West Side Vacations from ￥335,878
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The Latest West Side Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was ￥472,308, price is now ￥335,878 per person
￥335,878
per person
Oct 6 - Oct 13
found 19 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.2/10 Very Good! (2,096 reviews)
Quick and easy check in and check out, friendly and helpful staff
Reviewed on Aug 29, 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was ￥778,928, price is now ￥543,686 per person
￥543,686
per person
Oct 6 - Oct 13
found 19 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,694 reviews)
5 star hotel that goes above and beyond. My family loved staying at the Trump
Reviewed on Aug 29, 2025
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was ￥609,956, price is now ￥430,196 per person
￥430,196
per person
Oct 6 - Oct 13
found 19 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,100 reviews)
The best hotel for Navy Pier
Reviewed on Aug 28, 2025
Eurostars Magnificent Mile
Downtown Chicago
Price was ￥501,303, price is now ￥354,314 per person
￥354,314
per person
Oct 6 - Oct 13
found 19 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.8/10 Excellent! (3,067 reviews)
The staff was helpful &’ nice. The hotel itself was clean
Reviewed on Aug 24, 2025
The Allegro Royal Sonesta Hotel Chicago Loop
Downtown Chicago
Price was ￥487,238, price is now ￥354,164 per person
￥354,164
per person
Oct 6 - Oct 13
found 19 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (1,975 reviews)
The restrooms do not have built in ventilation and the hotel needs to be updated overall.
Reviewed on Aug 25, 2025
Where to stay in West Side
Find the best West Side areas and neighborhoods for the activities you enjoy most. Learn more about West Side
West Loop
1 out of top 10 points of interest in this area
Consider a visit to Milwaukee Avenue and take some time to enjoy the abundant dining options during your time in West Loop. If you want to see more of the city, jump on the metro at Racine Station or Ogilvie Transportation Center.
Find the Best West Side Vacation Packages
West Side Hotel Deals
Crowne Plaza Chicago West Loop by IHG
25 South Halsted Street, Chicago, IL
The price is ￥26,318 per night from Sep 2 to Sep 3
￥26,318
￥30,895 total
Sep 2 - Sep 3
includes taxes & fees
Holiday Inn & Suites Chicago - Downtown by IHG
506 West Harrison Street, Chicago, IL
The price is ￥22,202 per night from Sep 2 to Sep 3
￥22,202
￥27,827 total
Sep 2 - Sep 3
includes taxes & fees
8.2/10 Very Good! (1,016 reviews)
"Great property, pool is awesome and sits right under the Willis Tower"
Reviewed on Aug 26, 2025
Hyatt Place Chicago Medical/University District
1835 W Harrison Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ￥20,016 per night from Sep 1 to Sep 2
￥20,016
￥23,498 total
Sep 1 - Sep 2
includes taxes & fees
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Discover the most popular places to visit in West Side
United Center
Catch an event at United Center during your trip to Chicago. Amble around this vibrant area's lakeside or experience its entertainment choices.
University of Illinois Chicago
Enjoy the collegiate vibe at University of Illinois Chicago during your stay in Chicago. Stroll along the riverfront or experience the acclaimed art scene in this vibrant area.
Garfield Park
After visiting Garfield Park, make a plan to see the other sights and activities in Chicago. Discover the top-notch restaurants and acclaimed art scene in this vibrant area.
What to do in West Side
Self-Guided Illinois Scavenger Hunt: The Great Quest in Illinois
￥1,819
per adult
Wendella's 90-min Chicago River Architecture Tour
￥5,986
per adult
94% of travellers recommend
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.