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 Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

Downtown Chicago
¥244,796
per person
Oct 2 - Oct 5
found 24 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.2/10 Very Good! (2,992 reviews)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
¥286,662
per person
Oct 2 - Oct 5
found 24 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (5,106 reviews)
Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
¥262,404
per person
Oct 2 - Oct 5
found 24 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (3,577 reviews)
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

Downtown Chicago
¥276,288
per person
Oct 2 - Oct 5
found 24 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.8/10 Excellent! (2,341 reviews)
I booked this hotel through Expedia and when I checked in, I was told I was going to be charged $125 that would be refunded to me after my stay if the room was in good condition. I then got a notification that the entire cost of the trip was taken out of my account when it had already paid, so over $1000 was taken away from me that it wasn’t expecting. I did not get the money back until I checked out.

Reviewed on Sep 1, 2026

Freehand Chicago

Freehand Chicago

Downtown Chicago
¥246,278
per person
Oct 2 - Oct 5
found 24 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
7.8/10 Good! (3,328 reviews)
Pros - this hotel is conveniently located and its less expensive than some others in the area. Cons - the first room I was given had water damage in the ceiling and did not smell good. I also checked the AC unit and the filter was completely clogged with dust, this type of washable filter is supposed to be cleaned every month and it looks like it has at least 9+ months of dust on it. I complained about the water damage and they moved me to another room. The next room didn't have soap or shampoo in the bathroom for some reason, and I checked the air filter in this room also and it clearly hasn't been cleaned in forever. In addition to cleaning the air filters, this type of AC unit is supposed to be professionally cleaned once per year. This one has clearly not been cleaned in years. If you want a well maintained hotel, try somewhere else.

Reviewed on Sep 2, 2026

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5* Cheap vacations in West Side

Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
¥1,032,840
per person
Nov 6 - Nov 8
found 1 day ago
Roundtrip flight included
Tokyo (HND) to Chicago (ORD)
9.6/10 Exceptional! (2,003 reviews)
Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

Downtown Chicago
¥1,104,403
per person
Nov 6 - Nov 8
found 1 day ago
Roundtrip flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (1,004 reviews)
Everything was perfect!

Reviewed on Sep 2, 2026

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3 Night Cheap vacations in West Side

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

Downtown Chicago
¥244,796
per person
Oct 2 - Oct 5
found 24 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.2/10 Very Good! (2,992 reviews)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
¥286,662
per person
Oct 2 - Oct 5
found 24 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (5,106 reviews)
Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
¥262,404
per person
Oct 2 - Oct 5
found 24 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (3,577 reviews)
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Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

¥4,309
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Willis Tower Skydeck and The Ledge Ticket

Chicago: Willis Tower Skydeck and The Ledge Ticket

¥7,453
per adult
88% of travellers recommend
Chicago: Willis Tower Skydeck and The Ledge Ticket
Art Institute of Chicago

Art Institute of Chicago

¥6,404
per adult
92% of travellers recommend
Art Institute of Chicago
See all activities in West Side
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.