
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.

The Royal Sonesta Chicago Downtown
Downtown Chicago
Price was ¥968,554, price is now ¥663,375 per person
¥663,375
per person
Aug 13 - Aug 20
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (3,457 reviews)
Candice front girl helped ys checked in she is wonderfull nice. She needs raise.
Room was wonderful, view was 100/10.
Reviewed on Jul 3, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was ¥1,111,172, price is now ¥727,868 per person
¥727,868
per person
Aug 13 - Aug 20
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,554 reviews)
stay away, no one told us it had been damage and under repair, staff could not even help get me bording pass, room service sub par. We got a notice from Expedia after we checked in saying we could cancil, a bit to late.
Reviewed on Jul 3, 2026

Kimpton Gray Hotel by IHG
Downtown Chicago
Price was ¥1,098,030, price is now ¥736,571 per person
¥736,571
per person
Aug 13 - Aug 20
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,005 reviews)
Concierge was very helpful particularly ask for Shea
Reviewed on Jun 28, 2026

Pendry Chicago
Downtown Chicago
Price was ¥1,127,210, price is now ¥762,888 per person
¥762,888
per person
Aug 13 - Aug 20
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,128 reviews)
Wonderful hotel with attentive staff. Should bring back ice machines.
Reviewed on Jul 3, 2026

The Langham, Chicago
Downtown Chicago
Price was ¥1,528,190, price is now ¥1,043,539 per person
¥1,043,539
per person
Aug 13 - Aug 20
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,007 reviews)
Everything was mostly great. Except it was a bit overpriced (especially the spa) and minibar person kept adding stuff I didn't use to my bill. Also they don't tell you what perks you have depending on your reservation. You have to ask. Also I stayed in a junior suite for 8 days and they wouldn't give me a late check out. Finally, they begrudgingly have me an hour after I reminded them I spent almost $9,000 dollars there. Gee, thanks. Front desk guy at check in was mostly unhelpful although he was friendly and polite. Tons of great stuff.
Reviewed on Jul 2, 2026
5* Cheap vacations in West Side
Price found within the past 48 hours. Click for updated prices.

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ¥716,212, price is now ¥560,173 per person
¥560,173
per person
Sep 20 - Sep 26
found 8 hours ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.6/10 Exceptional! (1,899 reviews)
The shower temp was about on the hot side no matter how low you had it. The bed& room were overall great
Reviewed on Jul 3, 2026

The Langham, Chicago
Downtown Chicago
Price was ¥1,528,190, price is now ¥1,043,539 per person
¥1,043,539
per person
Aug 13 - Aug 20
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,007 reviews)
Everything was mostly great. Except it was a bit overpriced (especially the spa) and minibar person kept adding stuff I didn't use to my bill. Also they don't tell you what perks you have depending on your reservation. You have to ask. Also I stayed in a junior suite for 8 days and they wouldn't give me a late check out. Finally, they begrudgingly have me an hour after I reminded them I spent almost $9,000 dollars there. Gee, thanks. Front desk guy at check in was mostly unhelpful although he was friendly and polite. Tons of great stuff.
Reviewed on Jul 2, 2026

Four Seasons Hotel Chicago
Downtown Chicago
Price was ¥1,212,717, price is now ¥909,976 per person
¥909,976
per person
Aug 13 - Aug 20
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,006 reviews)
Excellent hotel. We love staying there whenever we visit Chicago.
Reviewed on Jul 3, 2026
4 Night Cheap vacations in West Side
Price found within the past 48 hours. Click for updated prices.

Hilton Rosemont Chicago O'Hare
Price was ¥313,972, price is now ¥296,036 per person
¥296,036
per person
Sep 18 - Sep 22
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.4/10 Very Good! (1,005 reviews)
The pool was not handicap accessible, being there for a wheelchair softball tournament, many of the teammates were unable to hang out together because there was no way to get to the pool.
The rooms were clean, a little outdated, but the walking distance to the parking was tough as well. Parking in garage, the skywalk was quite a distance. Not to mention when you have to pay to park in your hotel that you already pay to sleep!!
Reviewed on Jul 3, 2026

Level Chicago Fulton Market
Downtown Chicago
Price was ¥795,942, price is now ¥566,164 per person
¥566,164
per person
Sep 18 - Sep 22
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (512 reviews)
We had a great stay at Level. I think it’s a really good option for a longer trip, especially if you want more of an apartment-style setup and a convenient location. The staff was amazing from start to finish and truly made the stay stand out. Everyone was kind, helpful, and welcoming, and the service alone would make me come back.
The location is also very convenient and worked well for getting around Chicago, especially if you don’t mind doing a bit of walking. For our family, I think it felt a little more geared toward professionals or longer stays than a traditional family hotel, but overall we had a very positive experience. If you’re staying in Chicago for more than a couple of nights and want something comfortable and convenient, I would definitely recommend it.
Reviewed on Jul 2, 2026

Things 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.


