Maywood Holidays

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    Better together

    Save up to S$134 when you book a flight and hotel together*
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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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Maywood Flight & Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was S$989, price is now S$696 per person
S$696
per person
17 Oct - 20 Oct
found 1 day ago
Return direct flight included
Fort Lauderdale (FLL) to Chicago (ORD)
8.4/10 Very Good! (1,450 reviews)
I think this is a good hotel in an extremely convenient location whether you plan to walk or catch a ride. Close to everything and staff was pleasant.

Reviewed on 19 Aug, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was S$1,791, price is now S$1,134 per person
S$1,134
per person
17 Oct - 20 Oct
found 1 day ago
Return direct flight included
Fort Lauderdale (FLL) to Chicago (ORD)
9.4/10 Exceptional! (1,690 reviews)
This property is beautiful and located in a great area.

Reviewed on 19 Aug, 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was S$2,043, price is now S$1,388 per person
S$1,388
per person
17 Oct - 20 Oct
found 1 day ago
Return direct flight included
Fort Lauderdale (FLL) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Nothing beats a stay at the Park Hyatt when in Chicago!

Reviewed on 10 Aug, 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was S$1,206, price is now S$848 per person
S$848
per person
17 Oct - 20 Oct
found 1 day ago
Return direct flight included
Fort Lauderdale (FLL) to Chicago (ORD)
9.4/10 Exceptional! (1,059 reviews)
Loved the atmosphere and friendly atmosphere

Reviewed on 18 Aug, 2025

L7 Chicago by LOTTE

L7 Chicago by LOTTE

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was S$1,382, price is now S$984 per person
S$984
per person
17 Oct - 20 Oct
found 1 day ago
Return direct flight included
Fort Lauderdale (FLL) to Chicago (ORD)
9.6/10 Exceptional! (2,837 reviews)
Property was well located to be able to explore Chicago easily. Very clean hotel and the staff was extremely accommodating. The only thing missing was a pool but it wasn’t a huge issue. Very nice hotel and would go back for sure.

Reviewed on 20 Aug, 2025

Top hotels in Maywood

The Wade

The Wade

4.5 out of 5
644 N Lake Shore Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is S$228 per night from 1 Sept to 2 Sept
S$228
1 Sept - 2 Sept
includes taxes & fees
8.2/10 Very Good! (1,210 reviews)
"The room and view were super nice. Even with not being on the waterfront side of the build we werent disappointed. Check in staff could be nicer but the bar staff was excellent. Nice and informative for travelers. The pier was i. Walking distance. Food and shopping all around and spotless insude ..."

Reviewed on 20 Aug, 2025

The Wade
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is S$284 per night from 14 Sept to 15 Sept
S$284
14 Sept - 15 Sept
includes taxes & fees
7.8/10 Good! (9,026 reviews)
"Family had a great stay."

Reviewed on 21 Aug, 2025

Congress Plaza Hotel
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is S$230 per night from 3 Sept to 4 Sept
S$230
3 Sept - 4 Sept
includes taxes & fees
8.4/10 Very Good! (4,742 reviews)
"I loved the suite idea! The breakfast had a large and varied assortment and great dining area! The staff were obliging and convenient to text for additional towels or housekeeping! Although, trash pickup was noisy at 5am every morning facing the south toward the parking garage. Can you ask for a ..."

Reviewed on 21 Aug, 2025

Embassy Suites by Hilton Chicago Downtown River North
See all 5,075 properties in Maywood
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.

Popular places to visit

Wrigley Field which includes a sporting event, a city and central business district

Wrigley Field

Chicago’s world-renowned baseball ground, Wrigley Field is an iconic stadium where you can learn about the all-American sport and even catch a game.

Wrigley Field
McCormick Place

McCormick Place

Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.

McCormick Place
Millennium Park which includes modern architecture, a city and autumn leaves

Millennium Park

One of Chicago’s main focal points, where locals and visitors flock to see the striking art, architecture and landscape on show.

Millennium Park

What to do in Maywood

River tour boat in Chicago

Architecture River Tour

S$53
per adult
96% of travellers recommend
Architecture River Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

S$58
per adult
96% of travellers recommend
Chicago By Night River & Lake Cruise
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

S$52
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See all activities in Maywood

Frequently asked questions

How much does a Maywood holiday package cost?
Offering great value package deals from S$696 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?

  1. 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.
  2. 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.
  3. 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.
  4. 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.