Maywood Holidays
- Plan, book, travel with confidence
- Better togetherSave up to S$1,300 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
Top hotels in Maywood
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
S$161
8 Sept - 9 Sept
includes taxes & fees
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
S$217
31 Aug - 1 Sept
includes taxes & fees
8/10 Very good! (1,981 reviews)
"There was mold on the curtains."
Reviewed on 11 Aug, 2026
Hilton Chicago O'Hare Airport
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
S$345
11 Sept - 12 Sept
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.
Stay near popular Maywood attractions
Underground Railroad Memorial at McDonald's
This poignant memorial marks where enslaved people found refuge on the Underground Railway, featuring symbolic broken shackles. Visitors can reflect on this powerful history while viewing the plaque honouring Harriet Tubman.
What to do in Maywood
Chicago: Navy Pier Centennial Wheel Ticket
S$32
per adult
90% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
S$52
per adult
94% of travellers recommend
Frequently asked questions
How much does a Maywood holiday package cost?
Offering great value package deals on Expedia, you'll be thrilled with how little a holiday to Maywood costs! Our packages simplify travel planning and maximise your savings.
What are the cheapest months to go to Maywood?
To pick up cheap Maywood holiday packages, organise 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 holiday. 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 customise 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 holiday as a package?
You can enjoy significant savings on your Maywood break by booking a tailored holiday package. Check the "Package" heading, then enter your destination and travel dates to browse the best flight and hotel prices. Bundling can save travellers hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a holiday 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 favourite 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 customised Maywood holiday package.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.
