New Chicago Vacations from ￥120,093
Book a 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
The Latest New Chicago Vacation Packages
Price found within the past 48 hours. Click for updated prices.
SIRTAJ - Beverly Hills
South of Wilshire
Save 100% on your flight
Price was ￥353,237, price is now ￥197,610 per person
￥197,610
per person
Feb 27 - Mar 2
found 5 hours ago
Roundtrip flight included
Tokyo (HND) to Los Angeles (LAX)
8.4/10 Very Good! (1,001 reviews)
The staff were very nice and welcoming. The check in process was very simple and easy.
Reviewed on Jan 17, 2026
Surf & Sand Laguna Beach
Pearl District
Save 100% on your flight
Price was ￥480,105, price is now ￥307,624 per person
￥307,624
per person
Mar 12 - Mar 17
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Orange County (SNA)
9/10 Wonderful! (1,002 reviews)
spectacular, clean phenomenal views, good service.
Reviewed on Jan 6, 2026
Los Angeles Deluxe Suites - 2 Bedrooms & 2 Bathrooms
Hollywood
Price was ￥381,666, price is now ￥248,036 per person
￥248,036
per person
Apr 8 - Apr 12
found 9 hours ago
Roundtrip flight included
Tokyo (TYO) to Los Angeles (LAX)
9.2/10 Wonderful! (80 reviews)
Staff and management were amazing! Very accommodating and they communicate and respond back conveniently. Directions were clear and precise on check in and check out. The unit itself was really spacious for the 5 of us! I would highly recommend booking with this team!
Reviewed on Jan 10, 2026
The Sofia Hotel
Downtown San Diego
Price was ￥361,237, price is now ￥239,625 per person
￥239,625
per person
Mar 5 - Mar 12
found 22 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to San Diego (SAN)
8.4/10 Very Good! (1,627 reviews)
Overall everything was great!! From arriving to leaving. Even my son and his girlfriend stayed at the hotel and they loved it
Reviewed on Jan 19, 2026
Find the Best New Chicago Vacation Packages
New Chicago Hotel Deals
Red Hawk Resort & Casino
1 Red Hawk Pkwy Placerville CA
Fully refundableReserve now, pay when you stay
The price is ￥25,167 per night from Jan 26 to Jan 27
￥25,167
￥27,684 total
Jan 26 - Jan 27
includes taxes & fees
9.4/10 Exceptional! (543 reviews)
Yes
Reviewed on Dec 29, 2025
The Murieta Inn & Spa
7337 Murieta Drive Sloughhouse CA
The price is ￥23,703 per night from Jan 20 to Jan 21
￥23,703
￥28,763 total
Jan 20 - Jan 21
includes taxes & fees
9.2/10 Wonderful! (670 reviews)
Rancho Murrieta Hotel & Spa offers a truly welcoming and refined experience. The beds are exceptionally comfortable, making it easy to unwind and get a great night’s sleep. The décor is elegant without feeling stuffy—thoughtful, tasteful, and perfectly suited to a relaxing getaway. What really sets ...
Reviewed on Dec 25, 2025
Best Western Amador Inn
200 S State Highway 49 Jackson CA
Fully refundableReserve now, pay when you stay
The price is ￥13,790 per night from Jan 22 to Jan 23
￥13,790
￥15,444 total
Jan 22 - Jan 23
includes taxes & fees
7.6/10 Good! (1,002 reviews)
The egg & bacon breakfast was appreciated.
Reviewed on Jan 15, 2026
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.
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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.
