West Side Cheap Vacations
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Top Cheap vacation packages in West Side
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was ￥135,967, price is now ￥85,990 per person
￥85,990
per person
Mar 19 - Mar 23
found 1 day ago
Roundtrip flight included
Wilkes-Barre (AVP) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
The staff was incredible and the room was spotless.
Reviewed on Jan 25, 2026
Fairmont Chicago at Millennium Park
Downtown Chicago
Price was ￥127,078, price is now ￥92,774 per person
￥92,774
per person
Mar 19 - Mar 23
found 1 day ago
Roundtrip flight included
Wilkes-Barre (AVP) to Chicago (ORD)
8.6/10 Excellent! (2,008 reviews)
The room was clean. The staff was very nice. They even held on to our stuff on our last day after check out so we could explore the town luggage free!
Reviewed on Jan 23, 2026
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was ￥98,291, price is now ￥72,384 per person
￥72,384
per person
Mar 19 - Mar 23
found 1 day ago
Roundtrip flight included
Wilkes-Barre (AVP) to Chicago (ORD)
8.2/10 Very Good! (2,365 reviews)
I liked the hotel. The staff was very courteous and friendly. The room was cute. The location is fantastic.
Reviewed on Jan 20, 2026
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Price was ￥122,148, price is now ￥91,355 per person
￥91,355
per person
Mar 19 - Mar 23
found 1 day ago
Roundtrip flight included
Wilkes-Barre (AVP) to Chicago (ORD)
9.4/10 Exceptional! (3,392 reviews)
Beautiful hotel, stunning views, excellent location, amazing staff, and phenomenal rooftop!
Reviewed on Jan 26, 2026
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View all trips5* Cheap vacations in West Side
Price found within the past 48 hours. Click for updated prices.
The Peninsula Chicago
Downtown Chicago
Save 100% on your flight
Price was ￥255,752, price is now ￥201,810 per person
￥201,810
per person
Mar 19 - Mar 23
found 1 day ago
Roundtrip flight included
Wilkes-Barre (AVP) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
The staff was great. Everybody was friendly. The room was beautifully appointed, although maybe a little too heavy on electronics. I don't think every light switch needs to be a touch pad. And there were one or two things we couldn't figure out, such as the lighted mirror on the credenza: don't know where the controls for that were hiding. These are minor issues and do not take away from the splendid funishings in the room.
Reviewed on Jan 11, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥402,709, price is now ￥319,210 per person
￥319,210
per person
Mar 14 - Mar 18
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
The room was boring thought it would be cleaner updated for the price best part was the view
Reviewed on Jan 24, 2026
Waldorf Astoria Chicago
Downtown Chicago
Price was ￥299,862, price is now ￥244,036 per person
￥244,036
per person
Apr 15 - Apr 18
found 23 hours ago
Roundtrip non-stop flight included
Osaka (OSA) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
Completely loved our stay. Probably the best hotel in all Chicago. Amenities are great and the staff are even better.
Reviewed on Jan 26, 2026
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See all available trips from Wilkes-Barre to West Side
View all trips3 Night Cheap vacations in West Side
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥225,194, price is now ￥183,198 per person
￥183,198
per person
Apr 15 - Apr 18
found 23 hours ago
Roundtrip non-stop flight included
Osaka (OSA) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
The staff was incredible and the room was spotless.
Reviewed on Jan 25, 2026
Waldorf Astoria Chicago
Downtown Chicago
Price was ￥299,862, price is now ￥244,036 per person
￥244,036
per person
Apr 15 - Apr 18
found 23 hours ago
Roundtrip non-stop flight included
Osaka (OSA) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
Completely loved our stay. Probably the best hotel in all Chicago. Amenities are great and the staff are even better.
Reviewed on Jan 26, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥285,612, price is now ￥233,135 per person
￥233,135
per person
Apr 15 - Apr 18
found 22 hours ago
Roundtrip non-stop flight included
Osaka (OSA) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
The room was boring thought it would be cleaner updated for the price best part was the view
Reviewed on Jan 24, 2026
4 Night Cheap vacations in West Side
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was ￥135,967, price is now ￥85,990 per person
￥85,990
per person
Mar 19 - Mar 23
found 1 day ago
Roundtrip flight included
Wilkes-Barre (AVP) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
The staff was incredible and the room was spotless.
Reviewed on Jan 25, 2026
Fairmont Chicago at Millennium Park
Downtown Chicago
Price was ￥127,078, price is now ￥92,774 per person
￥92,774
per person
Mar 19 - Mar 23
found 1 day ago
Roundtrip flight included
Wilkes-Barre (AVP) to Chicago (ORD)
8.6/10 Excellent! (2,008 reviews)
The room was clean. The staff was very nice. They even held on to our stuff on our last day after check out so we could explore the town luggage free!
Reviewed on Jan 23, 2026
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See all available trips from Wilkes-Barre to West Side
View all trips* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
