Maywood Vacations from ￥213,975
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 Maywood Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was ￥279,034, price is now ￥213,975 per person
￥213,975
per person
Apr 20 - Apr 27
found 1 day ago
Roundtrip non-stop flight included
Osaka (OSA) 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
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥355,284, price is now ￥244,208 per person
￥244,208
per person
Apr 20 - Apr 27
found 1 day ago
Roundtrip non-stop flight included
Osaka (OSA) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Beautiful room, great location. Will definitely stay there again.
Reviewed on Jan 28, 2026
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Price was ￥362,754, price is now ￥279,852 per person
￥279,852
per person
Apr 20 - Apr 27
found 1 day ago
Roundtrip non-stop flight included
Osaka (OSA) to Chicago (ORD)
9.4/10 Exceptional! (3,392 reviews)
Excellent stay. The hotel is beautifully designed, with a perfect blend of historic character and modern comfort. The room was spotless, quiet, and very comfortable, with great attention to detail.
What really stood out was the staff — warm, professional, and genuinely helpful from check-in to check-out. The location is also ideal, close to everything yet calm and relaxing after a long day.
Reviewed on Jan 29, 2026
Arlo Chicago
Downtown Chicago
Price was ￥376,892, price is now ￥294,512 per person
￥294,512
per person
Apr 20 - Apr 27
found 1 day ago
Roundtrip non-stop flight included
Osaka (OSA) to Chicago (ORD)
9.2/10 Wonderful! (1,862 reviews)
The hotel itself was really nice, but we had to move rooms because the adjoining room was being really loud at 10 AM on a Saturday.
Very hard to find parking, but it’s an alright spot.
Reviewed on Jan 27, 2026
Staypineapple, An Iconic Hotel, The Loop
Downtown Chicago
Price was ￥342,692, price is now ￥268,196 per person
￥268,196
per person
Apr 20 - Apr 27
found 1 day ago
Roundtrip non-stop flight included
Osaka (OSA) to Chicago (ORD)
9.4/10 Exceptional! (1,003 reviews)
Clean shopping near by
Reviewed on Jan 18, 2026
Find the Best Maywood Vacation Packages
Maywood Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥13,897 per night from Jan 30 to Jan 31
￥13,897
￥16,314 total
Jan 30 - Jan 31
includes taxes & fees
8/10 Very Good! (9,832 reviews)
Yes perfectly clean
Reviewed on Jan 24, 2026
Embassy Suites by Hilton Chicago Downtown River North
600 N State St Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥16,325 per night from Feb 8 to Feb 9
￥16,325
￥19,164 total
Feb 8 - Feb 9
includes taxes & fees
8.4/10 Very Good! (5,617 reviews)
Friendly desk staff, clean room. Fridge didn't have temp adjuster and contents froze, bottles broke.
Reviewed on Jan 28, 2026
Hotel Riu Plaza Chicago
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥16,717 per night from Feb 11 to Feb 12
￥16,717
￥23,939 total
Feb 11 - Feb 12
includes taxes & fees
9.2/10 Wonderful! (3,254 reviews)
Love the place! Great breakfast buffet. The room was clean, service was great, and great
Reviewed on Jan 28, 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.
Discover the most popular places to visit in Maywood
Wrigley Field
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
Michigan Avenue
You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.
Navy Pier
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
What to do in Maywood
Chicago: Navy Pier Centennial Wheel Ticket
￥3,883
per adult
88% of travellers recommend
Chicago Crime and Mob Bus Tour
￥7,748
per adult
92% of travellers recommend
Explore a world of travel with Expedia
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
