥455,368, price is now ￥388,928 per person
￥388,928
per person
Sep 19 - Sep 22
found 12 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.6/10 Exceptional! (1,893 reviews)
Great location, wonderful staff.
Reviewed on Jun 26, 2026
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See all available trips from Tokyo to Northwest Side
View all trips4 Night Cheap vacations in Northwest Side
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥379,384, price is now ￥309,758 per person
￥309,758
per person
Sep 9 - Sep 13
found 11 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (4,518 reviews)
The Hotel is well located. The staff is friendly and helpfull.Very clean facility, nice roof top bar/restaurant. Breakfast is oustanding. Overall great experience.
Reviewed on Jun 27, 2026
Level Chicago Fulton Market
Downtown Chicago
Price was ￥387,118, price is now ￥320,492 per person
￥320,492
per person
Sep 9 - Sep 13
found 11 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (504 reviews)
Upscale amazing stay in trendy neighborhood in Chcago. Walking distance to coffee shops, great restaurants. The amenities were beyond what I expected/ great lap pool, hot tubs, sauna steam room and amazing gym with enough equipment to do a full strength training workout. We will stay here again!
Reviewed on Jun 25, 2026
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See all available trips from Tokyo to Northwest Side
View all tripsThings to do
Chicago: Navy Pier Centennial Wheel Ticket
￥3,853
per adult
88% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
