Maywood Vacations from ￥216,234
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ￥109,000 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.
InterContinental Chicago Magnificent Mile by IHG
Downtown Chicago
￥307,398
per person
Nov 18 - Nov 22
found 24 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.2/10 Wonderful! (3,269 reviews)
Great weekend stay. Everything was amazing, down to location of getting around in the city. The ONLY downside was the cost of parking. It’s valet only and the price was not listed anywhere. It’s $88 a night if you’re doing overnight.
Reviewed on Sep 14, 2026
Find the Best Maywood Vacation Packages
Maywood Hotel Deals
River Hotel
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
￥22,838
￥27,153 total
Sep 27 - Sep 28
includes taxes & fees
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
￥24,727
￥29,398 total
Sep 28 - Sep 29
includes taxes & fees
8/10 Very Good! (2,239 reviews)
"Everything was fine except that the mini-refrigerator in our room did not work."
Reviewed on Sep 14, 2026
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
￥24,089
￥28,638 total
Sep 27 - Sep 28
includes taxes & fees
8/10 Very Good! (10,248 reviews)
"Everything was really nice except the A/C unit wasn't powerful enough to cool the room. When we checked in the curtains were open and the room was extremely warm and never fully cooled. Luckily we had a travel fan that made the room bearable. All other aspects of our stay were great the staff were ..."
Reviewed on Sep 14, 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.
Stay near popular Maywood attractions
Underground Railroad Memorial at McDonald's
This poignant memorial marks where enslaved people found refuge on the Underground Railroad, featuring symbolic broken shackles. Visitors can reflect on this powerful history while viewing the plaque honoring Harriet Tubman.
What to do in Maywood
Chicago: Willis Tower Skydeck and The Ledge Ticket
￥7,453
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
￥3,886
per adult
90% of travellers recommend
Frequently asked questions
How much does a Maywood vacation package cost?
Offering great value package deals from ￥216,234 on Expedia, you'll be thrilled with how little a vacation to Maywood costs! Our packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Maywood?
To pick up cheap Maywood vacation packages, organize your trip outside of peak times such as public holidays. You'll typically find lower prices and better availability when it's less busy.
How many days is enough for Maywood?
Generally, a handful of days is enough to explore the top attractions during your Maywood vacation. But if you prefer to have more time to rest or go on day trips, think about extending your itinerary.
How to find the best Maywood package deals?
Finding a cheap Maywood package deal is a breeze with Expedia. After you've entered your trip dates and destination under our "Packages" tab, set your budget, apply some filters and browse what's available. You can customize your search by "Amenities," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to view the most wallet-friendly Maywood package deals. Want a simple trick to score even more savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are often lower.
Is it cheaper to book a Maywood vacation as a package?
You can enjoy significant savings on your Maywood break by booking a tailored vacation package. Check the "Package" heading, then enter your destination and travel dates to browse the best flight and hotel prices. Bundling can save travelers hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Maywood?
If you have your Maywood travel dates locked in, book early to bag some terrific deals. With Expedia, you can typically reserve some flights up to one year in advance. Prefer spur-of-the-moment adventures? Our last-minute deals are ideal for jetting off on a whim.
How to plan a trip to Maywood?
- Choose when to travel: Check your schedule and get packing. Your favorite season and the activities on offer will also help you decide when to escape to Maywood.
- Set your budget: Consider expenses such as flights, food and transportation when calculating how much to put aside for your trip to Maywood. Then, select a property that matches your budget, whether that's an economical stay or a high-end retreat.
- Decide how many days away: Start by compiling a list of the attractions you want to experience in Maywood. Then, estimate how long you'll need for each, as well as any travel time.
- Bundle your bookings: With your travel dates in place, you can combine your car rental, flights, hotels and more into a customized Maywood vacation package.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
