Maywood Holidays

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Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
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Top hotels in Maywood

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$204 per night from 4 Dec to 5 Dec
S$204
includes taxes & fees
4 Dec - 5 Dec
7.8/10 Good! (8,142 reviews)
"Ice machines! This was an issue here all summer long. I pointed it out to management over the summer but the issue has gone from bad to worse. Supposedly, there are ice machines on even floors. This visit, housekeeping directed me to the machine on the 4th floor as the only working ice machine. I ..."

Reviewed on 22 Nov,2024

Congress Plaza Hotel
River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is S$158 per night from 23 Dec to 24 Dec
S$158
includes taxes & fees
23 Dec - 24 Dec
8.6/10 Excellent! (3,542 reviews)
"Highly recommend ."

Reviewed on 20 Nov,2024

River Hotel
Club Quarters Hotel, Central Loop, Chicago
Club Quarters Hotel, Central Loop, Chicago
4 out of 5
111 West Adams Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is S$152 per night from 23 Dec to 24 Dec
S$152
includes taxes & fees
23 Dec - 24 Dec
8.4/10 Very Good! (3,264 reviews)
"This is a go-to hotel for me near a yearly event I participate in. It's the best value of any of the hotels in its immediate surrounding area."

Reviewed on 21 Nov,2024

Club Quarters Hotel, Central Loop, Chicago
See all 4,546 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.

Frequently asked questions

How much does a Maywood holiday package cost?
Explore the best of Maywood from as little as . We offer a great selection of rental cars, hotels and flights to suit every budget. You can pick up even more discounts when you add a few sightseeing activities to your holiday package.
How do I get a cheap travel package to Maywood?
Think of all the fun things you could do in Maywood with extra cash in your wallet. Watch your savings stack up when you bundle your flights, hotels and other bookings into a Maywood holiday package. You have loads of choice with Expedia too. In fact, you can select from more than 550 air carriers and 1,000,000 hotel options globally. Whether you’re enjoying a break with the family or surprising your special someone, organising a trip to Maywood is better with a package.
Where should I stay in Maywood?
With interesting attractions like Frank Lloyd Wright Historic District and Ernest Hemingway Museum and House in this neighbourhood, try to find a hotel situated near either of them. Concordia University Chicago is another sight that pulls the crowds.
How far in advance should I book my Maywood holiday?
Reserving your flights early with Expedia means one less thing to worry about. Most carriers advertise tickets up to a year in advance. This is typically the cheapest time to book. If circumstances have left you booking late, discount flights to Maywood are still known to appear in the weeks leading up to departure.
What does an Expedia Maywood travel package include?
From hotels and flights to car rentals, Expedia can help you put together a Maywood package that suits you. Heading away for a week or longer? Give some thought to a hotel, flight and rental car bundle. If you can only manage a quick getaway, a hotel and airfare deal may be more your style. Tours and activities can be added once you’ve made your booking. Our travel packages make it a breeze to plan and save.
What should I know before booking a Maywood travel package?
Booking all the parts of your escape together is a great way to save. Combine your airfares, rental cars and hotels into a tidy little package. But it’s not just hotels. Expedia features all kinds of properties, including holiday rentals like beachside villas and serviced residences. Your choices are almost endless!
Can I choose my airline with a Maywood Expedia holiday package?
Yes, you can. We have more than 550 airline partners across the globe, so go with the carrier that suits your budget and travelling style.
If I'm not able to travel, can I cancel my Maywood holiday package?
It’s difficult to predict what the future holds, so it’s good to know that you can cancel or change your Maywood holiday package. If you made your booking in the last 24 hours, you may be entitled to a refund. If it’s an older booking, your hotel, airline or car rental company may charge a fee. Check our Customer Service Portal to learn more.

Popular places to visit

McCormick Place

McCormick Place

4.5/5(36 reviews)

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

Wrigley Field

4.5/5(40 reviews)

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

Millennium Park

4.5/5(147 reviews)

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

Flyover in Chicago

Flyover in Chicago

S$50
Per adult
94% of travellers recommend
Flyover in Chicago
Chicago: Willis Tower Skydeck and The Ledge Ticket

Chicago: Willis Tower Skydeck and The Ledge Ticket

S$58
Per adult
86% of travellers recommend
Chicago: Willis Tower Skydeck and The Ledge Ticket
River tour boat in Chicago

Architecture River Tour

S$71
Per adult
94% of travellers recommend
Architecture River Tour
See all activities in Maywood

* 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.