
Northwest Side Adventure Vacations
Book a Adventure Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ¥45,448 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top Adventure vacation packages in Northwest 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)
Great breakfast buffet, incredible staff, very clean, close to everything we wanted to do! 10/10 and will certainly stay here again!
Reviewed on Jan 26, 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
Don't see what you're looking for?
See all available trips from Wilkes-Barre to Northwest Side
View all trips5* Adventure vacations in Northwest 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)
We went to celebrate my birthday. We had been there several times for work and for celebrations. Previously, the rooms had been spotless and service had been fantastic. This time was less than great. Upon arrival the room was fine upon initial appearance. However, after my wife took off her shoes the carpet was SOAKING wet. I called down to the desk they said they would send someone up right away to fix it. We waited over 45 minutes and no one came up. I called again - the attendant said they would send someone up, yet again. They sent someone up after an additional 45 minutes.
Upon arrival of the person to clean it/fix it, he noticed that it was *really wet* and quite large and would take a long time to fix and be quite noisy. The gentleman asked if we would be leaving the room so they could do so without bothering us. We changed our plans to accommodate that.
We ordered a bottle of champagne to celebrate while we were getting ready for our changed plans. The gentleman who brought the champagne to our room did not open it or pour it, rather just handed it to my husband. The champagne was corked and very unpleasant. We tried to call down to send it back or resolve it in some way but no one answered the phone.
We did have breakfast in the morning which was FANTASTIC and the highlight of our stay.
Reviewed on Jan 26, 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 1 day 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
Don't see what you're looking for?
See all available trips from Wilkes-Barre to Northwest Side
View all trips3 Night Adventure vacations in Northwest 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 1 day ago
Roundtrip non-stop flight included
Osaka (OSA) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Great breakfast buffet, incredible staff, very clean, close to everything we wanted to do! 10/10 and will certainly stay here again!
Reviewed on Jan 26, 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 1 day 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 1 day 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
Don't see what you're looking for?
See all available trips from Osaka to Northwest Side
View all trips4 Night Adventure vacations in Northwest 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)
Great breakfast buffet, incredible staff, very clean, close to everything we wanted to do! 10/10 and will certainly stay here again!
Reviewed on Jan 26, 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
Don't see what you're looking for?
See all available trips from Wilkes-Barre to Northwest 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.
